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KF #33. Strategic Mindset Archives - How to be Awesome at Your Job

704: How to Achieve Lasting Success by Thinking Long-Term with Dorie Clark

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Dorie Clark says: "The things you said yes to earlier in your career, if you're going to be successful, you need to stop."

Dorie Clark reveals the critical skills that help us think long-term and set ourselves up for future success.

You’ll Learn:

  1. The three barriers to long-term strategic thinking
  2. The top two skills that make you indispensable
  3. What to do when you’re stuck in a rut

 

About Dorie

Dorie Clark helps individuals and companies get their best ideas heard in a crowded, noisy world. She has been named one of the Top 50 business thinkers in the world by Thinkers50, and was honored as the #1 Communication Coach in the world at the Marshall Goldsmith Coaching Awards. She is a keynote speaker and teaches for Duke University’s Fuqua School of Business and Columbia Business School. She is the author of Entrepreneurial You, which was named one of Forbes’ Top 5 Business Books of the Year, as well as Reinventing You and Stand Out, which was named the #1 Leadership Book of the Year by Inc. magazine.

A former presidential campaign spokeswoman, Clark has been described by the New York Times as an “expert at self-reinvention and helping others make changes in their lives.” She is a frequent contributor to the Harvard Business Review, and consults and speaks for clients such as Google, Yale University, and the World Bank. She is a graduate of Harvard Divinity School, a producer of a multiple Grammy-winning jazz album, and a Broadway investor.

 

Resources Mentioned

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Dorie Clark Interview Transcript

Pete Mockaitis
Dorie, welcome back to How to be Awesome at Your Job.

Dorie Clark
Hey, Pete, it’s so good to be back with you.

Pete Mockaitis
Well, I’m so excited to dig into your wisdom once again. And one exciting thing that you’ve mentioned I think the world needs to hear is that you have written a musical.

Dorie Clark
Yes, I have.

Pete Mockaitis
What is the story here?

Dorie Clark
Well, this is a process that started about five years ago. I actually write about this in my new book The Long Game. I’m a big fan of long-term goals, ten-year plans. And so, in 2016, I decided that my ten-year goal was going to be that I would write a show that would make it onto Broadway. And so, I have been assiduously pursuing this. I was literally starting from zero because I had no training or experience in writing Broadway or musical theater-type shows.

And so, since then, as I was mentioning earlier, I was…well, first, I applied and was rejected, and then I applied and was finally accepted into a training program, a kind of a prestigious training program that BMI, the music publishing company, runs. And so, I’ve been through that, I’m part of their advanced workshop now, have learned to write musical theater, and, in fact, have written one, which I am now shopping around to produce into regional theaters.

So, it’s just working the network and getting it out there. But I have written a sexy, lesbian, spy musical called Absolute Zero. So, you heard it here first. God willing, 2026 Broadway season.

Pete Mockaitis
I just have so many follow-up questions in terms of how that’s going to unfold but I’ll just wait to see it in theaters.

Dorie Clark
You’re going to love it. It’s going to create a whole new genre.

Pete Mockaitis
I appreciate in and of itself when things cannot be easily defined. Original genres, appreciated. All right. Cool. Well, now something that you have a bit more experience writing is nonfiction books that help people be awesome at their jobs, and it sounds like you got another hit on your hands with The Long Game. Tell us, what’s the big idea here?

Dorie Clark
Thank you, my man. Yes, this is my fourth so I have been flexing my muscles for a while with business and career books. So, the new book is called The Long Game: How to Be a Long-Term Thinker in a Short-Term World, and, basically, it’s about how to apply the principles of strategic thinking to your life and your career so that you can get better results.

Pete Mockaitis
Well, yes, that sounds super helpful. And tell us, long-term thinking, is that something that professionals have a shortage of these days? Or, how would you assess the health of the long-term thinking game these days?

Dorie Clark
The broad state of affairs is not great, partly, of course, that’s human nature. Everybody likes a little bit of instant gratification if you get down to it, but, also, things have become harder for a couple of reasons. One is just in our society, in general, even pre-COVID, I think most of us recognize that there are a lot of forces conspiring to encourage short-term thinking.

We have at the corporate level, you have the push for quarterly earnings and how that trickles down to everybody about trying to get results sometimes with really negative consequences and corners being cut in the Volkswagen or the Wells Fargo type of situation. And in our personal lives, we’re 10, 20 years into our social media era, and a factor that has always impacted people, which is looking around and comparing yourself to other people, we always had that but now we’re comparing ourselves literally to the whole world. And that can be a little demoralizing sometimes, so there’s a push towards short-term thinking.

And then you take that and you put COVID on top of it where all of our plans got blown up suddenly. All we can do is react and be short-term because we don’t know what’s coming down the pike. So, it’s a lot of pressure in that direction. And so, it is my hope that this book, in some ways, can actually help us overcome that and put a stake in the ground because when we have been in reactive mode for so long, of course, it’s a good skill. You want to be agile, you want to pivot, you know how to, you want to know how to be able to respond to change, but, also, that can’t be the only thing you do.

We need to start making plans again. We need to be reclaiming our lives and coming up with the visions of where we want to go so that we are driving the train, not just responding to external stimuli. And, for me, that’s what playing the long game really is about.

Pete Mockaitis
Well, playing the long game seems like the prudent, wise thing to do when I’m thinking about reading some Aesop’s Fables type things to my children. And so, we’ve got those stories about the ant and the   grasshopper and storing things for the winter, and the tortoise and the hare, and kind of sticking with it over the long haul.

So, I think that I’m guessing the milieu is that, “Oh, yeah. Hey, long-term thinking is probably a good and virtuous thing I should be doing.” But could you lay it on us in terms of some of the benefits for people’s careers, like, “No, seriously, if you do this, you can expect these fabulous results to come to you, and if you don’t, here’s what you’re risking”?

Dorie Clark
Absolutely. Well, let me give you one example. I could ask sometimes, like, “Who is an example of someone who’s a good long-term thinker?” And one person who, honestly, stands out, of course, he has his own challenges in terms of his, essentially, world domination. But leaving that aside, Jeff Bezos is actually a really remarkable example of a long-term thinker.

And I think back in 2011, he did an interview with Wired magazine that I think was very telling. They asked him, “Okay, what is the secret to your success? What is the secret to Amazon’s success?” And, of course, this was 10 years ago, this was before Amazon became…it was successful but it was before it became the behemoth that it is today. And what he said was, “What makes Amazon special is that our competitors are only willing to plan on a three-year horizon. We are willing to plan on a seven-year horizon, and invest in a seven-year horizon. Because of that, we are able to take on bigger, more monumental, more potentially game-changing projects than they are. And that is the difference.”

And so, we go a decade out, and we see, oh, my goodness, Amazon Web Services. We see Amazon Prime. These were bets that they laid years ago, and they took time to pay off but now it’s created a massive competitive moat between Amazon and other players. And it’s the same thing for our own lives and our own careers. If you are willing to invest now and you keep at it assiduously while everybody else is just saying, “Ahh, that doesn’t make any sense. Oh, what a waste of time,” by the time they actually figure out the value of what you’ve done, they really can’t even catch up.

Pete Mockaitis
Well, I like that a lot and I think, and, Dorie, I don’t know, I read so much of the stuff you’ve written, and this might be from you, that with that Amazon example, I think Bezos is also said to have commented that he really tries to focus on things that he does not expect to change in terms of, he said, “Well, ten years from now, will people want to pay less? Yes, I think that will not change. People still like low prices. And, like, ten years from now, will people still want things faster or will that change in terms of, ‘You know what, I’d rather have it in five days’? Like, no.”

And so, with that sort of confidence, they said, “All right. Well, we’re pretty sure that people will want the prices low and will want it fast ten years from now, thusly, we can invest big on doing what it takes to make that happen.” So, yeah, that’s really resonant. So, maybe can you bring it into like careers then? If we’re playing the long game with our careers, what are some things that we can bank on as employers and the marketplace will really want from us years from now?

Dorie Clark
Absolutely. So, one of the sections that I have in The Long Game is actually talking about, again, to take a corporate example, but bring it down to the granular of how we apply it in our own lives, most of your listeners are probably familiar with Google and their famous 20%-time policy. And this is the idea that Google pioneered and, well, to be fair, 3M, the Post-It company actually came up with it originally as 15% time. Google adopted it, they even expanded it, made it 20% time, but it really came to public prominence with Google.

And their concept is that employees should be able to spend up to a fifth of their time working on, essentially, speculative projects outside the scope of their regular job, but it should be things that they find interesting, obviously, but things that they believe would help the company. And that is how some of Google’s biggest innovations, like Google News and Gmail, got created.

Now, the caveat, the asterisk on all of this, interestingly enough, even most Google employees don’t do this. About 10% of Google employees actually do 20% time, which is this very low statistic. You might say, “Oh, well, that’s ridiculous. Why should we even take seriously this thing if the company that’s preaching it doesn’t do it?” But actually, I think it’s an important point for us to plumb. We know that it is not easy to carve out 20% time. You have to really be forceful in creating a fence around it. It is always easier to just lean into doing your existing job, “Oh, I’ve got meetings. Oh, I’ve got emails to answer.” And so, you allocate that time accordingly. I get it.

But if you are fencing off time for, essentially, your own professional development, for learning things, trying things, where you are developing new skills and exploring new areas, this becomes your insurance policy for the future. COVID showed us that we have no freaking idea what is going to happen. We just don’t know.

And so, we can make educated guesses and we can plan for the future, but, really, the best thing that all of us can be doing is turning ourselves into Swiss Army knives where we are not overly optimized for one task because that task could change, the company could change, it might not need it anymore. What we need to do, and 20% time is a really good vehicle to do it, is to allocate part of our time to proactive professional development so we’re learning new things and have new skills that we can fall back on if we need to. And it’ll also open up new opportunities as well. So, I think that’s one clear takeaway that can be very useful for people in the present moment.

Pete Mockaitis
All right. So, I like the notion of becoming a Swiss Army knife, and proactive professional development, and being kind of a bullet proof, invincible, depending on the winds of change and sway and stuff. And so, I guess I’m thinking what are some of the top skills, or I’m actually visualizing literally a Swiss Army knife, the bottle opener, the screwdriver, the tweezers, the scissors?

Dorie Clark
Everybody’s going to love you if you can open bottles. I say go for that one.

Pete Mockaitis
And then the hook, the little hook. I always found that tricky. Apparently, it’s for when you’re carrying boxes wrapped in twine. Okay, now you know if you were curious. You can also pull out stakes with fishing wire. Anyway, Swiss Army knife has a lot of tools. What do you think are some of the top tool skills that professionals should work to be developing that are timeless? Because, on the one hand, I’m thinking, “Well, hey, a lot of sort of artificial intelligence stuff, for example, is hot.” And then a coding language like Python or something is something that you say, “Oh, maybe that’d be good to know, but then, again, maybe that’ll be irrelevant in six years.” So, help us, Dorie, how do we think through what are the skills are really worth investing and building?

Dorie Clark
That’s right, Pete. Absolutely. I’m going to answer it in a couple different ways. So, the first one, props to you, my man, is a really simple starting point that people can do is actually LinkedIn Learning courses. And I’m an instructor, you’re an instructor, and, in fact, both of us are fortunate enough that some of our courses were among the top 20 most popular of the year. So, actually just diving in and immersing yourself in that is a really good simple way.

These courses are not long. This is something you can do on your lunch break but that’s a good regular way that you can begin to just take time that often might’ve been deployed for other purposes, maybe just messing around, maybe answering emails. Actually, really investing in learning. So, that’s one low-hanging fruit.

But, also, I think it is true, of course, we can all kind of envision that, “Oh, I should learn about 3D printing or something like that. What are the things of the future?” If you are interested in those things, then, Godspeed, go do it. That’s great. I also want to argue that there is merit in learning about things that might seem completely irrelevant. And my example, in fact, I consider musical theater to be my 20%-time activity. And it might sound frivolous in some ways, like, “Well, what does that have to do with being a business author?”

And on the surface, hmm, I don’t really know but what I do know is I am not only learning skills about how to do a particular thing, lyric writing, book writing, whatever. Those are really powerful and you can argue that there are some overlays in terms of story arcs and narrative and how it applies to my book, but, also, from a networking perspective, I am meeting massively different types of people. There’s a lot of interesting development of who I’m connecting with and what I know, and it’s giving me access to a whole new canon of knowledge.

And so, I can tell you that it’s been…there are examples where I’m meeting people in the business world and I’m able to connect with them better because I have additional knowledge that I can bring to bear about theater if that is, in fact, one of their interests. So, even something that seems really like, “Oh, why would you do that?” There actually can be a lot of surprise hidden value in it. It’s sort of the equivalent of the well-worn example of Steve Jobs studying calligraphy. Like, “Well, what did that matter?” Well, it turns out, it can create a design orientation that actually can be very influential but we couldn’t have predicted it.

Pete Mockaitis
Yeah, that is cool. Okay. Well, so then in terms of the 20% time, it’s like it’s a combo then of, “What do you find really fascinating? Go for it,” and then, “What do you think you just can’t see any connection whatsoever? Don’t let that stop you.” And then LinkedIn Learning is one quick and easy and fun resource to get in there.

And so, I’m curious then, are there any – and I’m sure this will vary as the years unfold or maybe it won’t at all, and that’s the point – what will be some like the top skills you think, boy, every professional can really benefit from sharpening these skills?

Dorie Clark
Yeah, absolutely. Again, with the purview so that, honestly, if you want to keep yourself motivated, the most important thing is that it should be interesting to you. But I would say, in my own experience, things that are super valuable, one, probably the biggest that I’ve put at the top of the list, is public speaking. And part of the reason that I do this is there are some very interesting research that was done a few years ago by The Center for Talent Innovation, which is a think-tank in New York. And they were studying the concept of executive presence, which is, essentially, this idea, this very poorly-defined idea of somebody looking like a leader, or seeming like a leader. Like, what does that mean?

And so, they wanted to break that down because a lot of people talk about, “Oh, he’s got executive presence but he doesn’t.” And so, okay, what are they talking about? And one of the key components that it turned out people were implicitly referring to is people’s public speaking ability. And it kind of makes sense because if we think about, for instance, how our country, how countries, in general, elect leaders, what are the trials that we put them through? Well, it’s usually debates, it’s townhall meetings, it’s rallies, it’s all about your public speaking, so a very low-hanging fruit where someone can get a dramatic ROI from investing time and effort is actually becoming a better public speaker. So, I would put that at the top of the list.

I’m also, you know, I’m partially communications in general, given that I started my career as a marketing strategy consultant, but I would say that effective copywriting, persuasive sales writing is one of the most important skills, whether you’re literally selling something or whether you are a regular professional trying to sell your boss on an idea, or trying to get a client to take a concept and let you run with it. Sales copy, which is different than regular writing, persuasive sales copy is an incredibly valuable skill to have. So, I would probably put those two at the top of the list.

Pete Mockaitis
All right. Beautiful. And so then, beyond just simply learning, training, skills development, what are some other ways that you recommend we can shift our thinking away from the short term and to the long term? Are there any sorts of key questions, or prompts, or exercises you recommend folks go through to get more in the long-term zone?

Dorie Clark
Yeah, I love that question. So, when we think about, “How do we kind of reorient ourselves?” One of the most important starting points is actually just, at a very basic level, creating the white space necessary to be able to have those conversations, whether it’s literally a conversation with a colleague or just an internal reckoning with yourself. It is not that it takes a huge amount of time to do strategic thinking. It does not. But it takes some time.

And one of the problems that I see with a lot of the clients that I worked with and colleagues around me is that they literally have no time for this because they are so packed to the gills with their scheduling. They’re constantly racing around. They don’t have a moment to breathe. And, therefore, they really don’t have a moment to ask very fundamental questions about what they’re doing, why they’re doing it, if it’s the right thing to be doing. Nobody wants to be the person that is optimizing perfectly for the wrong goal, for the wrong outcome.

So, I think that one of the very best things we can do to begin to give ourselves the space to ask these questions is to actually just create a little room on our calendar. Obviously, it’s easier said than done, but I think we need to start becoming a lot more ruthless in terms of what we accept. Something that doesn’t get talked about, this is a skill you need to develop, although no one will tell you this, the things you said yes to earlier in your career, if you’re going to be successful, you need to stop. You need to regularly re-evaluate and create tighter and tighter criteria for what actually gets on your schedule. And this is an essential part of being a strategic and long-term thinker.

Pete Mockaitis
Ooh, I find that actually pretty inspiring, Dorie, and I don’t know if that’s the reaction you get very often, “Tighter and tighter criteria. Ooh, boy.” But I think it’s true in that I‘m thinking about just, hey, this podcast, 700 episodes in, that’s exactly what’s happened in terms of criteria get tighter and tighter and tighter with regard to what guest gets in, which parts of the interview stay versus get edited out. And then, likewise, just as a function, I think the percentage of incoming pitches that are thumbs up gets smaller and smaller as well.

Dorie Clark
Yeah, when you were first starting, you probably would’ve interviewed my cat. That’s what it’s like when you start.

Pete Mockaitis
I’m thinking about how I might make a case for that in terms of, “Well, cute animal photos have been shown to reduce stress.”

Dorie Clark
It could go viral.

Pete Mockaitis
“Cats have been known to go viral.” So, then can you make that all the more real and specific for us in terms of maybe in your own schedule or others that you’ve coached or worked with and how you’ve seen, “Hey, this used to be okay, and now it’s not. And here are some particular filters or rules or criteria I’m using now that determine what gets the yes”?

Dorie Clark
Yeah, absolutely. And I actually go into a lot of detail about this in The Long Game because I think your question points to something important, which is specifics actually really matter here because you can say all you want, “Oh, you should just say no more often,” and that’s great but people are like, “Okay, you jerk, like how do I do it?” So, you need to really understand the mechanics and the scripts and how do you draw these criteria.

Just to give you an example. When I first started my business, I’ve been working for myself for 15 years, I kind of didn’t know anybody. Like, when you’re starting any career, or you’re starting at a job, you don’t know anybody and so, therefore, you don’t even know who’s worth your time. And at that moment, it’s actually good to say yes to everybody because it’s not like you have so many other important things to do, and it’s not like there are so many people fighting to spend time with you. if you have an opportunity for a networking engagement, you should probably do it, right?

So, early on, the filter should be very wide. But, over time, people do begin to seek you out more, and so you’ve got to narrow it. So, some examples. Early on, I was so happy that anyone would like talk to me. I would immediately offer to go to them, “Oh, where do you want to meet? When do you want to meet?” And so, I would accept these things where I’d be taking like a 45-minute train ride into the city to go see somebody at some inconvenient place. I’d be coming back. I would literally have spent half a day in a networking meeting with someone.

Now, a half a day is extraordinarily valuable. I think about how much revenue or all the things I could be doing but, back in the day, I would say yes to that. So, over time, I slowly tightened it and say, “Okay. Well, maybe I’d meet with them but I’m not going to just offer to go to them. I would either make them come to me and meet near me, or I would only do it if I was already going to be in their neighborhood.” Also, I used to meet with people, “Hey, let’s have a networking meeting,” for like pretty much no reason. It could be, “Oh, somebody suggested we might like each other,” something like that.

Now, I actually need a pretty compelling reason, like, “Well, what do you want to talk about? Like, what’s the goal? Why is it that we should connect?” because, oftentimes, what I would discover, that I didn’t know, is that people actually had an agenda. They just wouldn’t state it. It was often to sell something to you. And so, it’s important to kind of understand what’s behind all of that. So, that’s a piece of it.

You can also, if you want, if you want to do the meeting, you’re not sure if you can say no, another strategy that I use is find a way that you can downgrade it but still say yes. So, you might say, “Oh, Dorie, can we have coffee? Can we have lunch?” and if I want to be careful, I don’t want to offend you or something, or I feel like I should say yes, I might say, “Oh, thank you, Pete. I’d love to do it. That would be great. My schedule is super crazy. I can’t do lunch but how about a call? Can we do a call next week?” And so, that way, instead of lunch, which might be two hours, two and a half hours, like getting there and then a lunch, the call is a tight 30 and then you can log off. So, you have, essentially, found a way to still say yes but save yourself 90 minutes, and all of that adds up over time.

Pete Mockaitis
Well, Dorie, I like this so much. It’s funny, just recently, I think I was getting a new insurance quote, and they proposed…because sometimes this is very easy to do, they said, “Oh, hey, when’s a good timing and we can hop on a call for me to walk you through a point-by-point all the elements of this plan?” I was like, “Wow, I never want to do that,” and maybe that might be prudent depending on the nature of the insurance product and what’s at stake and if there’s a lot of points of differentiation between that insurance product and the competition. Maybe that might be well worth your time. But for me, it wasn’t. It was sort of small potatoes insurance and I thought, “Wow, do people really say yes to this?

And so, I was able to say, “Oh, would it be possible for, instead, for you to email me the policy and share with me the key points and the price?”

Dorie Clark
That’s right.

Pete Mockaitis
And I think I know what they’re doing. I think from like a sales process, I’m sure the studies have shown, you get a higher conversion rate if you have like a relationship and some engagement and some conversation, but I probably just wanted to kind of say yes, thank you, get some insurance, and move onto something else.

So, sometimes it’s easy but for me it’s kind of rare. And it’s funny, as you share those things, I’ve had those thoughts. Let’s just get real about sort of emotions here. And sometimes I will also have thoughts to be like, “Pete, who the heck do you think you are? Oh, now you’re big time, huh? Oh, you’re so important now that you can’t be bothered to have lunch.” So, I’ve got some internal dialogues in terms of just like, “Well, no, I can have a spreadsheet I can show you that time it better placed somewhere else from a business development perspective. Like, that’s a fact.”

But sometimes it’s more fuzzy, like, “Well, I don’t even know what’s going to make a bigger impact. Hard to say.” But then there’s also a little bit of the, “Oh, so now I’m too good.” And it’s like I don’t want to become, I don’t know what the anti-hero I’m looking for here, the villain I’m trying to paint here, not Scrooge McDuck swimming in money, or like Scrooge…help me out here. Like, I still want to be a generous person who is not corrupted by success as I grow but I guess that’s part of the long game as our time will become increasingly more valuable. We will need to say no more often. How do we deal with that?

Dorie Clark
Right. Well, I think you’re pointing to something important, which is that there’s a lot of layers to this. It’s not just a strictly rational ROI calculator, essentially. But I think there’s a few ways to think about this. And, also, of course, it depends who’s asking. I think sometimes, again, when we are less experienced, we often, at least me, I would essentially fall prey to people, just anyone who’d be like, “Hey, want to have coffee?” and I would just assume like the correct answer is yes, “Okay, yes.”

And then, meanwhile, you come and it’s some kind of a sales pitch or something where it’s almost like you’ve been kind of tricked or strong-armed into it, or if it’s not a sales pitch, maybe it’s they want something, “Oh, hey, Dorie, I hear you write for so and so. Can you introduce me to blah, blah, blah?” And it’s like, “Oh, now I get it. Like, oh, you want a thing that’s why you want to connect.” And so, those are things I do not feel bad screening out. I don’t want some user who is taking advantage, and so I think, partly, it’s about learning how to be more mindful if you feel like that vibe is coming off of someone.

I think, also, the truth is I don’t feel bad about saying no to people that are coming at you, or coming at me, in ways that are a little inappropriate. I think that, for me, when I was 22, when we’re all 22, we would have the college career counselors, they’d be like, “Oh, you should reach out to people and pick their brain.” And many people, again, when you’re 22, fine, but many people just kept with that, and that’s still their approach, and it should not be the approach of a seasoned professional.

If you are dealing with someone, you want to be showing empathy for their situation. And if you know that that person is, and you got to think about it, but if you actually, when you rationally think about it, realize, “This person is probably getting 10, 20, 50 emails per week with people asking for something,” you have to be mindful of what your ask is and contextualize it properly. And so, if you’re just sort of blithely saying, “Oh, can I have, for no reason at all, an undifferentiated amount of your time?” that’s actually not really being a sophisticated consumer. And so, I think that we need to…we all need to be more thoughtful in terms of how we approach people.

I actually did an analysis of the emails that I received a while back, and I discovered that, in the course of a week, I got somewhere between 10 and 11 requests per day for something. Now, sometimes it was a coffee or a meal, sometimes it was a, “Hey, will you share this on social media?” Sometimes it was a, “Will you blurb my book?” or, “Will you do this?” And many of them were from great friends, and I would be glad to do it. That’s totally fine.

But we all have to recognize for ourselves and when we’re dealing with others, if someone is getting 70 requests in a week, it is just foolish for that person to say yes to all of them. You have to triage and protect it so that I can say yes to you, Pete, and not some random person who is sort of barging in with inappropriate request.

Pete Mockaitis
Yeah, that’s good. Was it Jim Carrey where he says yes? Is it Yes Man? With all the chaos that ensues with the yes to everything. Yes, that’s helpful and thought-provoking both in terms of as the requester and the potential grantor of requests, like how to do that well. Well, thanks, Dorie. We went really deep there.

Dorie Clark
Absolutely.

Pete Mockaitis
Let’s zoom out for a bit. Any other critical ideas from The Long Game that you think folks looking to be awesome at their jobs should know about?

Dorie Clark
Yeah. Well, I’ll just add one piece to where we were going before, which is, ultimately, if you want to actually be true to your vision, if you actually want to accomplish whatever your long-term goal is, it is not just about the people around you and saying no. We often fail to think about the opportunity costs when some requests or something is coming at us, some opportunity. We often think, “Should I do this thing or not?” And that’s not really the right question. It is actually, what we should be asking, is, “Should I be doing this thing or any other thing in the world that would take approximately that amount of time?”

And so, we have to contextualize it because if there’s a goal that you truly care about, that needs to be a north star in your mind so that you are carving out time so you can really do that and fulfilling your agenda rather than everyone else’s agenda for you. So, just connecting with that point, one area that I talk about that’s related in The Long Game is a concept that I call being willing to say no to good things.

Of course, we understand that we should say no to the bad things. It might be hard or that you worry that you might be hurting people’s feelings or something like that, but, ultimately, we get it. But where we really develop the kind of ninja-level skill, and this is very hard for all of us, is that if we want to leave room to pursue what actually is great, what is a great opportunity or a really important thing for us, if something is nearly good, we also need to be willing to say no to that. And the discipline to do that is really what can set us apart and make us extraordinary.

Pete Mockaitis
That’s powerful. Boy, Dorie, we’re two peas in a pod here when you talk about saying no and sort of the alternative is like everything else that you could be doing. And I remember the first time I learned about the concept of opportunity costs in an economics high school course, it freaked me out. I’m just like, “Holy crap, so you’re saying in choosing to do one thing I’m saying no to everything else on the planet every time. Whoa!”

It kind of shook me up actually for a few weeks. It’s like a random day in economics class, a day in high school. But it’s the reality of the matter with regard to where you can funnel your time, and that’s really powerful when you’re thinking about those long-term objectives that you’re shooting for and how to get there.

I guess I want to hear your take in terms of the…well, if it’s diet or exercise or smoking or video games, anyway there’s a whole host of ways we humans have a knack for going after that instant gratification at the expense of long-term stuff. So, do you have any tips or perspectives or reframes that could help people when they’re in the heat of battle and they have a temptation to do something that maybe feel good or short term when they’d be better to do something more long-term oriented?

Dorie Clark
Oh, as someone who ate a large ice cream sundae last night, I can totally speak to this. But to be fair, I planned. I planned that sundae. I saved up for that sundae but, nonetheless. I think there’s a couple of things that we can keep in mind. And one of them, in The Long Game I tell the story of a woman named Kim Cantergiani who was a busy mom, a busy wife, had a great job as she was a C-suite executive at a nonprofit. And the thing that always fell through the cracks was her health, and she had gained weight that she wanted to lose, and she just had not been able to do it.

And, ultimately, for her, what proved successful is she created a pound-a-thon campaign where she publicly pledged to all her friends, and she got them signed up, that for every pound she lost, that they would donate X amount of money to the local Battered Women Shelter. And so, at that point, it became about something bigger than herself. She was going to be letting down other people if she did not lose weight.

And so, she told me, she said, “After that, I really couldn’t be seen walking around with chips and a Diet Pepper after that.” So, I think sometimes it’s about external accountability and tapping into the bigger picture of a cause outside yourself. And the third point that I’ll make is that oftentimes it’s really about committing to a date certain for something, because humans, we love to kind of blur the lines or make exceptions or, “Oh, I could do this a little later.”

But I tell a story of a woman named Sam Horn who was a very successful speaker, author, just running herself ragged in the pre-COVID world, traveling everywhere, giving these talks. And she decided that what she really wanted to do, it’d been a longstanding goal, is she wanted to move near the water, and actually not just one place. Not like get a lake house, but she wanted to spend an entire year as kind of a digital nomad, living by the water in beautiful places, like Florida and Hawaii. And she ended up doing it but she said the only reason was that she just forced herself to commit. She circled October 1st on her calendar and she made herself happen. And she said, “If I didn’t have a date, I wouldn’t have done it.”

Pete Mockaitis
That’s good. Thank you. Well, Dorie, tell me, any final thoughts about the long game before we shift gears and hear about some of your favorite things?

Dorie Clark
Thank you. I appreciate it, Pete. I will just mention, for anybody that wants to dive in further to strategic thinking and creating a long-term vision, that I have a free resource, which is a Long Game Strategic Thinking Self-Assessment, and folks can get it for free at DorieClark.com/thelonggame.

Pete Mockaitis
All right. Perfect. Thanks. Well, now, could you share a favorite quote, something you find inspiring?

Dorie Clark
One of my favorite quotes is actually one from Theodore Roosevelt, and I love it because, fundamentally, to me, long-term planning is important but it’s acting toward those long-term goals. It’s about the action. And his quote is, “In any moment of uncertainty, the best thing to do is the right thing. The next best thing to do is the wrong thing. And the worst thing to do is nothing.” And so, I think we learn by taking action, and, to me, that quote exemplifies it.

Pete Mockaitis
Thank you. And how about a favorite study or experiment or bit of research?

Dorie Clark
So, I have to pick a sentimental favorite. I actually talk a lot about this in The Long Game as well, is the famous marshmallow study by Walter Mischel, talking about, “Do you take one marshmallow now or two if you wait 15 minutes?” If we can figure out how to crack that code, that’s the ultimate in long-term thinking.

Pete Mockaitis
And a favorite book?

Dorie Clark
One of the things that was most inspiring to me as I was starting my business and my business career was the book Influence: The Psychology of Persuasion by Robert Cialdini.

Pete Mockaitis
Had him on the show. So amazing.

Dorie Clark
He is. It’s so beautifully written. It is so engaging. And I think it just taught me so much about life, so I really respect the work that he’s done.

Pete Mockaitis
And a favorite tool, something you use to be awesome at your job?

Dorie Clark
Yes, a favorite tool that I use, actually all the time, is Google Translate. I feel like these days, I’m working with so many people internationally, and where I can, at least learn a few phrases or say something as kind of a tip of the hat for them and their culture, I try to do that. So, I enjoy using that tool for connecting with people across borders.

Pete Mockaitis
And is there a key nugget you’ve been sharing that really seems to connect and resonate with folks; they quote it back to you often?

Dorie Clark
Well, one of the things that I feel like seems to be resonating for people a lot, perhaps especially coming out of COVID, is a concept that I talk about in The Long Game called thinking in waves. And the basic idea is that, oftentimes, when we feel stuck, we feel like we’re in a rut, the problem is that we are, essentially, trying to just keep doing more of the same thing, and it’s the same thing that we’re good at, or the same thing that we’ve gotten results at. And, unfortunately, one of the things about being a successful human and a successful professional is that we actually have to do different things and we have to shift into a different wave.

And so, one of the most important things, I believe, is that we need to recognize, “Okay, which wave are we in? And where are we in the cycle? And how can we shift?” So, as just one example, for a lot of people, many of whom, frankly, have been kind of hard on themselves about this, they may have had a lot of extra home responsibilities or family responsibilities during COVID, and it’s not like you had a lot of choice in that. That’s sort of what the situation called for. We can’t beat ourselves up about it. But the important thing is to recognize that if we are playing the long game legitimately, then we need to lengthen the time that we’re looking at, and realize that it’s not necessarily about having perfect work-life balance, let’s say, during a set period of time.

During the past 18 months, you probably didn’t have very good work-life balance, but what you can do is actually make a choice to over-index in other areas. And once you are able to re-allocate some of that energy toward work, or toward non-family relationships, like friends, and deepening connections, and things like that, or if you’ve been going crazy with work, working way too hard, that’s fine in the short term. Sometimes you need to do that in order to be successful, but the problem comes when you do that always.

And so, it’s just understanding what wave are you in and how can you transition successfully so that over a long-enough period of time, you are getting the balance that you need.

Pete Mockaitis
Lovely. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Dorie Clark
One of the final challenges that I will suggest to people is in The Long Game I talk about a concept that I call optimize for interesting. And we all know that in our culture, oftentimes, things are a little bit polarized. It’s either, according to conversations, it’s either that we’re optimizing for our passion or we’re just making money, “Okay, let’s get some money.” I feel like those are fine options. They all have their limitations.

But because not all of us necessarily even know what our passion is, or it might change over time, or maybe your passion isn’t something that you can or that you want to monetize, what I like to suggest that we have as one potential orientation is the idea of optimizing for interesting. Because even if you don’t know what your passion is, for sure, you know what you find interesting. There’s hobbies, there’s things, you know what, some people really like birds. Guess what? If you like birds, you know it. If you’re not into birds, you also know that.

Some people are into wine, some people are into golf, some people are into football, some people are into theater. Optimize and try to direct your discretionary time and learning and knowledge and effort toward things that you find interesting. And you really can’t go wrong because you will enjoy the process, you will get more data, and you will learn things about yourself. And if it stops being interesting, no problem. Just pivot to something else.

Pete Mockaitis
Dorie, thank you. It’s always a treat. I wish you much success in the long game.

Dorie Clark
Pete, thank you. Always a pleasure to be here with you.

695: How to Take Risks Confidently with Sukhinder Singh Cassidy

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Sukhinder Singh Cassidy says: "When nothing is sure, everything is possible."

Sukhinder Singh Cassidy shares valuable insight on how to take smarter, more calculated risks with confidence.

You’ll Learn:

  1. Two easy ways to build your risk-taking muscle 
  2. How to stop the fear of failure from holding you back 
  3. One question to help you make smarter, more calculated risks

About Sukhinder

Sukhinder Singh Cassidy is a leading technology executive and entrepreneur, board member, and investor with twenty-five years of experience founding and helping to scale companies, including Google and Amazon. She served as president of StubHub and as a member of eBay’s executive leadership team. Sukhinder is the founder and chairman of theBoardlist, a premium talent marketplace that helps diverse leaders get discovered for board and executive opportunities, and the author of CHOOSE POSSIBILITY. 

Resources Mentioned

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Sukhinder Singh Cassidy Interview Transcript

Pete Mockaitis
Sukhinder, thanks for joining us here on the How to be Awesome at Your Job podcast.

Sukhinder Singh Cassidy
Thank you for having me.

Pete Mockaitis
Well, I’m so excited to dig into your perspectives associated with your book Choose Possibility. Can you tell us, what’s the big idea here?

Sukhinder Singh Cassidy
The big idea is that we all have a rather terrible relationship with risk-taking and a rather kind of, I would say, ill-conceived view of what risk really looks like. And so, the book was written to help us reframe risk for what it is, really the pursuit of possibility, and offer really pragmatic ways to rethink how you approach risk-taking in order for you to be able to unlock more of its benefits.

Pete Mockaitis
Well, I’ll take right away the pursuit of possibility feels a lot better than the word risk just in the gut, as you sort of feel the words side by side and their valance. So, very cool. Now, your own career has had some interesting possibilities and risks and wild successes and disappointments. Can you give us a little bit of view for some of the wildest rides and how you’ve thought about risk and what happened for you?

Sukhinder Singh Cassidy
Sure. Sure. Well, as you noted, I consider myself someone who’s taken hundreds of risks in my career. I have been at large companies when they were growing, like Amazon and Google. I’ve been a CEO of large companies like StubHub, but I’ve also started three of my own, been an early-stage investor, a mid-stage investor, a late-stage investor, a board member at startups, a board member at large public companies, and so I feel like I’ve navigated and traversed risk-taking throughout my career.

And if you said sort of, “What are some of the wildest rides?” Well, they include quitting my job as a president at Google when I was arguably among the top 15 executives in the company, and going to a startup as a CEO, and, honestly, having it fail ferociously as a career move within six months, only to have to figure out how to recover and navigate my way to my next career choice and, ultimately, find the unlock for myself in terms of the rewards I took for the risks I took. As you can imagine, that career left me feeling like risk-taking is not what people think it is, and the reward relationship with risk is anything but linear, which is how we tend to conceive it.

Pete Mockaitis
Well, I absolutely want to ask about that specific point, so let’s roll with it. So, the risk-reward relationship is not linear. What does it look like?

Sukhinder Singh Cassidy
I think of the relationship between risk-taking and reward is not only non-linear but, in some ways, very circuitous. And so, let me explain what I mean. When we make a move, any move, or take any choice, I bet you we’re looking for not just one reward but multiple rewards. We might be making a career choice that we’re hoping will fulfill us financially, that we’re hoping will unlock some outsized career, win like a title change, or step up in responsibilities, and maybe brings us a lot of personal happiness. So, we’re making a move that has effectively three choices within it that we’re trying to optimize for.

Yet, when it comes to sort of how things unfold, as we execute our way through a choice we’d made, the reality is we’re measuring it on these three different choices or goals we have, and we won’t get the results all at the same time. We maybe figure out if it’s going to be a financial win for several years. We may figure out if it’s a happiness win within a year. We may or may not achieve the career ambition we wanted in terms of title.

And so, when you think about all the reasons we take the risk to begin with, the rewards don’t unfold in sequence, they don’t unfold at the same time, and each reward may have its own relationship to our execution or to the factors that are entirely outside of our control on whether or not we sort of achieve we originally intended against that specific goal.

So, when I say it’s non-linear, I mean it unfolds at various points in time, big and little risks don’t correlate to the size of the ultimate reward, and so you look at the whole thing, and you say, “Gosh.” Whatever you imagine going in, you may or may not achieve it going out, but I bet you that you will still be able to collect the benefits of risks even if they don’t look like the rewards you originally imagined.

And I think that is the key, how you take risks and make sure that if it’s a non-linear and circuitous relationship, you can still gain benefit from the risk you take and understand what the relationships and the benefits might be every time you take a risk even if it’s not the ones you originally imagined.

Pete Mockaitis
Well, boy, I think you could chew on that for a while and really get to some great places. It’s funny, when I was thinking about a non-linear relationship doing risk and reward, I was just thinking from a strictly kind of a finance thing, it’s like, “As there is a higher standard deviation and the returns of the given asset class, risk, there is a higher reward, like percent, money, return.”

Sukhinder Singh Cassidy
Yeah, percent return. Right. Yes.

Pete Mockaitis
But as you sort of zoom out and think about kind of the long game and your life and time and how things unfold, it doesn’t look like that at all.

Sukhinder Singh Cassidy
Yeah. Well, it’s interesting. So, actually, let’s back away, let’s look at your asset, my view versus your view, and back way. First of all, there is a thesis that I have in the book that if you actually look over the extent of your lifetime, you will actually find maybe that linear relationship but through multiple choices and multiple cycles.

So, if people were to chart my career, they’d say, “Wow, Sukhinder, there’s a pretty linear relationship between risk and reward because you started at one place and you took a risk and, gosh, look where you ended up.” So, it looks like a straight line over your lifetime but, really, what you’re doing is mapping through a bunch of cycles of choices and individual risks and individual rewards, each of which may or may not have worked out.

So, to your point, it’s like a stock pick. Any given stock pick may or may not work out. You and I would agree. When you’re building a stock portfolio, what are you trying to do? You try and actually make multiple choices. You’re diversifying your risks in order to maximize your overall return. By the way, as you keep picking stocks and watch pattern matching, I bet you become a more calculated stock picker over time.

And over the course of a long timeframe, let’s say 10 years, in which you are managing a stock portfolio, you’re getting better and better, though never perfect, at picking stocks, diversifying risks, taking parallel risks at the same time. And over the course of that entire period, you may say, “Wow, there was a relationship between starting to be a stock picker in my ultimate value of my portfolio.” But that doesn’t mean every individual stock you picked worked out.

And I think therein is the opportunity, and therein is the miscalculation of how most people think about risk. Most people think about risk as one mighty choice for one mighty reward. And I think, to take your analogy further, you will see the compounding benefits over a long period of time, but it will be an amalgamation of many individual choices or risks taken, each of which may or may not have worked out. And that’s why I think risk-taking has to become a skill rather than a single event we imagine.

Pete Mockaitis
So, when we think about risk-taking as a skill, how do you recommend we go about getting better at this skill of risk-taking?

Sukhinder Singh Cassidy
First and foremost, it’s probably no surprise, I think about starting early and often. I will say to people, you imagine and look at the biggest risk-takers in the world, and we somehow celebrate their biggest choices and we act like that’s the only choice they ever made and that’s why they’re such a mighty risk-taker when, in fact, most started taking risks long before we knew it, and they took risks of different sizes.

So, if I were to say to you, “How did you become good at managing your portfolio?” or whatever it is you’re doing, I bet that it started by doing it early and often. So, I say to people, first and foremost, find reasons to take risks in your everyday life, in your everyday career. And most people will say, “Well, I took a risk. I made this choice to go into this career. I took a right turn and decided to join a startup.” Okay, well, that’s one risk but we have opportunities to take risks every day.

I always say to people you could take the risk to learn something new. You could take the risk to discover more opportunities. You could take the risk certainly to achieve an outsized ambition, or you could take a risk to avoid harm. Like, those are four different reasons we might have to take risks every day. And so, I say to people, early and often is the way to really build your risk-taking muscle.

The second thing I talk about with people is many people believe that risk-taking first requires a lot of planning. I don’t know. Have you ever seen this, Pete, the person who plans a lot, and plans judiciously, and plans in great detail before they ever take a risk? Because we think the more perfect our plans, the better our risk-taking will be and the more we can control the outcome.

And one of the other pieces of advice I say to people when they’re trying to get going and just start to take risks is, “Hey, as oppose to the perfect plan from afar, spend less time planning, create a rough plan, and then the most important thing you can do is get proximate to the choices you’re thinking about making, or the risks you’re thinking about taking.”

If you’re thinking about taking a risk to be an entrepreneur in a big company, one of the best ways to do it might, first and foremost, be proximate to people who are entrepreneurs. Learn what it looks like to be an entrepreneur. Get proximate by joining a startup. Become an apprentice before you make a final choice.

And so, I think people presume that risk-taking requires a perfect plan. And, instead, I kind of advocate for a rough plan, what I call a whiteboard plan, “What’s the direction in which you want to head?” And before you make your choice, take the little risks to get proximate and closer to the opportunities you seek, and learn before making your final choice.

Pete Mockaitis
Now, we’re using the phrase take risk a lot, so let’s get clear with definition, shall we? When you say, “Take a risk,” what precisely do we mean by that?

Sukhinder Singh Cassidy
Well, I think of a risk is anything that has an uncertain outcome in pursuit of a goal. So, if you look at the standard definition of risk in Merriam-Webster, it’s to avoid injury or harm. That’s the kind of risk-taking we all imagine that keeps us from ever acting. If you look at the definition of risk-taking, it talks about literally entering an uncertain situation for the pursuit of a goal.

So, for me, a risk could be speaking up in a meeting. That’s ego risk. That’s psychological risk. It’s not financial risk but why don’t people speak in meetings? It’s because there’s a risk involved to their psyche or to their sense of what others think of them. And then risk-taking obviously follows more classic definitions if you know. You might decide to, as we said, empty the money from your bank account and put it in your first startup. That’s a bigger risk but it’s still a risk.

So, I think of risks as micro-actions, medium-sized actions, and larger-sized actions, all of which are uncertain but they’re decisions you make to try and unlock more impact. And what keeps you from doing it is obviously these fears we have, whether they’re related to our ego, financial, or kind of personal risks.

Pete Mockaitis
Well, yeah, so let’s talk about the fear. And maybe we’ll zoom out for a moment and get to a conceptual or theoretical optimal relationship to risk. Like, is your take that we should neither be fearful and take zero risks nor reckless and just do every nutty thing that we think about? Or, what does optimal look like in the realm of risk-taking?

Sukhinder Singh Cassidy
Sure. Well, let’s start with what I call the universal risk-taking equation.

Pete Mockaitis
All right.

Sukhinder Singh Cassidy
So, I want you to imagine two phrases, they’re pretty simple. One is FOMO, fear of missing out. I’m sure you know FOMO. The other of FOF, fear of failure. So, many people have fear of failure, many people have FOMO. So, I think of the universal risk-taking equation, put this in your head, the one that guides us all.

It’s goes something like this. If our fear of missing out on something is greater than our fear of failure, we’ll likely act, we’ll likely move in the direction of a choice we’re contemplating that has some uncertainty. If our fear of failure is greater than our FOMO, we’ll likely fail to act, it will equal inaction. So, let’s imagine risk-taking framework that looks like that.

First of all, you’ll notice two things. In that universal risk-taking equation, there isn’t the absence of fear. There are actually two fears that we are managing at any point in time – our fear of missing out, which is kind of what we would all think of as a positive fear, it’s the fear that induces us to act, and this fear of failure.

So, if you think about that concept, I think the world largely tells you that if you want to act, you just have to visualize the positive. Keep visualizing the positive because we’re going to ramp our FOMO. Makes sense. It’ll be like, “Hey, if you want to get that risk-taking equation working in your favor to act, just ramp your FOMO.” That doesn’t really do much for the way most people live, which is with a lot of fear.

So, just visualizing the positive doesn’t really do anything to help shrink the denominator in the equation, which is fear of failure. So, you could have a lot of FOMO, like you could have a lot of positive visualization, but if you can’t conquer or find a way to shrink your fear, you just won’t act, even though you know intellectually that there are all these things you’re excited about.

So, I often say to people, first of all, embrace both fears. I have an executive coach that I’ve worked with for 10 years through a number of my career choices, and he says to me, that I think is absolutely right, most people have a rather immature relationship with what he calls our inner risk manager, that voice inside of us that is, on the one hand, sometimes goading us forward, but more often our risk manager is trying to keep us from acting by sort of signaling all the dangers that’s going to happen to us, they’re trying to keep us safe.

So, he always talks about this immature relationship with our risk manager, and managing that formula I just talked about is about having a more mature relationship with your risk manager. And so, while it’s all good to kind of visualize the positive and ramp your FOMO, and I certainly recommend it when you’re creating goals, or when you’ve made a big choice and you’re trying to keep yourself motivated every day. What I often say to people is, “Let’s work actively on reducing our fear of failure,” and, “What are the strategies we can use that would help us reduce our fear of failure and allow us to act also?”

And there are a couple that I strongly recommend. One comes from our favorite risk-taker of all time, Jeff Bezos. Bezos wrote in his very famous shareholder letter to investors when he was going public, that most decisions Amazon makes, and he says that, “Most decisions we make, as people, are what we call decisions with two-way doors.” We often imagine that we make a decision and it’s a one-way door, there’s no way back. But the vast majority of things we do or try, there’s a way back. If you say something in a meeting that it doesn’t work out the way you want, it’s not like you can never say anything again.

Pete Mockaitis
“You’re fired.”

Sukhinder Singh Cassidy
Yeah, “You’re fired. Are you kidding? You said that terrible thing. Nobody thought you were smart.” Like, that’s absolutely ridiculous. If we said, “Hey,” you want to take a new job opportunity and it’s at a startup. If you’re very employable, and your current company lets you, it’s not like there’s not a way back if you go and it doesn’t work out.

So, the vast majority of things we think about are not one-way doors; they’re two-way doors. And so, I often advocate, and I advocate certainly in the book, that if you want to have a good relationship with your fear of failure, let’s start by not avoiding what those risks are. Let’s name them. Let’s size them. And they get sized as big if they’re one-way doors. If they’re two-way doors, they’re likely smaller, medium-sized risks, and go one step further.

I say, like, imagine the choice after the choice. Imagine you say that thing in a meeting and it doesn’t work out. Well, what’s the very next thing you would do? Imagine you go to that startup and you hate the job. What’s the very next move you would make? And the minute you can imagine the choices after the choice, and if you can come up with several, well, that’s probably not as large a risk as you think it is. And imagining what you would do actually helps us confront those fears of failure as opposed to avoiding them.

So, I often think about that universal risk-taking equation, and while I’m all for FOMO, I actually believe that we own each strategy to sort of look and shrink our fear of failure in order to get us into action. And those are some of the things I think about a lot and talk about a lot when I advocate for people to take more risks.

Pete Mockaitis
And so, you say you advocate for people to take more risks, is it fair to say that most of us don’t take enough risks and relatively few of us are wild and reckless? Or, what’s your take about the breakdown of the…we’ll just say United States professionals?

Sukhinder Singh Cassidy
Well, you’re asking a question that’s near and dear to my heart. If you want to go to the website for the book called ChoosePossibility.com, you can take a risk quiz, interestingly, to figure out what your natural risk-taking style is because I wanted to know the answer to the same questions as I was writing the book and certainly bringing it to market as we launch it.

And so, we actually created a simple risk survey, and then we surveyed the US population, obviously not the entire population but a sample, before putting the risk quiz on LinkedIn and on the site where you can take it. And to your point, what we found is that we sort of named four archetypes for risks, and we found that the vast majority of people taking the risk quiz, like 60%, are what we call contemplators, which is very good at being calculated and measured in laying out the pros and cons of any decision.

But where they self-identify is having challenge is in actually making a decision. And these people self-identify saying, “Hey, I can look back and I have a decent amount of regret about choices I didn’t make and actions I failed to take.” So, the majority of the population in our risk quiz are contemplators. And then let’s think about what comes on either side of a contemplator.

A contemplator who is more negative, who sees more easily the cons of any given situation, who’s always trying to keep safe and keep away from harm, we call a critic. On the other side of being a contemplator is what we call the calculator, the person who also does the analysis of pros and cons in any big decision, and certainly probably does a faster analysis or more efficient analysis on smaller decisions, but is comfortable making a decision within a given time period. So, they’re always calculating and kind of biased towards making a decision more than the contemplator.

And then the last archetype we identified is what we call the change seeker. And you and I probably know lots of change seekers, which are people who are so easy to see opportunity that, in fact, they may move very spontaneously. Some would call them reckless, some wouldn’t. Some would say that they’re the life of the party and the people who never miss an opportunity even if it costs them overcommitting or, in some ways, moving rashly.

And so, when we look at these four archetypes, and as I said, you can identify which you are by taking the quiz on the site, I think the majority of people certainly are comfortable with the idea of a pros and cons list, but when it comes to action, they maybe sit on the sidelines a little bit more than they wish they would. And, obviously, that’s what prompted me to write the book.

Pete Mockaitis
Okay. Well, let’s talk about some particular strategies and tactics when it comes to doing some decision-making. So, I liked how you discussed how we can shrink our fear of failure by thinking through, “Hey, is this a two-way door? If this went south, what would be the very next step?” What are some of your other favorite approaches? Or, do you have a master framework when you sit down and say, “Okay, Sukhinder, decision time”? How do you get to your answers?

Sukhinder Singh Cassidy
Well, let’s put it this way. First of all, in our risk quiz, I’m a calculator, which means I’m never without my own spreadsheet. Make no mistake, I think of my own relationship with risks as, “Yes, here’s that formula.” But to answer your question, I do believe that for smaller choices, it’s about doing the rapid formula and moving yourself to action because as soon as you realize that a risk is of rather small size, hopefully you can get into action fairly quickly without needing a gigantic spreadsheet.

But, believe me, when it comes to bigger choices in my own life, I have a pretty gigantic spreadsheet too. And some of the things that you would find on it might surprise you. So, in my frameworks for taking risks and making bigger choices, there are probably two things that I do, and I weigh in my framework that most people don’t weigh.

When most people create a framework for making a bigger choice, they really do a pros and cons of like what we might think about like how they will execute, they say, “Gosh, this could go right and this could go wrong.” But they really act as if the entire risk and thing worth rating are like their own execution ability. Like you say, “Oh, this could go right or this could go wrong if I do this or I fail to do this.”

In my own risk-taking frameworks, actually, I not only look at how something compares to my goals or my own skills and capabilities, like, “Gosh, am I likely to succeed or fail in my efforts?” But I have two dimensions that I think most people fail to add. Number one is what I call the people factor. So, most people try and make a choice sort of on the what of the thing they’re pursuing.

So, let’s put it this way. I want to go to a startup. I’m thinking about the what that that startup does and is that startup likely to be successful or not? Is that a winning idea? I often, and this has certainly been something I’ve learned the hard way in my career, but I’ve also had the benefit of, I’ve really, in all of my frameworks, I overweight the people I am going to join in any new choice or endeavors. So, I call that the “I put the who over the what,” and that’s one big piece of advice I have for people when creating around framework and doing your own pros and cons list. You have to add and rate the people factor of any dimension.

And people say, “Well, why is that important?” I think it’s important because many of us have been told to take risks in the direction of our passions, as an example. Like, “Hey, go overweight moving towards something that’s in the direction of things you enjoy.” That’s great. But 99% of our careers and how successful we are on the job are done in collaboration with others, with peers, with a boss, with a CEO who might be guiding the direction of the company, so with people who share or don’t share our values, let alone complement our strengths.

And so, when I overweight the people, what I’m really overweighting is, like, “Hey, I’ll get to have fun in my job or do the things I’m passionate about or good at dependent on the people I go to work with every day. And if I go to work with extraordinary people, people who have skills I seek to acquire, or people whose values fit my own, there’s a far better chance that I’m going to enjoy the day-to-day of my job and do my best work.”

And, yes, all the better if it’s in the direction of my, let’s say, stated passions in terms of topic area. So, putting the who over the what is one big factor in my frameworks that most people don’t really rate enough or rate highly enough when they make their choices. And the other one that I often tell people is missing from their frameworks, and I would add to any framework or pro-con choice, is what I call the things that aren’t in your control, the headwinds and tailwinds of any situation.

We tend to believe that we go into any situation, and what I call the neutral state, like it’s just waiting there for our immense and amazing execution in order for us to be successful as if that is the only factor at play in things that work and don’t work. But if we take the time to rate the situation we’re entering, as it’s like, “Does it have momentum and tailwinds?” People often give me a lot of credit for my choices, but my friend, I came to Silicon Valley in 1997. Ahh, that was a good time to come to Silicon Valley.

Let me tell you, there are so many tailwinds that if I made a bad choice, I could still pivot into good choices. And, in fact, that happened to me in my first job in the Valley. I quit in six months but there was so much opportunity that I could pivot into and so many companies that had tailwinds, that I had plenty of what we call room to fail and still be successful.

And so, I think objectively rating the situation you’re entering, “Does it have headwinds or tailwinds? And what does that mean for your ability to execute?” is a huge other factor in the frameworks I build around any big choice.

Pete Mockaitis
I like that concept right there, room to fail. I guess I could just flip it around. As I was contemplating, “Should I launch this podcast? Oh, it’s going to be a lot of work. And, hey, I’ve tried a lot of business initiatives that didn’t work out.” And one of the things I loved about this, as a concept, was that there were just so many ways to win, financially. I already knew it was going to be fun talking to people like you about stuff I love.

Sukhinder Singh Cassidy
Of course, right?

Pete Mockaitis
But I thought that there are so many ways that this can win, whether it’s just from sponsorship, or selling courses, coaching and training, licensing and monetizing. Like, there’s a lot of ways. As opposed to a lot of businesses are like, “Well, hopefully people like this thing,” whether a product or service, and if they don’t, then that’s kind of all there is to it.

So, room to fail or many ways to win is a cool parameter to embrace and to value and to consider.

Sukhinder Singh Cassidy
I love it. This comes into like embrace your inner calculator. Like, lay out all of these things because sometimes, as you know, like one of the things I found in the book is if you look at the research, people often make decisions quickly because uncertainty feels so uncomfortable.

But when you lay out all of these paths, as you said, all the ways your podcast could monetize, like you’re not only ramping your FOMO, you’re also, in many ways, like dealing your fear of failure. You’re saying, “Oh, my goodness, here are like the three ways. If this one doesn’t work, this one could work. If this one doesn’t work, this one could work.” So, I bet you, that thought process got you into action by confronting all of these thoughts early and being calculated in taking this risk, not just like a hope and a prayer, but laying it out in order to get yourself into action.

And so, I mean, I love it. Yes, room to fail all the time. But room to fail means you take the time to confront the things that not only you would love about doing this, but the things that you fear, and laying out all the possible paths you could pursue. That’s what gets me into action, it’s not just sort of dreaming in the abstract.

Pete Mockaitis
And that’s a really compelling point right there about folks moving quickly because they don’t want to linger in the discomfort of those, the moments of uncertainty.

Sukhinder Singh Cassidy
Yes.

Pete Mockaitis
I think there’s some real wisdom there. And so, any pro tips with regard to if folks are in a position, like, “Ah, I’ve just been thinking about this too long. Aargh!” How do you recommend sort of calming the system, or, maybe just in general, like when emotions are running hot, like to get back to a place of calm, wise rationality?

Sukhinder Singh Cassidy
Well, I’ll tell you what I do because I certainly love to act and I’m somebody who makes decisions, relatively speaking, fast. But when it is a weighty decision, or when there is something bothering me, the first thing I do when something is like I’m prompted to act quickly, almost too quickly, and I feel myself becoming reckless, is I try and step back and ask myself, “What am I trying to solve?”

And, often, what reveals itself is that there is not a one-stepper but a two-stepper. So, first of all, when we’re feeling anxious, it’s because something in our current situation is maybe feeling threatening or negative to us. You know people who are like, let’s say, take the first job offer they get. And you say, “Well, why are you going to jump into that job? Like, just step back. What are you trying to solve?”

And when you ask yourself the question, “What are you trying to solve in making the decision now?” usually, what you find is you’re trying to solve in a one-stepper something that’s effectively of two-stepper. So, what do I mean by that? Let’s say your current job sucks. Like, you’re fighting with your boss. So, the first job that comes up, you feel like, “I’m going to take that. That’s the one. I’m saying yes on Monday.”

I would say, “Okay, figure out why you want to say yes on Monday. Before you say yes on Monday, figure out what you’re trying to solve.” So, first of all, you’re trying to solve your current discomfort at work. That might involve going in on Monday and having an honest conversation with your boss about something that’s not going right. That is a distinct decision and risk to take from the risk of what job to go to next. That’s the two-per. Like, number one, solve the current discomfort. Number two, then decide if you were in “a neutral state” and try and pick the best possible job choice, “Would you pick this one? Or, would you now take the time, having solved your immediate discomfort, to go lay out five job choices because maybe you’re going to find one that’s even better?”

And, certainly, I say to people, like, “Step back. Forget what you’re trying to solve. And if it’s a two-per, lay out your two independent goals because they may be solved separately. And that allows you then, my friend, to setup the next choice, that next possibility, and I’m not like, “Hey, go live forever in uncertainty,” then I’m more in there like, “Hey, if you were in a neutral place, maybe you would have the time to go figure out the three jobs that would be your dream job. Go have two more conversations and set yourself a timeframe to still make the decision but it doesn’t need to be yesterday.”

Pete Mockaitis
Well, I think that is an insight that’s applicable in many circumstances, that this isn’t a one giant leap but rather maybe two or three or four steps and components. And in asking that question, “What are you trying to solve?” you can see that and take appropriate action. And what’s fun is that you may feel all the more empowered and emboldened and equipped to have that conversation with boss because, like, “I don’t know if this is going to go well.” It’s like, “Well, hey, if it’s horrible, at least I have something.”

Sukhinder Singh Cassidy
Yeah, I have something. I have a bird in the hand. Yes, absolutely. But it’s just about forcing those things apart when we’re feeling reckless. So, the point is that I think our relationship with risk tends to be risk is for the risk-takers among us. Okay, not true. Risk is a skill that anyone can build, point one. And then, number two, on this point of like, “Okay. Well, if you want to build those risk-taking muscles, think about these choices in increments.” You’re often not making, as you said, one choice. You often have the opportunity to make two, three, four choices.

And you know what that does for us when we know we have the ability to make two, three, or four choices? It frees us from the pressure of one big choice, which is what people think it needs to be – one big choice. I call this the myth of the single choice, “I’m going to make one big choice and it’s going to be either a raging success or an abject failure,” and then there’s so much pressure on that one choice. The minute you say, like, “I have multiple choices and risks to take or choices to make,” it really frees us up from this myth of the single choice. And, in fact, we can get the compounding benefits of choosing again and again and again.

Pete Mockaitis
That’s beautiful. Well, Sukhinder, tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Sukhinder Singh Cassidy
Well, I think mostly it’s what I said. If you think that risk-taking is for the risky among us, reframe your thinking about what risk really is. It’s a small or big choice that you can make multiples times a day, a week, a month, a year that get you into action now and sort of unlock your learnings so you can choose again. And it’s about this freedom to choose and choose and choose again that really helps us create compounding benefit to the risks we take.

Pete Mockaitis
Lovely. Well, now, could you share with us a favorite quote, something you find inspiring?

Sukhinder Singh Cassidy
My favorite quote is probably one from the book, which is, “When nothing is sure, everything is possible.” And so, we often think about, as I said, this idea that uncertainty is daunting, but let’s just remember, like, uncertainty is literally the definition of possibility. When nothing is sure, everything is possible. So, that’s a pretty awesome place to dwell, right?

Pete Mockaitis
Yeah, thank you.

Sukhinder Singh Cassidy
And we don’t tend to think of it that way.

Pete Mockaitis
And how about a favorite study or experiment or bit of research?

Sukhinder Singh Cassidy
Well, one of my favorites is actually, I don’t know about, but have you ever read the book Good to Great from Jim Collins?

Pete Mockaitis
Oh, yeah.

Sukhinder Singh Cassidy
So, that’s one my favorite older books, but one of my favorite newer books, in fact, I had it in our book club at StubHub. I made the entire leadership team read it, it was this book Growth Beyond the Hockey Stick from a set of McKinsey partners. It’s one of my favorites. It’s a 30-year study of companies that non-linearly outperform over time.

And what it really finds, which I think is so fun, is it sorts of reinforces or validates through data the research that the companies most prone to failure over a long period of time are companies that fail to take any move rather than companies that made multiple moves, some of which were wrong, actually have a much better chance of what they call, what McKinsey calls moving up the power curve to become non-linear, you know, outsize successes over time in terms of shareholder returns. So, failing to move is far more likely to have you, what we call go, whereas making multiple moves, imperfectly, is far more likely to get you to grow. Very neat analogy, obviously, to the book.

Pete Mockaitis
And how about a favorite tool, something you use to be awesome at your job?

Sukhinder Singh Cassidy
My favorite tool to be awesome at my job, you would laugh, but it’s my iPhone notes. Like, when people talk about having, like, “I always have a plan,” but I’m moving all the time, so although I’d love to have a whiteboard. The reality is my iPhone notes is my whiteboard. If you went into it, you would see notes on everything from business ideas, to what I need to get done today, to my grocery list, to tips for what are the things I want to remember to mention on this podcast. So, I would say one of my favorite tools is a pretty simple one – iPhone notes. All the time. Goes with me all the time. I can erase it, modify it, but it’s always there.

Pete Mockaitis
And a favorite habit?

Sukhinder Singh Cassidy
These days it’s tennis. I don’t know what your favorite COVID habit is but I have become much more regular as a tennis player, and I’m loving it.

Pete Mockaitis
And it sounds like you may have already shared a couple of these, but is there a particular nugget that you articulate that gets quoted back to you frequently and people are loving?

Sukhinder Singh Cassidy
I have a quote I often give people that does get played back to me all the time. It’s called, “You manage me or I manage you. Which would you prefer?” And when people are like, “What do you mean by that?” I often say in leadership talks, “Okay, like literally, if you’re a leader, you have a choice, you can say to your people, ‘You manage me or I manage you. What would you prefer?’”

And most people presume that the right answer is, “Well, gee, like I would prefer to manage others.” And I say to folks all the time, I’m like, “Really? I prefer for somebody to manage me.” They’re like, “What do you mean?” I’m like, “No, no, I really prefer that they manage me. Like, I’m a CEO, so if you walk into my office and expect to be managed, and I’m an opinionated person, there’s a pretty good chance I’m just going to spit out whatever is in my head and tell you to do it. That doesn’t mean it’s the right answer. It’s also not a super empowering place to be.” So, if you presume that my job is to manage you, that’s not a particularly fun place to be.

Now, let’s reverse it. Now, if I say, like, “Gosh, your job is to manage me. That means you’re likely to walk into a meeting with me with an agenda of your own. You take control of the conversation. You probably have a problem and a solution you’d like to propose. You’ve thought it out. You lay it out.” Now, guess what that means for me as your leader and manager? It means that I get to have a really highly leveraged interaction with you where you’ve clearly thought it through. You get to lay out your vision. I get to respond to it and add to it my vision and my insights. And then you leave out my office in 10 minutes versus an hour. You’re feeling super empowered. And guess what? I’m feeling pretty leveraged and we both go on to have a better day.

So, I always say to people, like, reverse your thinking on management. If you think the purpose of management is for you to manage down to others, imagine what life looks like when you ask people to manage up to you, what it looks like for them and what it looks like for you. That, to me, feels like real leverage for both parties.

Pete Mockaitis
That is a beautiful perspective. And one of my mentors, Victor Cheng, in episode 500, he said that that’s how he would approach his conversations with new direct reports. So, he’s the boss, he’d say, “I work for you and here’s how it works. You tell me what you need, what resources, what decisions I need to provide to you so that you can do your best work. And then that’s what I want to with them, and get out of your way, and we’re going to have great things happen.”

It’s sort of a reframe but it is lovely. I could tell you, with employees, it is refreshing and wonderful for all of us when they say, “Hey, Pete, here’s what I need from you.” I was like, “Okay, cool. Well, hey, you’ve got it. Is that it? That was quick.”

Sukhinder Singh Cassidy
Isn’t nice? It’s awesome, right? It’s quick and efficient. Now, make no mistake, your friend sounds pretty graceful and patient. My problem is I’m actually impatient and fairly opinionated. So, I always say to people, “The problem is if you walk in with a blank sheet, you’re far more likely to walk out with my sheet, and I’m not sure that’s a good thing. It may or may not be but the problem is I always have something to say, so I would much rather you come in with what you have to say because that is a fun place for me to be as well.”

And sometimes personalities like mine, you definitely don’t want to be walking out just presuming that because I have an opinion, it’s always the right one. What I’d really love to do is get into an interaction with someone, which is quick, efficient, highly leveraged, and fun because we’re both learning something from it.

Pete Mockaitis
And if folks want to learn more or get in touch, where would you point them?

Sukhinder Singh Cassidy
Well, you can always find me on LinkedIn, just at Sukhinder Singh Cassidy. You can find me on Twitter but, honestly, I hang out more on LinkedIn because it’s a fun place to have career conversations with folks. And, certainly, you can, if you are so inspired, you can always preorder the book Choose Possibility on the website, and it comes out August 17th.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Sukhinder Singh Cassidy
I would say my call to action is take the risk quiz but, more importantly, understand that it doesn’t matter what your natural style is. Every single one of us can be what I call a chooser. And so, my call to action is be a chooser versus kicking the can down the road. Make the little choices today that unlock incremental possibility.

Pete Mockaitis
Well, Sukhinder, thank you for this. This is a real treat. And I wish you lots of luck in all your possibilities.

Sukhinder Singh Cassidy
Well, thanks so much. Thanks for having me.

614: Making Smarter Decisions When You Can’t Know Everything with Annie Duke

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Annie Duke says: "All decision-making is forecasting of the future."

Poker champion Annie Duke shares tools to improve your decision-making process and your ability to predict the future.

You’ll Learn:

  1. Why your decisions still matter, even when you don’t call the shots
  2. The shift in language that leads to more open conversations
  3. How a pros and cons list tricks us into making worse decisions

About Annie

Annie Duke is an author, corporate speaker, and consultant in the decision-making space. Annie’s latest book, How to Decide: Simple Tools for Making Better Choices, is available on October 15, 2020 from Portfolio, a Penguin Random House imprint. Her previous book, Thinking in Bets, is a national bestseller. As a former professional poker player, Annie won more than $4 million in tournament poker before retiring from the game in 2012. Prior to becoming a professional player, Annie was awarded a National Science Foundation Fellowship to study Cognitive Psychology at the University of Pennsylvania. 

Annie is the co-founder of The Alliance for Decision Education, a non-profit whose mission is to improve lives by empowering students through decision skills education. She is also a member of the National Board of After-School All-Stars and the Board of Directors of the Franklin Institute. In 2020, she joined the board of the Renew Democracy Initiative. 

Resources mentioned in the show:

Thank you, sponsors!

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  • Rise.com. Build your team’s learning library–the fast and fun way–with Rise.com/awesome 

Annie Duke Interview Transcript

Pete Mockaitis
Annie, welcome back to the How to be Awesome at Your Job podcast.

Annie Duke
I’m excited to be back. It’s been a while.

Pete Mockaitis
It has. Well, yeah, just looking at that, it’s been over two years. Wow, time is flying, because I still remember many of the things you said kind of closely, like, “Want to make a bet?”

Annie Duke
Nice.

Pete Mockaitis
And so, it seemed closer. So, yeah, I’m excited to dig into some wisdom you’ve formulated in your latest book How to Decide. But, first, I think we need to hear, we know about you being a poker champion, but I just recently learned that you’re also a Rock Paper Scissors Champion and I want to hear the whole story.

Annie Duke
Oh, my gosh. There’s, like, literally so little story to this. It sounds much more amazing and glamorous than it actually is. At the World Series of Poker one year, some friends of mine, like, they organized a Rock Paper Scissors World Championship which was designed like March Madness. And I quickly went over and asked my friend for some rock paper scissors advice, which he gave me, and I ended up winning.

Pete Mockaitis
Well, that’s good advice. So, what’s the trick?

Annie Duke
Well, first of all, a lot of luck. Well, the trick that he told me and, listen, I’m not certifying this advice, it happened to have worked for me, is that you should be thinking about how you can tie with the person. So, it’s a little bit like anything else that you’re playing that’s like that. You want to try to get into the other person’s head and think about what they might be throwing. So, if they’re throwing scissors, you should be trying to throw scissors back.

Pete Mockaitis
Okay. And so…

Annie Duke
And I think the reason for that is that if they were thinking about you being able to predict them, which is where people’s heads go, so if I’m thinking about throwing scissors, I’m worried about you throwing rock. So, if I changed my mind, I’m going to go to paper, but scissors beat paper. So, I think that’s what it is. It’s sort of you’re going those levels deep, that “The person is thinking I’m throwing scissors but what if they know?”

Pete Mockaitis
Yeah.

Annie Duke
“And if they know, then I want to figure out something that’s going to beat that.” And so, when you’re shifting off of your original intention, you’ll lose to the tie.

Pete Mockaitis
Oh, man, there are so many layers here.

Pete Mockaitis
I’ve looked a little bit in the world of championship rock paper scissors play, and I understand some people will just pre-memorize a script, like, “I’m going to go rock and then scissors,” and then just roll with it regardless of what you’re doing.

Annie Duke
Yeah. So, I’ve used that strategy before. So, basically, what you’re saying there is, “I don’t want to be predictable,” so you would do this if you thought that your opponent was actually quite good. In other words, so you felt like you couldn’t predict your opponent then you would want to go to, essentially, a random number generator. So, that’s basically what they’re doing. They just write down a script in advance, and they’re just saying, “If I’m not reacting to what they’re doing or reacting, whatever, then you can’t predict me.” So, the way that I did that, there was one…I don’t know if it was in that tournament, it might have been another one. I took out a dollar bill.

Pete Mockaitis
So, there’s multiple Rock Paper Scissors tournaments under your belt.

Annie Duke
Two. So, what I did, I think I came against somebody who I thought was actually quite good at rock paper scissors, and so I took out a bill. I just had like a stack of bills, like dollar bills, and basically that would give me a serial number, it’s like 10 numbers or something. That would give me 10 throws. So, I had like, if it was zero, one or two, I would throw rock. If it was three, four, five, I would throw scissors. And if it was six, seven, eight, I would throw paper. And then I ignored nine and moved one. So, it was that kind of thing, so that ends up accomplishing the exact same thing.

Pete Mockaitis
Yeah. So, you’re champion in the one. And how did the other one go?

Annie Duke
I think I got to like the semifinals maybe.

Pete Mockaitis
Well, so that’s what I find so intriguing. It suggests that if it’s repeatable that you’re doing well, then it seems like there’s more than pure chance at work here.

Annie Duke
Well, I think it’s probably just, you know, I played a lot of poker so I sort of crawl into people’s heads a lot. And so, I think that I’m probably maybe better than the average Joe of figuring out what your patterns are, what you’re likely to be doing. And if you can do that, obviously, you can defend against it. But then you also have to have this kind of second-order knowledge of, “What if I’m against somebody who might be better than me at that?” then you can go to a random strategy.

And I think what happened was, I think I lost in the semifinals or the finals, but it was starting in the semifinals, or the round before that, that I used the random strategy. And I know I won one or two rounds with the random strategy where I felt like I’d come across somebody who was really good. And then, by the way, it really frustrates your opponent because they want to be able to apply their skill. And so, if they’re really good, then you take out a dollar bill, they realized that you’ve completely unarmed them.

Pete Mockaitis
Yeah. Well, that’s intriguing. And I read that they made a robot that can win rock paper scissors every time but it’s cheating. It’s like it catches what you’re going to do like a split second.

Annie Duke
Well, that’s not really winning now, is it?

Pete Mockaitis
Yeah, it could cheat at rock paper scissors perfectly.

Annie Duke
Great. Yeah, a cheating robot. You know what we really need to add to this dystopia right now? Cheating robots.

Pete Mockaitis
Cheating robots.

Annie Duke
We could just add cheating robots into the mix.

Pete Mockaitis
Oh, more headlines. More headlines to trigger anxiety. Okay. Cool. Well, that was fun. Let’s talk about decision-making when there’s more than…

Annie Duke
Well, we just did.

Pete Mockaitis
We did, how to win rock paper scissors under different circumstances. Well, so I love dorking out about decision-making tools. And I’d love it if, hey, there are some listeners who are not yet as enthused as you and I, can you make the case for the benefits professionals can enjoy with enhanced decision-making skills? And maybe, specifically, or particularly, for those who think that, “You know, I don’t have a lot of decision-making authority at my role. I kind of got to do what I’m told,” what are the benefits to be had by being excellent at decision-making?

Annie Duke
Let me give you just sort of the broader point, which is there’s only two things that determine how your life turns out, and it’s left in the quality of your decision-making. That’s it. So, there’s a whole bunch of luck that happens in your life, like, “What year are you born in?” It matters that I was not born in 1600 for the outcome of my life. And, obviously, from my perspective or from your perspective, coronavirus is a matter of luck. I assume you did not create the virus and distribute it.

Pete Mockaitis
Sure.

Annie Duke
But maybe that’s a bad assumption.

Pete Mockaitis
Certainly. And I guess there’s decisions you make associated with how much you’re going to go out, what measure you’re taking.

Annie Duke
Right. Exactly. So, that’s a good example, the two things that matter. There’s a whole bunch of luck that has to do with coronavirus, like the wrong human, to steal that line from Contagion. Then there are decisions that you can make given that that luck has occurred, and that’s the only thing that you have control over. And the better that your decisions are, the better your life is going to turn out.

So, I mean, that’s literally the simplest argument, which is it’s the one thing that you have control over that will actually have an actual real impact on the way that your life is going to turn out. Now, I understand that someone may, in a business setting, not be the ultimate decider, but the better your decisions, the more likely that you’re going to accomplish your goals within that environment. And there’s a few ways that you can think about it.

One is, of course, that you’re responsible for your own decisions. And one would hope that the better your decisions are, the more it maps onto your ability to actually move up the ladder or accomplish the goals that you’re trying to get to professionally. And you want to become more educated, and you want to implement a better process just literally for yourself. That’s number one.

Number two, there are certain things, there are certain behaviors that you can engage in that actually will start to get implemented in the people around you. In other words, you do have some influence even if you’re not the ultimate decider. You have some influence over the people around you that you can start to sort of get some of these really good decision-making skills and tools into a group setting.

And the last thing is, honestly, like, let’s say that I’m in a crappy situation with a bad boss, and they don’t really listen to anybody, and I don’t like the situation I’m in, that’s actually, in some ways, a more important time to be a good decision-maker because you need to be able to navigate those situations well. You need to decide when you want to stay or when you want to go, “Do I want to quit? Do I not want to quit? What can I do about this to make my situation better and actually to be able to thrive in an environment that’s an unhappy environment?”

Because, in a variety of ways, we can all end up in environments that are really unhappy where there are external forces that are making it very hard for us to thrive. And, while that is true and we want to be able to work to be able to change the situation that we’re in as much as we can, sometimes we have very little control over that, so you want to sort of grab onto like, “What are the things that I do actually have control over and improve those?” because those little changes will compound over time.

Pete Mockaitis
Well, that’s exciting. And so then, it sounds about as important as it could get in terms of what we can control that will impact everything in life, in career and happiness, decision-making enhances. So, could you maybe inspire us? Could you share a story of someone who, they thought their decision-making was fine, but then they adopted some of your tools and approaches and, boy, they saw some awesome results with their enhanced decision-making?

Annie Duke
If I were to think about this from prior to getting into a business setting, from a poker setting, the fact is that in order for me to improve my poker playing, what I have to do is to be able to think about, “What kind of were my predictions of the world?” and then try to figure out, “How did the actual outcomes that I got mapped onto my predictions of the world, what were the other ways that I might’ve thought about the hand?” And then I need to be able to talk to people in a way that’s going to expose to me the ways in which they may have differences of opinion with me, because the differences of opinion are where things get really interesting, right? Like, if you and I believe the earth is round, that’s pretty interesting, like, “Okay, the earth is round.” You’ll find that out.

Pete Mockaitis
“I also agree.” Conversation over.

Annie Duke
Yeah. But if I found that you think it’s flat, and I think it’s round, that’s like a humongous opportunity. And your listeners may be saying, like, “Well, how is that an opportunity for the person who believes that the earth is round?” which is a very common response for that. Isn’t that only an opportunity for the person who thinks the earth is flat? And I have a couple of answers to that.

Number one is things aren’t usually as clear as “We know that the earth is round, not flat.” We’re usually talking about things that are much more subjective, like which candidate to hire. And you believe we should hire candidate B, and I think I should hire candidate A, and we don’t know what the truth is, right? Not in the same way of round and flat, and so we need to have that discussion in order to get to the discovery that the earth is round. That’s the first piece.

But the second piece is that even when we hold opinions that are generally maybe are even true, it’s actually helpful for me to actually have to defend those against somebody that believes that the earth is flat. I don’t know about you but my arguments for why the earth is round would be super weak, like, things like, “Scientists say so, and I saw the pictures,” which are not particularly good arguments.

So, by having to actually be able to explain it to you, I’m actually going to know my own position better. So, what I was trying to do as a poker player was actually find out where there are areas of disagreement. So, when I actually work with teams, most of what I’m trying to do is that, and that’s how we’re improving decisions because what we’re doing is we have processes that are in place by which we can talk about, which allow for you to surface the dispersion of opinion as opposed to linger over the agreement.

Now, I’m sure you’ve been in lots of meetings where basically what happens is somebody says something and then everybody goes around the room and says, “I just want to double-click on what Pete said because I have my own reasons for believing the thing that he said, and I also would like to reiterate the same reasons that he said those things.” And you sort of go around the room, and then I guess everybody feels pretty good about themselves. But what you’ve really done is said, “I think the earth is round,” “I think the earth is round,” “I think the earth is round,” “I think the earth is round,” which is not particularly good for informing a group. It’s not good for informing a decision. It’s not going to actually improve decision-making at all.

So, what I’m trying to do with groups is get them to surface the areas where they disagree, where there’s actual dispersion of opinion, and then spend most of their time on that, really exploring that. By the way, not with the goal that they end up agreeing because when you’re talking about subjective things, like candidate A or candidate B, you actually shouldn’t expect agreement. And if you do get to agreement, probably somebody is actually not agreeing, they’re giving in, which is a really different thing. But we want those different viewpoints to collide, and then that really improves the decision-making.

Now, it turns out that when you really do a good job of surfacing the dispersion in the first place, you also create this amazing record of why you think what you do, why you want the decision that you want, what you think is going to be true of the world in the future. And this, then, has a huge impact on your decision-making because, after the world starts to unfold, as it does, like after the future starts to happen and become the present, you’ll have like an evidentiary record that you can go back and look at. And this now allows us to actually create really nice closed feedback loops where we actually know what we’re supposed to be looking for in order to become better calibrated in our decisions.

So, what I can tell you is that the groups that I work with, when we actually get these kinds of processes implemented, the quality of the conversation shoots through the roof, meetings are shorter, but more informative, which I think everybody would really like. And then the way that they’re actually thinking about dispersion, like, “What does it mean for somebody to disagree with you?” moves out of sort of the defensive world into the open-minded world because it really reinforces these ideas that the goal of a meeting is to inform not to agree. And then it actually helps them to much more quickly to recalibrate if their calibration is off because you can close these feedback loops really quickly, and actually more accurately.

Pete Mockaitis
Well, I love that point you brought up about defensiveness there, and even the phrase dispersion of opinion, you know, feels emotionally a lot more comfortable than disagreement or conflicts.

Annie Duke
Well, that’s why I’m using that term actually.

Pete Mockaitis
Masterful. Good work.

Annie Duke
Yeah. So, it’s in my book, and I really recommend that people start to use this term, dispersion or divergence. Both of those words, I think, are really good. Where do we diverge? And where do we converge? Because I think disagreement has such a negative connotation. It sounds so combative. And when I feel like you disagree with me, it gets translated for us sort of just cognitively into like you’re attacking my identity as opposed to just like, “Oh, we have a disagreement about these things.” It feels like an attack on my identity.

And, generally, what happens is that when I view it through the lens of disagreement, I’m going to tend to shift into convince mode as opposed to convey mode. In other words, I’m going to want to bring you over to my side of the argument in order to certify my beliefs and certify my identity, and so the way that I’m speaking to you is going to be meant to convince. It’s going to create a lot of interrupting, me saying, “Well, have you thought about this? So, you weren’t thinking about this data, or I think you’re wrong about this,” and so on and so forth. As opposed to like a real honest exploration of me trying to understand why you believe what you do.

Pete Mockaitis
Yeah. Boy, it’s funny, this reminds me of a time when it was way back, I think maybe in high school, in which I was arguing with somebody, and we had some friends and we just decided that they were going to be the jury, and we would make our case and advocate for our perspective. And it was kind of funny, it was kind of a joke, but it got a bit heated actually. And then when the jury left, it was just the two of us, and we just sort of chatted out with a completely different intention of, “Well, let’s sort of really see what kind of went on there and what we should do about it.” And it was just sort of like night and day in terms of “Are we trying to convince to win the argument as opposed to kind of collaboratively jointly discover what’s as accurate as possible?”

Annie Duke
Right. Yeah, exactly. And I think that the other thing that we need to realize when we’re dealing with things that are in the subjective world, so we’re not talking about “2+2=4” or, “The earth is round.” For most of the decisions we’re making in our lives and in a business setting, by the way, we’re talking about things where we’re trying to discover what is subjectively true, but what is subjectively true is not known so we’re having to go through the discovery process in order to get there.

And so, the idea that you somehow know the truth and you need to convince other people of your side is really, really unproductive, and it’s going to create that kind of thing. It actually makes more sense that the two of you convey why you believe what you do, and then you can walk away not agreeing. And that’s okay because you don’t need to.

If you think about, for example, if you and I are in a hiring committee, and I really care about whether I think the person is going to be a generous team member, like cooperative, generous, someone who doesn’t take credit for themselves but likes to share credit and things like that, and you care, all you care about is what their sales production is, right? Literally, you’re just a numbers person, right? That’s okay.

I don’t need to convince you of what my values are and you don’t need to convince me of what your values are because, by allowing those two perspectives to just sort of live and breathe, and for me to express why I believe what I do and why I think that’s important, and you can express what you believe and why you think that’s important, we’re probably going to hire a better candidate, because what’s going to happen is that’s now going to get expressed in our hiring rubric and who we actually end up bringing in.

Pete Mockaitis
Yeah, I like that a lot. Well, so we’ve already covered some great tools and perspectives associated with in-group settings, how we can view it as a dispersion of opinion or divergence as oppose to a disagreement, and how we’re not trying to convince but to convey, and we’re all enriched as a result of having engaged in that.

I’d love to zoom into if it’s sort of an individual and it’s sort of I’ve got one person making decisions for himself or herself, and doing the research, and there’s not so much a collaborative exercise going on, what are some of the best tools in this context to make better individual decisions?

Annie Duke
Well, first of all, not a pros and cons list.

Pete Mockaitis
Okay.

Annie Duke
Which I think most people might find kind of surprising, I know that. So, the thing about a really good decision tool, like if we were to think about what’s a great tool, decision tool or otherwise, like, if we think about a screwdriver, right, it should be accomplishing the purpose that it’s meant to accomplish. So, like if I want to get a screw to actually go in the wall in a way that’s going to be safe and actually accomplish the job…

Pete Mockaitis
Ergonomic. Convenient.

Annie Duke
Yes. Which is why I want to be able to use a screwdriver as opposed to a hammer or a jack hammer. So I want the right tool for the right purpose. But here’s also the really important thing about a tool is that I need to be able to repeat the use in a way that’s going to create really high fidelity. And then I also need to be able to hand it to somebody else and then explain it to them so that they could actually use that tool in the exact same way.

So, when we sort of understand that we see where decision tools really go awry. So, like, “Your gut is not a decision tool.” “Well, why?” “Because I can’t actually look at it and explain it to you, right?” That’s where we’ll go. “Well, my gut told me so,” and you’re like, “Okay, but that doesn’t really…I can’t use your gut.” Right? But you know what I mean. It’s like, “Okay, but I can’t actually examine to see whether you screwed that in well, and then you can’t explain to me exactly how you got that screw in the wall, or what you were doing. And I can’t actually repeat that process because it’s a black box.”

So, a pros and cons list, in some sense, certainly is a tool in the sense that we know its purpose is to get you to decide about whether you want to proceed with an option. And I could actually sort of teach you it in a structural sense. So, that’s all okay. So, we’re getting part of the way there. It’s certainly better than gut. But here’s what that tool lacks that will actually reveal what the kinds of tools are that we actually want to be using.

So, the first thing that it lacks is that it’s a list, literally a list, which means that it’s flat. So, what do I mean by flat? It’s flat in two ways. One is that when we think about something that’s on the pro side or something on the con side, we don’t have a sense of the magnitude. So, it could be like I could get a hangnail and I could die. So, those are both there, because all I sort of have is this list.

And so, that’s one of the first problems is that sort of the magnitude of how positive the things on the pro side are, in terms of achieving your goals, is not actually anywhere explicit in the list, and the magnitude of how negative the cons are, it’s also not existing in the list. So, that gives us hint number one, is that we want to have an idea of this magnitude if we’re going to have a really good decision tool.

The second piece is that we also don’t have a sense of the probability of those things occurring.

Pete Mockaitis
Yeah.

Annie Duke
So, if we have a con, that’s like, “Well, I could lose $10,000,” you would want to know, “But how likely is that to occur?” Right? So, you could have a pro, which is like, “I could win a million dollars.” You could do this with the lottery, right? But the con could be, “I’m going to lose a dollar or two dollars,” and the pro is, “I could win the jackpot, so maybe that looks pretty good.” But what we need to understand is, “What’s the probability of winning the jackpot?” which is de minimis, versus “What’s the probability of me losing the two dollars?” which is basically every time.

And if we don’t have that information, it’s also incredibly hard to compare. So, when we see that, what happens is it becomes very hard to understand whether an option is good or not, and then we get into the problem of how on earth would you compare options. Like, if I had one option that had 10 cons and 2 pros, would that be worse than an option that had 5 cons and 4 pros? Well, I don’t know because I don’t know what the magnitude of those pros are and cons, and I don’t know the probability of those things occurring is, so it’s hard for me to compare.

And then we have this added issue, which is that it’s basically, literally, a tool for expressing your bias, like your cognitive bias, because you can imagine that you can take something that could sort of be one pro or one con, and you could divide it up into its little bits in order to create ten ways to express that. So, the con could be like, “Well, I might end up like really unhappy,” so that would be one, but it could also be like…

Pete Mockaitis
“I could be anxious. I could be stressed. I could be disappointed.”

Annie Duke
Exactly. Right. And now, all of a sudden, it’s ten things, right?

Pete Mockaitis
Yeah.

Annie Duke
So, what ends up happening is that as we’re sort of exploring those pros and cons, generally, as we’re entering into a decision, we’re already sort of somewhere in our head kind of know what our opinion is and know what we would like to be true, and then we do the pro and con list, and all it’s doing is kind of like expressing whatever that opinion already is, but it’s certifying it as objective when it’s not actually objectively. And that’s actually a super bad combination.

And you can see how this is a problem, like particularly if we’re trying to compare options because we’re going to do it just by list. And so, the option we don’t want to do, we can just create a lot of cons for. The option that we do want to do, we want to create a lot of pros for. So, that’s sort of through the negative frame of like, “Here’s a tool that everybody really understands,” that turns out to be sort of the equivalent of taking a jack hammer to get a screw in the wall. Okay, so we don’t want to do that. We’re going to ruin the wall.

So, that tells us, “Okay, so what does a good decision process going to do?” Well, it’s going to solve this problem of sort of dimensionality. So, for any option we’re considering, we want to think about what the likely outcomes of that option are. But then we want to think about how much is that option going to advance us toward our goal or way. So, that gets that idea of the payoff, what’s the magnitude of how good or bad we consider that option is for us. But then we want to take a stab at what the likelihood of those things occurring is.

And what that allows us to do is understand, for example, like in the startup world, you may have a really high likelihood of failure but the payoff is so large that if that payoff is likely enough, you would still do it despite the fact that mostly it’s going to be bad outcomes. But that’s okay because we’ve added this likelihood piece in, and we’ve added sort of like what does the payoff look, and we can start to bring that into our decision-making. And you can see that that now gives us a real way to compare our two options, because now we have a pretty clear sense of what’s the upside potential and the downside potential, and, “Does the upside outweigh the downside given whatever I’m willing to risk?” And then I can now compare those two things.

So, like a simple example would be, like let’s say that I have two candidates that I’m thinking about hiring, A and B, and I really, really care about retention, like my recruitment costs are out of control and I’ve got all these employee turnover, so this is something that I happen to be focusing on. And so, what I can do is I can say, “I want to think about kind of these three buckets that the person that I’m hiring is going to be with the company between zero to six months, six months to 18 months, beyond 18 months. Let’s say that we set those three things up.

And then, basically, what I can do is just have anybody on the hiring committee, for any candidate that we see, to say, “What do you think the probability of those three buckets is?” because that’s what I really care about, right? And now I actually have an apples-to-apples comparison. So, I’ve thought about, “What are my values? What are the payoffs that I’m trying to get? I want this person to stay here a long time. And I’m looking for the person who is going to stay here the longest. That’s what I care about.” And now I have a way to actually compare options.

Pete Mockaitis
Okay, so we covered some of the shortcomings of the pro-con list, we got it captured very clearly the magnitude of things, and the probability of those things occurring. And so then, I’m imagining kind of just a spreadsheet by this point in terms of I’ve got a few things, I’ve got some magnitude, I’ve got some probabilities. And I guess it gets a little tricky if it’s not just money in terms of like, “How do I put a number on my stress?” How do you do that?

Annie Duke
Well, so I think that it’s really interesting. When we get into things that we feel are more subjective, we think that we actually don’t know anything and so, therefore, we shouldn’t try, “What’s the probability I’m going to be stressed?” Or it doesn’t even have to be something that’s like so clearly subjective like stress, but like what’s the probability a candidate is going to be with a company, is going to leave within six months? Well, we don’t know. We’ve never hired that candidate before.

So, in the sense of, “Can I be exact?” or if I’m releasing a software feature and I want to know, like, “Oh, of the people who use my product, how many of them are going to start adopting this, like, the daily users of this new feature within the first month?” Obviously, these aren’t things that are like 2+2=4, and they’re not things like if I flipped a coin, it’s going to land heads 50% of the time where like I know for sure what the answer is because we have enough information.

What people end up doing in that case is very often just saying, “Well, I’m not going to try because I can’t come up with ‘the right answer.’”

And the problem with that is that then we just sort of get we get mired in the limitations of our own sort of lack of knowledge instead of thinking about, “Well, I want to be an educated guesser, and my goal as a decision-maker is actually to get more educated because I have all these uncertainty in trying to forecast the future?” which is really what we’re doing when we’re saying, “What are the possibilities or the probabilities and things like that?”

There’s all this uncertainty in my ability to forecast the future, but the more educated I am, while I may never get perfect, I’m going to get closer to the range of what is objectively true if I were omniscient, and that’s actually going to improve my decision-making. So, I can do an example of this with you. My computer is sitting on a stack of books. Now, obviously, you can’t see the books because it’s what my computer is sitting on. I’m on the computer looking at each other, so you don’t know how high the books are and you don’t know what type and you don’t know what number, right?

Pete Mockaitis
Right.

Annie Duke
Okay. So, how much does the stack of books weigh?

Pete Mockaitis
About five pounds.

Annie Duke
Okay. And what do you think the lowest amount of the stack of books weighs is? Do you think it’s possible this stack of books that it’s sitting on could weigh a pound?

Pete Mockaitis
I think it’d be improbable that a stack, implying multiple books, weighs less than one pound.

Annie Duke
Okay. Could it weigh 200 pounds?

Pete Mockaitis
No.

Annie Duke
Okay. So, I think this is really good, right? So, what we discovered is that you could’ve said, “I don’t know.” But what I just did was I said, “Well, but you know things about books.” And so, while you may not get the exact answer, you’re going to get an answer that eliminates a huge number of possibilities. In other words, it’s going to get you somewhere closer to what’s actually true of the stack of books that my computer is sitting on. And that’s a really important exercise and it’s a really important exercise for three reasons that I hinted at.

Reason number one is that the more accurately you’re thinking about the future, in other words, “Can you get in a target range?” Like, if you think about it like an archer. And, in fact, in the book I talk about like the archer’s mindset, right? Yes, you’d like to hit the bullseye but you get points for hitting the target. And the closer that you can get to hitting that bullseye the better off you are, but you’re still getting points. It’s like you still get points for showing your work, right?

So, even if you hit the outer edge of the target, you still get points because all the stuff that isn’t on the target, like you know that these books don’t weigh 200 pounds, is going to help you to actually have better decision quality because you’re eliminating all these different possibilities that the answer could be that’s going to clarify your decision and get you better at sort of calculating, really, in the end what’s the expected value of the decision. Like, how much upside potential compared to downside potential do I really think there is? So, that’s number one is that you’re going to be creating a more accurate view of the future even if it’s not perfect, and that’s good.

The second thing is that, which I had hinted at before, is that we have this problem as decision-makers, which is, generally, the stuff that we know is like so tiny it could fit on the head of a pin compared to the stuff we don’t know, which is like the size of the universe. Obviously, if you have the ideal decision tool, which I think would be a crystal ball, you would be set because that universe stuff that you didn’t know would be revealed to you in this psychic instrument that you have that caused an omniscience and an ability to foresee the future, but we don’t have a crystal ball. So, what we’re really trying to do is, “How can we create a set of tools that will allow us to cobble together something that is crystal ball-like?” And part of that is dealing with this problem that there’s this whole universe of stuff that I don’t know.

And by forcing yourself to guess, I made you think about that. I made you think, “What do I know about books?” so you’re exploring that world of things that you do know in order to try to make yourself get the educated into the guess, and then you may, in other cases, start thinking, “Well, what is the universe of stuff that I don’t know? And maybe that would actually help me with my guess.” So, like if we went back to something as simple as a hiring example. One of the things that we might do is say, “Well, maybe I could go find out how many candidates, like when companies hire into this particular position, what the average retention in the industry is.” That’s called a base rate. And that would be incredibly helpful for me to go find out as I’m trying to estimate what I think any candidate that I might see is.

Now, that doesn’t mean that the candidates I see are going to be right there on the base rate, but it’s going to give me a place to anchor to about kind of what’s true of the world in general that’s really going to help me. The other thing that I might do is to go ask for somebody else’s perspective where we know that two people can be looking at the exact same data and come to very different conclusions about it, right? So, I could ask one person, “What do you think these books weigh?” and then I could ask somebody else, “What do you think these books weigh?” And maybe you said five pounds, maybe they say 20 pounds. Great. Now, we go back to that earth is round and flat thing, and now I get Pete who’s the five-pound person and Susan who’s the 20-pound person to have a discussion about why they have that dispersion of opinion that’s probably going to get me closer to what the most educated answer would be, closer to what’s objectively true of the world. And that actually like incredibly important.

So, whether you’re forecasting, like, “What’s my stress level going to be?” or, “How long is someone going to be with the company?” or, “How many users are going to adopt this on a daily basis within the first month?” all of these things, which we’re lacking information about, not allowing yourself, “Well, how could I ever know that?” and not accepting that as an answer, is actually really crucial to a good decision process.

Pete Mockaitis
Certainly. And I think that’s a great perspective in terms of you don’t know it exactly but knowing it’s more than one pound and less than 20 pounds is way, way more narrow than it could be anything.

Annie Duke
Oh, my gosh. Right. And I think I make the point in the book that this is part of the reason why we want to communicate with precision.

So, I think I make the point that if I say 2+2 is a small number, I’m technically correct but it’s going to be harder for you to tell me things that might help correct my inaccuracy is because the target area is kind of broad that I’ve given you, and it’s going to be hard for me to get better at math. Now, I’m going to get somewhat better because if I say 2+2 is a very large number, you’re going to be able to correct that. So, it’s not that I can’t improve, but it’s going to slow down my improvement that I’m not willing to give an exact answer, like 4, right? And there’s ways, obviously, if I’m not being precise that I can game it because I can say 2+2 is somewhere between minus infinity and positive infinity and, okay, I’m technically right. But what is that value of the information there in terms of actually improving my decision-making because, if you think about it, this is the reason why a crystal ball would be such an amazing decision tool is because all decision-making is forecasting of the future.

When I make a choice, when I pick an option, what I’m saying is that, “I think that given whatever goals I have and what my values are and my resources are that this option is going to be the most likely to create the type of future that I would like to unfold, and so I am being like a soothsayer in that sense. I’m making a prediction about the future.” And what we’re trying to do is make those predictions higher quality.

Pete Mockaitis
That’s great. Well, tell me, Annie, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Annie Duke
Yeah, I think I’d like to just say, like, just one really important decision tool, when we’re thinking about, “How are we actually getting a better view of the future? How do we actually become better fortune tellers?” Those are what we’re trying to do. And I just want to give a real pitch for a decision tool that I think is somewhat counterintuitive, at least in popular culture, which is the power of negative thinking as opposed to the power of positive thinking.

So, the power of positive thinking is like so incredibly powerful in the literature from Napoleon Hill.

We know about The Power of Positive Thinking, and it’s very popular which is you imagine a destination that you’d like to get to, and then you imagine success along the way. And I think that that’s a really bad decision tool, and I’m not saying that people should not imagine positive goals. Of course, you should. But the whole key to unlocking decision-making is to imagine the obstacles, the ways in which you might fail along the way. Why? Because that is the only way you can avoid them.

So, the way that I kind of think about it is the difference between a paper map and Waze. A paper map, you look at the destination you want to get to and then its clear roads. And I think about that as the power of positive thinking, right? Like, “Here are the clear roads, and now I’m just going to go along my merry way along those roads.” But what does Waze do? Waze says, “Here’s the destination you want to get to. And, by the way, there’s a road closure over here, and there’s like an accident on this one, and there’s heavy traffic over here, and so I’m going to reroute you so that you can actually successfully get to your destination.”

And I think the problem with the positive thinking literature is that sometimes it’s explicitly stated when you get into some sort of cookier versions of it, like The Secret, but it’s certainly implied in all of it that if you imagine failure, that it’ll actually create failure. But what an app like Waze tells us is that if you imagine failure, it actually creates success because that is the only way that you can get out ahead of it. And the more that you can identify the obstacles that might lie in your path, the better off you’re going to be because you’re going to have a clear view of the future, and you’re going to have a clear view of the kinds of things that you might want to avoid, the kind of things that might get in your way.

So, one of the best decision tools that you can use is called a premortem. And it was originally developed by Gary Kline. I have an adapted version of it in the book. And, essentially, what it asks you to do is to imagine a goal or a decision that you’re making which has an implied goal that it will work out, and imagine that it’s however long it would take for you to know whether you’ve reached a goal. So, let’s say that you have a goal to increase sales by 10% in the next year. And so, you imagine it, a year and a date from now, and you failed to reach that goal, and you ask yourself, “Okay, why did that happen? Why did I fail?” And you divide it into two categories: matters of your own decision-making, “What are the decisions that I made that may have led to this failure?” and then matters of luck.

And, as I recommend with everything, you try to figure out how likely those things are, and then you can actually figure out what to do about it. You may say, “Maybe I should change my goal,” or you may keep your goal, and you say, “Well, here are a bunch of decisions that I might make that really would cause me to fail, so let me try to figure out how not to make those so that I don’t actually engage in these kinds of behaviors.” If I want to lose weight, I have to figure out a way, because I know a point of failure is people bringing in cupcakes for their birthday. I need to figure out a way to not eat the cupcakes when that happens. I need to see that that’s on the horizon, and actually try to figure out how to avoid it.

And then with matters of luck, you can think about, “Are there ways, are there decisions that I can make that can reduce the probability of these bad things happening?” I can’t control the luck but I might be able to reduce the probability of those things occurring. And even if I can’t, maybe I can have a plan for it so that I’m not just running around like a chicken with my head cut off and so I can figure out what those are. And maybe I can find a hedge which is just like buying stocks and bonds at the same time. And if you don’t actually think about, “How can I instantiate this idea of sort plan positive, think negative?” into your decision process, you’re going to be constantly surprised by the world. You’re going to be using a paper map when everybody else is using really solid GPS. And we know that people who use paper maps have a disadvantage in terms of getting to destinations on time than people who use Waze, so don’t be the person still using a paper map as it applies to your own decision-making.

Pete Mockaitis
Beautiful. Thank you. Well, now, could you share a quote, something you find inspiring?

Annie Duke
My favorite quote from Feynman just has to do with him saying, “If you can’t explain it to a child, you don’t actually know it yourself.” And this is a paraphrase of the quote obviously. But the reason why I like that so much is that it kind of really has to do with this idea of what makes for a really good tool, is I have to be able to explain it to you, and I have to explain it in simple terms.

And what I really love about that sort of second piece of not just, “Do I need to be able to hand you the screwdriver so that you can use it, but if I can’t explain it to you, I don’t really understand how to use a screwdriver.” And if I can’t do that, I butt up against the limits of what I know in a way that when we talk about that universal stuff we don’t know that we really want to be exploring, it makes me go look in that universe, and then I think it expands my knowledge, and everybody is better off for it because I explained to you how to use a screwdriver, and then I understand screwdrivers much better for having had to go through that process. And that’s why I love that Feynman quote so much.

Pete Mockaitis
And you might think I already know to screw nails on, or screw a screw, but sure enough you say, “You may have better experiences in terms of stripping them less often, giving them straight the first time, not having to redo stuff.”

Annie Duke
Right. When people are having success doing something, and they don’t start thinking about “What are the limits of my knowledge? And what are the limitations of the way that I’m thinking about this and my perspectives on the world?” what happens is that they get disrupted from without, and you’d rather be disrupted from within. So, you can look at IBM in the 1980s versus a Microsoft or Apple, and this is a big danger when you’re doing things pretty well, and your models of the world are pretty good.

But just as we talked about with things that are subjective, your model can be pretty good and it can be working, but that doesn’t mean that you have the objective truth. Like, you want to be exploring different ways that people could be looking at the problem, and always seeking new knowledge, and always sort of testing your ideas to see if there isn’t a better way, and also, sort of back to the idea of negative thinking and that causes you to have to sort of explore the limits of your own knowledge and your own ideas in a way that’s actually going to help you to improve them and disrupt your own ideas instead of allowing someone else to come in and disrupt you, which is something that we’re all trying to avoid.

Pete Mockaitis
And how about a favorite book?

Annie Duke
I’m just going to answer it by recent, right? So, I’m going to give you two favorite books right now, and then two that you should be looking out on the horizon. My two favorite books right now are Maria Konnikova, which is The Biggest Bluff which is amazing. It’s like a marriage of memoir and exploration of the influence of luck in your life. So, Maria decided she wanted to explore luck because she had just sort of stuff happened to her. Like, her husband lost his job, she got sick, I think one of her grandparents died, sort of like all at once, and she’s like, “Whoa,” and she wanted to explore it. So, she said she’s going to learn how to play poker from being a total novice.

She ended up really doing well. She won a huge poker tournament, and, it’s this really wonderful book. It’s really beautifully written and it’s a great exploration of just sort of the influence of luck in your life.

The other book that I’m really recommending right now is The Psychology of Money, which is by Morgan Housel, he’s so good with just kind of like taking really complex concepts and making them very understandable through really, really fun narrative. And he’s really just talking about, like, “What are the different ways that we think about money?” Like, what is money? It’s sort of an object that we can sort of explore and understand, like, “What is its purpose in our life? And how do we think about it? And what should we do about it and do with it?” It’s just a really fun book. I really think that everybody should be reading that book.

In terms of books on the horizon to have, to be on the lookout for. Katie Milkman, who’s a professor at Wharton, and has a book coming out in the spring called How to Change, which is incredible on just if you want to create better habits in your life, just understanding, “When does habit change occur? Why? What are the ways that you can sort of make that happen for yourself?” It’s a really wonderful book. It’s really fun.

And then Noise is going to be coming out soon from Kahneman, Cass Sunstein, Oliver Sibony, and I’m really excited about that. It’s like a contrast to Thinking, Fast and Slow which is more about cognitive bias, and this is just more about sort of noisiness in the system, and it’s a really good book. So, those are two for the horizon. And even winnowing it down, I gave you four, so I’m…

Pete Mockaitis
That’s great. Thank you. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Annie Duke
I would like people to practice, when soliciting opinions or feedback from somebody else, to try to not offer their own opinion first and see what happens. So, there’s this really big problem, like when we’re talking in the meeting sense about we all think that the goal of a meeting is to agree. That’s true one-on-one as well. It feels really to agree with people that you’re talking to, that’s why we end up in echo chambers.

So, your opinions are contagious. So, if I want to know what you think about like Perry Mason, which is on HBO, if I really want to know what you think, I should just say, “What do you think about Perry Mason?” But what we do is we say, “Oh, I watch Perry Mason. I thought it was really cool and interesting, and I think it was really fun to see his journey from detective to lawyer, and I like it that he was a flawed character as opposed to the Raymond Burr version. What do you think?” And that’s obviously something simple about a TV show that probably isn’t very impactful. But think about that in terms of when you’re really trying to get somebody’s help, is I’m not actually going to get your true perspective.

When we talked about surfacing the dispersion of opinion, how am I going to surface the dispersion of opinion if I offer you mine first? So, I really challenge people to start trying to implement that into their own life, and I think they’ll find that it really changes the communication, and how much you sort of get to what people really believe that can really spur these interesting conversations.

Pete Mockaitis
Excellent. Thank you. Well, Annie, I wish you lots of luck with your book How to Decide and all your decision adventures.

Annie Duke
Well, thank you very much. I’m so happy that we got to talk again.

596: The Six Skills of Proactive Professionals with Chrissy Scivicque

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Chrissy Scivicque says: "The more we manage the expected, the more capacity we have to deal with the unexpected."

Chrissy Scivicque discusses the crucial set of skills that keep you ahead in your career.

You’ll Learn:

  1. How to become 5000% more effective at your job
  2. How to keep the unexpected from blindsiding you
  3. The one question that leads to astounding career growth

About Chrissy

Chrissy Scivicque believes that work can be a nourishing, enriching life experience—and she loves helping professionals discover exactly what that means for them and how to achieve it. Her popular website, EatYourCareer.com, is devoted to this mission. As an award-winning writer, certified career coach and experienced corporate trainer, Chrissy brings a unique perspective to the world of professional development. She is the proud author of The Proactive Professional and The Invisibility Cure.

Resources mentioned in the show:

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Chrissy Scivicque Interview Transcript

Pete Mockaitis
Chrissy, thanks for joining us here on the How to be Awesome at Your Job podcast.

Chrissy Scivicque
Well, thank you so much for having me, Pete. It’s great to be here.

Pete Mockaitis
Well, I’m excited to dig in, and I’m also excited that you share my fondness for true crime documentaries.

Chrissy Scivicque
Yes. I’m glad to hear that you also have this morbid interest.

Pete Mockaitis
Yeah, I don’t know. I guess my favorite podcasts are in the true crime realm but they’re not about murder because that feels a little weird for me but, still, I think my wife and I watch like three JonBenét documentaries. Have you seen The Jinx?

Chrissy Scivicque
I haven’t but I’ve actually listened to a podcast about every single episode.

Pete Mockaitis
Oh, wow.

Chrissy Scivicque
That’s typically how I prefer to take in my true crime, so I just listen to podcasts. It really is very disturbing. My family is incredibly worried about me. But I think what I’m finding out is that when I disclose this information, so many people say, “Me too,” because we have this kind of morbid curiosity. I think it’s really…I tell myself it’s about problem-solving, that I love a good mystery, and I’m a little bit of an armchair detective, and I figure it’s a problem-solving exercise. That’s what it’s all about.

Pete Mockaitis
Well, yeah, the mystery is intriguing. So, you listen to a podcast about every episode of the documentary The Jinx, but you haven’t listened to The Jinx, haven’t watched The Jinx.

Chrissy Scivicque
I did. True crime obsessed, my friends, because we’re all obsessed.

Pete Mockaitis
Well, I think that was one of the most compelling ones. I can’t give away the spoiler but, like, I imagine, if you were a documentarian trying to cover a crime, this is like a unicorn dream come true for you.

Chrissy Scivicque
Right.

Pete Mockaitis
Like, “Wow!”

Chrissy Scivicque
There’s nothing better.

Pete Mockaitis
We’ll just leave it at that.

Chrissy Scivicque
I understand The Tiger King is the exact same though.

Pete Mockaitis
You know, I haven’t actually watched it.

Chrissy Scivicque
I haven’t either but I’ve listened to a lot about it.

Pete Mockaitis
That’s good.

Pete Mockaitis
Well, one of the mysteries that you’ve been working to solve is in the realm of being proactive. You’ve got a great book title, I’m digging it, The Proactive Professional: How to Stop Playing Catch Up and Start Getting Ahead at Work (and in Life!) That’s an appealing promise. So, maybe to get terms clear, how do you define a proactive? And can you make that real for us in terms of, “Here’s what proactive looks like versus reactive”?

Chrissy Scivicque
Yes. So, I define being proactive as doing the right things today to set yourself up for success tomorrow. So, there are so many great examples, and I’m just going to share the one that comes top of mind because I just heard from this individual recently. So, this gentleman reached out to me through LinkedIn, and he shared with me that he read the book last year, and he was happily employed, he was thinking he was going to stay at his company for the next few years, but the book inspired him to be proactive about his career management.

And so, he did things over the past few months. He updated his resume, he got on LinkedIn and he was nurturing his network. He got a professional certification. He did all of these things for, really, just the purpose of being proactive, a just in case sort of thing. And then, recently, 2020 hit, and he was laid off in May. So, he reached out to me, and the reason that he was contacting me, he said, “Chrissy, I’m not freaking out. Instead, I feel prepared for this. I did all of these things, not knowing what the future held, but now I’m ready to launch this job search where I’m looking at my colleagues, they’ve been laid off, and now they’re scrambling trying to update their resumes and do all of these things that I’ve been doing because I’ve been ahead of the game.” So, that’s just a perfect beautiful example of someone being proactive in their career.

Pete Mockaitis
Yeah. And so, that is a great picture right there in terms of if anyone is feeling the stress and wishes that they didn’t, had been proactive, for one person there, got them out of that. So, I’m intrigued. Let’s talk a little bit about the why on a global scale. I couldn’t help myself when we’re talking about being proactive. I think of Stephen Covey and The 7 Habits, with habit one being “Be proactive,” because I had to grab the number. And I don’t actually know what his underlying research base is so maybe you can give us one. But I trust he has one, and this is not hyperbole, but he says, “The difference between people who exercise initiative and those who don’t is really the difference between night and day. I’m not talking about a 25% to 50% difference in effectiveness. I’m talking about a 5,000% plus difference particularly if they are smart, aware, and sensitive to others.” So, 5,000%, 50x, does that sound about right to you? Is that squaring with your research and experience? Unpack that for us.

Chrissy Scivicque
A thousand percent, I couldn’t agree more. I believe that this is the skillset that really differentiates the average professional from the exceptional one, and I see it over and over again. I have researched this for years. I literally started to read about what it means to be proactive 15 years ago. I was working as an executive assistant, and the executive I supported at the time, he used to say, “Be proactive,” I mean multiple times a day. He would say it so frequently that I remember at one point, I was like, “Oh, is he losing his mind? Is he senile? We’ve talked about this a million times.” But, obviously, he was telling me he needed me to improve in that area.

So, I started this research process and I found that Stephen Covey has some great material on this topic, but other than that it is quite limited what’s out there. What we find typically, and what disappointed me in the process, was that business experts and leadership experts and trainers and coaches, everyone was saying, “Be proactive. It’s especially important in the workplace. It’s necessary for success,” but then no one was following it up to say how you actually do that and put it in practical terms. And that’s what I need. When I’m learning, I need practical step-by-step actionable advice, and that’s really what I set out looking for. And I found that I needed to talk to people, and I needed to talk to people who were ahead of the game, they seem to be always two steps ahead of people, and I needed to ask them, “How do you do it?” and break that down.

Pete Mockaitis
Yeah. Well, that’s a nice way to phrase that, “Always two steps ahead of the game.” And, indeed, to stop playing catchup, which is not fun. It’s sort of an exhausting mental place to be day after day. So, yeah, being, so 50 times as effective and not being stressed and exhausted and feeling behind like you’re catching up sounds like a real big why to deliver on. And I’m glad we’re going to dig into the how there because, you’re right, I think “Be proactive,” I think it’s also sort of like, “Be strategic.”

Stacey Boyle was a guest we had who said, “I kept hearing that.” I was like, “What does that mean and how do I do it?” So, yeah, lay it on us. How does one be proactive? What are sort of the fundamental skills and steps?

Chrissy Scivicque
Yes. Well, what I set out to do when I started this whole project was to create a framework. I’m a big believer in the step-by-step methodology. And so, what I came up with was basically a six-part framework. And so, as I’m digging into what it means to be proactive, I realized that we tend to think about it as being one single skill but, really, what it is, it’s this combination of six different skills.

So, it’s a blend of, I think of them really as cognitive skills and behavioral skills. So, it’s about how you think and it’s also about how you act. So, these six different skills all work together, and I can go through them at a really high level pretty quickly, and then we can dig in as you like from there.

Pete Mockaitis
Oh, I love it. And I can’t help but think of Liam Neeson right now since we’re going to talk about a particular set of skills, and not for tracking down a kidnapped daughter, and hunting the criminals, but maybe we’ll prevent you from having to do that if you proactively apply these six things.

Chrissy Scivicque
I like the way you’re thinking.

Pete Mockaitis
Okay. Well, yes, please, lay it on us.

Chrissy Scivicque
Okay. So, we’ll start with the first one. The first one is big picture understanding. So, big picture understanding is really all about understanding your context, understanding the broad environment in which you’re operating. In the workplace, you need to think about, at the highest level, things like the economy, things that are happening in your industry, things that are happening in your professional field within your organization, within your team. You’ve got to keep an eye on all of that because that’s going to help you to make smart decisions for yourself and your career, and then also just on a day-to-day basis.

So, an example from my own career, I started my career in banking, and that was in the late ‘90s all the way up until 2008, which was just an incredibly turbulent time in the US economy. And it was really important for me to keep an eye on those things happening within our industry and the economy, and to watch that not only for my clients so I could be proactive on their behalf, but also for my own career. And, thankfully, I was able to kind of look out and make some decisions for myself that allowed me to leave the bank where I was working about three years before it became the largest bank failure in American history.

Pete Mockaitis
All right.

Chrissy Scivicque
And, really fortunate, you know, to be able to take that kind of a proactive step where, unfortunately, so many of my former colleagues lost their livelihood in that process. It was a really disastrous situation. But that’s the importance of the big picture understanding.

Pete Mockaitis
And I’m intrigued there. So, I don’t know if you’re like The Big Short, like you put all the pieces together in terms of this is what’s going to go down. Or, how did you pull that off? Did you know precisely, “Okay, we got a problem with these mortgage-backed securities, and the ratings on them aren’t being…”? What did you know? And how did you get to know it? And how was that enough to say, “Uh-ok, let’s look around elsewhere”?

Chrissy Scivicque
I think it was paying attention. And I don’t want to, in any way, imply that I had some sort of unique knowledge. I don’t think it was that. I think it was just paying attention and really thinking through the implications of some of the things we were seeing. We were seeing extremely low interest rates. We were seeing mortgage standards had been incredibly deteriorated. People were over-leveraged. It was just this confluence of things happening that made me feel uncomfortable.

Pete Mockaitis
Got you. Like, something bad may be happening soon-ish that’s going to tend to hurt.

Chrissy Scivicque
Yeah, it’s kind of instinct and paying attention to that, and just the broader environment. I think a lot of people probably did see but they didn’t take action soon enough, and they kind of were hoping for the best, and they saw those same things happening, but one of the biggest problems with people being proactive is that it’s risky. For me to leave a secured job where I was making a lot of money and go somewhere else is a risk and with no guarantee of a successful outcome, and a lot of people don’t want to take risks. They’re willing to kind of wait it out until action is forced upon them. So, that’s the opposite of being proactive though. Being proactive, you’re taking that intelligent risk. You’re taking the information that you glean and making some intelligent choices.

Pete Mockaitis
Okay. That’s cool. So, there we go. First, big picture understanding. And then what?

Chrissy Scivicque
So, then, second, we have situational awareness. So, situational awareness is a term that we typically hear in things like self-defense classes.

Pete Mockaitis
Yeah, I’m thinking about FBI agents, being like, “Count how many lightbulbs there are in the room,” that kind of thing.

Chrissy Scivicque
Totally. Yes, exactly. It plays into our true crime stuff. But that’s exactly what it is, it’s being aware of your immediate surroundings. So, big-picture understanding is the high-level stuff, and then situational awareness kind of narrows it down to say that you’re paying close attention to the immediate things happening around you in the workplace. You’re not going on autopilot. You can’t be proactive if you’re on autopilot. You’ve got to be engaged. You need to be not only physically present but mentally present as well.

And sometimes it’s just really basic things, like you see that your boss is looking stressed out, and you know that he or she has a deadline coming up at 3:00 p.m. today, probably not a great time to barge in and say, “Hey, we got to talk about my career growth opportunities,” right? That’s just being aware of the situation and observing and listening with your eyes and your ears and your head and your heart. Being truly engaged in what you’re doing is a requirement to be proactive.

Pete Mockaitis
Well, yes, that’s great. And then I could see all kinds of proactive opportunities already being opened up there, it’s like, “Hey, can I take something off your plate? We’re going to work through lunch, do you want me to grab you something?” It’s like, “I love this person.”

Chrissy Scivicque
Exactly.

Pete Mockaitis
It’s like, “This is the kind of proactive team member that I want to promote. Or I don’t want to promote because I’ll lose him. I want to give more money to keep him or her.” Something good will happen.

Chrissy Scivicque
Right. When I was an executive assistant, I remember, at first when I was working, I was supporting this leader, and he was notorious for at about 2:30-3:00 o’clock in the afternoon, we used to call him Hurricane Herv because he was just a hurricane. And I would always joke, “Oh, we can downgrade him to a tropical storm.”

But I finally put two and two together, situational awareness, I started to realize, “If he doesn’t have some true breaktime away from his desk, away from just the mental strain of what he’s doing in the middle of the day, by that 2:30-3:00 o’clock time, he’s going to be a hurricane.” So, I started to be more proactive about, “I’m going to block that time on your schedule, I’m going to walk into your office and make sure that you’re taking care of yourself.” And that was something that was additional, that kind of takes me from being the average assistant to being that whatever it was Stephen Covey said, that 5,000% improved assistant.

Pete Mockaitis
Certainly. And so, now we started the story again. So, then that unfolded, what did Herv say? “Chrissy, you’re just the best ever, and I need to reward you for how wonderful you make my life”? How did that unfold?

Chrissy Scivicque
You know, I did pretty well in that role. I can honestly tell you that my title actually adapted over the time that I was there, and besides being an executive assistant, I also became the director of client communications because that was a key skill of mine that I was able to leverage in that role in kind of an unexpected way, and definitely earned some monetary rewards as well. I think that the biggest reward though is that that partnership that I was able to build with the person that I was supporting. It wasn’t just about checking the boxes and doing the tasks. It was about truly, “How am I helping you to be more valuable? How am I helping you to achieve your goals in unexpected ways, in ways that aren’t necessarily defined in my job description?”

Pete Mockaitis
Excellent. Okay. So, we got the big-picture understanding, the situational awareness. And then what?

Chrissy Scivicque
And then the third one is future focus. So, this is just about keeping one eye on what’s coming up. So, while you are paying attention in the moment to what’s going on with your situational awareness, you’re also thinking about what’s coming next. So, what’s coming up tomorrow, next week, next month, even next quarter and next year? Thinking about not only the events and the deadlines and those types of things that you need to be managing backwards to figure out what you need to do today to be successful with those things, but also thinking about your own future, and what you want to be building for yourself.

So, if you’re keeping your eye on the future and thinking, “Next year, I’d really like to get a promotion,” well, great. So, that means that this year, there’s things that you should be doing to set yourself up for that. Perhaps getting some more professional development, and perhaps speaking with your manager and finding out what those opportunities might look like, and letting them know what your goals are. So, you’re constantly thinking about the future and working backwards to say, “What do I need to do now so that that future becomes a reality?”

Pete Mockaitis
All right. And how about the fourth skill?

Chrissy Scivicque
So, then the fourth one we go into is strategic foresight. So, this is where I think the magic happens. It’s really what connects the dots. So, we start with big picture understanding, big high level. We then go to situational awareness which is all about where we are, future focus is all about where we’re going, and strategic foresight says, “Well, how do I get from here to there?” It connects the dots. It fills in all of those steps.

So, it’s kind of where you’re thinking about what the possibilities of the future might look like, and saying, “Okay. Well, what steps can I take to avoid problems, to leverage opportunities, overcome obstacles?” It’s basically filling in those gaps. Our former Secretary of State, Colin Powell, used to tell leaders to look for people who can see around corners. And that’s what this is. This skill is seeing around corners and figuring out, “Okay, what’s coming next? And what can I do to prepare for that thing that’s coming next?”

Pete Mockaitis
Yeah, okay. And the fifth skill?

Chrissy Scivicque
The fifth skill is intentional action. So, you’ve gone through all this, you can see what’s coming next, and you then take some action to go ahead and implement. You have more of a kind of a bias to action instead of waiting to have certainty about the future, instead of waiting for someone to direct you or instruct you, you go ahead and you do what you know needs to be done. So, that’s where Stephen Covey talks about taking initiative. That’s what this is, taking initiative, taking that intelligent risk even if it is you know uncertain but you go ahead and you do the right things to get yourself to that next step.

Pete Mockaitis
Right. And sometimes the intelligent risk and the action-taking can be…it doesn’t have to be all or nothing. I think with the risk, you say, “Hey, I noticed this and so I went ahead and took the liberty of doing that. Shall I order this thing I found, or should we book this?” As opposed to committing thousands of dollars to something that nobody asked for. You can invest a little bit of time identifying the thing and just asking for the approval.

Chrissy Scivicque
Yes. And sometimes the proactive thing that you can do is opening up the conversation, “I noticed this and I’m thinking that we can do this.” So, I don’t want to ever encourage anyone to take unnecessarily risky steps in the spirit of being proactive. Sometimes it really is just opening up that conversation, having a proactive conversation.

Pete Mockaitis
Okay. And what’s the sixth and final skill?

Chrissy Scivicque
And then the final one is self-evaluation. So, this is where you look at how this is all working out for you, as Dr. Phil says, “How is it working out for you?” And asking yourself, “Am I staying ahead of things or are things catching me off guard?” And when things catch you off guard, asking, “Okay, was there something that I missed? Should I have seen this coming? Should I have done something different to prepare for this?” And in all of that, you develop these lessons and this new understanding that then goes right back into your big picture understanding. So, it’s all this wonderful beautiful cycle that continues.

Pete Mockaitis
Well, this is great stuff, and I kind of went a little bit quickly through the six skills, or asked you to go through them quickly, because I guess I want to see them all in action from one through six. And, in terms of an example, if I could, I might put you on the spot in terms of, okay, this podcast. You did your homework, and you may already have noticed some things that I should do or you could do, or you might recommend that I have somebody do. So, if I could, could I put you on the spot? And it’s okay if we get it wrong or you mis-assume. But could you maybe give us a demo from one through six, big picture understanding, “Hey, Pete and How to be Awesome at Your Job podcast, what are some proactive stuff one might do?”

Chrissy Scivicque
Interesting, Pete. I like this little thought experiment. Okay. Well, I think that we’re in a really interesting time to think about big picture understanding, right? Thinking broadly about everything that’s going on, you might want to think about how all of this work-from-home stuff is potentially going to impact what it means to be awesome at your job, right?

Pete Mockaitis
Certainly.

Chrissy Scivicque
So, big picture, thinking about that and thinking about how perhaps the needs of your audience are changing.

Pete Mockaitis
Certainly.

Chrissy Scivicque
Situational awareness would just be you’re continuing to look for immediate feedback from your audience, and interaction with them to find out what’s really speaking to them, especially right now in this time. Future focus, continuing to think about where you want your podcast to go for you and for your audience. And the strategic foresight piece would be connecting those dots, “Okay. Well, where we are right now and giving people what they need right now in this moment, how can we also be setting ourselves up for where we’re going in the future and how we’re expanding as a brand and our offerings?” Taking intentional action? Doing it, getting going, moving fast on it, so that you’re making moves. And then self-evaluation, always just looking back and thinking about, “Okay, what worked, what didn’t, what can we tweak for next time?”

Pete Mockaitis
Okay. Great. Thank you. And so then, I’d love another example in terms of…that was one piece of listener feedback when you said, “I love it when you ask, ‘Can you give me another example?’”

Chrissy Scivicque
Yes.

Pete Mockaitis
So, here we’re doing it, we’re taking some intentional action.

Chrissy Scivicque
Perfect.

Pete Mockaitis
So, we heard about Hurricane Herv and the support you offered there. We heard about for me and the podcast and some proactive things to do. Could you tell us a fun story about someone who made the leap from, yeah, mostly reactive to mostly proactive and saw some great things happen through taking the six steps?

Chrissy Scivicque
Yeah, I have so many fun stories. I work a lot with support professionals and administrative professionals. As I said, I’m a very proud former executive assistant myself. So, last year, in fact, I worked with an executive assistant, she reached out to me when she had just been promoted to supporting someone in the C-suite at a global technology firm. It was her first time supporting at that level so she really wanted to set herself up for success, and really go in there with a strategic plan for how she was going to stay two steps ahead of this incredibly busy and very powerful woman she was going to be supporting.

And so, we developed together, essentially, kind of an interview list, some questions, again, that proactive piece being opening a conversation, some questions for her to ask and discuss with her new partner in the first few days of working together. And these were questions like, “What’s your preferred communication mode? What’s your communication style? How do you typically deal with stress? And how can I best support you when you’re under stress?” These great, high-level questions about how they can build this partnership.

And so, the new assistant had this conversation, and the executive was just floored by this approach and loved it so much that she said, “I want you to go and have this same conversation with these other executive leaders that you’re also going to be working with in this role, and do this exact same thing with them. And then let’s teach the other assistants to do this as well.” It’s a proactive approach to developing a relationship. You can apply the proactive approach to any aspect of your career: relationships, career management, tasks management, customer service. Everything.

Pete Mockaitis
I love that so much. And we had Mary Abbajay on the show talking about managing up, and this being sort of just a super powerful action that any professional can take. And in her experience, fewer than 1% do, to say, “Hey, what are your preferences in these ways?” And in so doing, I love it because a lot of people, when I suggested this, “Oh, that’s kind of weird.” It’s like, “It’s only weird because you haven’t done it, and it’s only weird because now you’ve been working with the person for two years, you feel like maybe you should’ve done it earlier. Now, why are we talking about this now?”

So, it’s just weird because it’s different but it doesn’t mean it’s bad. And so, in fact, being on the receiving end of that, I can tell you I just love it as a manager/leader. And you’re telling, with that story, that this senior executive loved it so much, she said, “Please spread this far and wide. This is fantastic.” And then other senior leaders made the time to do that with delight as opposed to, “Oh, why are we doing this? I’m too busy.” It’s all positive when you go there.

Chrissy Scivicque
Yes, absolutely. It sets you up for success, and that’s what I think is also important when you’re framing the conversation is that you’re letting them know that, “This is about designing the partnership that’s going to work for both of us, that’s going to allow me to be a better support for you.” And so, if they understand the value of taking that time, they’re much more willing to do it.

Pete Mockaitis
All right. Well, so then, tell us, if we’re trying to get going with our proactive selves and practicing these six skills, are there some top best practices and worst practices we should keep in mind to maximize our progress in building these skills?

Chrissy Scivicque
Absolutely. Yes. So, I would say the best and easiest thing you can do right now, aside from anything else we’ve talked about, if you’d just only do one thing, start asking yourself with everything you do, “What’s next? What else? What’s the next question? What’s the next need?” And then go ahead and answer that question or provide for that need before it is specifically asked for or requested.

So, I’ll give you a quick example of this because I look for it everywhere I go, and once I give this example, I’m betting you will too. So, customer service is a really easy place to see this. A lot of customer service people, unfortunately, they end up being very reactive, they only answer the specific question you ask, they are order-takers. And when they are more proactive and do this answering the next question thing, it’s very powerful and you notice it right away.

So, last year, I was in a hotel in Las Vegas, and I woke up at 5:00 in the morning, called down to the front desk, and I said, “Hey, do you have a Starbucks in the lobby?” And the front desk agent said, “Yes, we do.” And I was getting ready to say, “Great. Thanks,” and hang up the phone and head downstairs in my PJs to get my coffee, and then he stopped, and he said, “And it doesn’t open until 6:00.” So, he gave me this additional information that I didn’t think to ask. It was 5:00 a.m. in the morning, I’m not thinking about that. I’m just asking, “If you’ve got the Starbucks,” but he gave me the information that I really needed before I even thought to ask for it myself. And thank goodness because I didn’t want to be walking down there in my PJs for it to be closed.

And so, when you start to see that, and you go, “That was really proactive.” It’s a super small teeny tiny little thing, but thank goodness. And we can do that for our clients, we can do that for our managers, we can do that for our colleagues, even if they aren’t asking the direct question, even if they aren’t saying the direct thing they need, we know it a lot of the times. We have to own our own expertise, and say, “I know what it is that you aren’t thinking to ask. Let me go ahead and give you the information you need, and let me go ahead and get you that thing that you aren’t thinking of that you need.” We can do that.

And all it is, it’s that simple shift of starting to think about, “What else? What next?”

Pete Mockaitis
What’s so great about that example is, you’re right, anyone can do it, and there’s situational awareness in terms of, “Oh, I have a feeling I know what you’re driving at, it’s that you would like to have caffeine inside of you.” And then that’s so simple, “And it doesn’t open until 6:00.” And I guess, boy, this is a continuum. You can go all the way the distance in terms of, “However, there’s one across the street which is open right now.” And it’s like, “Okay.” Or you can take it even further in terms of, “You know, our staff is happy to acquire that for you and bring it up to your room. What would you prefer?”

And you can sort of then choose for yourself in terms of, “Hey, given my availability and my bandwidth and my boundaries and what’s appropriate, I can sort of draw the best line as opposed to just sort of defaulting to question answered. We are done now.”

Chrissy Scivicque
Right. It really puts you in a very powerful place of being, of true service to people. This is a skill that is trained at the Disney University. I don’t know if you’ve heard the story that the most common question that Disney cast members at Disneyland hear is, “What time is the 3:00 o’clock parade?”

Pete Mockaitis
“Where is the bathroom?”

Chrissy Scivicque
“Where is the bathroom?” is probably pretty common too. But, “What time is the 3:00 o’clock parade?” They don’t really mean that. The 3:00 o’clock parade is at 3:00 o’clock. Duh. But they’re frazzled and they’re pulled in a million directions, and, really, they want to know, “What’s the best place to watch the parade? What time will the parade get to me where I’m standing right now?” They’ve been standing in the hot sun in lines for hours so they’re not thinking clearly.

And Disney guest service people are taught to anticipate the true need. Don’t just answer that the 3:00 o’clock parade is at 3:00 o’clock. Give them what they really need and find that out. Inquire. Have some proactive conversations with them and anticipate their needs, “Well, right around here, if you watch from here, it passes by at 3:15 but I’d go over there by the ice cream shop.” Give them what they really need. You know what they need. They don’t know. They’re frazzled.

Pete Mockaitis
And what’s great about that example is that your knee-jerk reaction, “That’s 3:00 o’clock, idiot,” in terms of, it’s like, “Why are you bothering me with this?” You can very much take an indignance sort of selfish knee-jerk reaction to it. But I think it’s also it just feels better from a humanity, happiness, energy experience in terms of thinking and operating that way, not so much, “How can I get through this interaction as quickly as possible because I have too much to do and I’m exhausted and frazzled to, ‘Oh, this person has a need, and I have an opportunity to delight them’?”

And I don’t want to seem too, I don’t know, Pollyanna or unrealistic, but I really did, with my first job, it was at Kmart, my first job like with the normal I delivered newspapers and did lawn stuff, but in terms of like a paycheck was at Kmart. They called me Pantry Pete because I worked in the pantry, that’s why.

Chrissy Scivicque
It’s good to have a nickname. Always good.

Pete Mockaitis
And I remember, they said in one of our training videos that we had the power to please, which meant like doing substitutions in terms of, “Oh, we’re all out of the 24-pack of Pepsi, that sale, but we can give them two 12 packs at the 24-pack price.” So, I just thought that was the coolest thing, one, because I’m 17 and I don’t have a lot of authority in a lot of ways, and that was just kind of cool, like, “Oh, I could do that. Yeah, power.” And, two, it was really nifty that it kind of got my creative service juices flowing, and it really was fun in terms of, “Oh, how could I delight someone?” It’s like, “Oh, we don’t have that, but you know what, there’s this other brand of thing which is almost really it’s the same thing. It’s nuts and caramel corn in a bag.” I could define that it’s just about what you’re after, it’s like, “Oh, I never heard of that. Okay. I guess Poppycock, Fiddle Faddle, Cracker Jack.”

Chrissy Scivicque
Same difference.

Pete Mockaitis
Pretty close.

Chrissy Scivicque
It’s great though. It brings us back to that big picture understanding, right, because it reminds you of your big picture purpose in your role. Pantry Pete is there to help delight customers and get them what they need. And so, you’re then given the power to proactively prevent a customer from being dissatisfied, so I love that. I think Disney does the same thing, right? It reminds their employees, “Big picture, we’re here to make magic, and these people have paid a ridiculous sum of money to be here. So, any opportunity you have to make magic, let’s do it even in super small ways. Answering the 3:00 o’clock parade question, you can make magic.” So, I think companies get it right when they empower their employees to do those kinds of things.

Pete Mockaitis
Well, Chrissy, tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Chrissy Scivicque
I think I’ll just add that one of the things I hear frequently from people when they go through my training or they read the book, they come back and they tell me about the moment that it happens, that finally their boss or whoever finally says, “You read my mind,” because it’s such a powerful moment when you’re able to proactively anticipate someone’s needs and you come off looking like a mind reader. And I think that’s one of the coolest things about learning to be proactive is that you start to get that kind of reputation, “Oh, I’m a mind reader. I can figure out what you need before you even know you need it.”

And the first time that happens, it feels so good. And I’m not suggesting that I’m really teaching you how to be psychic. We never really know what the future holds, but we can always take some proactive steps to set ourselves up for success. So, I love that. And if you get that, anyone listening, if you get that moment when somebody tells you, “You read my mind,” and it feels great, let me know about it. I love it.

Pete Mockaitis
And, boy, that’s just powerful in so many domains in terms of what’s up with your colleagues as well as I’m thinking about marketing now in terms of, well, the term mind reading makes me think of I took Ramit Sethi’s copywriting course, and there’s some useful stuff. And he talked about trying to understand people’s hopes and dreams, fears and pains, and barriers and obstacles. And, sure enough, once you get some of that, it’s like, “Oh, hey, I made content that’s quite relevant to you.” And that is really fun when you get those emails, like, “Yes, that’s exactly what I wanted.”

And then even when you’re making a landing page or a marketing communication or whatever, it’s just so much more resonant in terms of, “Yes, that is what I need. You, you get me. You read my mind.” And so, whether you’re collaborating, you’re marketing, you’re selling, you’re just being a great partner and friend.

Chrissy Scivicque
Yes, personal life as well, absolutely. Yes, we can be proactive for one another. We’re on the bus and we see somebody who needs a seat, we can stand up before they have to ask or beg for it. We can be proactive in literally every single aspect of our lives.

Pete Mockaitis
Beautiful. Well, now, could you share with us a favorite quote, something you find inspiring?

Chrissy Scivicque
Yes. So, the biggest one that I rely on, this comes from Nelson Mandela, and he says, “Let your choices come from your hopes, not your fears.” And I hope to live my life like that. I don’t want to ever look back and regret that I didn’t do something because I was afraid. And I always encourage my coaching clients to do the same. Aim for what you hope for.

Pete Mockaitis
And how about a favorite study, or experiment, or bit of research?

Chrissy Scivicque
I love the marshmallow study…

Pete Mockaitis
Oh, yes.

Chrissy Scivicque
…where there’s kids and they’re given the option, “If you can not eat this one marshmallow, when I come back in 15 minutes, I’ll give you two.” And it’s all about the ability to delay gratification and self-manage. They followed the kids and what we find is that, with these skills, you have more success in life. The kids who were able to not eat the one marshmallow, and they earned the two marshmallows, they scored better on their SATs, and they were better at stress management. So, those are really important skills, they’re learnable skills, but they’re really great requirements for success in life and at work.

Pete Mockaitis
And a favorite book?

Chrissy Scivicque
The newest one that’s been added to my list is called Work Clean by Dan Charnas, I believe is the last name. And it’s such a fresh perspective on the topic of organization. He basically talks to and researches with world-renowned chefs, and talks about them working in these incredibly busy restaurant kitchens and how they manage the physical environment and create systems to be able to do that. So, it’s a really new idea, new way of looking at cleanliness and organization, and he applies it to the corporate world, which is really cool.

Pete Mockaitis
And how about a favorite tool?

Chrissy Scivicque
I’m going to go old school on you, and I’m going to say good ole paper and pen, the Bullet Journal method. Ryder Carroll just did a book on this recently, and I’m loving it. Right now, I use a lot of tech systems, obviously, for just running my business, and sometimes I don’t want to look at another screen. I just love having my Bullet Journal.

Pete Mockaitis
Okay. And a favorite habit?

Chrissy Scivicque
I’m going to give you probably an unusual one. I am a doodler, and I think that doodling is…I’ve been doing it since I was a kid. Every piece of paper, literally, that I’m looking at in front of me right now is covered in doodles. It’s a very relaxing habit. I know that it helps me to concentrate and listen more, particularly if I’m in a learning environment. So, as a trainer, whenever I see somebody doodling, I don’t mind it. I know it’s a really helpful way to kind of distract one part of the brain to concentrate on something else.

Pete Mockaitis
And is there a particular nugget you share that really seems to connect and resonate with folks; they quote it back to you frequently?

Chrissy Scivicque
Yeah, probably the one that I hear repeated most is that the more we manage the expected, the more capacity we have to deal with the unexpected. So, it gets back to the idea that certain things in the workplace are absolutely expected and predictable, and we want to manage those things as much as possible because crazy, unexpected things are going to come up. And when they do, we need to have capacity to deal with them. So, go ahead and manage anything that’s expected so that you can have that capacity to deal with the unexpected.

Pete Mockaitis
And if folks want to learn more or get in touch, where would you point them?

Chrissy Scivicque
I would love it if they would go to EatYourCareer.com. And you can check out my blog, you can join me for free training webinars, Q&A sessions, all sorts of great materials there for you.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Chrissy Scivicque
Final call to action is to trust yourself and trust your experience and your expertise, and realize that much of the time you know what to do. You don’t need to wait for anyone to give you permission or instruction. You have the figure-it-out skill, so trust yourself and be proactive, and just do it.

Pete Mockaitis
All right. Chrissy, this has been a treat. I wish you much luck in all the ways you’re proactive.

Chrissy Scivicque
Thank you so much, Pete. It’s been great to be here with you.

551: How to Save Massive Time, Energy, and Frustration by Solving Problems Before They Happen with Dan Heath

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Dan Heath discusses how upstream-thinking can help solve problems before they even show up.

You’ll Learn:

  1. The power of “upstream thinking”
  2. How to get to the root of the problem
  3. How to avoid the blame game at work

About Dan:

Dan Heath and his brother, Chip, have written four New York Times bestselling books: Made to Stick, SwitchDecisive, and The Power of Moments. Heath is a senior fellow at Duke University’s CASE center, which supports entrepreneurs fighting for social good. He lives in Durham, North Carolina. The Heath brothers’ books have sold more than three million copies worldwide and have been translated into thirty-three languages.

Items Mentioned in the Show

Thank you, sponsors!

  • Pitney Bowes. Simplify your shipping while saving money. Get a free 30-day trial and 10-lb shipping scale at pb.com/AWESOME

Dan Heath Interview Transcript

Pete Mockaitis
Dan, thanks so much for joining us here on the How to be Awesome at Your Job podcast.

Dan Heath
Hey, thanks for having me on.

Pete Mockaitis
Well, I am so excited to speak to you in person and digging into the wisdom of your book here “Upstream.” And so, I want to maybe hear from you on the personal side, talking about preventing problems instead of reacting to them, is there an area in your own life where you’ve applied some “Upstream” mindset principles to get some good results?

Dan Heath
Yeah, there actually is one, and it’s so utterly mundane, I’m almost embarrassed to share it, but here was my epiphany. And, keep in mind, this was while I was writing a book on upstream thinking, and by upstream, I mean the quest to solve a problem before it happens. So, anyway, as you know, I’m a writer and, for whatever reason, I tend to do my best writing in coffee shops. So, I had this coffee shop I go to every morning, and I sit in the same place, and I order the same thing. And so, as a result of that, I’m constantly shuffling my laptop back and forth. I have a proper office that stays largely abandoned, and then I go to this coffee shop to write.

And so, I go to the coffee shop, I plug in the laptop, and then when it’s time to go, I pack everything up, I pack up the power cord, I get back to the office, I unwind the power cord, plug it in there, and it’s just a lot of power cord shuffling, and it’s just like an everyday annoyance. And I’ve been doing this for years. I mean, for years, I’m packing up, unpacking my power cord a couple of times a day. And then, in the course of this research, it occurs to me, “Hey, what if I bought a second power cord, and one of them could stay in my backpack when I go to the coffee shop, and one of them could stay permanently wired on my desk, so when I get back and I put my laptop down, I just easily plug it in.

And it was like this great relief where this little everyday annoyance was just gone forever. And then I started kicking myself, like, “How could I get in this mode where for years…?” I mean, it’s not like this was some major hardship obviously, but it was an annoyance, and it never needed to be one. And that’s the spirit of “Upstream” the book, in a very mundane personal story.

Pete Mockaitis
Well, I actually totally connect and relate to that. And I think about travel in terms of I’m always sort of reassembling my toiletry bag 3-1-1 and just get two of the things, and just leave the thing in the suitcase forever.

Dan Heath
Exactly.

Pete Mockaitis
So, lessons learned.

Dan Heath
And I think this is also true in relationships. Like, every couple has something that they bicker about, “Oh, you left the toilet seat lid up again,” there’s just some recurring irritant, maybe many, depending on your relationship. And so, I also got to talk to some people who’d figured out how to solve those kinds of problems. I met this guy named Ritch Marissa, and he and his wife, their thing was the hallway light. So, Ritch would go outside, often just to take the dog out or something, and he would flip the hallway light on. He’d come back in and he would inevitably forget to turn the hallway light off, and that bugged his wife, and so this was just like a little nagging problem for them.

And one day, Ritch Marissa has this epiphany, and realizes, “Hey, we don’t ever have to do this again. I’ve got it. I know how to crack this.” And so, the next day, he filed for divorce. No, I’m kidding. That is just a cheap joke. No, what he did was he went to Home Depot and he bought something I didn’t even know existed, which is called a light switch timer, and this is like a little panel that goes where your light switch is, and there’s buttons on it with different timestamps, so he can just press the five-minute button, the light comes on, and after five minutes, it turns itself off.

What is just so profound to me about this, I know these are little things, but it’s just a signal that, in our lives, it’s so easy to get into these patterns where we can fight the same problem again and again, and it’s like it takes a miracle for us to snap awake and realize, “Hey, with the right intervention, this could be gone forever.”

Pete Mockaitis
Yes, that’s resonant and it’s exciting, and I think it really just, even for the relationship itself, that’s a loving action. That’s going to say, “Hey, honey, I heard you, I listened to you, and I’m doing something about it,” and so not only do we have that irritant gone, but we have kind of, “Oh, that was really nice of you. Thank you,” going for you.

Dan Heath
If only more of our relationship problems could be addressed with a $10 gizmo from Home Depot, the world would be a better place.

Pete Mockaitis
Home Depot on Valentine’s Day is a peak day for them. Well, cool. So, then we talk about upstream and this notion of solving problems before they happen. I’d love to hear, have you made any particularly surprising counterintuitive discoveries about our human nature while digging into this stuff?

Dan Heath
I think what really captured me about this topic, because I’ve been thinking about this, I checked the other day, and literally my first Word file where I started taking notes on this upstream topic, was in 2009, so this has been on my mind a long time. And what kept me with it really involved the definition of a hero. So, when I say hero, what associations start popping to mind? It’s probably a policeman, or a firefighter, or a first responder, or a lifeguard who saves someone. It’s people who save the day, that’s a hero.

And it occurred to me at a certain point that there’s a whole another class of people who keep the day from needing to be saved. Someone invented a smarter building code that reduced the incidents of fires in buildings. And someone else consulted with lifeguards at public pools and taught them how to scan the pool in a better way and to position their chair in a smarter place. And a high school coach who’s mentoring teenagers in a way that keeps them out of trouble with the law. And these are upstream heroes.

These are people who stop emergencies from happening, and yet they hardly ever get any glory. In fact, their work may be largely invisible. We may have no idea what they did. I mean, how would we? How would we know that the consultant at the swimming pool kept a child from drowning one day? And so, that idea just captured me that there’s this whole invisible set of heroes whose identity we may never know even though they’re having a profound influence on us.

Pete Mockaitis
Yeah, that is powerful. And so, you’ve got a number of excellent tales that you’ve got some of the best story teasers on the back of your book that I’ve ever encountered, so well done. Well done.

Dan Heath
Thank you.

Pete Mockaitis
You and editor and team for those. So, maybe let’s just bring this to life with a little couple of those. So, tell us, all right, so there’s a school district, they had an issue with dropouts, and they did something upstream to prevent a whole lot of dropping out. How’s that story unfold?

Dan Heath
Oh, this is one of my favorites in the book. So, this is the Chicago Public School district, massive school district, I mean, this district has a $6 billion budget which is the same as the city of Seattle. So, when you talk about a difficult change environment, I mean, this is it. and if you want to hear a depressing stat, back in 1997, the graduation rate at CPS, Chicago Public Schools, was 52%. Like, if you were a student at CPS, you basically had a coin-flip’s chance of graduating. And it had been true for years.

And in a situation like that, people start to habituate to that level of success. If you were a teacher, or an administrator in this system, you’d certainly bemoan the fact that you’ve got a poor graduation rate, you regret it, but it almost comes to seem inevitable that, “Well, it’s a shame, but this is a complicated world. These kids come from difficult environments. Their K through 8 education didn’t serve them very well. And so, what are we going to do about it?”

Well, there was a point that came when they realized, “Maybe we can do something.” So, some academics, including Elaine Allensworth, figured out that there was a test they could perform in the ninth-grade year that could predict with 80% accuracy which students would graduate and which wouldn’t. And the test, I don’t mean like the SAT. All I mean is the test was, “Did the student take five full-year course credits and passed them successfully?” and, “Did they fail more than one core course?” Core course like Math or English. And if they received five full-year credits, and they didn’t fail more than one course, one was okay, but two was a real warning flag, then that meant they were off track for graduation.

And so, for the first time, it’s like they had a kind of smoke detector for dropouts, they advanced warning, they had time to do something about it. And so, this becomes a way of opening the door to changing the way the system worked. And some of the things they did, I’ll give you two examples, one was they realized some of their own policies were sabotaging kids. So, this was like the “get tough on discipline” era in schools, and it was routine at the time. For a couple of kids who shoved each other in the hallway, they’d get a two-week suspension. They just doled those out like candy.

But the research shows if you take a kid who’s kind of on the borderline, and you kick him out of school for two weeks, what happens is they come back, they’re lost, they feel bad that they’re lost, they end up failing the course, and then if they fail a couple of courses, they’re off track for graduation. It’s this absurd situation where nobody realized that by handing out a two-week suspension, they might well be dooming them to dropping out of high school, but that’s what the research showed.

The other thing is they reorganized the way that they worked. So, all of the freshmen teachers, traditionally, they would just stick to their own within the discipline. The Math teachers would meet with Math, and English with English, and so forth. Now, they formed what they called freshmen success teams where they met across departments and they would go student by student. I mean, they would be sitting around the table, literally saying, “Okay, Michael. How are his grades and his subjects right now? How has his attendance been the last couple of weeks? Have we been calling his home when he’s missing school? Can we get him some extra tutoring?” And they’re figuring out, on the fly, how to take these kids who are at the risk of being off track and getting them back on track.

And what happens is, as the years go by, and as they learned how to get ahead of these problems, how to encourage attendance, how to get extra resources for the students who need it, they start moving the needle. They start moving the needle at the freshman level. More and more students are now on track versus off track. And then, four years later, when it comes time to graduate, this early warning system pays off. And, now, the graduation rate in CPS is something like 78% or 79%. I mean, I can’t overstate the magnitude of a change that has to happen in a system like CPS to move the graduation rate by 25 points. It’s just astonishing work.

And for every student that graduates that, in an alternate reality probably would’ve dropped out without this work, their lifetime income is going to go up by $300,000 to $400,000. I mean, this is a massive, massive effort that started with the upstream notion to think, “Hey, what if we could prevent some of these kids from dropping out?”

Pete Mockaitis
Absolutely. So, that’s so powerful right there. It’s like, “What is the smoke detector, or the early warning system, which then, in turn, lets us prioritize and wisely concentrate resources or interventions to prevent the issue from occurring there?” So, I think that can have all kinds of applications in all kinds of settings, professionally and personally, in terms of, “What might make high-performing, high-potential employees want to drop out or exit the organization? What are some of those tests you can run?”

Dan Heath
That’s actually a great example. And I think a lot of organizations, we constantly hear about the big data revolution, and I think in many cases it’s overblown. But I think this is one case where it’s not, where what data is so powerful at doing is figuring out ways to detect that problems are coming. And I’ve spoken with a number of HR leaders that have figured out very diagnostic tests for knowing when employees are in trouble, when they’re at the risk of leaving.

I’ll give you another example on the customer side. So, LinkedIn, we all know LinkedIn, they sell a very expensive package to employers who are doing a lot of recruiting on the site, and it’s a subscription. What they figured out years ago is the way it would work is the employers would subscribe to an annual thing, and then about month 11, the sales reps would start really putting the full-court press on the customers just to make sure that they were going to renew because that’s how everybody was measured, is what’s the retention rate. And, churn, as most of you probably know, churn is a measure of how many people are not renewing. And so, churn is always what you’re fighting in a subscription business.

And so, they would send in the rescue troops in month 11 to make sure these customers are going to renew. And somebody started digging through the data, and they made a curious discovery that they could predict as early as the first four weeks of a customer’s subscription who was likely to renew and who wasn’t. And, at first, they were puzzled, they’re like, “How could we possibly know from the very start who’s going to renew and who’s not?” You would think that it would take time to figure that out. And they dug in and they realized the deal was people either got value from LinkedIn almost immediately or they never did.

So, they realized, “Aha, we’ve got to get out of the business of rescuing customers, and we’ve got to get in the business of making sure customers have a bang out first month.” And so, they put a lot of resources into onboarding customers, and they would do a lot of handholding where if you’re hiring a developer in Atlanta, they would get on the phone with you and walk you through step by step, “Okay, here’s how to define your target profile. And I’ve actually written some copy for you for emails that you can send out to prospects.”

And the effect of this work is, over a period of four or five years, if memory serves, churn rate was cut in half, even as the company’s revenue absolutely exploded. And that is an intervention that’s probably worth tens if not hundreds of millions of dollars in value, simply by paying attention to, “How can we see problems before they happen?”

Pete Mockaitis
Yeah, that’s huge and it totally makes sense in terms of you’re getting the value or you’re not getting the value, and you can know that pretty early. So, Dan, hey, keep it coming with these stories. So, you also mentioned that there’s an online travel website, and they were able to cut 21 million customer service calls by doing something a little different with their website. What was that?

Dan Heath
This story is almost hard to believe. So, this is a story about Expedia, and in 2012, there’s a guy named Ryan O’Neill that was digging through a bunch of data, and he found something that even today I find hard to believe, which is that, at that time, for every hundred customers who booked travel, a flight, or a hotel, or rental car, whatever, 58 of the hundred would end up calling the customer support center for some kind of help.

Pete Mockaitis
Wow.

Dan Heath
Which would seem to nullify the whole point of the online travel model. It’s sort of like if you went to a gas station where you could swipe your credit card at the pump, and then 58 out of 100 times something went wrong where you had to go inside. Like, you’d be pretty irritated with that business. And so, he starts to dig in, “Well, what in the world is going on? Why are so many people calling us?” He figures out the number one reason that people are calling is to get a copy of their itinerary. That’s it. Number one. Twenty million calls were placed in 2012 of people asking for a copy of their travel itinerary, and he’s just kind of slapping himself in the forehead, and he’s thinking, “How could this happen?”

Well, there’s a good reason why it happened. I mean, Expedia is a big profitable business. It’s not like these people were ignorant or unskilled. What happened was they were organized to neglect this problem. So, there was a whole set of people whose job it was to get customers to the site, and then there’s a whole another set of people whose job it was to make sure that people who came to the site, ended up booking something, and there’s a whole another set of people whose job was to keep the website running smoothly, and a whole another set of people whose job it was to take the customers’ calls and resolve them quickly.

But if you look across this whole ecosystem and you ask, “Whose job is it to make sure customers never need to call us?” The answer was, “Nobody.” It was nobody’s job. And if that goes even worse than that, that nobody would even benefit if that were true. And so, the top executives at Expedia realized they’ve got a problem, and they formed a special taskforce and put them in a war room, and they challenged them, “Hey, let’s keep these customers from needing to call us.” That’s the shift upstream. “Rather than get more efficient at handling customer calls,” which had been the way they’ve measured themselves to-date, “let’s just keep these calls from happening.”

And the solutions came very quickly, as you’d well imagine. They gave customers ways to get their own itinerary, and they added different trees to the IVR, “Press 2 if you need a copy of your itinerary,” and they changed the way they sent the emails with itineraries so they wouldn’t get in the Spam folder. And what happens is those 20 million calls essentially vanished, they go to zero over a very short period of time.

And I think what this tells us is something interesting, which is organizations always push for specialization. We’re divided into silos, we’re pressed to specialize, and there’s good reason for that. It makes things more efficient. It makes us more productive. But it can also be a deterrent to solving really thorny complex issues because we stay in our silos, and those silos create blinders. And so, all of a sudden, really obvious questions like, “Hey, why do all these customers need to call us if we’re an online website?” It’s like it gets purged from our existence because of the way we’re organized.

And I think that’s the promise. If you’re listening right now, and you’re in a big organization, let me promise you, there are issues just like this, these silos-spanning issues, that are waiting for someone to discover them and organize a response, and that’s the upstream mindset.

Pete Mockaitis
And those are great opportunities to bring your career upstream or up the hierarchy when you identify and you get proactive, and then you make some real value happen by tackling it. That’s huge.

Dan Heath
Exactly.

Pete Mockaitis
Well, so then we’ve heard some fun stories. Now, I want to get your view on kind of what are the fundamental principles or key questions to ask to surface these opportunities all the more readily and to not let them just sit under the radar for months and years?

Dan Heath
Yeah, let me identify, I’ve got a couple of skills that I think people can consciously build that will make them better upstream-thinkers. And the first is anytime you’re trying to prevent a problem before it happens, you’re going to be dealing with complicated systems, and you’ve got to understand the system, and, in particular, you’ve got to find some point of leverage, somewhere you can tinker with the system to get a different result.

So, in the case of Chicago Public Schools, they had this discovery that, “Hey, ninth grade is the critical time when we can take a student who’s off track and get them back on track.” So, one way to get closer to problems to identify a point of leverage is to immerse yourself in the specifics of the problem. So, I’ll give you an example. There’s an organization called the Crime Lab that’s associated with the University of Chicago, and they do a lot of research on, “What policies could potentially help reduce the crime rate?”

And so, years ago, during the forming of the Crime Lab, they were asked to work on the problem of gang violence, which is a recurring problem in Chicago. The problem there has to work on was homicide, and the lore was that the homicides were the result of gang violence.

And so, they started by questioning that premise and tried to get closer to the problem. And the way they did it was they went to the medical examiner who always writes a report on why young people died, or why anybody died, and they went through the last 200 reports of homicides of young people and they just read through the situations to train their intuition. And, yes, there were some that were the result of gangs jockeying for power or what have you, but what was far more common was a situation where some teenagers got in a fight over something stupid.

One example was a couple of groups of guys, one of the groups accused one of the guys on the other group of stealing someone’s bike, and the fight escalated. And in some places, a fight like that might’ve ended in throwing some fists. In this case, one of the kids had access to a gun and somebody got shot. And that became, what they discovered in these medical examiner reports, as they got closer to the problem, they saw this is not fundamentally about gang violence, that if they wanted to intervene to reduce the number of homicides, we got to somehow be able to speak to these situations that are normal teenage disagreements that escalate out of control.

And what they eventually did is they created a program that trained young men in high schools how to resist that urge to go nuclear when you get mad or when you get in a disagreement, to build a little bit of self-control and reflectivity in situations like that. But the way they discovered that point of leverage, which turned out to be quite successful, was by getting closer to the problem.

Another example, the same thing, that I write about in the book is there were some architects that helped design big public spaces like airports, and they’ve been asked to think about how to make those spaces more convenient and more accessible to older adults, and these were young architects. So, how do you get closer to an issue like that when you’re not in the target population? And they discovered something that’s called an age simulation suit, which is something you can wear to help you feel, not just learn about it, not just hear about it, but feel for yourself what it’s like to be older.

So, there are elbow braces that mimicked the reduced movement you get in your elbow joint. And as you age, you lose dexterity in your fingers, so they have these gloves that simulate the loss of dexterity. And they wear something called overshoes which simulate nerve loss in your feet, which makes it a little bit harder for you to perceive where the ground is. And so, they wear these age simulation suits, and they walk around DFW just to feel what it’s like to be old. And any business traveler listening to this knows DFW will make you feel old, just in general, much less without an age simulation suit.

But they start figuring out, “Hey, we need another step on the escalator because it’s really hard to get your balance when it’s moving as quickly as it is.” And they realized that there aren’t enough opportunities to take a rest, that these big hallways are intended to help people get where they need to get quickly, but older people need breaks, and there just aren’t good spots where they can put their hand on a railing or take a seat for a moment, and they realized they need some rest stops.

So, just to zoom out to the bigger issue here, what I’m saying is whatever industry you’re in, whatever role you have, there’s always going to be recurring problems in your organization. And one systematic way that you can get better at helping your organization solve those problems is to be the person who has the instinct to get closer to the problem, to go through those medical examiner reports, to put on an age simulation suit to give yourself a better instinct about what it’s like to navigate these spaces. I think that’s an upstream skill that we can all cultivate.

Pete Mockaitis
Certainly. And I imagine the hang-up and the reason people don’t do that is they might say, “Oh, my gosh, who has time to look at 200 of these reports or to find this special suit and to go through it?” And so, I guess, in the moment, I would imagine that can feel like, “Where will I find the time?” But if you zoom out, boy, I imagine there’s huge multiples of time saved associated with doing this stuff.

Dan Heath
You have put your finger on what may be the fundamental tension of upstream thinking. And I want to tell you about a study that I think really brings this tension to life. So, a woman named Anita Tucker, who’s just a fascinating thinker, at one time she ran a frosting plant for General Mills, I believe. And now she is an organizational researcher, and, at one point, for her dissertation at Harvard, she followed around nurses. So, she shadowed them during their day, and she figured out that nurses are basically professional problem-solvers. There’s always something weird popping up that they had to deal with, and sometimes it’s small stuff, like they ran out of towels, and they had to figure out where to get a towel for a patient.

Sometimes it’s bigger stuff. Like, Anita Tucker tells a story of a nurse who was trying to check out a new mother from the hospital ready to take her baby home, but the security anklet that they put on babies had fallen off and so you can’t check out the mom without that, so they went on this frantic search, “Where is the anklet?” It turns out it was just in the baby’s bassinet. So, easy, they checked out the mother and were done.

Three hours later, the same thing happens again with a different mother, and this time they do another search, they can’t find it, and so they have to go through another set of protocols to resolve the situation, but they managed to get the mother out. And so, when Anita Tucker first encountered this story, she thought, “Hey, these are nurses being really resourceful. They’re scrappy, they manage to work around problems, they don’t let things stand in their way, they don’t go running to the boss every time something goes wrong. It’s an inspiring portrait.”

Pete Mockaitis
These were the heroes.

Dan Heath
Until you realized that what she’s describing is an environment that never learns, that never improves, because when you work around problems, and when you heroicized people who work around problems, what you’re guaranteeing is that those problems will recur.

Pete Mockaitis
Because you get glory by addressing them.

Dan Heath
Exactly. And it didn’t occur to the nurse who check out two mothers in three hours that had problems with the anklet falling off to ask, “Hey, why is this happening? What can we do to stop this from happening? What’s the root cause? How can we make sure we never have to solve this problem again?” And I want to be clear here, I’m not throwing stones at nurses. I think that this study could’ve been done on any profession that it would’ve come down to the same conclusion, which is our lives are so busy and so full of emergencies and issues to be dealt with that we get in this trap of, “Let’s just get through it. Let’s just work around. Let’s figure out how to get by.” But what we have to realize is that is a trap. When we work around problems every day, we guarantee ourselves to have to deal with them again tomorrow.

And so, when you said, what it feels like in the moment is, “Oh, my God, where am I going to find time to go through to 200 medical examiner reports?” that’s exactly the issue, is in the short term, it is extra work, it is stepping outside of that cycle of workarounds, but it’s basically the only ticket out of that self-perpetuating cycle of firefighting. And that’s something, that trap of firefighting, is something that I call in the book tunneling. It’s actually a term from some psychologist in a book called “Scarcity.”

But I love that mental image of tunneling, that that’s the trap we get in where we kind of lose our peripheral vision and all we’re doing is making our way forward, “How can I get through these problems as quickly as possible to get onto the next set?” And we start to lose sight of the big questions, which is, “Is this tunnel going the right way? Is there an easier way to get where we’re trying to go? Are we even pursuing the right goals?” When you’re in the tunnel, the only real direction is forward.

Pete Mockaitis
Yeah, and that totally connects and resonates. Like, even just biochemically, it seems like, “Okay, all right, my back against the wall. We got to hustle. We got to hurry. Let’s do, do, do, go, go, go,” and then it’s that vicious cycle.

Dan Heath
It is. And I empathize with the nurses because what are they suppose to do? I mean, honestly. So, the mother is trying to get checked out, they can’t find the anklet. What would we advise of the nurse in that moment? Is she suppose to conduct a root-cause analysis of the circumference of the anklets and contact the manufacturer and talk about product improvements? It seems absurd. It’s almost like we can’t envision another reality other than the tunneling reality.

But just to give you a feel for a way out of the tunnel, what many health systems have done is start to hold standing meetings, sometimes called safety huddles, where a bunch of nurses and doctors and staffers get together in the morning, it might be a 20-minute meeting, and they talk about, “Okay, what near misses did we have yesterday where someone was almost hurt or we almost gave somebody the wrong medication? What can we learn from that? How can we improve our processes to make sure it doesn’t happen again?” And then they look forward to that day, “What’s coming today that’s more complex than usual that we should think through?”

And I think that’s a perfect example of how you can escape the tunnel, even if it’s just for a 20-minute meeting, because that’s the forum where that nurse could’ve said, “You know, something weird happened yesterday. We had two mothers with the same problem happened to.” And that’s a meeting where you could deputize a subgroup to work on that and figure out what was going on and solve it. So, I think it may be too much to ask of humanity to figure out how to get out of our tunnels because it’s such a powerful instinct. But if we can even escape them for short periods, we can make much smarter choices.

Pete Mockaitis
I’d love that. And so, maybe while we’re just sort of imagining workplaces at large and recurring problems that may have the potential to be solved once and for all, what are a couple of things that just leap to mind for you that we should have our eyes open toward as professionals?

Dan Heath
One thing, I think, has to do with a sense of ownership. So, in the book I talk about what’s curious about downstream actions is that they’re often obligatory. If someone shows up at the hospital having a heart attack, the surgeon can’t opt out of that work. Or if a preschooler has an accident, the daycare worker can’t opt out of the diaper change, right? When there’s a problem that presents, we have to deal with it. Versus, upstream problems, curiously, are sometimes voluntary. People have to step up and say, “This problem, it wasn’t something that I created but I’m going to be the one to fix it.” And that’s something that relates to accountability.

I’ll give you an example from the work world. I talked to an administrator named Jeanie Forrest who works in the Yale Law School. And when I talked with her, she was having this staff issue that she was dealing with. So, there were two staffers, these are disguised for obvious reasons. The boss, let’s call her Barbara, and the director, we’ll call Dawn. So, Dawn had filed a complaint about Barbara, her boss, for belittling her and kind of undermining her in certain situations, and this had landed on Jeanie Forrest’s desk. So, she asked the two women to come in, and Jeanie Forrest said, “You know, this situation is my fault. I had heard rumors that you two weren’t getting along, and I sensed it myself. And you know what I did? I just stuck my head in the sand and I thought, ‘Well, maybe this will go away.’ So, that’s on me. This is my fault.”

And then she turned it around and she said, “I want each of you to tell the story of this situation as if you’re the only one in the world responsible.” And at first, the women had a hard time honoring the spirit of that request, so Barbara, the boss, said, “Well, every time I ask something of you, you shut me down and you give me weird body language.” And Jeanie Forrest said, “Barbara, that sounded awful lot like you’re blaming Dawn. Can you try that again?” And Barbara said, “Well, you know, I could’ve done a better job explaining. I thought that you should just accept what I said and I dismissed your questions. But I could’ve done a better job being patient.”

And Dawn, for her part, said, “Well, I just accepted your huffing and puffing, but the truth was I just really didn’t understand, and I should’ve made it clear. Hey, I‘m not being resistant. I just don’t understand what you want. Can you help me?” And so, they end the meeting on this kind of detente and they tried to change their relationship. And I emailed Jeanie Forrest six weeks later just to see what have happened with this, and she wrote back and said, “They’re working together productively and cheerfully, it’s a little insane.”

And what I want to highlight about this is I think it’s a kind of metaphor that so many times in life, we have the sense that the problems are happening to us, that we are the inheritors or the victims of problems, but this reframing thing that Jeanie Forrest did of telling the story as if we’re the only ones responsible, it helped all three of the people involved realize, “Hey, we have agency here. Like, we could’ve made different choices, and we can make different choices going forward. We have influence here. We have power.” And I think what that means for upstream efforts is, often, we may find ourselves voluntarily taking charge of something that we had nothing to do with causing.

I was talking to some people from a large software company who were organizing a taskforce on sexual harassment. And it wasn’t a problem of their making. They weren’t the harassers, they had nothing to do with the environment. But they said, “This is a problem that needs solving. What if we sign up to be the people who try to solve it?” And that kind of enlightened volunteerism is something I find very, very inspiring about upstream work, and it goes back to that notion of upstream heroes, the people whose work can be invisible even though it has profound impact.

Pete Mockaitis
Dan, this is so much good stuff. Tell me, anything else you want to make sure to mention before we shift gears and hear about some of your favorite things?

Dan Heath
The final thing I might mention is, and this is something I feel you could carry through with you your whole career, is to be cognizant of the downside of measurement and metrics. We live in a measurement-obsessed culture, especially in business these days. And measurement is wonderful, it makes us more efficient, it gives us clear targets, but there’s always a downside to measurement, and much of that downside has to do with gaming and the way that measurement alters our behaviors in ways that are sometimes good and sometimes bad.

So, as a concrete example of the bad side, there was a policy passed in the UK for hospitals where they required hospitals to see patients in emergency rooms within four hours of their arrival, so enlightened intent, “We want to make sure that patients are seen, that these crazy wait times, 12 hours, 16 hours, would go away forever, and that we force hospitals to reinvent their processes.” So, very enlightened. What happens is a lot of hospitals started doing this thing where ambulances would bring patients and stay in the parking lot until they thought the patients were within four hours of being seen, and then they would rush them inside so that they can meet the four-hour rule, right? A perversion of the intent of the policy even though they technically met the statistical definition of it.

And that’s something that you’re going to see in your career again and again and again and again every time there is a sales incentive or a bonus offered. You can bet it’s going to do some good and some bad. But I’ll tell you, most of your colleagues are going to be woefully naïve and think only about the good side, and you can be the one that says, “Hey, let’s kick the tires a little bit here.” One test you can run is what I call the lazy bureaucrat test, and that is if someone wanted to ace the measures or incentives that we’re setting out with the least effort possible, what would that look like?

Or another one you might call the defiling the mission test, which is imagine that we ace all of these measures that we’re setting, and yet our work ends up harming the mission, the reason we’re all here. What would that look like? Like, in the case of the ambulances waiting in the parking lot is a great example of defiling the mission. You’ve aced the measures but defiled the point of healthcare which is to pay attention to patients and their needs. So, I just want to leave that as a provocation that you can be the person whose attention to the dark side of measurement keeps your organization out of a lot of nasty traps.

[39:03]

Pete Mockaitis
Boy, Dan, I can’t resist now. You dropped a couple test on us and those were so good. Do you have more that you can reveal?

Dan Heath
Yeah, actually, there’s another one that I’ll steal from Andy Grove, the former CEO of Intel, and that is he said, “Any time you’ve got a quantity measurement”’ so you’re paying people, maybe you’re paying the janitorial crew based on square footage cleaned, or you’re paying your data-entry people based on the quantity of documents entered.” He said, “Any time you got a quantity measurement, you’ve got to counterbalance it with a quality measurement,” because what you’ve got to realize is if you incentivized people to clean more floors, what comes part and parcel with that is they’re going to do a worse job per square foot in the service of getting to a larger area.

Or they’re going to go so fast on the data entry that they’re making lots of mistakes for the sake of getting through more documents. So, the way to balance the scales is to combine quantity with quality, where quality might be some kind of spot checking of how good the rooms looked after they’re cleaned, or with data entry, to make sure that there’s some metric that specifies how good the precision was between the entry and the original document.

And ever since I became aware of that test from Andy Grove, I’ve started seeing situations where really smart people put it into place. Like, even in the police force in L.A. For years, police were adopting these metrics of reduce crime, reduce crime, reduce crime, and that leads to things like stop and frisk. Stop and frisk is effective at reducing crime but it has this just grotesque side consequence of subjecting a lot of innocent people to abusive treatment. And so, they’ve learned to counterbalance the focus on reducing crime with a measure of community trust, “How much do you trust the police? Do you feel like they’re doing a good job looking out for safety?” And that’s a beautiful way to kind of restore order or a sense of balance to the work. So, that’s another one I would add to the quiver.

Pete Mockaitis
That’s good.
Well, then could you share with us a favorite quote, something you find inspiring?

Dan Heath
My favorite quote, this is from a guy named Paul Batalden, who’s a healthcare expert, he said, “Every system is perfectly designed to get the results it gets.” And that quote has become just like a brain worm for me. It’s so enlightening because it tells you in situations like Chicago Public Schools that at one time failed 48% of its students. It tells you the way CPS is setup is designed to fail half its students. So, if we’re going to get different results, we have to change the system.

But I think it’s also true in our own lives. I think that’s what’s so powerful about this quote, is if you find yourself perpetually dealing with the same dissatisfactions or the same frustrations, it’s a sign that the system is setup wrong. How do you change the system? We can’t just hope our way to a different result.

Pete Mockaitis
And how about a favorite book?

Dan Heath
This is definitely not my favorite book but I thought, in the wake of Clay Christensen’s recent passing, he wrote a wonderful book called “How Will You Measure Your Life?” that I think is a great excuse for all of us, just to be self-referential here in this podcast, to step out of the tunnel and think about the big picture and where we’re headed, and “Are we making the right micro choices to get the kind of macro results we want in our lives?”

Pete Mockaitis
And a favorite tool?

Dan Heath
Let me give you a small one. There’s an online tool called Toggl, and it has turned me into a time-tracker, and that’s what it is, it’s a time-tracking software that allows you to just see how you’re spending your time and devoted to categories. And I’ll tell you, I am not like a natural personal productivity person, okay? I am not the kind of person who puts labels on file folders, so this was unnatural for me. So, take heart if you’re a naturally-unorganized person. And it has really changed my day-to-day work. It’s made me much more cognizant of how I spend my time, and I’ve gotten strategic about it. Like, I’ll actually, from time to time, just do a check-in and see, “Am I putting hours against the things that are most important to me?” And that little tool made it a lot easier.

Pete Mockaitis
Oh, thank you. And how about a favorite habit?

Dan Heath
I’m going to throw out my coffee shop habit. And, look, I know everybody’s going to have a different one. But something about going to the same environment really brings out the best work for me, and I think it’s because it’s just like everything in the environment at the coffee shop now is a trigger or a cue to me to get into writing mode. It’s like it helps me get over that hump because I have so many associations with the look of the place, and the smell of the place, and the taste of the coffee, and it’s like my sensory environment is helping me replicate that state of getting into thoughtful writing mode.

Pete Mockaitis
And is there a particular nugget that you share that really seems to connect and resonate with folks, they quote it back to you often?

Dan Heath
With this new book, what I found that resonates with people is this idea that the need for heroism is usually evidence of systems failure. If you think about we celebrate a lifeguard who jumped into the pool at the YMCA and saved a drowning child, obviously we want to celebrate that lifeguard, he may saved a life, but the need for them to jump in the pool and do the saving, maybe evidence that something was wrong with the way things were operated. Was the lifeguard chair too far from the pool and they have blind spots? Or was the lifeguard on their phone? Or was the lifeguard looking at something interesting happening in the pool and they had dropped their discipline of scanning the pool every 10 seconds? So, I think we should distrust heroics in a way, that if we’re repeatedly relying on heroics to get the job done, then maybe something bigger is at stake.

Pete Mockaitis
Perfect. And if folks want to learn more or get in touch, where would you point them?

Dan Heath
Come visit me at UpstreamBook.com and there’s resources on the site that are free, there’s a lot more about the book if you’re interested, so, yeah, come there.

Pete Mockaitis
And do you have a final challenge or call to action for folks looking to be awesome at their jobs?

Dan Heath
I would say in the next week, let me challenge you to find a way to get out of the tunnel that you’re in, whether that is just taking an hour off of work and going and sitting in a coffee shop with your phone off and thinking about the big picture. Whatever that looks like for you, escape the tunnel and think about how you might knock down some of those recurring problems and irritants in your life.

Pete Mockaitis
Dan, this has been a treat. Thank you. I wish you tons of luck with “Upstream” and all your adventures.

Dan Heath
Thanks so much, Pete. It’s been a real interesting conversation.