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

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

Ross Dawson
Wonderful to be talking to you, Pete.

Pete Mockaitis
Well, I’m excited to dig into your wisdom about Thriving on Overload: The 5 Powers for Success in a World of Exponential Information. But, first, could you tell us a little bit about your knack for musical instruments? I understand you can play many. How did you learn how to play them all? Any tips and tricks, or any special performances that really leap to mind?

Ross Dawson
Well, it’s just at the age of 14, I said, “I just want to play guitar,” so I gave a little money to my dad, he bought me a guitar, and I actually, at the time, had some cassette tapes and a little book, and I taught myself. So, I teach myself just about everything, and so it was the guitar included, and then I sort of worked out, “Okay, well, that note on the guitar, is that a note on the piano?” And so, I looked out on how to play the piano, and learned a couple of other instruments. It’s all self-taught.

Sometimes it’s useful. Often, it’s useful to have teachers but I think there’s so much we can discover ourselves in the way we find our own ways of doing things if we do them ourselves. And that’s certainly been my musical journey where I just do what I want to do, and I enjoy it, and not necessarily following what anyone’s suggesting to me I should be doing.

Pete Mockaitis
Fun. Okay. And were you in a band at some points along the way or any noteworthy performances?

Ross Dawson
Yes, just lots of bands along the way, mostly pretty early on when I was at school, when I was university, and then after that, yeah, a number of other bands, and playing guitar, bass, keyboards, percussion. And I’ve been certainly keen to get back to it for quite a while, and it’s a bit harder when you have kids and you got busy and so on, but working on some ways to use technology plus instruments to be able to create my own one solo show live.

Pete Mockaitis
Oh, fun.

Ross Dawson
So, working it too.

Pete Mockaitis
Looking forward to it.

Ross Dawson
So, see you if I actually get on stage at some point.

Pete Mockaitis
That is good. Well, one final question on the music scene, did any of your bands have funny names? Band names are our favorite.

Ross Dawson
Nothing that I…well, funny, I don’t even remember them all. Platinum Blues was one of the sorts of bigger bands that I was in. So, this idea of those blues but we were sort of gilding it. So, that was, I suppose, one of the steps along the way.

Pete Mockaitis
Cool. All right. Well, Ross, now tell us a little bit about Thriving on Overload. Any particularly surprising or counterintuitive discoveries you’ve made along the way on this stuff?

Ross Dawson
Well, I suppose, in a way, Thriving on Overload is counterintuitive in the sense we live in a world of overload, but we can thrive on it. I think this is a fundamental belief that our brains are not adapted to the world that we have created. Incredible inventors that have made, among other things, a profusion of information, and screens, and always on, and this is something is what we have brought ourselves, but it is not something that our brains are ready for, so we are overloaded. We are overwhelmed. It’s just natural. It’s impossible not to be, in a way.

But I do believe that it is possible to thrive on that. And this is, I suppose, a way where we can become, you know, learn, change how we do things, what we do, our attitudes, practices. And that, in a way, means we can transcend who we have been to be more adapted to the world that we live in. So, this is a journey, we can learn things, we can progress, and so that’s something which is not obvious but I think this really is our most important capability that we need to develop.

Pete Mockaitis
Okay. Well, so then can you paint a picture for, if there’s any cool studies or data or research, which really reveals just what’s possible in the realm of thriving on overload? Like, what’s the typical level of thriving/floundering in the midst of overload versus what can really be possible if you master this stuff?

Ross Dawson
There’s a whole set of capabilities to develop the capability to thrive. So, the subtitle of the book is, The 5 Powers for Success in a World of Exponential Information. Those five powers are purpose, framing, filtering, attention, and synthesis. So, we need to be able to dig into each of those and how all those fit together. But if we want to distill this, I suppose, to research and some data and some one frame, one piece of research or sort of now what is compounded research is into multitasking.

And some people think they’re good at multitasking, and the reality is that now more recent studies on what’s actually happening in our brain shows that when we think we are multitasking, as we think we are doing two things at the same time, our brain is actually switching from one thing to another thing, and then back to the other thing, and then back to the other thing.

Now, if we’re simply listening to a podcast while we’re cooking dinner, that’s probably achievable. That’s not too hard to go back and forth. But if we’re doing something which is contemplatively taxing, and we’re then checking our email, or trying to watch TV, or whatever it is, it’s simply not functional. So, studies have shown, in fact, that those people who think they are good at multitasking actually underperform those people that don’t think they’re good at multitasking because they’re trying to do something which is literally not possible. Our brains cannot multitask.

So, this is where we are put in a world with so much wonderful things going on, and we try to pay attention to multiple things at the same, and it’s simply, yes, you can do it by switching your attention, but you will perform less than you’ve done before. Now, taking research at the other end of the spectrum, those who are trained in the single practice which takes our attention the most sustained is meditation, which is simply the practice of keeping our attention sustained on one thing for a period of time where we can continue to be on attention on one thing for a period of time.

And you don’t need to be a meditator to get there. There are other ways to be able to get there, and there are people who switch everything off, and for three hours at a time, aside from getting up and stretching and having a drink of water or whatever they need along the way, will be focused on task for a period of hours.

And the reality is that it’s only a very small proportion of people that are able to and do take that time and capacity, develop that three hours of attention, spend it on one thing in which they can achieve incredible things. Whereas, the vast majority of people, it’s literally, their attention is not on one thing for more than literally a few minutes at a time, at best, because they’re just strayed by thoughts or notifications or alerts.

And those are the two poles. One is eternal distraction, eternal attention watering all over the place where we can never achieve that much. And those people that demonstratively can keep their attention on one thing achieve extraordinary amounts of things in quite limited periods of time.

Pete Mockaitis
Okay. Well, that does sound exciting in terms of what’s possible. Now, to zero in on that three-hour figure, I’m thinking about ultradian rhythms and just what’s possible for the human organism. Is that three hour like three hours but with, like, a couple minute bathroom and beverage break? Or, how does that unfold, that three hours?

Ross Dawson
Yes. So, to your point, the basic rest activity cycle is generally understood to be 90 minutes, where our brains do go through cycles of, amongst other things, ability to be more focused and less focused. And so, we do need to take that into account, and our brains are different, we could be more or less tired, those all sorts of different factors, but 90 minutes is a reasonable guideline.

So, three hours is something where it is very possible for anybody to spend three hours in reasonable degrees of focus but that’s probably more than as much as most people would want to achieve in a day. The way I put it is that everybody should, for at least 90 minutes, at least once a week, have a complete focus time.

And that’s something which, again, is already challenging for most people. Most people don’t take 90 minutes out where there’s no distractions, nothing interrupting them, where there’s only one thing, they can’t escape from it, and they do get on with it. It actually takes practice to get into that but you can still achieve a lot as you get to that 90-minute period and I think that’s a good starting point for most people.

If you’re used to just being distracted and checking your email all the time, whatever it may be, make sure you have a time of 90 minutes, no distractions, no notifications, nobody’s going to interrupt you unless it’s the end of the world, and you have one task to get on with, and you just do that for 90 minutes, and do that once a week. That’s just incredibly starting point. And from then, you can start to build it.

So, in terms of some of those cycles, one of the most famous is the Pomodoro technique, which you spend 25 minutes of focus, five minutes break, 25 minutes of focus, and five minutes break, sometimes a bit longer break, and then you do that three times, which basically takes you to 90 minutes, have a little bit of a longer break, and then you do that three times again, 25 minutes plus five minutes break. And that works for a lot of people.

Personally, I think that the more flexible approach, as in if you feel you’re in the groove, then why suffer 25 minutes, or if you just feel a little bit of a break first that’s earlier. So, we can let our…some people work to that structure, having a time run, 25 minutes and five minutes break, that works for them perfectly. Other people, I feel that 25 minutes, often I’ll just want to keep on going, I won’t want to stop. But when I’m ready, I can take a stop, wander outside, pick up the guitar, whatever it may be.

So, I think if we get into this practice, what we do need is find our practices, find our routines that work for us, find what times of day is the best time to do this, but just making sure that you are starting with at least carving out some time, which is this what I call deep-dive time. That’s when you can achieve an incredible amount in very limited periods.

Pete Mockaitis
Okay. Well, then so we’ve got a sense for what that means with regard to minutes of focused attention, which is handy. Could you share a cool story if there’s a particular case or poster child, if you will, that really illustrates what that can mean in practice for one’s results, career, productivity when they get there?

Ross Dawson
I think the reference point for, certainly for me, and I think for a lot of people is writing books. There’s pretty significant proportion of people say they aspire to write a book at some time in their life. You are never going to get there unless you have the focused time and you’ve blocked that out. So, that’s where anybody can say, “All right, I would love to write a book.” It could be a fiction book, it could be a memoir, it could be about this big idea you’ve have, it could be to show you’re the expert in your field, whatever it may be.

And, yes, when I wrote my first book, before I wrote my first book, I said, “I think society overweighs the value of a book. Being an author is an incredibly wonderful thing and society gives a lot of value to authors and, yeah, it’s a good thing but it’s…so I’ll play that game, if that’s what it is.” I have to say that after writing the first book, I say, “Well, actually, probably authors do deserve some respect.”

But it is something where you do need to carve out the time. So, anybody who writes a book will have an incredible accomplishment, it doesn’t matter how many books or copies are sold, you will have achieved something of value, something to point to, one which will advance your reputation, your career, your abilities, you’ll learn a lot through doing that. So, I think it is a wonderful endeavor, and that is something which can only be done with focused time that is blocked out, it’s simply for that.

Pete Mockaitis
Okay. So, there it is, it’s kind of binary, on or off. Certain accomplishments such as writing a book are just impossible without the ability to have that focus for an extended period of time that is 90-ish minutes or thereabouts or even greater. And then I think in this age where there are different media and creations, we could maybe think of the book as a proxy or a representative for any sort of, I don’t know, magnum opus or great work of sorts that they’re not cranked out in 15-minute break in between Instagram sessions.

Ross Dawson
Exactly. To your point, if you want to be a YouTuber, today the bar for YouTube videos is pretty high, as in it’s a very high quality. If you want to do X videos on a particular topic and show you’re the expert, you’ve got to be pretty good because there’s a lot of other really good people out there. And, again, that’s not going to happen by itself.

You’ve got to say, “All right. Okay, I’ve got to work out. All right, what’s my topic? What’s my script? Where do I get my video assets? What are the overlays that’s going to be?” This is, again, going to take focused time. It’s not going to happen just by filling in in between other things. And what you can do, for example, in 90 minutes of focus will far exceed what you can do just trying to do bits and pieces while you’re interrupted along the way.

So, this is a way of amplifying your productivity, but it’s also a way of just being more…creating more value from the world we have. And I think that this fundamental equation for almost all of us are input as information. It’s what we read. It’s what we experience. It’s our conversations. It’s what we see in the world. It’s what we live, what we notice. It’s what we make of the world. It’s our knowledge. It’s our understanding.

And then it’s sharing it. it’s creating value with that. It’s building a startup. It’s applying it to our work. It’s making better decisions. It’s seeing opportunities. It’s creating YouTube videos. It’s creating blogposts. It’s creating articles. It’s having more intelligent conversations that add value to more people. It’s the input and the output. And both of those require this structure to how it is we bring our information together and building knowledge. And the structure in our work lives and to how it is we create something of value from it.

Pete Mockaitis
Okay. Well, so you mentioned these five powers: the purpose, the framing, the filtering, the attention, the synthesis. Can you expand upon those in terms of, I guess, a definition, and maybe some top do’s and don’ts for really developing each of these powers?

Ross Dawson
Certainly. So, just at a high level first. Purpose is simply knowing why. Why is it that you deal with information, do what you do in the first place? Second is framing, which is being able to literally build frameworks for your knowledge, for your understanding, for your information so you can piece together how they are connected. Filtering is being able to look at the information source that you have, and to be able to discern what it is that serves you, that serves your purpose, and what it is that doesn’t, and being able to make sure that you leave the ones, the information, that’s not useful.

The fourth mode is attention. So, we’ve been talking about this idea of deep diving. We have extended focus for a period of time, but that’s not the only attention mode. For example, we might have scanning, we might say, “All right, there’s a period of time when I’m just going to look at all my information sources. I’m going to stop and then move on to then perhaps reading and taking that in,” so there’s different attention modes.

And the fifth one is synthesis. And this is, in a way, pulling everything together so that it’s rather than just be lots of information, we can make a body of knowledge, we can understand the system, we can be able to have the foundations to build something of value. So, these are the five powers, and we can sort of perhaps flip over the year digging into specific questions. I can obviously go into greater depth on any of those, but I think laying those out as the five is critically important.

So, where would you like me to dig into from those topics?

Pete Mockaitis
Well, I guess I’d like to hear what sorts of practices enable us to develop and deploy each of these powers well versus what is the antithesis, the kryptonite, of each of these powers that are to be avoided?

Ross Dawson
So, we have to start with purpose, and the way I frame that in my book Thriving on Overload is around our relationship to information. So, we have a relationship with money, we have a relationship with food. In the same way, we have a relationship with information, there’s a lot of parallels with our relationship with food and relationship with information where we can have a not very positive relationship with food where we snack on chocolate all the time or eat when we’re stressed and so on.

And, in fact, there are some quite similar habits, sometimes, which people have with information. But we can also have a positive relationship with food, where we eat healthy food, and we feel that is sustains us, and we don’t have too much food when it’s not something that we truly want. So, with information, the same thing, where we can have a positive relationship with information, which is formed by going to what actually is good for us, which makes us feel happier, which inspires us, which informs our ability to achieve what we want to achieve, and is something which we’re not always indulging and snacking in all the time.

And so, I propose this idea of intermittent fasting information diet. So, some people, for food, they say, “All right, I’m not going to eat for a period of time. Come back and eat a meal, whatever, but I won’t eat anything at all in between.” And I think that’s a very valuable approach with information as well. We can say, “Well, I’m not going to check social media, I’m not going to check the news headlines, I’m not going to indulge in those things because, for a period of time, there are things that I want to do. I want to play with my children. I want to read something which is important, which I’ve decided is something I want to spend my time on, and I want to be able to write my book,” whatever it may be. So, we can vary those things.

But this all comes from purpose in the sense of understanding what it is we want to achieve, what it is we think is worthwhile, and, as a result, being able to determine the information that’s not useful. And the antithesis of that is simply not knowing, “Oh, that’s interesting. A bit about the celebrity news,” or, “Oh, see this horrible thing about what’s happening in politics, and spend some time looking at that.” And none of that serves us because we’re not clear on our purpose.

And so, having that purpose is an absolutely fundamental starting point to simply being able to prosper and know what it is that is valuable to us in a world which is often overwhelming.

Pete Mockaitis
Well, Ross, I’d love to expand on that notion of purpose in the specific context of reading the news. Sometimes, when people read the news, they say things like, “I want to be informed.” And that strikes me as a little bit vague as far as a purpose or a goal goes because, in a way, there is infinite news one might be informed or not informed about. And so, it seems kind of thin in terms of, “My goal in reading this news is to be informed.”

And sometimes I wonder, maybe just because I don’t like reading a lot of news. I guess my purpose, the way I go into this is say, “I’m going to spend approximately 40 minutes scanning the headlines of The New York Times and The Wall Street Journal so that I have a general clue as to the happenings in the world so I am able to converse with people,” as opposed to going, “Huh? What?” And so, that’s my purpose when I’m going to the news.

And it doesn’t take that long, and I find that if I spend too much time on the news, one, I’m pathologically curious, which is great for a podcast interviewer but not so great for a news consumer because, like, two hours later, it’s like, “Okay, I’ve read all about the chess cheating scandal, but how does that serve me?” I found it very interesting and I know I can comment a lot about it, Ross, if you have any questions, but it’s not really enriched me much.

So, can you share with us some example articulations of what might be some rich, useful, best-in-class articulations of purpose when it comes to approaching information of the news?

Ross Dawson
So, a couple of points just with what you’re saying. So, I think that’s wonderful in the sense of, first of all, you mentioned you take 40 minutes, and that’s exactly what I say. We need to have a period of time when we say this, “I’m going to scan the headlines and no more.” But news is one category, in a way, of information. It’s what I framed in the book as society, in a sense of, “What do we want to know about what is happening in society at large?”

And we said, the purpose is, “What is our purpose for it? Why is it that I read the news?” And you articulated, again, a quite clear purpose, so you can have intelligent, or at least, somewhat formed conversation with people, and you only need the headline for that to be able to not know…or, to actually know what’s happening as opposed to having the idea of what’s happening. And that’s entirely valid.

So, some of the reasons why you would want to go in the news is to be an informed voter. Now, that’s something which you probably can catch up with just before you need to vote. You don’t need to be constantly…

Pete Mockaitis
The day before, binge.

Ross Dawson
You don’t need to be constantly reading the news all year round in order to be able to vote, whatever it is that you vote. But that’s one valid reason. Another is to be able to have intelligent conversations with your friends you want to have conversations with. Another is to be aware of the things which are changing in your community, and so that gives you a geographic for this, “All right, I would like to see news about my local community.”

Another is to say, “Are there any things which are going to impact my children’s opportunities?” I might say, “All right, if they’re at a particular age, I might be looking at developments in university or college admissions,” or something like that. So, these are things which you would start to be focused. But this comes back to the domains for our relationship with information.

And one of the first ones, one of the most important ones is expertise. We do have to choose our area of expertise to be clear, “This is what I am an expert in, or I’m aspiring to be an expert in, or something which I think I’ll be useful to be an expert in in a few years from now,” and being quite clear around that, writing that down, “I will become…” or, “I am an expert in a particular area,” quite clearly defined, and that gives you clarity on what information, what sources you need to take in, what you need to distill so that you can become that expert. If you’re just skimming across the surface, you’ll never be an expert in anything, and that is not very useful in the current state of the world today.

Another is in wellbeing, “So, what is it that I’d want to know about my own wellbeing, well, the wellbeing of my loved ones? What is it that’s going to help me to have a better diet to be able to help support the conditions of people in my family?” So, it’s perfectly valid to have some passions. All right, so sports teams or there’s nothing wrong with celebrity news as long as you don’t let that expand to take over all of your news.

So, I think there’s different categories around helping you decide what your purpose is. There is information you can look for. You can look in your expertise, your ventures, whether that’s a startup, or whether it’s a community garden, whatever it is, in terms of your wellbeing, in terms of your relationship to society. These are all things that we can think through in order to become effective.

Pete Mockaitis
You know, Ross, what you really are crystallizing for me is, and this is so helpful. Thank you. Hopefully, it’s good for listeners too. But I find, internally, I have a response of frustration or irritability when I see a news headline or blog article, or whatever, it says, for example, “Topic: What you need to know.” And I’m thinking, “There is no possible way you know what I need to know because our contexts are so wildly different.”

Like, the person running the political campaign for this politician needs to know way more and way different things than someone who may or may not vote for that person months down the road, or someone who’s managing the budget or employees in that industry. I guess maybe because I’m a content creator myself, I’m prickly or snobbish about the quality, but it’s like, “What you need to know, there’s no way one article can provide what everyone needs to know because everyone’s contexts are so different and their purposes that they establish are so different.”

So, Ross, thank you for clarifying what was simmering under the surface for me. And is it fair to say you’re going to have a hard time writing a piece of content that’s what you need to know for all peoples in one fell swoop?

Ross Dawson
Well, I think you’ve hit the nail on the head.

Pete Mockaitis
I guess I just wanted to make sure. Thank you, Ross.

Ross Dawson
But what it comes back to is saying we need to know it is health, and we don’t necessarily know that. So, what I described is we need to develop our own personal information plan. So, to complement the book, I’ve created some software or course where it takes people through that journey of identifying their purpose, and their expertise, and their areas, and their sources, and how they can use that, and the times they’re going to use that and do that.

You don’t need the book or the course, though they’re obviously designed to be as useful as possible. But we all need to decide, “What is my own personal information plan? What is it that matters to me? What time am I going to spend on that? What time am I not going to spend on the things that don’t matter? How am I going to structure my day? How am I going to structure my time? How am I going to spend time to be focused? How am I going to make space to synthesize this and pull this together?”

Information is the core and the value, I would suggest, of almost all of your listeners, and it’s something which most people haven’t spent the time to think about, is to, “How can I do this better?” And we can all build our own personal information plan, and that starts with this idea of, “Why? What’s important to me?” And from that, a lot of that starts to flow into, “What are the structures and the habits and the practice which will enable you to achieve what you want in your life, and be happier because you’re not drowning in the things that somebody else thinks is important to you but actually isn’t?”

Pete Mockaitis
That’s powerful. Well, you got me thinking about email outsourcing, but we’ll move on in terms of thinking about what’s important to me, and what’s not important to me, and what’s important to other people that land in your inbox, and how can you navigate that effectively, whether it’s software or helpers or different levels of support. So, we’ll just let that percolate in people’s heads for now. But let’s hear about framing next.

Ross Dawson
So, framing is building a framework. So, we got lots of information, but that’s all just bits of information. It only becomes knowledge and understanding when we connect that, when we say, “What are the relationships between these ideas? How does this fit together? What are the foundations of my understanding of this area of expertise that I’m developing?”

So, there’s a number of tools, a lot of visual tools that we can use. So, we can use things like mind maps. We can use things like concept maps. We can just sort of just draw things on a piece of paper and draw lines with them. And there’s now more and more software which helps people to not just note, “Ah, that was interesting. Oh, that’s interesting. Oh, that’s a really good study there,” and then to actually make links between them.

So, there’s a whole new generation of software tools, including around research and obsidian, but also other ways of just using simple software tools, such as note taking tools and so on, that enables us to practice this way of framing by drawing connections in, building a lattice of knowledge which is the foundation for how it is we can become an expert, to understand things, to be able to know what the reference points and the researchers that supports what are valid ways of thinking about these spaces.

Pete Mockaitis
And can you paint a picture or give us an example of what a frame looks and sounds like?

Ross Dawson
So, on RossDawson.com/frameworks, I’ve created a whole set of what I find is useful frameworks about the future, but any mind map. I think mind maps are one of the most people are most familiar with, where you have one idea and you lay that out as a kind of visual representation of some of the ideas and how those fit.

So, one of the good things about a mind map is it combines a hierarchy. You have a central idea and then subsidiary ideas, and then subsidiary ideas, but also being able to lay that out to be able to show some of the potential relationships between these ideas. So, these are forms of structuring, and it’s different for every person as to what is most useful for them and the way in which they think.

And some people like putting things in a linear document but we’re trying to move beyond linear. So, how do we draw connections between things? And I think, often, just being able to sketch things on pieces of paper, write down ideas on a piece of paper, draw lines between them as to what the relationships between those ideas are, and then you can start to literally build a picture of an area of expertise, of what it is you’re looking at.

Pete Mockaitis
Okay. And now let’s hear about filtering.

Ross Dawson
The filtering requires, first of all, understanding what information sources you’re going to go to. And this is not just going directly immediately. You might be using feeds, or you might be using aggregators, or you might be using different tools, but it’s building more and more this discernment of what it is that serves your purpose. So, clarity on your purpose, being able to guide that, and what it is that you need to discard.

And more and more, this is around being able to make sure that we are not succumbing to our confirmation bias, that we are not just looking for things that affirm what we want to know, but we are looking for things that complement our knowledge. So, one of the, I suppose, ways of shifting our thinking is to say, rather than being certain about things, whether that be in politics, or society, or in our area of expertise, is to start attributing probabilities to things.

So, we can say, “I think it is 90% likely, or 60% likely, that this is the case,” and then you can start to look for evidence that either increases or decreases the probability of you being right. So, there is a study of super forecasters, these people that are very good at predicting the future, and they have this implicit way of thinking about the future, or thinking about what it is they know as a probability. They’re never 100% certain on anything, because you can’t be.

But what you can do is to say, “I believe this. This is what I understand. This is the probability I attribute to that,” and then being able to look for evidence that will make your assessment that more accurate. So, this is a way of being able to actually go to the most surprising information to you and assessing that, and whether that’s valid so that you can then start to incorporate that into your mental models, or your ways of thinking, or your hypothesis around, for example, what will be a successful business.

Pete Mockaitis
Okay. And then, I’m curious, when it comes to arriving at what sources you think are winners versus ought not to be delved into, are there any core criteria or questions that really helps separate the wheat from the chaff?

Ross Dawson
So, it’s context. So, I frame this as, first of all, thinking about yourself. So, what is it that you want to be true, for example? Or, what is it you’re looking for? Or, what are your ideas already around this? You need to be thinking about yourself first, in a way. Second is the source, and you say, “Well, is this generally reputable, to generally other people consider this to be worthy? How much research did they do?” And being able to assess.

And no source is completely accurate. The most credentialed scientific journal in the world, Nature, has had 50 retractions in the last 10 years of things where they published it, and then they say, “Oh, actually, no, that’s not right. Ignore it.” And so, we can go to the most reputable sources and then we can’t actually be completely confident. There are certain sources where you can say, “Well, okay, there’s not much credibility,” but it doesn’t mean that any source is completely off the table either, but we need to have an assessment of that.

And the third one is actually looking at any specific piece of content, one of the most important things to do is to go back to its sources in whatever way to be able to corroborate that, “Is there anything which would suggest this was also true?” And it’s incredible, when you skirt into practice of going back to original sources for what it is you read, how often it is distorted or, in some case, a complete misrepresentation of what it is it says to be reporting on, or simply just misleading.

So, the single best practice is not to take anything at face value, but to then go back, and, of course, only if it’s important enough to you to warrant that, to go back and to do your research, to delve back, to say, “Well, let’s see, where does this actually come from and how do I assess that?” So, I think this requires a curiosity.

Yes, you are trying to say, “Yes, this is a more likely to be true source, more or less likely to be a true source,” concentrate on the ones which are more reputable, of course, but also to take everything with a grain of salt, and to dig back and to build your own reference point just what you believe is true, and be able to find the evidence you can to support that.

Pete Mockaitis
Okay. Well, now, could you give us any top do’s and don’ts in the zones of attention and synthesis?

Ross Dawson
So, attention, there are six modes that I identify in my book. So, the first, which we discussed, is scanning, so just looking across existing news sources. Second is assimilating, where we assimilate, and we say, “This is worth spending time on.” It could be a book, it could be an article which you identified, and just rather than being distracted, you spend time and you take that into your body of knowledge.

Seeking for knowledge, explore, and I think it’s important to spend time where you’re deliberately trying to find things you would never normally find. Deep diving, which we discussed from the outset, that way of just spending focused time for a period of time. And the critical one, and one of the most ignored and most important really of the attention modes, is regenerating, which means stop doing, taking in information. And going out in nature is the most powerful way to do that.

It doesn’t need to be a forest. It can be a single tree in a park or whatever it may be. Just getting out in nature is a form of regenerating our attention. So, the best practices, the time box, let’s say, “This is the time I’ll spend on this. This is when I’ll do it. This is the time I’ll spend on that, and I’ll do that.” And to make sure that you’re spending your time deep diving each day, you’re spending time scanning each day, you’re spending your time assimilating each day, and you are spending time regenerating each day.

And the don’t is simply just to go from one thing to another all the time, just continually distracted by the next thing, “Oh, I should be doing that. Oh, I should be doing that. Oh, I might do this instead,” and you never get to a fraction of what you could achieve otherwise.

In terms of synthesis, it really is about getting to a state of mind where you can pull all of the things which you’re exposed to into understanding, into knowledge, into something where you have insights that other people don’t. And that requires this going between the intense focus but also the breath, giving your mind the space in which it can piece together all of the different elements in order to build that understanding.

So, in my book, I describe some of the different ways in which we can get to the state of mind where insights happen, where we can synthesize the ideas, where can come up with insights. And I suppose the don’t on that thing is simply just to burrow down all the time and not give our mind the space which it needs to be able to do what humans are incredibly good at, uniquely good at, is to pull together, connect the dots, and make sense of the whole.

Pete Mockaitis
Okay. Well, Ross, tell me, any final thoughts before we shift gears and hear about some of your favorite things?

Ross Dawson
Simply that this is the foundational capability for success today, is this ability to deal well with information and create value with it. And I think that anybody, whether you’re a beginner, as it were, or an expert, everyone can get better on it. And I just believe that we can all and should be spending time trying to get better at our information capabilities because that’s what will drive our abilities to create what it is we want in our lives.

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

Ross Dawson
So, one of my very favorite quotes is from James Carse, and it is “Finite players play within boundaries; infinite players play with boundaries.” And it’s from his book Finite and Infinite Games, and that’s so many things. People are so much stuck in their boundaries, and so we need to play with the boundaries of our life and work.

Pete Mockaitis
All right. And could you share a favorite study or experiment or bit of research?

Ross Dawson
One of my favorite bits of research which studied normal people and then meditators, and they put on a metronome, and the metronome started ticking. And for normal people, the first tick, they had this strong brain response, and then, quickly, it went down and they just didn’t notice it anymore. The Zen meditators, the first tick, they noticed. The second tick, they noticed it, and they keep on noticing it. They are continually seeing the world afresh. They are not becoming habituated to it as almost all of us do. So, this shows that we can continue to see the world afresh even as it stays the same, or seems to stay the same.

Pete Mockaitis
Okay. And a favorite book?

Ross Dawson
One of my favorite books I’ve read recently is The Beginning of Infinity by David Deutsch, pointing to the infinite potential we have as the human race.

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

Ross Dawson
Favorite tool, well, just in terms of information access, Techmeme is just one way, one place where I can just quickly get on top of all of the important technology news of the day. So, just a quick, easy, and simple tool, and makes me informed in that area.

Pete Mockaitis
All right. And a habit?

Ross Dawson
The habit which I am developing more and more is when I feel like a break, is doing one of two things. One is picking up my guitar, and the other is rather than browsing through things, is turning to a book just to read for a few minutes, and then turn back.

Pete Mockaitis
And is there a key nugget you share that really seems to connect and resonate with folks; they Kindle book highlight it and retweet it and such?

Ross Dawson
Simply that we have to believe that we can create a better future in order to be able to create it. And I think a lot of people are very negative today. There’s a lot of negative news reported, people getting some poor states of mind, but I think the first thing is we need to believe that a better future is possible. And it doesn’t matter whether we think that’s highly probable or not very probable at all, as long as we believe it is possible to create a better future, that gives us the foundation to say, “Well, what is it that I can do in order to be able to create that?”

So, I think that’s, in a way, the foundation of my work, and I think it’s a lot of what resonates with people is this starting with this potential, this belief that we can create something better to drive the action, which means that we can work towards that.

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

Ross Dawson
For my work, in general, RossDawson.com but for the book, ThrivingOnOverload.com. There’s a wealth of resources there, there’s free parts of the book, the exercises, the introduction, there’s the overload course, there’s a podcast, there’s a whole set of resources. So, ThrivingOnOverload.com is a wonderful place for those people who want to go further on this journey.

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

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

Roger Martin
It’s great to be here. I’m looking forward to this.

Pete Mockaitis
Oh, me, too. Well, so I’m so excited to dig into your wisdom. Tell us, what’s the big idea behind your book A New Way to Think: Your Guide to Superior Management Effectiveness?

Roger Martin
The big idea is you got to be careful to not get owned by thinking models. You get told, “Oh, this is the way you should think about this problem.” If it doesn’t work, don’t go back and say, “Well, because people say that’s the model that should be used. Keep on using it.” That’s being owned by your model. Instead, you need to own your models. They need to work for you. And if they don’t, you need to change it. That’s the big idea.

Pete Mockaitis
All right. Makes sense. Now, the word model, I figured we’ll be saying it a lot. So, could you give us maybe four or five examples of models that professionals use just so we have a real clear sense for what we’re talking about there?

Roger Martin
Sure. A model would be, in order to align the interests of management with shareholders, you should give them stock-based compensation, and that will create alignment. Or, you should always make decisions based on data. That’s the only good decision, that’s a decision made on data. That’s a model. The job of a corporation is to make sure it controls and coordinates the various businesses underneath it. That’s its primary job. That would be a model.

Another model would be customer loyalty is the most important thing about customers.

Roger Martin
Those would all be models that we use that then guide our behavior. So, if you say, “Oh, I must align the interests of management and shareholders with stock-based compensation,” you will have a stock compensation plan that’s based on the performance of the share price as a key feature of executive compensation. So, these models drive behavior.

Pete Mockaitis
So, is there any distinction, not to play too much of the semantic wordplay game, between a model and a rule or a principle?

Roger Martin
Not really. I guess what I would say is a principle tends to be a portion of a model. So, our principle is alignment, and the way we’ll make that happen is through stock-based compensation. So, you’ve got a principle that informs other aspects of a model. That’s how I would distinguish them. You could call a model and a rule kind of relatively similar.

I just think of a model not in a better way but it’s a slightly more comprehensive than either rule or principle. It’s a set of things that we will do because we say if we do those things, it’ll get the result we want.

Pete Mockaitis
And is it possible that we operate from some models that we’re not even aware of?

Roger Martin
In fact, we do that all the time. Let’s say you’re a CEO and you kind of walk into a retailer that sells your product, you don’t like how it’s merchandised, let’s say you’re a fashion line.

Pete Mockaitis
I’m fashionable. Okay, I’m with you.

Roger Martin
Yeah, exactly. Like you, Pete. And you go to the people who are running the store and say, “You, people aren’t following the corporate guidelines on this. I’m outraged, dah, dah, dah.” That’s a model. It’s a model that says it’s their fault, not yours. Your instructions weren’t confusing. Or, your way of merchandising actually doesn’t sell stuff. It’s, “You’re morons,” or you’re not so much morons, “You’re insubordinate,” in some way, “in not following it.” Your model is you have to observe when people are being insubordinate and not following instructions, and chastise them for doing so, and that will improve things.

Pete Mockaitis
And that we know best in terms of the optimal approach for merchandising versus that you may be in a surprise, like, “We tried your way but this way is 30% better, so we’re going that way.”

Roger Martin
Absolutely. Absolutely. And that executive probably wouldn’t have articulated that in the corporate jet on the way to visit the retail outlet, “My model is to make sure they’re obeying and to chastise them if they’re not.” But, in fact, that’s what naturally flows because, in fact, that is his or her, probably his, managerial model.

Pete Mockaitis
Okay. Well, so you say that folks have a tendency to double down under existing models even if they’re not working. What’s behind that?

Roger Martin
It just seems to be, Pete, a human tendency from what I can tell, which is we like to have models because, otherwise, you have to think about everything from first principles. So, you have a way of doing things, so there’s affinity with the idea of a model. And then there’s sort of social adoption. So, if everybody else is doing it, if everybody else is doing stock-based compensation, and there are stock-based compensation consultants who come and tell you how to do it, and the board gets evaluated on the basis of whether it’s got stock-based compensation, all that stuff.

If that becomes the standard, it’s easiest, that’s because we’re sort of social human beings to say, “Having a model is better than thinking from first principles and I might as well adopt the model that’s the one that’s being used most because that’s probably a good idea.” And so, you’re a plumber in ancient Rome, and all the other plumbers are saying, “This great material, lead, is really malleable and makes for good water pipes and so let’s do that, too.” And because, boy, it seems to work, ten years later all the people die from lead poisoning, but at the time it seemed like a good idea.

So, I think those two things cause people to feel a certain level of concern, anxiousness, outright fear when they have to do something other than the existing model.

Pete Mockaitis
What you’re saying there is in contrast to first principles really resonates. I’m thinking about when I was just getting my start, I’m thinking, “Okay, you don’t want to do the speaker-author, guru biz in terms of, ‘Oh, yeah, you got to have Twitter, you got to have a blog.’ Okay, so this is what I do.” And I didn’t really find those to be especially effective tools, versus reasoning it from first principles would suggest, “Okay. Well, fundamentally, what is my offer?”

“How is it distinctive from alternatives and competitives available? Who is my customer? What do they want? What are their preferences? How can I make my prospective customers aware?” And so, that is a whole lot more work than, “Oh, you got to have a Twitter, you got to have a blog.”

Roger Martin
No, no, exactly.

Pete Mockaitis
But it would’ve served me better.

Roger Martin
And that, if I can go on that, that makes for a very interesting case. What I’d say is you took something that maybe would’ve been a model that a consumer package goods company would utilize and ported it over to another domain rather than accepting the domain’s kind of model. And that I find is kind of interesting.

A similar story, as you may know, I was dean of a business school for 15 years, and that was my first academic. I was never dean before. And all the development people, the fundraising people came to me, and said, “Well, this is how you do it. Get a list made of all the rich people in the country, and rich graduates, and then you go ask them for money.”

Pete Mockaitis
Okay, “This is your job now.”

Roger Martin
And I was thinking, “Okay, like I know a lot of rich people, and let’s just put me in their shoes and say, ‘How appealing would that be to me?’ So, you’re going to come and see me because I’m rich, no other reason other than that, and because, apparently, I should want to give you money. All you have to do is ask and I’ll give it to you.”

And so, I said, “I guess you could do that but it doesn’t seem like a good idea. How about this as an idea? I find people who have means and have something that they’re really interested in that the school is also interested in, and let’s get them involved in that because they care about it and they want to be involved in that. And, in due course, they will say to us, ‘Can we support this cause in a greater way?’”

And all the fundraising people said, “Well, what does this guy know about fundraising? This guy is crazy.” Well, on the basis of that, we got the University of Toronto, which is a big gigantic university, have been running forever. University of Toronto is only a six-figure unsolicited gift ever, where it was not asked for. Its first seven-figure unsolicited gift and its first eight-figure unsolicited gift. Literally, one guy, he was into real estate and got involved…who didn’t think there was nearly enough good real estate courses producing the people, and Toronto is a big real estate town, producing the real estate folks. I said, “I agree. We need to serve the community. Would you be willing to teach a course if we got you the appropriate help?”

He did. He loved it. Students loved him. He started hiring all sorts of students from it. We hired other real estate professors. We got to a point where we were one of the best two or three business schools for real estate in North America. We then built a new building. And he came to me and said, “You probably need somebody to give you the cornerstone gift for this, the building, right?” I said, “Yeah.” And he said, “Here’s eight figures.”

So, that was a different model, a completely different model than the dominant model because, in that case, I wasn’t even prepared to sort of spend my time on the dominant model because it just seemed silly to me. But you’re right, that requires thinking from first principles, which is not as straightforward. And if my approach had failed miserably, rather than succeeded, they would’ve said, “Yeah, he is a nut.”

Pete Mockaitis
Well, I think there’s one reason right there, is it’s riskier to do something novel and different. And I’m thinking the old saw, “No one ever got fired for buying IBM.” Like, “Yeah, that’s the thing. Yup, IBM, they make the business machines, that’s their name so buy them from there.” And so, I guess that’s one reason why folks might double down.

Roger Martin
It’s a perfect metaphor, “Nobody got fired, nobody ever got fired for using the dominant prevalent model of the day.” Full stop. So, absolutely. And that’s why I’m not saying to people in the book, “Whatever the dominant model is,” I don’t say reject it.

I say, “I could understand you trying it but just make sure you kind of write down, ‘What I expect to happen when I try this model,’ and then check what actually happened. And if there’s a big negative delta there, then here’s what I’d encourage you to do. Don’t just keep doing it because everybody else is doing it. That might be the time for you to think about, ‘Is there another way to think about it?’”

So, if the dominant model is working, keep doing it, is my view. It’s just when it doesn’t work.

Pete Mockaitis
Okay. Well, I was about to ask, how do we know if something isn’t working anymore? Are there any indicators or telltale signs it’s time to shift away? It sounds like one master key is simply write down in advance what you’re hoping the thing will do, and then check later, “Did it do the thing?”

Roger Martin
Yes. And that may sound kind of trivial but it doesn’t happy very often, Pete. And that leads to sort of…there are a bunch of human dynamics problems that you have to take into account. One human dynamic problem is human beings have an infinite capacity for expose rationalizing.

Pete Mockaitis
Oh, yeah.

Roger Martin
Right? You can expose rationalize anything. And we know this in a sad, sad, sad sort of way from war crimes trials, where often somebody is on the stand and who’s committed just a horrible, terrible crime that they know is horrible and terrible, but they rationalize it in saying, “Well, I had no choice.” So, you can rationalize anything.

And so, you have to help the mind not rationalize. And the only way I believe you can do that is by writing things out because, otherwise, if you say, “Oh, well, we’re going to build a new factory. And with that new factory, it’s going to cost $100 million but we’re going to increase sales by 50% within five years, and that will pay for the factory and a good return on our $100 million investment.”

If you don’t write that down, five years from now when sales are up 35%, you’re going to say, “Yeah, exactly. This is exactly what we said, sales increased 35%,” and you would never ask the question, “Hey, what didn’t go the way we thought that made it 35 rather than 50, which actually made it a return that’s below our cost of capital, not above our cost of capital?” You wouldn’t do that because it’s sort of lost in the mind’s mist of time what you actually thought your model was going to deliver for you.

So, I want you to write it down so that when it happens, you can compare what’s happened to that. And that will give you the information you need, “Did it perform the way I wanted it to perform, that I assumed it would perform when I used it?”

Pete Mockaitis
Okay. Very good. Is that sort of like the master key or any other key questions or things to do there?

Roger Martin
That’s the master key.

Pete Mockaitis
Okay. Got you. Well, so could you maybe tie this together for us with a story of someone who they had an outdated model, and then they made a shift to a new way of thinking and got some cool results?

Roger Martin
Sure. So, I could talk about customer loyalty. So, the dominant model is that the most important factor for you in kind of being profitable is having high customer loyalty. And what that is, customer loyalty, is a conscious act. So, that would be, I don’t know, what toothpaste do you use, Pete?

Pete Mockaitis
Colgate Total, paste not gel. Thanks for asking.

Roger Martin
Perfect. Colgate Total paste. And so, it’s worked for you in the past, and so you are consciously driven to show loyalty to that brand when you go to the toothpaste aisle. You sort of consciously say, “Hey, I’m loyal to that. It’s worked well. I will do that.” It turns out that all the behavioral science, all that research is telling us that, actually, the much stronger driver of that habit is unconscious.

Pete Mockaitis
Okay. You’re right.

Roger Martin
It’s actually your unconscious. So, literally, the way the mind works for you, since you’re a Total Colgate paste, if your hand reaches for Total Colgate, or Colgate Total gel, your subconscious starts yelling at you, saying, “What the hell are you doing? The paste. Paste works. Paste is most comfortable. Paste is most familiar. You’re asking me to do something new. I’m worried. I’m nervous.” So, it’s actually an unconscious driver. And Lord forbid that you reach for Pepsodent or something else, then you’ve gone completely off the rocker, “Oh, my God, cats and dogs sleeping together.” It’s going to be horrible.

So, it turns out, the subconscious loves comfort and familiarity more than anything. So, what you want to make sure that you’re kind of not messing with is habit. And so, one thing that companies can’t help doing is refreshing and redesigning. And it turns out that colors and shapes are really important visual cues before you actually can read the lettering on most things. And that would be the case in Amazon when you see the little chicklet there. We first see colors and shapes. And so, when you change the color of something, or change the name of something to, it’s a huge negative for habit.

And so, Procter & Gamble, Tide, unbelievably profitable and venerable brand, have been around for 70 plus years. And what it turns out is that people have a Tide habit more than they are loyal to Tide. And so, when Tide, 40, 50 years ago, when the transition was starting to be made from powdered detergents to liquids, the first liquids came into being, Procter & Gamble said, “Okay, Tide is the dominant detergent, the largest market share, but people see that as a powdered detergent. And so, to make sure we do best in the now nascent liquid detergent business, what we need to do is have a brand-new brand new, it’s called Era, and that will be our liquid and Tide will be our powder.”

The Era launch was an unmitigated disaster. It never got any traction, anything. And then some bright person at Procter & Gamble said, “Hmm, what if we launched Tide liquid? And why don’t we put it in an orange bottle with the same logo, the bullseye logo kind of on it, and call it Tide, and put a little Tide Liquid beneath it?” Blammo, it quickly became the dominant liquid detergent brand and has been ever since. Why? Because people had a Tide habit, and they had a habit of buying the laundry detergent that was in orange with a bullseye on it, with four letters on it, Tide.

Then, as time went on, Tide did smart things like when they figured out how to put bleach in the Tide itself, in the detergent itself, so you didn’t have to have a separate bottle. They had learned their lesson. And guess what they called it?

Pete Mockaitis
Tide with bleach.

Roger Martin
Yes, that’s very good.

Pete Mockaitis
And then a Tide Pod.

Roger Martin
And a Tide Pod. But, every once in a while, they forget. And so, when they came out with the innovation of how to have a Tide, a detergent wash as well in cold water as in warm water, forgetting the lessons that they learned, they said, “You know, orange is a warm color, perfect for Tide. But cold, we need a cool color for that.” And so, they came up with a cold-water Tide, in what? Blue bottles. Guess how that went?

Pete Mockaitis
Not well.

Roger Martin
Not well. Disastrously bad. What was their incredibly insightful fix for that?

Pete Mockaitis
Go back to the old color.

Roger Martin
Put it in orange bottles, then it became the dominant cold-water detergent. So, that would be an example of a company that began to really understand at a deep level the power of habit over loyalty. Does loyalty matter? Yes, it for sure does. Having a warm feeling, a conscious feeling about it is good. But if you interrupt habit, and interrupt the subconscious, it overwhelms loyalty. Like, think about it, it’s amazing, at least to me. When you think about it, everybody who loved Tide, when you come up with Tide in cold water, which is an added feature that should make your Tide better, it flops because it’s in blue bottles? Holy smokes.

So, the dominant model tends to be, with marketers, “Oh, we have to refresh. Our logo is looking dated. We have to have a new logo. We have to have a new modern color scheme. Maybe we’ll even change the name of it.” All of that stuff is bad, bad, bad, bad, bad but it’s done all the time.

Pete Mockaitis
Well, I guess, in terms of if habit is driving your beautiful market share position, then, certainly. I guess if you’re an upstart and there’s not very many people who’ve got the habits, and your colors and shapes aren’t nailing it amongst the consumers, well, then sure, have at it. But, yeah, I could see how it’s costly to shift there.

Roger Martin
And can I give an example on that, Pete, because it’s good? Myspace versus Facebook. Myspace, of course, was the dominant first kind of social media site, and, actually, in its peak year had more traffic than any other site of any sort, Google, anything. But if you look at the history of Myspace, Myspace kept, from day one, completely changing its look and feel so that there was no consistency, no consistency in the way things were presented, new features that were put on it. It was referred to in the press as a dizzying array.

Think then about Facebook. Like, it has utterly consistent look and feel from the word go, even when they made their painful transition where there was the only real dip in Facebook’s history was when they made the transition to mobile. Mobile looked just like look, feel, everything. Facebook understands habit. Myspace didn’t. Myspace is gone. Facebook is worth a trillion. It is so important. If you’re a startup, you must establish a look and feel.

Netflix did a good job of that. They changed their underlying product entirely but they kept as many other things consistent as possible that helped people kind of feel comfortable. And, again, it’s an issue of you feeling comfortable and familiar, not being upset. And for what it’s worth, this relates directly to RTO, return to office, because, in essence, you could argue that COVID was the greatest force habit break since at least World War II and maybe the Great Depression, where lots of habits just had to be broken.

And one habit that was broken was, people like you and me, and tens of millions of others, waking up every morning, getting in the car, or getting on public transit, and commuting to an office, and working all day in an office, and then commuting back at night. That was the habit. And this was a habit that had a bunch of negatives to it, especially if you lived in the greater New York area, greater Chicago area, greater L.A. area, it would be a painful long commute, but it became the ingrained habit. It was just you did it unthinkingly.

And then what happened was a force majeure break of that habit. You couldn’t blame your company on the habit being broken. It was the government saying, “You must do this.” And so, you had to adopt a new habit, which was painful. For many people, they said, “Oh, my God. Kind of working from home, I had a setup, I had to seize the guest bedroom, or seize the sun porch, or the kid’s basement play area, and turn it into my kind of Zoom office, instead of I couldn’t talk face to face with my managers and my employees, and, dah, dah, dah.”

But what happened after probably six months? It was your habit. It was like, “Oh, roll out of bed, make your coffee, go to the guest room, sit in front of my computer and do Zoom calls.” So, that became the new habit. So, that was first called working remotely and then became the new habit. Then, two years on, companies say, “You must return to office.”

They thought of it, these companies thought and still think of it as getting back to where we were, going back to what is standard, you being at the office. That is not, at all, what the subconscious thinks. The subconscious says, “Oh, my God, they’re making me do a brand-new thing. They want me to work remotely.” The office is the new remotely, and can you see, what happens with the habit?

The way to think about habit is that whatever you’re doing, your habit, so for you it’s Colgate Total paste, that’s your habit, and the alternatives are Crest and Pepsodent and Colgate Total gel, which apparently is abhorrent to you. And so, every time you have a purchase occasion, there’s a race and it’s a hundred-yard dash, and Crest and Pepsodent and Colgate Total gel are at the starting line, and Colgate Total paste is on the 90-yard line. And the gun goes off, and guess who wins?

If, for some reason, Colgate were to say, “You know, we’re totally tired of that Total name. We’re going to call it Colgate Fantastimo, and we’re going to change the paste. That paste is dull and old. And we’re going to make it sort of something that’s a combination of paste and gel, like in a twirl.” What they’ve done for Pete is moved the thing he automatically bought from the 90-yard line to the zero-yard line along with all the other alternatives. And you’ll win some of them because it’s a fair race at that point, but it goes from being a profoundly unfair race in your favor, if you’re Colgate, to a fair race. That’s what’s happening with the return to work.

Your job, which you had comfort and familiarity going for, that was Zooming from home and not doing the commute, that was on the 90-yard line, just got back put back to the zero-yard line, to be compared with, “I’m going to quit for a year. I’m going to find a new job out here in the burbs, or I’m going to change to a company that continues to allow people to work from home.” And so, it’s just massively destructive for the companies asking you to return to work.

And they think it’s disloyalty, “Pete is not loyal enough to come back to the office.” No, it’s habit. It’s Pete just has this visceral thing that he can’t necessarily even understand fully that says, “You know, Pete, it’s time to think about doing something else.” So, this misunderstanding, loyalty versus habit, is going to cause big American employers who are asking you to come back to the office massive turnover. The stats are 67% of people who are being asked to go back to work are considering alternatives.

Pete Mockaitis
Yeah, that’s a great metaphor with the race and having a huge head start because it’s like, “Huh. Okay, so I have to do something different. Do I want to do that? Well, let’s look at all the options.”

Roger Martin
Yeah, exactly.

Pete Mockaitis
As opposed to, “Just keep doing what you’re doing, and don’t ask any of those difficult questions, employee, and don’t just rock the boat.” Okay.

Roger Martin
And I can give a personal example. So, I’m a big of a sportsaholic, and I had a go-to sports app. It was CBSSports.com. I don’t even know why I started using it but it was the one I went to. And I put up with CBSSports.com IT people deciding that they would do refreshes and updates to make the site better and work better and everything. But then they came up with a total redo that they were exceedingly proud of. They sent me messages about, “Hey, get ready for the brand-new site. This is going to be awesome. The navigation, everything, was completely different. The look and feel, completely different.”

And after it being, I don’t know, seven-year a constant user of it, I just said, “Oh, okay. Now is the time to test out all the sports sites and see which I like best.” And now, on the first page of my iPhone is ESPN.com, and CBSSports.com has lost me, not forever. They’ve lost me until such time as ESPN screws up in the same way as CBS Sports did.

For the subconscious, possession is way more than nine-tenths of the law. I am an ESPN.com sports app guy now. And that game is over, it’s on the 99th yard line.

Pete Mockaitis
Okay. Well, rest in peace. You’ve got a chapter I find intriguing when it comes to strategy. You say, “In strategy, what counts is what would have to be true, not what is true.” And that is one of my favorite things to teach, so I want to hear you take the floor. What do you mean by this question, “What would have to be true?” How do we apply that when we are doing decision-making effectively?

Roger Martin
Yeah, most of strategy is about analyzing, doing analyses to come up with your strategy, a very analytical exercise, and most people who are going to strategy are kind of analytically inclined. Kind of the problem is, by analyzing what is, you’re never going to find out what might be. You’re never going to create the future, lead the future.

And so, rather than focusing on that, “What is true?” which will direct you towards what is and focus your mind on what is, if you ask the question instead, “What would have to be true?” you can imagine possibilities. You can say, “Here, I’m going to imagine we do this rather than what we’re doing now.” Now, if you just do imagination, you’ll come up with all sorts of crazy things that are just dumb ideas. But if you say, “What I’m going to do is ask, ‘What would have to be true about the industry? What would have to be true about the customers? What would have to be true if there’s a distribution channel, about our capabilities, about our costs, about competitors, for that to be a great idea?’”

Then you can create a logic structure that says, “If those things were true, that would be a great idea.” Then you can imagine another possibility, and say, “What would have to be true for that one? Well, if these other set of things were true, that would be a great idea.” You can do another one, A, B, C, you’ve got a third one, “What would have to be true for that?” Then you can ask the question, “Of those things that would have to be true, which are we least confident are true?”

And then we can focus our efforts on saying, “Well, if those things would be necessary for this to be a good idea, but aren’t true today,” sort of like we’re Steve Jobs, and it’s like, “Here’s an idea. Why don’t we sell people an MP3 player that is three times the cost of price of the best MP3 player out there? We’re going to make it white and have a wheel on it. How about that for an idea?” What would have to be true is people want to kind of throw money away, like they get three times X for an MP3 player with no greater capability than anybody else’s new technology anymore.

What would have to be true though would be, “This would be of greater use because they would be able to more seamlessly download songs in a more user-friendly way onto that machine. They can’t now. But how about we do this? How about we go to all the record companies and arm-twist them into selling single songs for 99 cents rather than an album, and we’ll put it on a site called iTunes and make it super easy for them to pay and super easy for them to download?”

So, he asked, “What would have to be true?” You’d have to have something special, then you go and figure out, “Can you make it true?” You figure out that you can, then you go do it. And, sure enough, you start selling the dominant market share of MP3 players, expanding the MP3 player market dramatically, and doing it at 3X the price.

That’s the power of saying not what is true but, “What would have to be true? And can we make it true?” And by asking, “What would have to be true for it?” you can focus your efforts on the few things that aren’t true now that you’d have to make true to create a great strategy. So, that’s why, “What would have to be true?” is way more powerful than “What is true?”

Pete Mockaitis
I dig that. That’s fun in a creative invention, being ahead of the game, sort of a way. I’ve often asked myself this question just in terms of, “What would have to be true for this option to be worth picking?” and then sort of list those out, and say, “Okay. And then how can I test that?” And it’s amazing how you can figure out things to do and not to do.

One time I was trying to promote a book and I saw this publication that was distributed to a bunch of producers for radio and TV shows, and it was kind of expensive to be included in this, but I thought, “Okay. Well, this would be really cool if I got on a few shows, get the word out. This is probably a worthwhile investment.”

It wasn’t, I regret spending that money. But then, months later, someone called me and said, “Hey, Pete, I noticed that you were advertised in this publication. How did that go for you? Was it worth it?” I was like, “Wow, if I had followed my own sort of teachings, I would’ve done exactly what you did. What would have to be true? It’d get you a lot of bookings and sell a lot of books. How can you test that? Call some people who bought it and see if it worked out that way for them.”

Roger Martin
Exactly.

Pete Mockaitis
Of course.

Roger Martin
Yeah. And then this is what we did with the re-launch of Olay, creating this sort of masstige positioning of it, where you had a prestige, like a Nordstrom’s first floor or Macy’s, whatever, experience in your Walgreens or your Target. And it wasn’t true that there was such an experience, nor was it true that retailers would say, “Yes, that’s a great idea.” But we went to Target, did an arrangement with Target where we helped fund a transformation of some stores to test out the idea. The product flew, I mean, flew off the shelves in the test, and then the rest is history.

Target said, “How fast can we do all the rest of the stores?” and then everybody else said, “Why are you, bad people, just doing something with Target and not with us?” And we said, “Well, because they said they would do it. Are you saying you’ll do it?” “Yes.” And, blammo, it turns the seventh-, eighth-place skincare product into the number one skincare brand on the face of the planet massively profitable. But it was asking, “What would have to be true?” and then figuring out a way to test that.

You’re not going to test it by launching a product nationally everywhere where you don’t have the experience. You work and spend some money. You spend some money and time with Target to figure out if you could make it true. Would it succeed?

Pete Mockaitis
Oh, beautiful. Well, Roger, tell me, anything else you want to put out there before we hear about some of your favorite things?

Roger Martin
No, I think you’ve done a really nice job of talking us through the core essence of the book, so, no thank you.

Pete Mockaitis
Well, thank you. All right. Well, could you share with us a favorite quote, something you find inspiring?

Roger Martin
I guess I would go all the way back to JFK, “Ask not what your country can do for you. Ask what you can do for your country,” because it is consistent with the advice that I give all my students and proteges, “I follow the doctrine of relentless utility. If you’re just relentlessly useful, good things will happen.”

Pete Mockaitis
All right. And could you share a particular favorite study or experiment or a piece of research?

Roger Martin
The favorite piece of research that I ever did in my entire career was in ’89 when I convinced somebody at Procter & Gamble to do a study that they didn’t want but that I knew there was something we would find.

The question was, “How should Procter & Gamble think about its customers?” Now, they consider you, Pete, although you don’t buy Crest, they consider you a consumer, and they consider Walmart, Walgreens, etc. customers. And at that point, they said, “Well, we’ve got mass merchers like Walmart and Target, drugstores like CBS and Walgreens, and supermarkets like Ralph’s, Kroger’s, Whiteman’s, etc. and we’ve got C stores.” And it just struck me that that wasn’t the right way to think about it.

And so, I just started looking at their top hundred customers, and trying to figure out whether there’d be a better way to think about it. And one day, it struck me that maybe a better way to think about it is, “What is the merchandising philosophy of the customer base?” because what was emerging then, because Walmart was still very small then but growing quickly, was this notion of EDLP, every day low pricing. And Walmart, and a bunch of other chains were doing EDLP, and everybody else was what was called high-low. They have things that are high price most of the time, and then have it on deals for part of the year.

And the entire CPG industry was set up, including Procter, was set up to support high-low.

The idea at P&G at the time was, “These high-low people are more like us, like Whiteman’s and Ralph’s, they’re differentiated. And these EDLP guys, like Walmart and Foodline and a few others at the time, they’re sort of these big brick warehouses and cinder block kind of warehouse look and places, and they’re down and dirty. And so, they’re not really like us.”

So, anyway, did the study and looked at those two segments, and came to the relatively stunning conclusion for Procter & Gamble, that the same store sales growth in high-low, all of their high-low customers together, the same store sales growth of their customers was zero. The same store sales growth in EDLP was 7% a year, compound. The growth in stores in high-low was net zero, and it was 7% compound annual for EDLP.

And then what I discovered was our market share, cutting category, I just added them all up, our market share in EDLP was higher than our market share in high-low.

And on the basis of that, and probably other stuff, Procter & Gamble was the first CPG company to flip and orient all of their systems to serve EDLP, and that got them a jump in their north American sales growth in the ‘90s, which was, especially the first half. It was phenomenal because, while everybody else was sticking with their sort of high-low focus, they were EDLP, and that’s when they created the Walmart team that put a whole bunch of people that enabled to kind of work closely with them.

So, that’s my favorite piece of analysis I ever did because it helped transform the way Procter thought about its customers in a way that it almost benefitted them for a while. Now, everybody else figured it out in due course. They had to move on to what the next thing that’s going to move the needle but I always liked that and I liked it because it was so hard to convince anybody there to let me do the study.

Pete Mockaitis
All right. Thank you. And a favorite book?

Roger Martin
They’re sort of nerdly but probably John Dewey’s Art as Experience. That was life changing for me. If you’re less nerdly, Lord of the Flies, my favorite fiction book, William Golding. And the best I’ve read recently, though it’s an old book that just came to my attention recently was the Social Limits to Growth by a guy named Fred Hirsch. Fantastic book.

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

Roger Martin
I guess it’s my relatively new MacBook Pro 13 inch.

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

Roger Martin
To my website. All my writing is organized on that, and that’s www.RogerLMartin.com. And you got put the L in or it’ll take you to a real estate broker in Houston, who’s very nice. Roger Martin is a very nice guy. He sends me all sorts of emails that come his way. I send him my books. He likes my books and reads them, and so we have a good friendship but it is strained by the number of people who forget the L. So, RogerLMartin.com or @RogerLMartin is my Twitter handle.

And I write a, web is increasingly popular, weekly piece on Medium, if you’re a Medium person, called Playing to Win Practitioner Insights series, 89-long, 90th the coming Monday. So, those would be the places to find me.

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

Roger Martin
Yeah, relentless utility. Think first about, “Am I being useful? Can I say from other people’s perspective I am providing utility?” And if you do that, good things will happen to you. Don’t sweat anything else. Just be relentlessly useful.

Pete Mockaitis
All right. Roger, thank you. it’s been a treat. I wish you much fun and interesting new ways to think.

Roger Martin
Terrific. Thanks for having me.

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.