Learning Archives - Page 3 of 10 - How to be Awesome at Your Job

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

Barry O’Reilly
Yeah, no, it’s a pleasure to be here, Pete. Thanks for having me.

Pete Mockaitis
Well, I’m excited to hear your wisdom about your book Unlearn: Let Go of Past Success to Achieve Extraordinary Results. Could you kick us off by sharing a key thing that you’ve unlearned that has proven quite valuable in your own career?

Barry O’Reilly
Yeah. Well, even writing the book is probably one of the best examples. I have a solid history of D minuses in English literature through school. I’m dyslexic. I think if I told my teacher that I managed to write one book, never mind two, that they wouldn’t actually believe me. So, it was kind of, for me, one of the big unlearning I had to have is actually how to write a book.

And as conventional wisdom, I always say that writers sort of sit there by a roaring fire with a perfect velvet jacket on and a glass of wine, and just like tearing out pages and pages of content. Believe me, I tried that but it didn’t work for me.

Pete Mockaitis
Too hot?

Barry O’Reilly
Yeah, not too good. And, yeah, I would sit there for hours just with writer’s block and I couldn’t quite get the words on the page, and it was really frustrating because I felt like I was doing everything, the tips that people told me. And it’s a real challenge. So, then I started to think about, for me, “Well, how can I sort of reframe what I’m looking at? My existing behavior is not working, so, therefore, I need to unlearn. I’m not getting the outcomes that I’m aiming for writing whatever it is, 10,000 words, 10,000 words a day. Whatever I’d set myself.”

So, I started to actually think about, well, reframe my thinking away from just typing as the only way to create content, and I actually started thinking about content. It’s actually really like creating a book is content. And there were suddenly many ways to create content. Typing is just one of them. So, I started to think about other ways to create content. I could record it. I could speak it. I could interview. I could have someone help me.

So, I landed on the idea of actually talking because that was the most natural way for me to share my stories. And what I did is I got a journalist to interview me. So, we would write down, like some bullet points that I wanted to cover in each chapter, and a journalist would interview me, and I would just tell stories about what the chapter would be about. And we would record it and transcribe it using an AI transcription service.

So, we’d speak for 45 minutes, and I’d get in the region of 20,000 words, record it and get a copy of it in text very, very quickly. And the journalist would then sort of go through that copy, edit it really fast, and send me like this sort of early version of a chapter that was sort of relatively raw but it was edited. And it gave me something to react to. It’s like an MVP or minimal viable product or chapter.

And, suddenly, as I would read through it, then I’d be like, “Oh, no, that doesn’t need to go here,” and I’d remember things I’d forgotten to say. So, we got into this iteration really fast. And that literally got me there. I actually unlearned how to write a book by learning how to speak about the ideas that I wanted to talk about.

And the product of that is Unlearn. And then, yeah, many people are often surprised when they realize when I say I didn’t write hardly any of it. I spoke most of it and I got somebody to work with me, and an AI to transcribe it, edit it, and ship it.

Pete Mockaitis
That’s cool. That’s cool. So, you unlearned the notion of what writing a book looks like. And in so doing, you found an approach that worked for you, and that’s beautiful. Well, tell us, when it comes to zooming out a little bit and broadly speaking about people and unlearning, any other big surprises or aha discoveries you’ve made while researching and putting together Unlearn?

Barry O’Reilly
Well, the notion of unlearning was the thing that probably struck me the most. So, the first book I wrote was Lean Enterprise: How High Performance Organizations Innovate at Scale. It was part of our recent series, or the lean series, and it was more successful than I could’ve imagined, to be honest. And when we released that book, a lot of, sort of medium to large scale enterprises or scale of startups were sort of saying, “We’re not a startup. We’re actually scaling our business, so what do we need to put in place to make us successful?”

And, suddenly, I was in the room with like Fortune 500 executives or startups in Silicon Valley that was scaling rapidly to work with them, to help them grow and innovate their businesses. And I was fortunate to spend time with these people, some of the most competent talented people you could ever hope to meet. And what I kept discovering was that while learning new things was hard, what was even harder was letting go of their existing behavior, especially if it had made them successful in the past.

So, the unlearning even in itself was a big aha moment for me, is that the real skill is not learning new things; it’s actually recognizing when your existing behavior and thinking is actually limiting your success, and then how do you find ways to adapt or innovate yourself to meet the sort of changing market or situation that you’re in.

And that was really my big inspiration for sort of writing Unlearn and the stories and the examples and so forth that are captured sort of within it, and have just sort of been really the things that have driven me on continuously to sort of do this. And for many people, it’s interesting because unlearning is sort of an act of, if you will, sort of vulnerability. You have to sort of say that, “What I know is actually limiting my success, and, really, I have to sort of shift out of it.”

And for many people, that’s very difficult because their success is tied to their behavior. Their behavior and actions are tied to their identity. You’re asking someone to change their identity, in a way, and that is extremely difficult for people.

Pete Mockaitis
Well, could you maybe walk us through an example that illustrates the unlearning process that would be helpful for professionals looking to become all the more awesome at their jobs?

Barry O’Reilly
Yes. So, probably sort of one of the classic examples that I cover in the book is working with a senior executive from a Fortune 100 bank, and she took over the role or went into the role, and everywhere she went, first day, people just kept asking her to make decisions, everything from what direction should the company go in, right down to what paperclips they should order. Every single person was just turning to her to say, “What do we need to do here? What do we need to do here?”

And, for her, that was a signal. She was like, “There’s a decision-making problem here. I shouldn’t be worried about what paperclips we’re ordering. That should be people are confident and inspired enough to do that. Like, why is everything from paperclips right through the company direction landing on my desk and everyone freezing?”

Now, the process for unlearning is it’s a three-step process. It’s first about this recognition to unlearn, identifying or diagnosing where your existing behaviors are not working. In fact, the way I defined unlearning is it’s a process of letting go, reframing or moving away from one’s useful mindset and acquired behaviors that were effective in the past but now limit our success. So, it’s not forgetting, removing, or discarding your knowledge or experience. It’s the conscious act of letting go of outdated information and making space for new information to come in to inform your decision-making and action. So, the first step is a diagnosis.

So, straight away, this executive could diagnose that nobody was making decisions, and that is not the outcome that she was aiming for. She wanted to have a high-performing organization where people could take responsibility and have an accountability to make decisions at the appropriate level, depending on the decision to be made. So, that was a signal for her.

And so, I sat down with her, and I got her to say, “Well, let’s describe it. Let’s describe what success would be. If this is the behavior that needs to be unlearned, how could we talk about division or the objective or the outcome you’re aiming for the people would be achieving?” And I got her to sort of write a story about it, write a vision statement for what would be true in the world if they had unlearned this challenge.

So, she wrote down things like people would be making safe-to-fail decisions, that they’d make small decisions to understand. If they had to make a big decision, they’d break it into smaller parts and learn along the way what works and what doesn’t. And this sort of learned helplessness to make decisions would be removed, and all of her direction would be what success is and why it matters. None of her direction would be how to achieve it. The teams would offer opportunities on how to do that.

So, writing this sort of story, it gave her these sorts of outcomes that she talked about, the learned helplessness disappears, her direction of what success is and why it matters. She wouldn’t be saying how to achieve it. And, straight away, we wrote those down in an unlearning statement that would basically say, “The company would’ve unlearned when 100% of her direction is what success is and why it matters. Zero percent of her direction is how to achieve it. Zero percent of people displayed this learned helplessness when making decisions.”

So, suddenly, she had sort of had this statement that would encapsulate this unlearning of decision-making as a problem within that company, and she actually shared this with a bunch of her team to sort of for them to understand as like what would be success criteria for unlearning it. And then the next step is to sort of re-learn. It’s like getting people to try new behaviors to try and move towards these objectives or outcomes that we’ve described.

And so, I always get her to sort of like pick one of these outcomes that she originally had described to sort of focus on. So, there was the learned helplessness, how to achieve a decision, or what success is and why it matters. And we picked actually that this one, zero percent of her decisions would include how to get there.

So, she took this sort of very bold sort of stance. And I often say to people, “If you want to re-learn, it actually means you have to do something uncomfortable,” and people mostly write down like simple things that they would try that they’re used to, like just be quiet for a moment, or don’t be the first to speak when someone offers a problem, or let all the team speak before she did.

But the one she chose was even more uncomfortable. She said she wasn’t going to make any more decisions. So, if someone came to her and asked her to make a decision, her immediate reaction would be, “What do you think?” So, introduce this tiny little new behavior. Now, you can imagine when you’re a Fortune 100 executive, and you sort of announced that you’re not going to make any more decisions. It would cause panic across the company.

But the way that we made it sort of safer, rather than just sort of never make a decision again, she was just going to try it for one day. So, for one day, make it sort of safe-to-fail, she’d think big but start small about trying to conduct this new behavior of not making decisions, and asking people what do they think.

And this is sort of the moment that we call a breakthrough. So, a breakthrough is literally when you start to get this new information, new behavior, new action, and the results that actually give you a feedback statement that you should keep doing what you’re doing or do something different. So, literally, she went into work, I think it was on a Tuesday. I think it was a Tuesday. And every time one of her team came in to ask or to make another decision on something, she sat there and said, “That’s interesting. What do you think?”

And what that did was something really magical. It allowed her to learn. It allowed her to learn about the people and what help they might need. Because some people, when she asked somebody, “What do you think?” would freeze, would be sort of “Ah, I don’t know. I really need you to make this decision. I don’t have enough confidence or control to do it.” So, she could realize straight away that person would need coaching.

But other people, when she asked, “What do you think?” would say, “Well, we’ve got three options. We can do option A, and here’s the pros and cons of that. We could do option B, here’s the pros and cons. Here’s C and pros and cons. I think we should do C, and here’s why.” So, instantly, she could go, “Great. Let’s do C,” because she could see the rigor and the thinking that her team had actually performed, and it gave her confidence to say, “Right, that’s the direction we should try. Let’s do it.”

So, this simple act of just not making a decision and asking people to sort of say what they think sort of revealed all these insights about who is able to make decisions and should be encouraged to make more, versus who was hesitant to make them and needed coaching and support to sort of get there. And instantly then, she just gets this uplift in performance because once she starts doing that, all her teams start replicating that. And then, suddenly, you’ve got this big performance improvement where you can start to eradicate decision-making problems.

So, that’s an example of a sort of unlearning statement and going through the diagnosis of decision-making, the re-learning of actually thinking big and starting small, defining outcomes, and taking a small new behavior, which was not to make decisions, and ask people what they think. And then the breakthrough was seeing this insight or learning from the team about who could respond well and who needed help. And that sort of informed her to keep doing, and that’s literally the cycle of unlearning.

Pete Mockaitis
All right. Well, thank you for that story. That’s really cool. And I’m curious, as we zoom into individuals listening here, are there any key questions or prompts you find super useful to surface, to highlight, to assess, to diagnose, “Aha, I may have an outdated or suboptimal belief or practice or mentality that I would do well to unlearn”? Like, what’s sort of the canary and the coal miner, some key indicators that I should be on the lookout for?

Barry O’Reilly
Yes. And the simple question many people that ask is, “How do I know what I need to unlearn?” And to diagnose, there’s a set of questions that I ask people. It’s basically getting you to think, “Is there a situation where you’re not living up to the expectations of yourself? Maybe there’s somewhere you’re not achieving just sort of outcomes that you desire. Maybe you sort of tried all the things that you can think of and you’re not getting a breakthrough. Or, maybe there’s a situation that you’re avoiding altogether because you just can’t think, ‘How am I going to tackle that?’”

These are all the sort of signals that your existing behavior is not working. So, not living up to your expectations, not achieving the outcomes you’re aiming for, situations you’re avoiding or struggling with, or maybe you’ve tried everything that you can think and you’re still not getting a breakthrough. I’d even ask you that, Pete, and you probably can come up with four or five answers straight away. And these are all signals that our behavior is not actually helping us achieve the outcomes that we’re aiming for. And, therefore, we have to unlearn, we have to try something different.

Pete Mockaitis
Okay. And as you’ve seen a lot of workplaces, are there some common examples that pop up again and again and again in terms of, “Oh, these are some things that would be great to unlearn”?

Barry O’Reilly
Yes. So, I think like risk-taking is always a big one, like people’s risk aversion, getting comfortable with being uncomfortable, trying new things, being willing to fail. These are all decision-making. It actually comes up quite a lot. These are sort of like the commonalities, I guess, that I hear from a lot of people, is how to help them sort of get those breakthroughs, is trying new things that they’ve never done before.

A lot of it is about, I think, when people perceive that there’s risks for both personal and perception, that if they try something and it doesn’t work, how they’d be perceived. That one really comes up a lot, I think.

Pete Mockaitis
Well, that’s juicy. And so then, if I was working on that, how might you help coach me through that emotional stuff?

Barry O’Reilly
Yeah. Well, first of all, it’s just a recognition, people diagnosing that that’s the heart of the issue. Most people sort of write it up as, “My boss won’t let me do something,” or, “We’re stuck in the status quo. We’re struggling to do new things. We don’t innovate in my business.” Like, a lot of people would sort of deflect it off to company not allowing them to do things.

And a lot of it is sort of then helping people recognize, well, first of all, you have agency and you can try. So, how do we make it safer for you to try? Or, you feel safer that if you fail, how you’ll be perceived? And one of the mantras in the book was this notion of thinking big, start small and learn fast. So, it’s important to have a big aspiration or big outcome that you’re aiming for because that allows you to sort of shift your thinking and your behavior, potentially, to get there.

But the way when you’re trying to make big changes is you don’t take big leaps. You take small steps and learn your way through. So, when somebody has a big idea to change their business, what I often say to them is, “Right. Well, write down that big idea.” Amazon has a famous practice where they get people to write press releases to describe what the world would be like if their product was in the market in two to three years’ time, what would be fantastic about it.

Now, with the way that they start is they don’t do a huge big project. They start small. They run some experiments with small customer bases to see what works and what doesn’t, and then sort of grow it from there. So, what I often say to people is if you have a big idea to change the way your company works, don’t expect that you can walk up to the CEO and get millions of dollars of funding and a new team, and then just sort of start working on it.

Do something small to start testing if that idea is going to work. Pick maybe one or two customers and sort of show them a very naïve version of the product that could work or could not, and get feedback and show that it’s working or not. And even if it doesn’t work, it’s okay. You will have learned something from those one or two customers about what success could be or what’s the right product that they’re looking for and iterate it.

So, these are the ways that you can think big and start small, to start tackling uncertainty and be successful as you try new ways of working new products, etc. And so, that’s what we do most of the time is just coaching people how to think bigger but start smaller so they can learn what works and what doesn’t in a safe-to-fail manner. And once they sort of get into that habit, then they’re able to take on these more audacious goals as they sort of see success moving towards it.

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

Barry O’Reilly
No, I think, like the message from me always with this is, like I experienced that I’ve got to unlearn stuff all the time. It’s tough sometimes to recognize the actual reason you’re not being successful is yourself, that you can’t get out of your own way. So, I think a bit of humility, a bit of not trying to beat yourself up too much when you’re not getting the success, I think, is quite important, and recognize that a lot of this is a sort of journey, a learning journey, if anything, a constant iteration and experimentation on yourself. And if you see it like that, it can be a fun journey to go on rather than beating yourself up along the way when things don’t work.

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

Barry O’Reilly
One of my favorite ones, and people will have to buy the book maybe to find out what chapter was this one, is that something always gives up. Either the problem gives up or the person gives up. But if the person doesn’t give up, ultimately, you’ll get the breakthrough that you’re looking for.

And that was really interesting for me as a notion to sort of think about. It is a little bit of a battle of wits between the problem you’re trying to tackle and the person, or yourself, trying to tackle it. And, really, half of the way to succeed is to keep showing up. If you just keep showing up, something will give. Either the problem will sort of give and you’ll get past it, and, hopefully, before the person gives up because then the problem wins. So, that’s always motivated me to keep being persistent and to keep showing up, and I really enjoyed that quote.

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

Barry O’Reilly
Well, I think my favorite example in the book is Serena Williams, and her story is just purely phenomenal. She’s sort of an against-the-odds story. And also, the success that she had and continues to have is sort of totally unheard of and a total outlier for the sport that she plays in. She actually is getting better as she gets older, which is sort of unheard of. Most tennis players retire at the age of 27. She’s 40 and she’s still competing at the highest level, getting to finals and being successful. So, yeah, really a fantastic story that I open the book with, and would highly recommend people check her out.

Pete Mockaitis
And a favorite book?

Barry O’Reilly
It’s called Maverick, and it was basically written about a small little factory in Brazil where the CEO, who took over, whose son who took over from his father, started using all these contrary methods to manage people that were much more about empowering people rather than the typical, let’s say, corporate institutional management techniques, and they had massive success. So, I highly recommend people check out that book. It’s one of my favorites.

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

Barry O’Reilly
I like the Shure SMB mic. Sounding good when we’re on podcasts, I think that’s one. One thing I learned, I think, through the pandemic especially, is that it’s really important to have good sound when you’re communicating because when the sound is bad, it makes it harder for people to listen. When you’ve got good sound, it makes it easier for people to listen and more of the information goes in. So, yeah, get a great mic. That would be my tip for people.

Pete Mockaitis
Agreed. And a favorite habit?

Barry O’Reilly
At the moment, well, there’s two. One is making a really nice coffee in the morning when I wake up. That’s definitely, that’s my special time. And then exercising as much as possible. I think one of the things I really learned as well, especially as I work in a venture studio called Nobody Studios, and I work with a bunch of biohackers. And this idea of like persistently improving your whole, both like mental activity, like doing exercises like this, reading, writing, etc. but also the physical aspect of how important it is to exercise and sleep.

We’re actually working on a sleep company at the moment, and it’s just been fascinating to me to realize and learn how important sleep is to our actual performance, in general. So, now I’m somebody who…I used to stay up and think I could get by on six hours of sleep at night, but now if I don’t get eight, I get angry at myself. So, it’s been really interesting to learn some of these habits.

Pete Mockaitis
Well, Barry, now you got me curious about, if you’re allowed to disclose, what’s the sleep company and what transformational insights have you gleaned thus far?

Barry O’Reilly
Well, the first one is how important sleep is. I think most people sort of undervalue how important it is. It’s the most restorative process that we have, so no surgery or amounts of vitamins or supplements are going to improve your wellbeing as much as sleep. So, it’s actually one of the most important things that we have to do.

So, yeah, some of the habits that I have had to unlearn was like going to bed late, or a routine to actually optimize when you do go to lie down to sleep, that you get the maximum sleep, that you can get a high-quality sleep at that. And it’s everything from the triggers, simple things that people might say to you, like don’t drink coffee, or don’t have high amounts of sugar, or don’t let your body be in a stress state when you go to sleep because you actually can have negative sleep, which hurts you more.

So, all of these things have been really fascinating to sort of learn and discover. And, yeah, if you follow our venture studio, Nobody Studios, you’ll see the sleep company when we launch it to the public in the next couple of weeks. I’m pretty excited about what it’s going to do.

Pete Mockaitis
Alrighty. And is there a key nugget you share that really seems to connect and resonate; folks quote back to you often?

Barry O’Reilly
Well, I think just even the word unlearn. It seems to be one of these provocative words that people go, “Yeah, that’s it. That’s exactly what we need to do. We don’t need to learn more things. We need to unlearn some things.” And I think it’s been a fascinating way to connect with people in terms of the interest area, or a way to describe something, or a notion that many people have felt but weren’t able to put word on it. So, yeah, I think unlearn, that’s it. It’s a fun one. Let go of past success to achieve extraordinary results. It’s all in the title.

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

Barry O’Reilly
Yes. So, I’m pretty much Barry O’Reilly on every social platform you can imagine, or BarryOReilly.com. And if you’re interested to follow our studio, we’re at NobodyStudios.com. Go check us out on the web and similarly on most social media platforms.

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

Barry O’Reilly
Yeah, just think big, have a big bold aspiration that you’re aiming for, that something you think could change, but start small. What’s the first small step you can do to start moving towards it? And you’ll learn fast what works and what doesn’t. So, that’s my message to everyone.

Pete Mockaitis
All right. Barry, thank you. This has been a treat. I wish you much luck with Unlearn and all your adventures.

Barry O’Reilly
Thanks very much. Thanks for having me, Pete.

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

Katy Milkman
Thank you so much for having me. I’m excited to be here.

Pete Mockaitis
Well, I’m excited to learn how to change once and for all. You’ve literally written the book on this and I can’t wait to hear your insights.

Katy Milkman
Well, I’m excited to share.

Pete Mockaitis
Well, maybe to kick it off, could you share maybe what’s maybe one of the most surprising, fascinating, counterintuitive discoveries you’ve made about us humans doing behavior change while researching the book How to Change?

Katy Milkman
That’s a great question. I love starting with that question. Probably it’d be a study I ran at Google that had the most counterintuitive finding to me. And it was a study where, actually, my collaborators and I were trying to figure out if we could create more durable habits around exercise in people if we got them to build really consistent routines, which is what our read of the habit literature suggested makes habits sticky, like, “Always at the same time of day, I’m really, really grounded in that routine and now it becomes like second nature to me.”

And if we could build that, we thought, then we sort of let go and we’d see these lasting habits. So, we ran this experiment with Google employees where we basically, for a month, gave them rewards for either visiting the gym at the same time of a day, a consistent time that they’d said was ideal for them, or for any time, whatever they wanted. So, about half of their visits ended up being at a consistent time but the other half were all over the place.

Pete Mockaitis
And so, one group was rewarded only when they went during the time they said and the other was rewarded regardless?

Katy Milkman
Exactly.

Pete Mockaitis
Okay.

Katy Milkman
We actually varied the size of the incentives so we got variance in how often people went, and we basically ended up with two groups who went the same frequency but in different patterns. One is going very consistently, the other is more variable when they go. And then the question was, “What happens at the end of this month?” And we were sure, we knew, it was going to be the people who had that consistent routine, and we were wrong.

And what we found out is that the reason we were wrong is not that we had our model completely messed up, it was true that the people who had been really consistent in their exercise who would basically train to be automatons, the same time, same time each day. Those people actually were a little more likely to keep going at that same time, but if they didn’t make it to the gym at that time, they didn’t go at all.

And the folks who had built a more flexible habit ended up with a more durable habit because they went a little less often at that magic time, it was the best time each day for them, but they went at other times too, and at that they went more. And that was really surprising to us that, it turns out, and I write about this in the book, I call it the power of elastic habits. I really expected, from everything I’d read, that those consistent cues would be critical to durable habit formation but what we found instead was that it bred rigidity, and that if you’re going to get something done, you need to be flexible, and just say, “I’m going to do it no matter what,” not, “I’m going to only do it under this narrow set of circumstances.”

So, I think that’s really interesting and it was a really important takeaway and counterintuitive to me. Although, now it makes sense, in hindsight I can see why that’s important but it’s not what I expected. And we surveyed professors of psychology in all the top universities, and 80% of them also were surprised. They predicted strongly, “Oh, yeah, that consistency, that’s what we know about habits. Consistency breeds habit,” and it’s just not what we found.

Pete Mockaitis
Yeah. Wow, that’s striking. And so, well, there’s one gem right there, so thank you.

Katy Milkman
You’re welcome. That’s a great opening question.

Pete Mockaitis
Well, let’s zoom out a little bit in terms of, okay, your book How to Change: The Science of Getting from Where You Are to Where You Want to Be. Can you lay it on us sort of the big idea or key theme or thesis associated with this work?

Katy Milkman
Yeah, absolutely. So, the key idea behind this book is that there’s a lot, of course, of great books and a lot of great knowledge out there about how to change and, yet, it’s not getting us where we want to be for the most part. People are still looking for these kinds of books, still trying to figure it out, a lot of us aren’t where we want to be. And one of the things I have found in my career, devoted to studying this topic of where change comes from, is that I think part of the problem is we often don’t focus on what is actually obstructing change for a given individual, for a given challenge or a given goal they’re trying to achieve, and tailor the solution to that obstacle.

We sort of grab one of those big ideas off the shelf that sounds sexy and appealing, like, “Set big audacious goals and then break them down,” or, “Build a really tiny habit and piggyback.” Like, there’s all these ideas that are out that are appealing but they won’t work if they’re not solving for what’s holding you back.

So, that’s kind of the big idea behind the book. There’s all these different things that can be barriers to change, whether it’s, “I don’t enjoy doing the thing that I need to do to change,” or, “I keep forgetting to do the thing and flaking out because I’m too busy and it’s just, I can’t prioritize it,” or, “I’m having trouble getting started,” or, “I don’t have the confidence to change. I don’t believe I really can and that’s holding me back,” or, “My peer group is not showing me the ways to do it and is a bad influence.”

Like, what is the challenge and the solution then will be different. And we can make more progress if we actually diagnose what’s standing in the way, and then use the best science to solve that specific problem. And I see this all the time in my work with companies, that they have some behavior, “We want get people to save more for retirement,” or to get their flu shots, or to be more productive. Like, let’s just grab from this bag of tricks from behavioral science and we think we’ll be able to slap a solution on it, but if there isn’t an understanding of, “Well, why aren’t people saving? Why aren’t they productive? What’s holding them back?” that is matched to the solution, we don’t get very far.

Pete Mockaitis
Okay, that’s resonating a whole lot. I’m getting chills in terms of like there’s much truth here.

Katy Milkman
Thank you.

Pete Mockaitis
So, in a way, it seems like self-evident, “Well, of course, you should figure out what’s the challenge and address it.”

Katy Milkman
It does seem self-evident.

Pete Mockaitis
And, yet, we don’t.

Katy Milkman
It’s astounding how often we don’t, yes.

Pete Mockaitis
Well, can you lay it down, lay it on us then, what’s maybe the menu of categories of obstacles and the best practices for deconstructing or addressing those obstacles? And then, maybe even before we go there, how do we go about identifying it and zooming in on it very well? Because, for example, when you say, “Why don’t people save?” like, “Well, I just don’t have enough money. I don’t have any spare money to save. I guess we’re done.” And so, it’s like, “Well, no, not quite. I think we got to dig deeper.” So, yeah, let’s start there. How do I identify, like, what’s the crux of the obstacle here?

Katy Milkman
I think the answer is probably most people will recognize themselves and a specific problem when they see these different discussions.

So, for example, I mentioned it’s not fun. That’s a really common one. I don’t know if that’s not a super common one for retirement savings. Most of us aren’t like, “I want it to be fun to save. And I find it dreadful and dreadfully unpleasant in the moment to do it.” That’s more like exercising or eating right or really focusing at work instead of scrolling social media. But that’s a category of obstacle.

Another category of obstacle is, “I don’t see how I can do this. This doesn’t seem doable.” I think that’s a big one, and retirement savings is actually is like, “Wow, it doesn’t feel feasible.” And that can come down to confidence, it can come down to what you’ve seen other people like you accomplish, and how, if you’ve learned their techniques and skills for doing it.

Another category can be, as I mentioned before, just flaking out, like, “There’s just a lot going on and I can’t get this to the top of the list, and I keep spacing it when it’s time to actually setup the 401(k).” So, it depends on which one you see yourself in, and I think it’s not like a category of problem, it’s always the same answer for different people. For some people, savings is also about procrastination, like, “I mean to do it but tomorrow I’ll get around to do it,” and then tomorrow never becomes today.

So, I think the goal of the book is that the reader will be able to see themselves as they see the classes of challenges and see what the solutions are. And there really are some experimentation individuals have to do, like, “Oh, I thought this was right solution for me. I tried it. Oops, I had diagnosed my barrier wrong. Really, that wasn’t what was holding me back. It wasn’t that I wasn’t going to the gym because I thought it was incredibly unpleasant. It was that I just hadn’t made the time to do it with the right people and I didn’t have the right social network and the right structures.”

So, there’s different problems for different people even for the same outcome, there are some commonalities.

Pete Mockaitis
Well, so then it sounds like one way that you diagnose kind of like the core obstacle is you try something and you realize, “Hey, it turns out that wasn’t it at all. Okay.”

Katy Milkman
That’s one way. Hopefully, I think that will be one way. I also think another way will be looking, for the book and even for this conversation, and seeing yourself in the challenge. So, I do think people will be able to self-diagnose if they just give a little thought. I think normally that’s not the prompt we get. Instead, we get a solution, like, “Here’s your solution. This is going to work for you because it works for lots of other people,” instead of some thought about, “Why is it that I can’t motivate myself to do X.” And often, introspection is going to be enough. We’re not that hard to understand when we look internally in a lot of cases.

Pete Mockaitis
Well, so let’s say that if I am thinking about, “Hey, what’s my obstacle?” and then what I come up with is something lame, like, “No, I just don’t have enough time”? Like, what does that really mean and how do we get deeper?

Katy Milkman
Yeah. Well, “I don’t have enough time” isn’t the kind of obstacle that the book is about because that’s not an internal obstacle. So, the book is really about how are you holding yourself back. “I don’t have enough time” is an external obstacle, like the way you structure your life needs to change. And I think you’d get some ideas about that once you’ve read the book about, “Oh, okay, does that mean you really don’t have enough time or do you just need to restructure yourself and your life differently?”

But the book is more about, so, if you’re like, “I don’t have the resources,” that’s a different kind of challenge than, “I can’t get myself to and I need to find a way to get myself to do something differently.” Does that make sense?

Pete Mockaitis
Oh, I hear you. And I guess maybe you’re kinder than I am to our imaginary interlocutor here. I guess when I hear “I don’t have enough time” I guess I just don’t buy it as my default.

Katy Milkman
Oh, yeah. And it can also be like, “I don’t have a priority to do this.” So, the book is not to convince you that you need to change. The book is for someone who has a goal, they want to achieve it, they haven’t been able to get there, or maybe they haven’t tried yet, they’re ready to try, and it’s going to offer the best science has for them about how they can set themselves up for success.

It doesn’t guarantee success by any stretch changes really, really hard but, hopefully, I think my career has been devoted to understanding what is the best knowledge out there, what’s the best science out there on how we can change, and I’ve tried to put it all in one place so that, for someone who’s motivated and ready to give it a shot, it’ll give them the best chance available.

Pete Mockaitis
I hear you. And I think that precondition right there says it all in terms of, like, if you’re really motivated, “I don’t have enough time” is probably not going to be what you say is your obstacle because, by definition, you think it’s important enough to make some time, and it might just be tricky to actually figure that out in a calendar, like, “No, for real, where do these 30 minutes actually emerge from?”

Katy Milkman
Right.

Pete Mockaitis
So, maybe can you lay it on us, perhaps like the top three obstacles and some of your favorite solutions to those obstacles?

Katy Milkman
Sure. Okay, I can give you one that I love because I’ll probably pick on ones where I have done the most research personally which doesn’t necessarily mean they’re the most important ones but they’re the ones I find most interesting.

Pete Mockaitis
Okay.

Katy Milkman
So, one of them is impulsivity, and I’ve touched on this a little bit already and things I’ve said, which is like people are wired to look for instant gratification and to dramatically discount things that are good for us in the long run, which is why it’s so hard to drag yourself to the gym and eat that healthy food when there’s a pizza right next to it or a brownie calling your name, stay off social media, study for a test when there’s more exciting options that, even though you know clearly what’s good for you in the long run, is just not fun to do in the moment.

And I think one of the really interesting things research has shown is that people, generally, when they face a challenge like this to motivate themselves to do something that’s not that enjoyable in the moment but that’s good for them in the long run, our inclination is to just try to push through and look for the most effective way to achieve our goal.

So, if we’re, I’m going to go back to the gym, but there’s lots of places you can think about this, if you’re choosing to work out at the gym, most people are like, “I’m going to do the most effective workout on this first trip to the gym,” as opposed to an alternative, which would be, “I’m going to do the most fun thing I can do. I’m going to do the Zumba class. It’s not going to burn as many calories per minute maybe but I’m going to enjoy it.”

Same thing with healthy foods. We look for the basket of foods that’s most sinless as opposed to a healthy food that we actually enjoy eating. Or, you need to study and do work, like do you try to set up an environment where you’re really going to actually enjoy it? Maybe there are some people around that you’re studying with, or you’re in a coffee shop that you like, and you get yourself your favorite drink and you feel great. Or, are you just going to try to do it in distraction-free environment because that’s the most effective?

So, most of us think effective, and what research shows is we’re actually better off trying to do the fun workout, eat the tastier, healthy food even if it’s a little worse for us, and study in a way that’s a little less effective but more fun if we want to persist because we’re so wired for that instant gratification. We won’t push through, we think we will, but we won’t, if it’s not fun.

So, I think that’s a really important insight and it actually is really related to some work I did early on in my faculty career on something that’s a very specific solution to this. I call it temptation bundling. And the idea is only allowing yourself to enjoy some indulgence that you look forward to but maybe you shouldn’t indulge in too much, some guilty pleasure, while simultaneously doing something that’s good for you and productive so that now you start to crave.

Maybe it’s trips to the gym to binge-watch your favorite TV show, or trips to the library because you’re always going to pick up your favorite Starbucks Frappuccino en route, or folding the laundry or home-cooked meals because you’re listening to your favorite podcast at the same time. So, if you can temptation bundle, suddenly, this thing that was a chore, actually becomes something you look forward to.

And I’ve studied this and show that it can help people exercise more, and found in my own life, of course, that it also is very effective for solving all sorts of dual self-control challenges. So, in general, a principle is, make it fun, and then temptation bundling is one tool to do that, and the obstacle is when something isn’t instantly gratifying, and because of impulsivity, therefore, you aren’t making progress on it.

Pete Mockaitis
Well, I love it. And that just seems like a game-changing insight distinction right there. Because of our impulsivity, don’t go guns blazing for the most effective path, but rather the most enjoyable path if what you want is consistency and persistence, like, that’s huge. Thank you.

Katy Milkman
That’s beautiful, yeah. And I only gave you one, you asked for three. I was like, “I have to breathe in here.”

Pete Mockaitis
You’re allowed to breathe. Your temptation for breathing can be bundled to more insight, Katy.

Katy Milkman
I will breathe while giving insight, okay. A second one that I like, is actually, I’ll call it the getting-started problem. And that is even though we want to do something, or motivated to do it, like finding the moment where you’re like, “Okay, and now I’m going to take action. I’m going to do something. I’m going to do something about it. This is the moment action is beginning.” It’s hard to get over that hump from visualizing it to doing it.

And I had this really interesting conversation with one of the HR leaders at Google about a decade ago when I was visiting and presenting. It’s actually as a precursor to doing the gym study I mentioned earlier on habits, I was telling them about some of my other work on nudging better decisions, helping people through use of behavioral science, make better choices at work about everything from enrolment in 401(k) plans to getting flu shots, you name it.

And this question was, “Okay, Katy, totally sold. We should be using behavioral science to encourage more productivity at work, more use of health and wellness programs, more retirement savings. But is there some optimal time to encourage that change? Is there some moment when people are particularly likely to hop on the bandwagon if we offer up tools that will help?” And I thought that was such a fascinating question and I didn’t know of any research that really addressed it so it ended up guiding my work for the next several years.

And what I immediately thought of, which came to mind, for you, too, when I posed that question was New Year’s. We all know that at the beginning of a new year there’s like this huge boost in people’s enthusiasm for starting resolutions. Forty percent of Americans set some sort of resolution. Many of them fail but they at least give it a shot which is more than we can say for many other times of the year. And I wondered, and my collaborators and I wondered, too, like, “Is there something bigger going on there? Is it just New Year’s or are there moments like that? And why New Year’s?”

And what we realized is, of course, there’s this like, it’s a social construct now, there’s norms around it, but part of it, what’s going on, is that at these moments, like New Year’s, that feel like a breaking point in life, we step back and think bigger picture, and we also feel some sort of dissociation from our past failures, because, “Oh, like, that was the old me last year, and the new me has a clean slate and I’m going to be able to do the things that were tough before and that seemed insurmountable.”

So, that sense of a clean slate and identity shift, boosted optimism, the tendency to step back, actually arises at a lot of moments in our lives that basically serve as chapter breaks in the way we structure our narrative. So, there are small ones like the start of a new week. There are big ones, celebrating a birthday, moving to a new job or a new city, becoming a parent. All of these moments turn out to make us feel like we have a clean slate and a new beginning, and people are more likely to do things like create goals on goal-setting websites, search for the term “diet” on Google, go to the gym, at these moments, and so I think that’s really interesting.

So, my team has studied specifically temporal landmarks, so moments that actually don’t involve a change in our lives but there’s also research that’s shown when you move to a new place, you move to a new job, those moments are productive times for change because, literally, you have a clean slate. You don’t have old bad habits to fall back on and you have an opportunity to build and structure new routines and not walk by the Dunkin Donuts on the way to work on this new commute.

And so, whatever it is that has been tripping you up, you have that clean slate in addition to the psychological clean slate. So, in that sense, I think the obstacle there is, “How do you find the motivation to get started?” And our research points to looking for these moments that have fresh-start resonance as jumping off points, and also nudging other people to notice them.

So, we found, for instance, if you just mark your calendar with the first day of spring on it and give you an option, like, “When might you want to start getting reminders from us to pursue a goal you’ve been meaning to get around to?” and March 20th is labeled first day of spring. Now, it triples your excitement about getting reminders to start your new goal in that day than if we gave you a calendar without labeling March 20th the first day of spring.

So, we can do, and we ran a study where we invited people, thousands of people who weren’t saving adequately for retirement, to sign up for our retirement program at their employer to start setting aside a portion of their paychecks in retirement savings. And everybody got an identical offering, you could start saving right away or you could delay a few months. But some people that delay, we labeled, and it corresponded either to a birthday or to the start of spring, and we said, “Do you want to start saving after your next birthday? Do you want to start saving at the start of spring?”

So, we’re literally making an apples-to-apples comparison because everybody is getting that same offering but some people don’t have it labeled for them as their birthday. It just says in three months. And we see a 30% increase in savings over the next eight months when we’ve invited people to start saving after those fresh start dates.

Pete Mockaitis
I was just going to ask, Katy, so not only do we have more enthusiasm to start but the proof is in the pudding. They actually do it afterwards.

Katy Milkman
Well, I do think a really important note is that, in that case, we set ourselves up for success because it’s an auto…it’s like a self-fulfilling thing.

Pete Mockaitis
You flip the switch once to do it, yeah.

Katy Milkman
Yes, and those are the best things to do at fresh-start moments because the motivation wanes and that’s why so many New Year’s resolutions fail. So, it only solves one problem, which is getting started, and the rest of my book talks about how you solve all the other problems so you stick to it and actually get somewhere with your goals. But if you can put it on autopilot, how about if that’s my third answer, but it’s not a super original and it is a super powerful one.

Anything we can put as a default so that it is just self-perpetuating, that’s a huge win because an obstacle to change is laziness, but you can turn it on its head and make it into a solution if you set defaults, like in that moment of motivation, you sign up for the retirement savings plan on January 1st, and now it’s going to just kick in. You’d have to actually lift a finger to change it and, goodness knows, you’re never going to. Or, cancel all of your subscriptions that you don’t really need, one day a year, when you’re feeling motivated after your birthday. Those are the kinds of things that can sort of be gifts that keep on giving. Or, signing up for an educational program or subscription of some sort that’s really valuable. Those also can carry you forward and sort of have like riptide-like effects.

So, if you can use that moment, when you’re feeling motivated to do something and lock in a change that will continue, that’s really valuable.

Pete Mockaitis
Well, that is cool. So, let laziness work for us if you can somehow shift it such that the default of doing nothing benefits you, then that’s awesome.

Katy Milkman
Exactly, which is what happens when you sign up for a savings program once, that just keeps going. Or, when you enroll in school, I mean, you still have to show up, but you’re going. It’s hard to get out. Like, the path of least resistance is to go for the thing that you’ve put a down payment on.

Pete Mockaitis
Yeah, that’s great. Well, Katy, tell me, anything else you want to make sure to mention before we shift gears and hear about a couple of your favorite things?

Katy Milkman
No, this has been so…you’ve asked such good questions. I feel like I’ve been giving you really long and detailed answers, like highlights of the book.

Pete Mockaitis
Oh, I love them.

Katy Milkman
So, I’m excited. Thank you for the great questions.

Pete Mockaitis
Okay, maybe I’ll give one more. What should we not do? And maybe something counterintuitive, like, “Hey, I’ve heard I should do this, but maybe I shouldn’t.”

Katy Milkman
I’m not a big fan of setting like really big audacious goals, like that model, and just assuming that will carry you forward, because without actually getting into the nitty-gritty structures, like I do think people try to think about a north star huge objective and that having that could be really valuable, and I think it can be distracting, it could be overwhelming. There’s also research showing that if you make too many, set too many goals, and then plan for each of them, that’s really demotivating because you can’t do it all and you sort of throw up your hands and give up.

So, I think sort of too big and distant and dreamy and not broken down is bad, and too many objectives that you do break down and plan for is bad. Like, focusing on one thing at a time, that’s a little bit of a stretch but it’s doable and you can plan for it, and then you can use these tactics to help you is the right way forward.

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

Katy Milkman
Is it “Well done is better than well said”? Is that Ben Franklin, I believe? I like that one.

Pete Mockaitis
Sure thing. And how about a favorite book?

Katy Milkman
My favorite book is Nudge by Thaler and Sunstein, and that actually has a new edition coming out later this year which I’m really excited for. Though, I’ll also say, my second favorite book, and it’s really close, is Influence by Bob Cialdini. I know you’re a big fan too.

Pete Mockaitis
Oh, yeah.

Katy Milkman
I assign both of those books, by the way, to all of my MBA students at Wharton. I love them and read them every year, and they’re just classics and truly wonderful and have changed the way I think about the world.

Pete Mockaitis
And how about a favorite habit for you?

Katy Milkman
That’s interesting. I wouldn’t call it a habit. Can I say a favorite behavior?

Pete Mockaitis
Oh, sure.

Katy Milkman
Because habits have this very narrow definition in academia where we’re like it’s on autopilot. Okay, so like a favorite behavior or this thing I do, which is I choose to work with people I really, really admire and enjoy spending time with so that work for me is a treat intellectually but also socially. And I feel really lucky to have the privilege of being able to choose who I collaborate with. And so, that has made my career tremendously fun, and I think it’s part of what’s helped me be productive and successful in my career as well.

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

Katy Milkman
My website which is KatyMilkman.com. It has all sorts of information about my book How to Change, about my podcast Choiceology, I have a newsletter called Milkman Delivers, which is a name that I was shying away from but my MBA insisted I had to go with, and about my research.

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

Katy Milkman
I would say one of the biggest takeaways from all of my research on behavior changes that, and we sort of started here, it’s super important to expect that there will be things that don’t work out, that if you are too rigid in your expectations of yourself, if you set up habits that are too rigid, if you set up goals that are too rigid, and let yourself be discouraged when things don’t work out according to plan, and don’t push through, you just won’t get very far.

And in change, anticipating setbacks and being prepared for them, having a backup plan, is just absolutely critical. Even in habits, we found that it was critical to be flexible and build flexible habits. So, it’s “I’ll always…” not “If only…” kind of habit. And I think that’s critical to everything. It comes up again and again in my research, how important it is to find ways to get back up after you’ve fallen down, and to be expecting that that could happen and planning for it.

So, my words of wisdom would be don’t let yourself be discouraged too easily, expect that there’s always setbacks. But on the path forward, it’s, hopefully, two steps forward and one step back, and just be prepared for that and set yourself up for success when you hit those roadblocks.

Pete Mockaitis
Well, Katy, this has been a pleasure. Thank you. I wish you lots of luck with the book and all the ways you’re changing.

Katy Milkman
Thank you. So lovely to chat. Thanks for having me on the show.

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

Michelle Weise
Great to be with you, Pete.

Pete Mockaitis
Well, as I was reading all about you, one thing that I found, I guess, touching or moving or wanting to touch up on for a moment was we’ve spoken with some people who have worked and written books with Stephen R. Covey, and it was just sort of beautiful to hear some memories of that great man and teacher who’ve lived on, and, likewise, I wanted to hear a bit from you, to start us off, about working with Clayton Christensen. What’s something folks should know about him and who he was when you were collaborating with him?

Michelle Weise
He was one of the most generous people. He would always kind of make you feel like you were the most important person talking to him at that moment. And, it’s funny, I had a lot of folks who would see him speak at large events and they could sense his sort of folksy tone from him and his kindness, and he would say these beautiful things, and people would turn to me and say, “Is he really that nice? Is this for show?” and it really wasn’t.

He was sort of rooted in that way. He was driven by a really intense faith. He was a Mormon. At his funeral, it was kind of amazing to hear the incredible amount of service he did on the sidelines. And that just sort of…that feeling of just kindness and generosity that was emanating from him, I think it just showed through every action.

And, for me, it was life-changing to work with him directly and to write with him and to learn from him, and to go very deep into the theories of disruptive innovation and sort of see where he would get frustrated with kind of the misuse of his theories. And everything I learned about storytelling, I learned from him.

Pete Mockaitis
Well, that’s beautiful. Thank you for sharing. And so, oh, yeah, we’re going to be doing a little bit of storytelling, I suppose, here about your insights associated with long life learning. I keep almost saying life-long learning every time, it probably happens to you a lot with your collaborators here. So, well, hey, let’s go meta for a second. Michelle, tell me, how can we tell this story most effectively?

Michelle Weise
Yes, so the reason why we’re getting tripped up on long life learning is we’re so much more familiar with this concept of life-long learning that we should be constantly learning how to learn throughout our lives. What I tried to do in this book was to move us into action. I was just noticing a lot of inertia around this concept because we know we need to reskill throughout our longer more turbulent work lives. But where is the actual infrastructure to sort of take these on and off ramps, in and out of learning and work, or do both at the same time and not have it feel so painful?

And so, for me, this mental shift comes through this concept of a longer life. If we extend our life spans, which we know since 1840, we’ve tacking on three months of life to every single year since 1840, so our life spans are just definitely extending but so are our work lives. When you look at early Baby Boomers and how long they’re staying in the workforce and how many job changes they go through by the time they retire, it just helps us kind of snap us into attention, and to say, “We have to start building a better functioning ecosystem in which we can access the education and training we need in order to thrive in the labor market.”

Pete Mockaitis
Okay. And that thesis seems to just make sense as a natural implication of living longer and such. So, could you maybe share with us something that’s surprising or counterintuitive as a discovery that you’ve made along the way as you’re putting this together?

Michelle Weise
Yes. So, I have been doing a lot of research on the future or work, and what I noticed in a lot of the literature and the analyses out there by chief economists as they’re trying to sort of forecast all the different kinds of ways in which jobs are going to become obsolete or this industry will become decimated by these technologies, what I realized was this kind of intense focus on the “it”, or the things or the jobs, or the tasks and numbers.

And so, what I realized is if we actually kind of move away from thinking about the future of work to the future of workers, and all of us having to somehow kind of move through this learn-earn, learn-earn cycle, to me it kind of helped surface some of the most intractable issues and barriers that we need to solve for today.

So, what my book does is it really actually elevates the voices of people who only have a high school degree, who are constantly being overlooked for work they could actually perform, and noticing where the barriers kind of coalesce. So, these concepts that I come up with around better career navigation, or better wrap-around support services, or more targeted educational pathways, or more integrated learning and earning, and more fair and transparent skills-based hiring practices, those aren’t just coming from me thinking what we need to do. It’s really kind of trying to gather all this qualitative data.

We did over a hundred hour-long in-depth interviews with folks to sort of sass out, “Where do people keep kind of bumping up against pain points?” And if we designed this future system better, then all of us are going to actually end up benefiting. It’s the same idea of the curve cuts that we did when we kind of created the Americans With Disabilities Act.

When you’re cutting into the curve and you’re making a sloping curve, you’re not only helping folks who are disabled who need to use a wheelchair, but you’re helping mothers pushing strollers, or FedEx delivery folks with their dolleys, you’re helping runners, cyclists, skateboarders. It’s this idea of universal design. But when we want to target our focus, because it just seems like this huge, expansive challenge, we focus on the people, the future of workers.

Pete Mockaitis
Lovely. Okay. Well, so then, as we got a lot of workers listening right now, can you sort of frame things up for us a little bit in terms of…? So, you make a point that the old model of, hey, there’s education, then there’s work, then there’s retirement isn’t what we should be relying upon going forward. Can you expand upon that?

Michelle Weise
Yes. So, just the notion that we could have one or a handful of jobs and retire in comfort, that’s already become sort of a quaint notion. And when you look at the amount of job changes that people are experiencing by the time they retire, folks are already going through, on average, 12 job changes by the time they retire.

And so, as we think about that longer more turbulent work life that is shaped by rapid advancements in technology, we can only extrapolate from there, “Wow, we may have to somehow entertain 20 or 30 job changes by the time we retire. And so, how in the world are we going to navigate that when one is just so difficult to navigate?”

Pete Mockaitis
Yeah. Well, lay it on us, how should we navigate these optimally?

Michelle Weise
Yes. So, I think the perfect illustration of what’s not working today is when we look at what the pandemic has shown us, which is when retail and hospitality were just completely decimated as industries, we had no way for people who were in those customer service roles or those frontline worker roles to actually transfer their skills from retail or from hospitality into something totally different but to identify their kind of transferable skills.

And I think, all of us, we believe that we have really important kinds of skills. Those transferable skills that can help us port our assets from one specific area to another. But, in general, when you think about the job market, we think about it in such a linear format. We kind of, if we start off in retail, or if we start off in office admin, when we think about advancement, we think within that line of work. It’s harder for us to sort of think about moving beyond that industry that we started in.

And the reason why we feel that way is because that’s what employers tell us, right? The employers want to see exact work experience in hospitality to move you up to a manager role. We don’t have ways of validating other kinds of experiences. So, one of the key solutions for us that are exciting for us to anticipate, and we already see these different kinds of AI-powered platforms.

What they’re doing is they’re helping us surface maybe some of our hidden skills. The skills that aren’t necessarily recognized by a formal credential, like a degree or a certificate or a certification. And what they’re doing is, as we’re typing in, I used to be a barista, that signal of the barista helps the platform actually surface, “Oh, did you know that folks who were baristas they have these specific competencies and skills.”

So, there are ways in which these platforms can not only help us surface our own skills but then help us envision pathways where we might actually be 75% of the way there towards something in human resources, or 85% of the way there towards something in advertising and marketing. We just didn’t know it; we couldn’t envision it for ourselves.

So, these kinds of tech-enabled platforms are interesting kinds of seeds of innovation to look at that might help us not only kind of validate our own skills whether we’ve acquired them through taking care of our own families or through work experience, and also understand the kinds of gaps we might have to fill in order to move into these other opportunities.

Pete Mockaitis
Well, that’s really interesting when you mentioned that if you’re a barista, you can very well have under the surface like all of these skills that you’re applying there. And that reminds me of a previous guest we had, Todd Rose, talking about dark horses and how what might seem like completely different skills are actually, if you zoom way in, super similar in terms of, “Oh, actually, well, you’re using your hands to shape these things into other things so that they fit. Those are similar.” Much like, “Oh, you are optimizing a manufacturing production schedule is sort of like solving a puzzle over in the realm of math or physics or something that, who would’ve known, those are quite common or quite complementary.”

Michelle Weise
Yeah.

Pete Mockaitis
Well, these platforms you speak of, how do we get our hands on one? So, can I go to some website right now and it’s going to tell me all my hidden skills?

Michelle Weise
So, that’s one of the challenges. There is like a free one off of Emsi called Skills Match where you can start to surface and kind of build a resume using these technologies. But this is one of the challenges and this is what I’m trying to point out in my book is that there are hundreds of thousands of innovations and solutions out there. The problem is for any normal person to understand where to go, like if we’re suddenly laid off, we don’t know who to call, where to go, who to talk to.

There are so many of these solutions out there but they’re not knit together in a way that’s easily understandable and navigable for any person. It’s not that we need a whole slew of new innovations. We need these things to become just more accessible so we can understand and comprehend how to navigate this who to go to for, “How do I know that when I pick this learning experience, a future employer is going to validate it and understand what it means? And how do I know precisely which skills I need to acquire? And which school actually offers those three competencies? I don’t need a degree, maybe. Maybe I already have a degree. I don’t want to go back to school full time. How do I get just what I need in order to move on?” And that’s one of the challenges.

But there’s a bunch of these groups, like Skyhigh, FutureFit. And what they’re doing right now is they’re more B2B, they’re more working with enterprises and trying to help them get a better understanding of who’s in their workforce. Because a lot of companies, and it’s very odd to think about it this way, but most companies don’t actually know what their people can do.

They know job titles, they know names. They don’t have a real granular sense of the skillsets, the competencies, all those hidden talents that folks have. So, that’s where these innovations are starting is trying to help employers be less wasteful, not always recruit externally, but look at the talent that they have right in front of them, and think, “Maybe I could actually take 30% of these folks and build their skills in X, Y, or Z technique or strategic goals for the future.”

Pete Mockaitis
Yeah, that’s exciting, and, indeed, it just seems like a huge opportunity that’s just waiting to be plucked. A great manager would know a lot of what their team is capable of. Yet, how is that information captured, collected, and transmitted elsewhere? And one of the incentives for doing so, you’re like, “No, Michelle is a rock star. She’s working for me. Get your hands off. I don’t want you to snag and do a completely different function.”

Michelle Weise
That is a real challenge within the companies. Yeah, this kind of like zero-sum game of, “Oh, if you take my person, you’re hurting me versus helping the company.” It’s hard to get out of that mindset.

Pete Mockaitis
Totally, unless you have sort of a widespread culture and reciprocity and such so that you say, “Hey, you know what, there’s give and take, I might lose Michelle for a couple months, but I’m going to get Phil who’s amazing and fills another role that we really need,” so there’s that trust there that can be handy.

Well, now, you just got me dreaming big, Michelle. I remember I once, I don’t know if I’m going to do this or not, but I hope someone is doing this. But when you talked about the high school folks who did not have diplomas and yet are capable of doing so much but it’s hard for them to sort of prove that. I kind of imagine just like forming this whole business where we just sort of like assess the crap out of people in terms of like all of these batteries of things because I come from strategy consulting and we did case interviews, and I found that that was a pretty excellent means of identifying if some folks have a particular set of skills. And so, that’s one kind of a test for one set of skills.

Likewise, there’s many tests for many other skills. Wouldn’t it be cool if folks could go to some sort of facility for a week or something and get a rundown on all their skills in a language that firms could read and understand, and then open up opportunity for people as well as savings for the companies? It seems like someone should have invented that. Maybe it needs to be me or maybe that’s in the works. But, Michelle, give us your take on to what extent does that exists, a means of identifying and appreciating hidden skills so that companies can save money and not have to hire the Harvard grad, and professionals who don’t have the degree can see some cool opportunities?

Michelle Weise
Yeah. So, what you’re identifying when you’re talking about seeing how someone responds to a case study is you’re testing their problem-solving capabilities, you’re trying to see, “What kind of systems-thinking, critical-thinking capabilities do they have?” I was just talking to a colleague who used to work at Arthur Andersen and they had this very open-question format where they would do the same things where they’d be trying to assess out someone’s sense of initiative and collaboration and these more fuzzy things, but trying to see how they talk about this in the context of solving a problem.

The good news is that there are these innovators who are working on new kinds of ways of assessing curiosity, problem-solving, all these really important kinds of skills that we know are going to be deeply valuable in the future of work. Because as we think about the rapid advancements of AI and how intelligent these AI are, where it’s not only able to read, drive, see, but it’s also able to write poetry, it can paint Picassos. It’s getting scary how far these technologies are sort of infiltrating our lives. What is our human advantage? What is our competitive advantage when we compare ourselves to these machines who can usually do some of this work far more flawlessly than we can? And it comes in these human skills.

So, places Imbellis and Mursion and all these different groups are trying to figure out ways to test out someone’s problem-solving capabilities where you’re on a computer and you’re thrust into this setting where you’re in this natural environment in the mountains and something is dead in front of you, and you need to kind of poke it and look at it, sort of see what is going on, and you’re trying to figure out what happened.

And so, on the backend you have psychometricians kind of figuring out what all those clicks mean, what are you doing when you’re putting these two datasets together. So, there’s really interesting ways in which groups are trying to democratize the process, and say, “We’re looking for the best problem-solvers in the world. If you can kind of solve this problem, this is really exciting.” And it makes me think of what you’re talking about with Todd Rose’s concept of the dark horse.

One of the most valuable assets that we will bring to the table is our ability to take concepts from seemingly unrelated domains and make them make sense in the context of the problem we’re trying to solve. So, InnoCentive, as an example, this was a platform that was created partly because at Eli Lilly, these chemists and scientists couldn’t figure out a problem so they posted it online and they found out that a lawyer could actually solve the problem using his sort of different kinds of contextualized expertise to help them figure out a way forward. Or, when they tried to figure out how to create more efficient ways of solving for oil spills in oceans, it was actually a pastry chef who talked about the process of making chocolate mousse and how that might actually help us think through how you remove oil from water.

And this is all, I’m totally stealing this from David Epstein’s book Range, but it’s this idea of, “How are we going to cultivate not only problem-solvers but people who can display that sense of range?” And it doesn’t always come from a four-year college degree. We don’t always get that real intensive interdisciplinary learning that we probably should. And, for me, for the next steps for higher education, that is a real opportunity for them to kind of break down silos across disciplines and departments. But, as we think about those skills that are going to make us most valuable, it’s going to be those kinds of hidden ways of thinking about problems.

Pete Mockaitis
So, let’s hit that for a minute there. So, AI can do a lot, and right now we’re very much evaluating humans being able to draw from different disciplines and putting them together. So, What are the fundamental kinds of principles or distinctions that…? Like, we think human brains are going to be able to do this better than machines even 20 years from now. What are those things? It’s not playing chess or Jeopardy, but what is it?

Michelle Weise
I think probably the most helpful way of thinking about it is when I talked to an executive from Apple who, he actually went to Stanford for a mechanical engineering degree, but as part of his general curriculum he took a class on ethics. And he mentioned that that class is probably one of the most valuable classes he had while he was an undergraduate, because when they’re producing technology, new technologies, new products, the thing they have to think about is, he called it sort of volume impact repercussions, where they have to think of second-, third-order effects of what they’re building, because, in an instant, millions of people are going to be leveraging whatever it is they are producing. And so, they really have to kind of anticipate forward and think, “What are all the ways in which this can go wrong?”

And if we think about where we are today with social media, we didn’t do enough of that. We didn’t extrapolate enough far forward. And when you hear the co-founders of a bunch of these different social media companies, you hear them say, “I didn’t think that this is the way that it was going to be used.” But this is what humans do bring to the table when we sort of bring ethics and judgment and values, and try to think forward.

And this also has implications on the kinds of people you bring around the table to do that sort of analyses. It has to be a diverse group. It cannot just be young white male undergrads kind of thinking about this problem. It has to be a diverse group of folks kind of thinking about those volume impact repercussions. So, I think those real skills in exercising judgment are going to be critical, that we can’t rely on the AI to do.

Pete Mockaitis
Okay. So, second-, third-order things. And I guess that makes sense to me in terms of like as I think about things that are like playing chess or Jeopardy or even like composing or painting, it’s sort of like they’re all kind of bounded in a way in terms of find the right answer, or the right move, or apply a principle of color or sound.

Michelle Weise
Right, they’re finite. Yeah.

Pete Mockaitis
Versus saying, speculating as to what social media and how it will impact us with widespread adoption. That does seem harder to stick inside code. Anything else that we humans do great?

Michelle Weise
So, a couple of years ago, Amazon had tried to leverage AI to diversity their hiring processes, and they thought maybe AI could do a better job than humans. And so, they kind of built out this new system, the AI started kind of going through the diverse set of applications. And then it was the humans kind of watching and seeing the output to sort of identify, “Huh, kind of strange that so many of these folks are named Jarod. Or, a lot of them played lacrosse.”

And they started to realize, “Oh, my gosh, we’ve trained the AI on flawed data.” They kind of looked at their existing talent pool. They tried to sort of say, “These are the senior leaders at our company that do great work.” But what they did was they trained the AI to search for people that looked and sounded exactly like their existing leadership, and that is not a way that you diversify your talent pool.

And so, it took humans to kind of notice and sort of exercise some judgment to say, “Wait, something is wrong. Interrogate it. Look deeply, look into the data,” and sort of say, “Oh, okay. We’ve got a problem here.” Because the AI will only just kind of repeatedly get smarter and smarter with the data that it is trained on. And we see this also happening, unfortunately, in the legal system where we’re developing sentencing structures based on deeply inequitable past data of how we’ve punished people.

So, we need this kind of deep-thinking humans for the future who have enough domain expertise to be able to question the AI because we cannot just let it…the crazy thing is that most companies…

Pete Mockaitis
Right. Jarod is in here. Whatever you say, robot.

Michelle Weise
Yeah, most companies like don’t know if they can trust their AI right now. I have a statistic in the book where they are not comfortable auditing the sort of their existing AI.

Pete Mockaitis
Not comfortable auditing it?

Michelle Weise
Yes, so this is from an Accenture study that basically fewer than a third of companies surveyed have a high degree of confidence in the fairness and auditability of their AI systems, and less than half have similar confidence in the safety of those systems. So, we’re so reliant on these technologies and yet we don’t fully trust the algorithms that undergird them.

Pete Mockaitis
Well, I buy that even in a very easy example. I think about machine-generated transcription, which, I mean, that’s existed for 20, 30, 40 years and yet it’s still not great. I don’t know. If you have 98% accuracy, okay, that sounds really impressive, but that’s really still like three errors every minute. And so, in this conversation we’d have a hundred or two, and so I wouldn’t call that good.

And so, anyway, I just find that, I don’t know, not to be quite grouchy, but I’m a little skeptical myself in terms of maybe eventually it will be awesome but right now I’m not super impressed, and maybe I just haven’t been looking at the right places to blow me away.

Michelle Weise
No, what you are pointing out is what this MIT economist named Daron Acemoglu calls so-so automation. So, like when we think about just the rise of ATMs in the last few decades, what’s interesting about an ATM is that it is far better than a so-so technology because it actually completely made obsolete the role of a person counting money because it could do it really well.

And we don’t actually have a lot of technologies that we’re building today, the transcription one is a perfect example, or the robots that we use in warehouses where we have to depend on people as pick-and-packers to be able to sort of get the thing out of the robot’s sort of treasure trove and put it into a box.

So, we’re creating technologies that are just so-so. They’re not great enough to completely obviate a certain task. And, as a result, we’re not creating enough forms of truly creative labor. Because when ATMs kind of took over, what was fascinating to see is the sort of burgeoning of the services industry in banking. It wasn’t that people just became useless, it’s that they actually transferred their skills into different domains.

Here, what we’re having is a lot of kind of unfulfilling what researchers called ghost work. It’s this kind of interstitial stuff that we have to do on the backend even when we’re training AI. You have tons of people, these mechanical turkers who are working for cents on the dollar, who are identifying all the photos that are coming up from the AI to say, “That’s a face. That’s the same face as that one. That’s a body part. Ooh, that’s not a body part we want to show.”

Pete Mockaitis
“That’s a cat. That’s not a cat.” Right?

Michelle Weise
Exactly. And, “Not a hotdog. A hotdog.”

Pete Mockaitis
Silicon Valley.

Michelle Weise
But we have a lot of terrible work that’s emerging because of that not-great-enough technology. Right now, we’re in this awkward phase where we’re not creating enough forms of creative labor.

Pete Mockaitis
Well, Michelle, these are a lot of interesting ideas. I’d love it if we could sort of zoom in here now for the professional who are maybe in their 30s or 40s who got a lot of work left in their career before retirement, likely. So, what’s our game plan in terms of learning the right stuff effectively and well and keeping our careers moving in a great trajectory?

Michelle Weise
Yes. So, I think one way forward is, unfortunately, for us as job seekers, a lot of the burden rests on us, and a lot of the financial risks also rests on us to make these decisions on our own. But moving into the future, what we really need to see and what, I think, will signify the kind of company that we want to work for are the ones who stop this kind of dis-investment in training their existing workforce and start to realize, “I have all this talent within. How do I help them acquire the skills they need to be successful?”

And I think the most powerful indicator of a company that is truly invested in us as job seekers are the ones that tell us, “You don’t have to do this on your own. We’re not going to just dangle tuition assistance or tuition reimbursement dollars and say, ‘Hey, we’re glad that you would like to advance your education. Go do it on your own time on top of everything else you’ve got going on in your lives.’”

The most competitive forward-thinking companies are going to realize that the workplace is really the classroom of the future. And I’m not talking about on-the-job compliance training, risk mitigation work, like sexual harassment training. I am talking about real new skills-building activities. So, it’s critical that the company not only identifies really transparent internal mobility pathways for you and for us, but it also has to be very explicit about carving out time in the flow of the workday for you to acquire those skills because it’s not fair for us to have to somehow squeeze it in on top of stitching together multiple part-time jobs, or all our caregiving activities. It’s too hard to just kind of stack that on top of everything else.

So, I think the things that we need to look out for the future are the companies that are truly invested in our reskilling and upskilling who kind of figure out ways to make that learning bite-sized, or for an hour a day, or an hour a week where we can be doing this in the flow of work. And, also, for educational institutions and providers to be able to modularized their learning in ways that’s more accessible where we’re not always bending to the sort of linear structure, the college or the university, but that it’s much more flexible and easily consumable.

Pete Mockaitis
And that’s a beautiful world that I’d love for us to live in. And I guess part of why this podcast exists is that we’re not there, and it is a little bit of a do-it-yourself proposition for a lot of folks these days, and fair or not, pleasant or not, stressful. So, let’s talk to the professional who’s in an environment that’s not so enlightened with regard to offering some great learning opportunity, and let’s say even, hey, they’re a little mercenary, they’re just going to go take it, “At 11:00 a.m., when there’s no other meeting on the calendar, I’m just going to do me some learning.” What are some of the top resources you’d recommend to them? I’m a huge fan of LinkedIn Learning myself, but what else would you say in terms of, “All right, you got an hour. You’re going to do some learning,” what are some of your favorite places to go?

Michelle Weise
So, one that I talk about in the book is called GLEAC. And what they do is they make this kind of mobile-friendly learning apps where they just take minutes and they have folks, for instance, who are customer service or retail folks in Prada stores, as an example, where they’re building up their reflection and communication of this kind of human skills that they’re developing where they’re exercising their judgment. And they are these bite-sized learning applications that a worker can kind of leverage while they’re working.

Another one would be Mursion that I’m kind of really interested in.

So, we tend to think of executive coaching as reserved for people kind of mid-level managers and up. What Mursion enables us to do is practice those really important human skills in a low-stakes environment. So, giving feedback, receiving feedback, these really critical skills for success in the workforce but we generally only practice them in a high-stakes environment, when we actually have to give someone really tough feedback or when we’re receiving it from our bosses.

And, generally, I know whenever I do this, I leave the conversation sort of thinking about all the different ways in which I could’ve done it better. And this environment actually has avatars in front of you, and the quality of the imagery is good enough where you can notice different people’s nonverbal cues, and you hear their voices change, and so you have to be responsive in that moment.

And it’s actually this kind of interesting AI-powered platform that’s puppeteer-ed by one human also in the background, where the human can play the role of like six or seven different people with different voices and different characteristics. And so, it gives you that chance to practice negotiation, all these different kinds of skills that we need to get better at because the fascinating thing, just in general, with human skills is even though we’re human, we’re not very sophisticated at them. We actually have to practice these skills. And just because we take a LinkedIn Learning class on empathy, we’re not somehow going to become more emotionally intelligent just from taking that one class. We have to figure out ways to practice this. So, those are the kinds of innovations that I’m excited about.

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

Michelle Weise
One thing that might be important for job seekers to know about is the existence of different kinds of alternative learning providers kind of outside the traditional realm of colleges and universities. I think most people have heard of these things called coding bootcamps where you go and you get pretty savvy in web development or frontend development and you do this for 6 to 12 weeks, you pay $20,000 out of pocket, and maybe you get this great job.

Those have typically kind of been more geared to folks who already have a degree, sort of more affluent who can actually afford to pay out of pocket. But there are these interesting other set of providers that I call on-ramps where they do this kind of really important human skills-building work but they also help learners get skills in healthcare, advanced manufacturing, cybersecurity, data science, enough to get hired by.

There are amazing stories of a US Postal Service worker becoming a quality assurance engineer for Facebook through this data science immersive program. And what they’re doing is that they’re actually stitching together that kind of career navigation with a very precise educational pathway with a direct connection to an employer.

And so, there are these kinds of opportunities available. It’s a matter of trying to, again, it’s back to us as the individual job seekers, the burden is on us to kind of find some of these. But a really interesting example of another one is one called Climb Hire we know that Salesforce administrators, they are a job that are in demand, that are in high demand. And so, what they’re doing is they’re building these skills but they’re also embedding social capital building into the learning process where they’re helping folks, who may not have the best professional networks, learn how important it is to build relationships, build professional networks.

And when a person actually gets a job at a company, as a Salesforce administrator, the onus is on them to refer and bring someone else into the company from Climb Hire because the CEO realized from LinkedIn data, as an example, that people are nine times more likely to get a job through a referral so they’re helping job seekers and learners really build this skill because it is something that you kind of have to learn how to do unless you’re sort of born into an incredible network.

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

Michelle Weise
So, you heard me talk about David Epstein who wrote Range, and he talks about deep learning, but he says, “The most effective learning looks inefficient. It looks like falling behind.” And I love this quote just because I think when we think about all the ways in which we are kind of channeled and incentivized to achieve, we’re always measuring through this kind of testing that is actually not measuring what matters.

And if we were actually to sort of really understand what kind of learners and that kind of deep learning in folks, it would actually look like failing. And I think that’s, I don’t know, that’s important for us to know.

Pete Mockaitis
And how about a favorite book?

Michelle Weise
Probably Beloved by Toni Morrison.

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

Michelle Weise
I have one of those keyboards that are split into two and kind of at an angle.

Pete Mockaitis
Oh, me too.

Michelle Weise
I have some tendonitis, so.

Pete Mockaitis
That’s good. I’ve got the Freestyle2 from Kinesis.

Michelle Weise
That’s what I have.

Pete Mockaitis
But you got the tents going. I didn’t get the tents. I just got the split because I’ve got, I guess, some wider shoulders and so I always found that I was…Yeah, so I like being able to stretch out and be me without having to crunch them in.

Michelle Weise
Yeah. I have the same exact one, the Freestyle2. Underneath you can flip out the thingies.

Pete Mockaitis
Oh, that’s right.

Michelle Weise
You know what I realized, I think I pressed the delete button so much that I actually really kind of hurt my wrist and needed to re-shift my posture.

Pete Mockaitis
Well, I think that there’s something beautiful hiding in that. Perhaps it’s revision, commitment to excellence, iterating, learning, that meta stuff there.

Michelle Weise
Yeah, nothing you write is golden.

Pete Mockaitis
Not at first anyway. And how about a favorite habit?

Michelle Weise
Oh, walking.

Pete Mockaitis
And is there a particular nugget you share that you’re kind of known for, people quote back to you a lot?

Michelle Weise
Oh, I think maybe because I learned this from Clayton Christensen, one of the most powerful parts of the theories is when you see something that looks less than, our immediate kind of reflexes is to sort of scorn or disparage it or to dismiss it as, “Ah, it’s not an important innovation to pay attention to,” but Clay always said it could be just good enough. And that is something that I try to convey to folks. When we have that very human reflex, when we perceive newness as danger, that might be actually the precise time where we need to take a beat and look at the thing more carefully.

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

Michelle Weise
I’m always available through Twitter and LinkedIn @rwmichelle or I have a website called RiseAndDesign.io.

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

Michelle Weise
I think, in general, it’s still this concept of collaboration. I think we, generally, just because of the way we trained from K-12 on through college, it’s so often kind of this notion that things are a zero-sum game, where if you’re winning, I’m losing. But in this concept of kind of long life learning, there’s no winning list. And so, how do we actually change our behavior instead of always sort of trying to be the leader? How do we actually make sure we’re collaborating in truly distinctive ways? I think that’s something that I think about a lot. It’s a hard behavior to turn to given the way that we’re trained.

Pete Mockaitis
Well, Michelle, thank you. This has been a treat. I wish you lots of luck in your long life learning.

Michelle Weise
Thank you. You, too.