Barry O’Reilly shares his strategies on how to unlearn the mindsets and behaviors that hold us back.
- The key to breakthrough improvement
- How to identify what you need to unlearn
- How to overcome the fear of change
Barry O’Reilly is the founder and CEO of ExecCamp, an entrepreneurial experience for executives, and the management consultancy Antennae. A business advisor, entrepreneur, and sought-after speaker, O’Reilly has pioneered the intersection of business model innovation, product development, organizational design, and culture transformation. He works with the world’s leading innovators, from disruptive startups to Fortune 500 companies.
He is a frequent writer and contributor to The Economist, Strategy+Business, and MIT Sloan Management Review, as well as a coauthor of the international bestseller Lean Enterprise: How High Performance Organizations Innovate at Scale―included in the Eric Ries Lean series and a Harvard Business Review “must-read” for would-be CEOs and business leaders. He is also an executive advisor and faculty member at Singularity University.
- Book: Lean Enterprise: How High Performance Organizations Innovate at Scale
- Book: Unlearn: Let Go of Past Success to Achieve Extraordinary Results
- Studio: NobodyStudios.com
- Website: BarryOReilly.com
Book: Maverick: The Success Story Behind the World’s Most Unusual Workplace by Ricardo Semier
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Barry O'Reilly Interview Transcript
Barry, welcome to How to be Awesome at Your Job.
Yeah, no, it’s a pleasure to be here, Pete. Thanks for having me.
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?
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.
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.
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?
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.
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?
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.
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?
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.
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”?
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.
Well, that’s juicy. And so then, if I was working on that, how might you help coach me through that emotional stuff?
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.
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?
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.
All right. Thank you. Well, now could you share a favorite quote, something you find inspiring?
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.
Well, thank you. And how about a favorite study or experiment or bit of research?
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.
And a favorite book?
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.
And a favorite tool, something you use to be awesome at your job?
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.
Agreed. And a favorite habit?
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.
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?
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.
Alrighty. And is there a key nugget you share that really seems to connect and resonate; folks quote back to you often?
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.
Okay. And if folks want to learn more or get in touch, where would you point them?
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.
All right. And do you have a final challenge or call to action for folks looking to be awesome at their jobs?
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.
All right. Barry, thank you. This has been a treat. I wish you much luck with Unlearn and all your adventures.
Thanks very much. Thanks for having me, Pete.