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A Powerful 3-Step System for Breakthroughs with Barry O’Reilly

Leading Innovation · 2023-11-20 · 43 min

0:00--:--

Key moments - from our scoring

Substance score

40 / 100

Five dimensions, 20 points each

Insight Density8 / 20
Originality7 / 20
Guest Caliber11 / 20
Specificity & Evidence9 / 20
Conversational Craft5 / 20

Barry O'Reilly, serial entrepreneur and author of *Unlearn: Let Go of Past Success to Achieve Extraordinary Results*, explains why unlearning is the critical skill missing from organizational innovation conversations. Drawing on 20 years coaching Fortune 500 executives at companies like Capital One, American Airlines, Spotify, and Slack, O'Reilly argues that learning new skills isn't the bottleneck - leaders struggle because they cling to the behaviors and mindsets that drove their past success, even when circumstances have changed. His three-step framework begins with diagnosis: identifying specific obstacles (stress, perfectionism, risk aversion) preventing desired outcomes. Next, leaders reframe those obstacles as positive behaviors to build - for instance, "I will unlearn stress" becomes "I will spend 25% of my time on personal development." Finally, they run small behavioral experiments to test new approaches, creating breakthroughs through iteration rather than willpower. O'Reilly illustrates this with vivid examples: how he wrote his books by talking rather than typing (adapting to dyslexia), and how Serena Williams hired coach Patrick Mouratoglou at age 30, abandoning her father's longtime methodology to win more Grand Slams in the next five years than the previous ten combined.

Key takeaways

  • →Unlearning is not about forgetting past knowledge - it's consciously letting go of once-useful mindsets and behaviors that now limit results in changed circumstances.
  • →The diagnosis phase should identify specific obstacles (stress, perfectionism, risk aversion) and reframe them as positive outcomes you want to achieve, not problems to escape.
  • →Breakthroughs require experimenting with uncomfortable, unfamiliar behaviors you're initially bad at - comfort and repetition in old methods won't work when the game has changed.
  • →Writing vision-based unlearning statements (like 'I will unlearn stress when I go home feeling accomplished 4 out of 5 days') creates measurable behavioral targets more effective than generic goals.
  • →The system is iterative and renewable - leaders can continuously diagnose new areas to unlearn, reframe outcomes, and run experiments to achieve breakthroughs in different domains.

Guests

Barry O'Reilly

Topics in this episode

SpotifyAmerican AirlinesCapital OneUnlearn (book and framework)Nobody StudiosLean EnterpriseDiagnosis-Relearn-Breakthrough systemBehavioral experimentationVision statements and unlearning statementsSerena Williams and Patrick Mouratoglou coaching example

Questions this episode answers

What is unlearning and how is it different from forgetting?

Unlearning is the conscious act of letting go of once-useful mindsets and behaviors that are now limiting your results, not discarding all your knowledge or experience. It's a process of reframing outdated information to make space for new information, as knowledge becomes obsolete when reality changes.

What are the three steps of Barry O'Reilly's unlearning system?

The three steps are: Diagnose (identify specific obstacles preventing your desired outcomes), Relearn (design small behavioral experiments to move toward the positive outcomes you want), and Breakthrough (iterate through these experiments until you achieve measurable shifts in performance and behavior).

How do you write an effective unlearning statement?

Frame it as 'I will unlearn [obstacle] in [timeframe], and I will know I have succeeded when [specific, measurable behaviors occur]' - for example, 'I will unlearn stress in three months, and I know I have succeeded when 4 out of 5 days I go home feeling accomplished and spend 25% of time on personal development.'

Why did Serena Williams hire Patrick Mouratoglou as her coach at age 30?

After suffering unexpected losses at age 30 - losing in the first round of the French Open to a player ranked 140th - Serena met coach Patrick Mouratoglou, who gave her feedback she'd never received before (moving too slow, hitting too late). She fired her father as coach, hired Patrick, and through small iterative changes won more Grand Slams in the next five years than she had in the previous ten.

How did Barry O'Reilly write his books if he's dyslexic?

Rather than typing (his limiting behavior), O'Reilly hired a journalist to interview him chapter by chapter. He talked through bullet points, the interviews were transcribed by AI, the journalist lightly edited for grammar, and O'Reilly iterated on the MVPs - resulting in a book readers describe as feeling like a conversation with him.

What our scoring noted

Our reviewer’s read on each dimension, with quotes from the episode.

Insight Density

8 / 20

The episode offers a coherent three-step framework (diagnose, relearn, breakthrough) with a few genuinely useful operationalizations - like writing a measurable unlearning statement with specific behavioral targets - but much of the runtime is consumed by setup, host affirmations, and anecdotes that circle the same point. A smart B2B operator will extract a handful of ideas but won't feel pressed for time taking notes.

I will unlearn Stress in three months. And I know I have succeeded when four out of five days a week I go home feeling accomplished. 25% of my time is spent on personal development activities.
the ability to sort of label it and say, well, I'm stressed and how I know I, I, how I will unlearn that is that I'm spending 25% of my time on personal development tasks. Great. Now you're designing experiments not to be not stressed, but to spend 25% of your time on personal development tasks.

Originality

7 / 20

The 'unlearn' framing is genuinely useful as a label, but the underlying framework is largely lean/agile experimentation repackaged for personal behavior change. The Da Vinci 'to-learn list' idea is credited directly to another author's biography, and the Amazon press-release technique is well-worn. The episode rarely argues for anything counterintuitive - it mainly restates growth-mindset orthodoxy with fresh vocabulary.

the first reference I came up with, with, with unlearning, was actually from bo henberg in 1981
He didn't ever have a to do list. He had a, uh, to learn list or questions to answer list

Guest Caliber

11 / 20

Barry O'Reilly is a credible practitioner - co-author of a respected Lean Enterprise book, direct executive coaching experience with named Fortune 500 clients, and a working venture studio - but he operates primarily as an author, advisor, and coach rather than as an operator who has built and scaled a business at significant depth. The Nobody Studios venture is mentioned only in passing without substantive exploration.

I've had the honor, really, to work with execs from companies like Capital One, American Airlines, Spotify, Slack, you name it. Through the pandemic, with Slack executive team, I formed a cohort of 500 executives
we're building 100 companies in five years and we've got 11 in production

Specificity & Evidence

9 / 20

The episode has pockets of genuine specificity - named companies, the measurable unlearning statement format, the Serena Williams narrative with concrete career milestones, and a real executive anonymised as 'Abigail' - but no financial data, no before-and-after organisational metrics, and none of the Fortune 500 case work is developed beyond name-dropping. The evidence leans anecdotal rather than empirical.

she won more Grand Slams from the age of 30 to 35 than she did in the 10 years previous in her career
she fired her dad as her coach and hired Patrick

Conversational Craft

5 / 20

The host rarely probes beyond surface-level summaries and frequently asks Barry to confirm the host's own paraphrase ('Do I have that right?'). He uses interview time to promote his own book and offers extended personal commentary that displaces follow-up questions. There is no challenge, no productive disagreement, and no attempt to pressure-test claims.

Do I have that right?
I join you in the author ranks. Um, and it took me about 10 years to get my book done, um, just finding the time to dedicate to it. But that finally happened and the book Negotiation Made simple was released last week.

Conversation analysis

Computed from the transcript - who did the talking, and the words that came up most.

Share of words spoken

  • Speaker B75%
  • Speaker A25%

Most-used words

unlearn30book26learn18trying16terms15leader15world14barry13different12obstacle12first11process11unlearning10writing10started10system9

Episode notes

There’s a learning curve to running any successful business. But once you begin to rely on past achievements or get stuck in outdated thinking and practices that no longer work, you need to take a step back - and unlearn. This innovative and actionable framework from executive coach Barry O’Reilly shows you how to break the cycle of behaviors that were effective in the past but are no longer relevant in the current business climate, and now limit or may even stand in the way of your success. 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.

Full transcript

43 min

Transcribed and scored by The B2B Podcast Index.

Speaker A: Welcome to Leading Innovation. I'm your host, John Lowrey. On this episode, I want you to get ready for an inspirational conversation with Barry O'Reilly, who's a serial entrepreneur, best selling author and an innovation Expert with over 20 years of experience creating high performing organizations across the world. Barry is the co founder and the chief incubation officer of Nobody Studios, which is a venture studio that works with pre seed stage business ideas and helps them figure out how to scale and be investment. He's also an author. His latest book is Let Go of Past Success to Achieve Extraordinary Results. He is also the author of Lean How High Performance Organizations Innovate at Scale. Barry's got some incredible ideas on how leaders can unlearn in order to create the capacity to learn new things. This is an important conversation for leaders who are looking to overcome the challenges of moving their organization forward in a difficult and changing world. Barry O'Reilly I'm so excited about our conversation. Most of the time we think about learning on this show. Today we're going to think about Unlearning based upon your new book. Thank you so much for being part of the Leading Innovation podcast.

Speaker B: Yeah, look, it's a pleasure to be here, John, and yeah, happy to share all the things I've had to unlearn, relearn, and get some breakthroughs along the way with you and the listeners.

Speaker A: Well, I'm really excited about having this conversation because I think you're onto something in terms of, uh, this new skill that leaders have to develop as far as unlearning goes. And you've written a book called Unlearn Let Go of Past Success to Achieve Extraordinary Results. And that subtitle right there is a bit counterintuitive. Tell us a little bit about how you came to writing this book and how this really, this idea kind of captured your attention to want to study it, write about it and share it with the world.

Speaker B: Yeah. So, um, the first book I wrote was Lean Enterprise. It was part of Eric Reese's Lean series. And that book sort of went gangbusters and suddenly I was sort of thrust into all of these, uh, rooms with executives from Fortune 500s and scaling startups and like really some of the most brightest, smartest people you could ever hope to meet in your life. And they all wanted to innovate their businesses. They all wanted to change and grow and work in different ways. Um, and what I could constantly see with these folks is that learning new skills was actually never the problem. They were quick to pick up ideas, uh, and apply them the actual hard part was actually letting go of a lot of the skills that had made them successful to that current point in time. So they learned all these skills that made them successful at one moment. But now technology was changing, customer demand was changing, their business was changing, and yet they were sort of holding on tightly to the sort of tools that made them successful to date, and a little bit fearful, if you will, to try these sort of unconventional, unfamiliar, or uncomfortable, ultimately, new behaviors. So that was sort of the lightning strike for me. I was sitting there as everyone was talking about learning organizations, and we need to learn, learn, learn, and it's all about learning. But nobody was really talking about the unlearning part that goes with that. And it was funny. Then as I started to do research around it, the first reference I came up with, with, with unlearning, was actually from bo henberg in 1981. And he talked about this notion where he said, as our knowledge grows simultaneously, it becomes obsolete as our reality changes. So really, learning involves taking in new information, but also recognizing what's outdated information and to let go of. And we sort of go through this in our entire life, right? The lessons we learn as children are often simplifications of reality that as we get more sophisticated in our thinking experiences, realizes, um, actually what we believe that one time is no longer true. So this is sort of one of the fascinating things for me, and that's where it really got started. And on the back of that, essentially, I built a system to coach executives, leaders, how they could constantly innovate their behavior to meet the situations that they were facing. And like I said, I've had the honor, really, to work with execs from companies like Capital One, American Airlines, Spotify, Slack, you name it. Through the pandemic, with Slack executive team, I formed a cohort of 500 executives that were dealing with transitioning to remote work through the pandemic. And I'm learning how to do that. So it's been an amazing experience. Uh, as I say, I also do a podcast on it as well, too, and excited to share some of those lessons with you and your audience too, as well.

Speaker A: Well, that's fantastic. Let's jump into the system. You referenced the system, and I'd love to kind of hear your process for how it is that people unlearn so they can create the pacity to learn again.

Speaker B: Yeah, well, the first step really is, if you will, like, diagnosis. Right? Like, can I actually identify the obstacles that are getting in the way of what I'm trying to Achieve. So, um, first of all, the way I describe unlearning, when people hear that, they often sort of get a bit upset and they're like, are you saying everything that I know is wrong? And, uh, often like, well, nothing could be further from the truth. No, the way I describe unlearning is it's a process of reframing and letting go of once useful mindsets and behaviors that were effective in the past, but are now limiting your results. So it's not forgetting, discarding, or throwing out your knowledge or experience. It's simply the conscious act of letting go of outdated information to make space for new information to come in. Right. So once you help people understand that you're not saying everything they know is wrong, that there's actually a system at play here that sort of opens them up a little bit to the possibilities of doing this. Right. So the way I help people essentially self diagnose is I have a series of questions that I ask them and you can answer these yourself or you can play along at home where the listeners can, can do this for themselves. But, um, the way I help people sort of identify areas that they might need to unlearn is I ask these couple of questions and, you know, you can write down your own answers if you wish. Right. So the first one is, can you think of a situation where you're not achieving the outcomes that you're aiming for? Maybe you're not living up to the expectations you have for yourself. And maybe there's a situation where you sort of tried everything you can think of and you're still not getting a breakthrough. Or maybe there's one that you're just totally avoiding altogether. You're like, you know what? I just can't even think about how I'm going to tackle that. Right. So not living up to the expectations you have for yourself, situations you're avoiding. Maybe you've tried everything that you can think of and you're not getting a breakthrough or somewhere where it's like your secret sauce has just stopped working. So if I ask you that, did anything pop into your head?

Speaker A: Absolutely.

Speaker B: I'm watching you frantically scribble down about five things here. Right.

Speaker A: And I imagine I'm writing notes based on your questions right here. I'm engaging with you. So, yeah, uh, I've got something in my head for sure.

Speaker B: Right. So the thing is, when I ask people that question, it's often not just one thing that pops up, a few things pop up. Right. And so the good news is, John, we've all Got problems. So don't worry about it. You know, everyone out there has written

Speaker A: I'm not alone in my list of five things. Is that what you're saying?

Speaker B: Not at all, not at all. You're all good. But, but this is the thing, like, because what we tend to write down are obstacles that we're facing, right? Maybe people often write down their, their to their perfectionism gets in the way of what they're trying to do, or they don't take enough risks, or they wish they were healthier and they had a better lifestyle or spend more time with their kids and their family or whatever, whatever these things are, right? These are sort of the obstacles. Now what we're really trying to get people to think about is first of all, identifying the obstacles. But they're just in the way of the outcome that you actually want, right? And so for me, I'll give you example. When I, uh, started writing this book, I was starting another startup and I was terribly stressed all the time, right? And really when I started to like, ask myself these questions, the things that sort of started surfacing for me, I was like, oh, that's it. Like I'm, I'm working long hours, I'm not doing enough of the things I enjoy. I'm sacrificing in other areas and not finding sort of replenishment in others, right? And so for me it was stress. It was very obvious that something I needed to unlearn. But, um, the way I then thought about that obstacle was, well, I sort of wrote a vision story for myself in sort of two to three years time. What would be happening if I had totally unlearned stress? And maybe people who are familiar with writing vision statements. I think Amazon popularized the idea of writing a press release for their products when they launch it, right? You write this press release of how the world's going to be in two years time when the products in the market. So for me, I was writing this press release, if you will, of how my life was going to be. And I was writing things like I'd go home feeling accomplished from work, um, I'd spend more time on personal development, I'd do more exercise, I'd read more. And all of these things were sort of really examples of the behaviors that I really wanted to have more in my life. Not so much that I wanted stress, but I wanted to be feeling accomplished spending more time on personal development. So once I was able to sort of describe those new behaviors, they're essentially the outcomes that I wanted. So the way I sort of encapsulate all of that is I write it in an unlearning statement that sort of says, I will unlearn Stress in three months. And I know I have succeeded when four out of five days a week I go home feeling accomplished. 25% of my time is spent on personal development activities. Uh, most evenings I get to have dinner with my family, whatever these things are, right? And those sort of then gave me, if you will, a direction. It's almost like an objective or a key result that would tell me this is what I'm actually aiming for. And then once I've sort of framed up both diagnosing what I need to unlearn and examples of what the success I'm looking for is, then relearning is just a series of experiments, like behavior design experiments, where I'm going to try and create tiny shifts in my behavior to move me towards these outcomes of feeling accomplished 4 out of 5 days a week or spending 25% of my time on personal development. You're essentially experimenting, right? Just like with a product when you're experimenting and trying to grow your customer base by 10%. And then through that experimentation process of relearning, you ultimately get breakthroughs. You suddenly realize shifts in your behavior, performance are moving towards your essentially defined goals. And then the great thing about this system, as I continually taught it to people, is it wasn't really like a sort of one and done type system, right? You could just keep putting more and more into this system where people could diagnose other areas that they wanted to unlearn, reframe it as the outcomes that they're aiming for, and then devise experiments, if you will, to sort of move towards the space you wanted to get to. And like I said, I've coached this to Fortune 500 CEOs scaling, um, startups. I've used it on myself to help grow startups and companies I've been involved with. And m. Yeah, it's been amazing to see people pick it up and run with it. And, you know, I get messages all the time from folks saying they've done everything from quit smoking to get healthier to, you know, lead happier lives and be more performant in their, their careers they so desire. And then, um, yeah, so lots of sort of fun examples and anecdotes I'm sure I can share with you along the way.

Speaker A: So break that system down for us into just a few words. If I listened and heard it correctly. Uh, it starts with the diagnosis, yeah,

Speaker B: you need to unlearn yeah.

Speaker A: Unlearn. Yeah. Diagnose identifying what you need to unlearn. And then within that there's a vision of the future, um, in terms of the outcomes that you are trying to achieve. And then it sounds like from there it's an experimentation process in terms of how to treat the behavior.

Speaker B: That's it, what you're trying to relearn and then looking for the breakthroughs that you're getting from that as you experiment with new behaviors. So unlearn, relearn, breakthrough. Just like that.

Speaker A: That's great. And then breakthrough to finish it off. That's fantastic. And so what's interesting about that to me is I listened to that system and what's so brilliant about it is, um, I love how you skipped the source of the stress and went straight to the stress. And so, so many people I would probably do this as well is I would say, well, I'll stop being stressed once I get the business to this place. And, and I think sometimes that's self deception, right? Because once you get the business to that place, you're still stressed. You're just stressed over something different. And what's so brilliant about your approach is you say, no, no, no, no, no. Like, regardless of where the business is in its journey, let's figure out how to eliminate the stress, uh, so that you become more productive and you unlearn that, um, reaction to all that is coming at you in terms of being a leader and you relearn how to be more effective with all that's coming at you as a leader. Do I have that right?

Speaker B: Yeah, it's very interesting, right? I think until we sometimes label stuff, it's hard for us to actually go, you know what? That's the obstacle I'm facing. Uh, stress is the obstacle I'm facing. Perfectionism is the obstacle I'm facing. This is the thing I need to unlearn. Right. But it's often hard to say, well, how do I unlearn perfectionism? Or how do I unlearn not making sort of risky decisions or how do I unlearn? Right. Like, it's hard for people to do that because the reason it's an obstacle is because you currently don't have the tools to get past it. That's why it's an obstacle. That's why you're bumping into it. M. Right. So even the process of sort of labeling, if you will, the obstacle that you're facing is massive in terms of you recognizing then that you're going to have to try new Behaviors to get past it. Right. Like classic one is fitness. Right. January one's coming up, you know, everyone's going to be like signing up for gyms. Left, right?

Speaker A: You bet. Yeah, yeah, yeah.

Speaker B: Getting themselves healthy again.

Speaker A: All of the Orange Theory classes will be full for a month and then they'll be wide open again.

Speaker B: You know it. Right. And, and it's, but it's, it's sort of that thing. Right. And, and so this, this ability, though, if you can sort of identify, like, I'm, um, I'm going to start to change my behavior. Right. So when people want to get fit, they're like, I'll go to the gym earlier, I'll sign up to that class, I'll do. They'll do all the things that they've done before and haven't worked for them because it's what they know how to do. Sure. And often the sort of counterintuitive thing about all breakthroughs is you're often going to have to do something that's uncomfortable, that you've never done before, that you suck at. But, uh, it's actually the pursuit of doing that is actually what makes you better, which is the odd thing. The first time you play an instrument, he suck. First time you try to ride a bike, suck. Yeah. But it's the repetition and the practice of doing something that's uncomfortable, unknown, that becomes more familiar and more competent. And that's sort of the thing where people sort of shy away from and the ability to sort of label it and say, well, I'm stressed and how I know I, I, how I will unlearn that is that I'm spending 25% of my time on personal development tasks. Great. Now you're designing experiments not to be not stressed, but to spend 25% of your time on personal development tasks. Right. It's to move you to a better place. And that's actually a better place to design from. It's where do you want to get to rather than what are you trying to get away from? Or what's the obstacle you're just trying to solve incrementally. And that's sort of been one of the huge aha's of this. And, you know, so many examples, like, even for myself, like writing a book. And so I'm dyslexic. You know, I have a solid history of D sort of minuses in English literature all through school. I still joke, if my English teacher knew that I'd written two books, they wouldn't believe, they wouldn't believe it. And, um. But one of the things that was sort of a huge sort of obstacle for me, even with writing, is I had this sort of inertia that I couldn't spell or I'd get the grammar wrong or. So it was just massive obstacle in the way. But. Excuse me. One of the things then I, I started to think about reframing is like, well, actually. Right, so, um, the obstacle here. What, what am I actually trying to do? Well, I'm not trying to write. I'm trying to create content. And actually there's lots of different ways I can create content. Books, uh, don't have to be just created by typing. You could talk them. You could get, uh, interviewed. What I ended up doing is I hired a journalist. And what we would do is that we would map out the chapters of each of the books around a couple of bullet points, and then the journalist would interview me and I would just talk. Because the easiest way for me to create content was talking. So we would record, uh, a, uh, conversation. We'd send it to an AI that would automatically transcribe it. The journalist then would take that transcription and lightly edit it, right, to make grammatical sense from a written point of view. And then they would send me, literally within like three or four hours, a sort of MVP of the chapter, which then I would start reacting to and iterating, going, oh, no, I forgot that story. Or I didn't add this in. So literally for unlearn, I didn't type the book. I talked it, the whole book, and basically worked through iteration. Then after we created these MVPs of chapters, and the most fun thing about it is when people, um, read the book now, they say to me, barry, I feel like I'm sitting in a room talking to you as I read this. Which is sort of like the ultimate aim you want for in capturing your voice in the written word. And that's what I did. I didn't type a word of it. I talked it all.

Speaker A: That's great. I mean, that's so brilliant in terms of thinking about how it is that you're gifted, uh, where it is that you have challenges. And that's true for every single one of us because all of us have different giftedness and different challenges. And for you then to be innovative enough and creative enough to learn how to play off of your giftedness and how to unlearn, how to be limited by your challenges is an outstanding skill in terms of being successful. Share with us some other stories. Like in your book, you share a story about Serena Williams Uh, give us some other examples, uh, about this process and where you've seen it lead people to such great success.

Speaker B: Yeah. Well, Serena is, um, a phenomenal example. Right. Not only is she had to sort of face the trials and tribulations of society for her, her competency, but tennis is one of the most rigorous, toughest sports. Ah, there is. Right. Kids are trained from a very early age, like literally like 8, 9, 10. They go into these very rigorous training programs. And famously, Serena and. And her sister Venus were trained by their father, right, who had built this sort of training plan for them since the age they were born. Right. Famously created by Will Smith. But, uh, duck from the microphone in case it tries to hit you. But this is. This sort of was the rigor that she was brought up in. And at the. You know, most tennis players sort of retire at the age of 27. And so when Serena was 30, she was sort of number one in the world at the time. And she stepped on a piece of glass in Munich when she was at a match there and ended up getting an infection and went and played a match the next day, lost a match, um, and sort of, anyway, continued on for a little while. She went to the US Open and lost in the final. Then she went, uh, on to Wimbledon or, sorry, uh, or, sorry, Australia, where she lost in the fourth round. Never had lost at that stage. Then at the French Open, she lost in the first round to somebody that was ranked 140th in the world. And, um, the tabloids were sort of writing her off. You know, she's finished, her career's over, whatever. You know, she was 30 at that time. So she went off to sort of practice around Paris and she came across this place to play. Um, and the person who, uh, owned the practice center, his name was Patrick Monroe and his dad was, uh, a famous entrepreneur in France. He actually was the most famous renewable energy, uh, entrepreneur in all of France. And he wanted Patrick to sort of take over the family business. But Patrick didn't really have much of an interest in the business. He was more fascinated by tennis. So at the age of sort of 25, he told his dad he was leaving the family business and he was going to open up a tennis school, which you can imagine how a, uh, multi billionaire entrepreneur felt when his son said, I'm leaving the family business to do that. So anyway, this is the pat Patrick chose. And anyway, Serena found her way to his training center near Paris after the loss in, um, the Grand Slam. Um, and she was just practicing and he approached her and gave her some pretty rigorous feedback to say, you're moving too slow, you're hitting the ball too late. And her instant reaction was one of curiosity, where she was like, hm, that's interesting. Let's work on it. I've never had that feedback before. So they ended up practicing together for a week. And, um, she went home to Miami after that and was preparing for Wimbledon, which is sort of like the premier event, I guess, of the tennis calendar. And then just as she was about to go back to Wimbledon, she fired her dad as her coach and hired Patrick. Basically, what happened from there is almost like the stuff of legends. And she started winning. She won Wimbledon, and, uh, she started winning more. She started beating more players in the top 10. Her win percentages went up. She won more Grand Slams from the age of 30 to 35 than she did in the 10 years previous in her career. And all of this was about small, little changes that her and Patrick kept constantly making to the way she would prepare for games, the way she would play in games, ah, the way she would hit rackets, choose rackets, and sort of. This was the whole thing where it went against the norm. Like I said, most tennis players were retiring. At 27, Serena was still getting to Grand Slam finals until she was 40. Wow. You know, and, um, it was kind of funny, like, one of the fun things about the book, and this is one of the stories I told in the book. Ah. Just as I was launching it, um, I ended up, uh, getting in contact with Patrick, the coach, via Twitter. And I. I told him I'd been working on the book and him and Serena, and he was like, sure, send me to. Send me a couple of copies. And then just before she took part in the next Australian Open, somebody sent me a photo from a newspaper, uh, in Australia, where Patrick and Serena were sitting down on the side of the course, reading. Reading the book together.

Speaker A: That's so cool.

Speaker B: It was so cool.

Speaker A: That is awesome. Yeah.

Speaker B: You know, one of these things, like, you never sort of know when you put these things out into the world, how they're going to play out. But there you go. There's my little, uh, anecdote story on it.

Speaker A: Well, that's a great story. And, um, my parents actually, um, would always say this quote to me. Um, they would always say, you're doing more good than you know. And that's one of those stories, right, where you're doing more good than you know. I think that's true for, you know, everyone in terms of that are trying to do Good out there. You actually do more good than you actually know.

Speaker B: Right on. You know, and, and I'm a big believer in this. Like, if you put good energy and good vibes out into the world, it comes back to you, you know, and for sure, for me, I was sort of, um, you know, that was a great moment, you know, because she inspired me to, to find that story and share that story. And, um, it was great to see the loop closed, if you will.

Speaker A: So let's talk a little bit about leadership and take this concept and apply it kind of to leadership. Um, first thing that I'd love to kind of pick your brain on is this kind of mindset of a leader. And you've mentioned something around kind of adopting a questioning mindset. Uh, talk a little bit about that in terms of how questioning and curiosity become valuable leadership skills.

Speaker B: Yeah. Well, it sort of goes back even to Serena's example. Right. It's very easy for her to dismiss the feedback that Patrick might have shared with her when she was practicing. Sure. Um, would have been easy for me to sort of say, you know, I only ever got D minuses. I'll never, I'll never be able to write a book. Right. And sort of this is, I think, why intellectual curiosity and pursuits of these things are so important. Right. Because, um, there are ways that maybe are not obvious to you, are not visible to you at a moment in time. And that's why experimentation and curiosity and asking questions is so important, because it encourages you to explore, to look outside the known, you know, to try new things. And then often that's where all the novelty and the breakthroughs are, is in non conventional ways that you've approached things previously. So I just think it's really key for any leader. Um, if you're going to be serious about doing innovation, you have to be actively curious. You have to get outside your comfort zone. You have to try things that you've never done before. And for me, it's sort of a. It's almost like a part of my mantra, if you will, where I always say uncertainty is opportunity. Um, and I almost like try to find things I've never done before and give them a go, just to see, you know, like, is there something there? Like, should I. Most recently, I've got very interested in picking up martial arts. I never thought I would do that, but then I started practicing it and I've really enjoyed it and it's opened up a whole new realm for me, you know, of something that I never thought I would do more. But I, but I really enjoy it. Right. And so these are all like little things where you just as you experiment and try, you'll never know. And I'm always a big advocate of people giving uh, that things a shot and staying curious.

Speaker A: So next leadership idea really comes down to thinking about, um, goals. And I'm interested in hearing your thoughts on, as we think about kind of the creating those visions that you talk about and setting goals that determine whether those visions are successful or not. How is it that leaders can ensure that their goals, uh, not only lead them to success, but their goals are also something that inspire others around them that have to contribute to the achievement of that particular goal?

Speaker B: Well, I always, um, encourage people when they're starting to unlearn. A huge part of the process is also to share what they're trying to unlearn with their peers. Right. It creates accountability, it creates a shared experience and it's humility. Right. It shows that you're trying to get better at something. Right. And it's one of the things I often always ask the execs to do is say, one of my favorite ones is I was working with this lady who's one of the maybe top five leaders and the top five bank in America and decision making was a real challenge for them. Right. She everywhere, people would just keep coming into her office to make her, ask her to make decisions. And it's everything from like, should we open up in a new country to should we order new post it notes next week? Like, she was literally like, I don't think anyone knows I was trying to make decisions around here. We've got to, we uh, need to unlearn decision making. And one of the sort of bold, brave steps that she made is she said, right, team, I'm going to stop making decisions for the next. And she actually was only going to try it for a day, but she sort of made a statement as if she was going to give up making decisions just to sort of almost like shock the folks into like, hang on, what. So what happened is anytime someone came into her office and said, and let's just call her Abigail, ah, we need to decide if we're uh, opening up in um, Brazil or Argentina. What should we do? And her automatic response was, I don't know, what do you think we should do? And then some people would sort of cower and go, well, but you're the executive, you need to tell me what we need to do. And then other people would go, well, if we go into Brazil, here's the pros here's the consultant, here's the tradeoffs that we need to be aware of if we go into Argentina, pros, cons. I think we should go into Argentina. And here's why. Instantly, she would learn what people were capable of making decisions and just needed to be encouraged versus those who needed coaching to help them get there. Right. And she couldn't have learned that if she made the conscious decision not to make a decision, but to change her behavior and ask a question and say, I don't know, what do you think? Right. And these tiny little cues offer, uh, amazing insights if you let them happen. Right. Conventional wisdom being the leader should know the answer. We should ask the leader, they'll tell us the answer, versus the leader should first ask questions and hear what other people think and then use all the information provided and then, then make a decision if needed. Right. They're totally different systems of operation, but, uh, guaranteed, the one that gets the best results, the best buy in, the best sort of best in their teams, is leading with a question rather than an answer straight away, um, and engaging people to make things better.

Speaker A: I love that. And I describe that, Barry, as the leader's trap. And most of the time when I'm describing it, it's in the context of conflict management, where people bring the leader a problem and say, how should we solve this problem? And they trap the leader because many times those problems are disputes between different employees on the team or in the organization. And they say, okay, you're the leader. You decide who's right and who's wrong. Well, it's a trap because the leader can't win in that situation. Right. Uh, because no matter what decision they make, uh, there's going to be someone that feels like the winner and someone that feels like the loser and someone that may get rewarded for very bad behavior in terms of not dealing with it the right way. Way. And then someone that is going to disengage in terms of saying, well, if that's how it's going to be, then the heck with this. And so that's really interesting in terms of that important skill of a leader of saying, okay, here's the challenge, here's the opportunity, here's the problem, whatever it is, uh, and asking questions and inviting people into the process of solving it to where the leadership doesn't take full ownership of the problem, but actually makes it a problem for the entire team or the entire organization to solve. I think that is incredibly valuable. So building on that problem solving, uh, you also tell a story about Leonardo Da Vinci and um, one of his approaches to problem solving from way, way back when. Talk about that in the context of this cycle of unlearning.

Speaker B: This is a classic example of sort of non conventional wisdom, right? Because one, one of the things that um, Leonardo had, and it was, it was actually included in his book that Isaac Watson wrote as well, which is another great book, he wrote, uh, like biographies, most recently of Elon Musk and, and Steve Jobs and so forth. But the thing that ah, Da Vinci had is he didn't ever have a to do list. He had a, uh, to learn list or questions to answer list, right? So people would go through his notebooks and it would never say things like get coffee.

Speaker A: Yeah.

Speaker B: It would say things like figure out how water floats or you know, how this device floats in water, right? Or figure out, um, how long it takes to get from Rome to Venice if we were flying. They were always like questions, right? They were never like, uh, things to do. They were like things to learn and things to discover. And um, for me, I always really liked that about just a philosophy about how to approach the world. It's better to sort of think about the problems that you're trying to solve rather than just the activity that you're going to do, right? So instead of, it's like get up, uh, drink coffee, do email, drop kids to school, pick up family, do that, whatever it is, right? Like he would think in terms of outcomes that he's aiming for, like solve why this sphere floats in water. Figure out the distance between Venice and Rome, right? These are, these are like great ways to think about the world. And, and yeah, so I, I just really liked that when I was reading that book and it just sort of gave me another like little anecdote to throw into the book about different ways people approach the world and the benefits that it is offered them.

Speaker A: I love that. And so I join you in the author ranks. Um, and it took me about 10 years to get my book done, um, just finding the time to dedicate to it. But that finally happened and the book Negotiation Made simple was released last week. And in that book I talk about being a learn it all negotiator and really got that concept from Satya Nadella, the Microsoft CEO that talked about being a learn it all leader. And I love this idea of the learn list as opposed to uh, to do list. Like, that's really a very, uh, cool concept. Uh, Barry, as we wrap this up, uh, let me ask one kind of last question here. And um, as people think about uh, this notion of unlearning, um, you talk about how people need to get outside their comfort zone and all of that. Like for folks that find reluctance in others to unlearn, how do you inspire that in other people? So for example, if I'm leading a team of people and we need to unlearn something that's holding us back as an organization or as a team, it's one thing to motivate myself to unlearn, but how do I motivate others to unlearn when it's such a difficult task?

Speaker B: Yeah, well, you know, it's funny and I'd love to hear your, uh, thoughts on this in terms of negotiation too as well. Right. But like, often I find that the gift you can give people is new insight. Create an experience where they see something, uh, that they had never seen before. You sort of like have to break their mental model of the world, but in a safe way. Uh, the classic way we uh, do that in startups is we get people to talk to their customers.

Speaker A: Right.

Speaker B: So they might have built a great product, but the sort of the test and the gold standard test, if you will, is getting them to show their product to customers and listening to the feedback that they customers give them. Right. To help them calibrate it. Ah, with negotiation, I always think is an interesting one. Right. Where people might think of it as a zero sum game, but yet the best negotiators see it about creating a great relationship actually and finding win win scenarios. Right. And so um, these are sort of some of the like non conventional approaches, right, where you sort of um, flip the wisdom that people think about things like entrepreneurs should know all the great details of how to build their product. Well, no, most entrepreneurs are the great ones. We're just really good at listening to their customers and then building solutions that solve their problems, not coming up with all the answers. So that's sort of always a fun thing for me. And I try to do that by creating little opportunities, uh, for people to just sort of see a different perspective. And often when they get that new information, that new insight, that's actually what shifts their mental model of the world. How a customer used a product different than they thought they would, or um, a process that they thought worked in a certain way, but then you bring them to the shop floor and see people not performing it in that manner. All of these little insights that just help people calibrate their view of the world. Often as long as you don't do it to make them look foolish or make them feel Uncomfortable. They really appreciate it. That's why I think about this idea of safely creating spaces for people to sort of learn that maybe some of their assumptions are incorrect. And then that's a great way to start a learning journey.

Speaker A: So, Barry, tell people, how do folks learn more about you? You're doing this interview from the Manila, Philippines, uh, which is awesome that, uh, technology literally has brought us together, even though we're on different sides of the globe. But tell us how people learn more about you.

Speaker B: Yeah, sure. You can go to barryorilly.com I blog there. Um, I've got a podcast too, that are released twice a month. Blog every month. So there's lots of things you can learn about product development, strategy and innovation. I also have a venture studio or an incubator called NobodyStudios.com we're building 100 companies in five years and we've got 11 in production. So we're 11% of the way there having, um, fun doing that. They can also check me out and yeah, I just want to thank you again, John, and congratulate you in your own book. I'm looking forward to reading this. Can already see you're up to like 5.9 and 25 reviews on Amazon a day out. So congratulations to you and well done with that. And yeah, again, thank you very much for having me in the show and getting to spend time with you and your audience.

Speaker A: Thank you so much, Barry. This has been awesome. Barry's book is Unlearn. Let Go of Past Success to Achieve Extreme Extraordinary Results. He's also written Lean Enterprise, How High Performance Organizations Innovate at, uh, scale. This has been an inspirational conversation. Thank you so much, Barry, for being part of the leading innovation podcast.

Speaker B: My pleasure, Joe. Cheers.

Speaker A: What an insightful time with Barry O'Reilly. I've taken about a page of notes here in terms of some. Some ideas that just struck me as really powerful that I'm frankly excited about putting to work today. This whole idea of creating a to learn list as opposed to a, uh, to do list. The story of Leonardo da Vinci and how it is that he prioritized learning and discovery in addition to all the things that he has had to do today. I am going to be a different leader because of this conversation with Barry O'Reilly. His process for unlearning, which involves diagnosing what you need to unlearn, creating a new vision for overcoming the obstacle and achieving the outcome you want to achieve, experimenting by relearning new processes and new behaviors, and then decide, discovering and observing your breakthroughs. This is a process that can transform leaders and transform organizations. I hope you're as excited about jumping into this as I am. Thank you for listening to Leading Innovation, and I'll look forward to seeing you on our next episode.

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