Master “Unlearning” To Build A Successful Business With Barry O’Reilly [Interview]

Barry O’Reilly, is a business advisor, entrepreneur, keynote speaker, and is the author who has pioneered the intersection of business model innovation, product development, organizational design, and culture transformation.

Barry is the founder of ExecCamp, the entrepreneurial experience for executives, and management consultancy Antennae.

He wrote  an amazing book, “Unlearn: Let Go of Past Success to Achieve Extraordinary Results” and he is also the author of “Lean Enterprise: How High Performance Organizations Innovate at Scale.”

We’re diving deep into “unlearning” and how it can help organizations thrive in this era.

How did you get into the study, research and practice of unlearning?

Barry O’Reilly: After we wrote “Lean Enterprise,” I was coaching a lot of senior executives and business leaders in scaling of startups or larger organizations about how to create high-performance organizations to innovate at scale.

One of the things I constantly came up against was while learning new things was hard, the significant inhibitor to helping people, especially high-performance individuals get better, was not their ability to learn new things. It was their inability to unlearn their existing mindsets, behaviors, and methods that were once effective, but now they were starting to limit their success.

So it was very interesting to me because a lot of the behaviors that make these people very successful when they tried to take the next step, some of them can actually be inhibitors to taking that step and succeeding.

A change in mindset

And a simple example might be, you know, if you can imagine when you were just a contributor in a team, say you were a software engineer and you are really great at writing code, and you come into work and you write code all day and then you were great at that. Very competent.

So you suddenly started to have to manage other people who were writing code, and often, the transition from being a contributor to be a manager, people try and often get stuck using the same behaviors that made them successful when they were a contributor when they were trying to be a monitor.

Often you need to flip your emphasis. Instead of measuring your success and the amount of output you create, stories you deliver, features you shift, your success becomes helping other people to deliver and improve their practice and get better rather than you do all this work.

These are very simple like examples, but where we often get trapped, and we have to recognize that maybe we need to let go of some of the behaviors that made us successful in our last role and innovate the way we work to be successful in our next role.

What’s the learning organization and what’s unlearning instead?

Barry O’Reilly: In the 1990s, Peter Senge published his book, “The Fifth Discipline,” which was the art and practice of learning organizations. That concept sort of exploded into the world. Everybody was becoming a learning organization and sending people to Stanford, Harvard, Cambridge, and Oxford to get these certified learning organization leadership programs.

But it was interesting because at the same time, while Senge was talking about learning organizations, another mention of by Bo Hedberg talked about unlearning. The interesting thing is while knowledge grows, it sort of simultaneously becomes obsolete as reality changes. Understanding involves both learning new knowledge but discarding obsolete or misleading knowledge.

Recognizing what’s not working

And Bo Hedberg sort of described this as a process of both learning and unlearning. What most people forgot or missed that trick with learning organizations is they thought it was just about doing more stuff.

But the real trick is to recognize what’s not working and let go of and then incorporate new things to help you learn at speed what works and what doesn’t. And you know the reason I think you see this huge disruption happening in business models is for a long time companies didn’t recognize that pattern.

Learn fast and rapidly innovate

Even in 1990 when Senge’s book came out, the largest organizations in the world were big organizations that scaled through hiring people, being number one in their market, building a moat around their business that they had high barriers to entry.

Even in 2008 that was still the case, the largest companies in the world were Exxon, General Electric, Microsoft, AT&T. But now if you look today, the largest companies in the world have fundamentally shifted the way that they work.

They’re building these platforms that allow them to both learn what works and unlearn the behaviors that are not working for their customers and rapidly innovate its speed. The reason companies like Amazon, Apple, Alphabet, and Facebook are powering ahead of the competition is they recognize that they can scale through technology infrastructure rather than people.

They build platforms that allow them to learn at huge fidelity, high accuracy about what features customers use and don’t use, what features work on don’t work. So they’re learning to unlearn at the same time.

That’s allowed them to have an exponential impact relative to the rest of the organizations in the world and truly sort of out-innovate them both in business modeling, product design, process delivery, and customer delight.

Is disruption organizational or it happens at an individual level?

Barry O’Reilly: What I always say is disruption doesn’t happen to organizations. The truth is it applies to individuals. Because organizations are just led by individuals. And often what happens is people get into leadership roles and they believe that the things that made them successful in the past will continue to make them successful in the future.

People with 20 years experience in a certain industry start to fall into the fallacy that they’re an expert, that they know everything. But technology is changing. Customer demand is changing. The world is changing all the time. You’ve got to have a system to continuously adapt your behavior to changing circumstances that you’re facing.

When you think about the best leaders of the world, they’ve cultivated a capability within themselves to innovate and adapt or even anticipate the future. They invest in experiences that enable them to grow.

They seek situations that are uncomfortable, uncertain and the results unknown. They’re experimenters. They’re constantly trying new things to find out what works and what doesn’t.

When you pair that mindset with the ability to leverage your technology to help you experiment at speed, I think that’s where you see the rise of people like Jeff Bezos who is continuously trying new things for Amazon to see what works and what doesn’t and the massive success that they’re realizing as a result.

How does the Cycle of Unlearning work?

Barry O’Reilly: What I was constantly finding with these leaders is that when they start to recognize that they’re not living up to the expectations that they have for themselves or they’re not achieving the outcomes that they wanted, they were signals that they needed to unlearn.

Their behaviors were not driving the outcomes that they want. Often how I try and explain this to people is just like a product has features and you’ve got to continuously innovate your features to stay relevant in the market with your product, humans have behaviors, so you need to continuously innovate your behavior to stay relevant in the market. I think leaders sort of understood this.

When they sort of recognized when they needed to unlearn, what we would do then is take a next step of relearning, teaching them new skills, strategies, behaviors where they could experiment with these by thinking big and starting small and experiment with all many behaviors, they could find the behavior that started to drive them in the direction that they wanted and get some of the breakthroughs that they were aiming for.

Breakthroughs are really a disability to recognize new information and new perspectives. That’s what sort of starts to shift your behavior, is you get these new behaviors, they get new insights, new information, which impact your mindset, and then you can start to go through this process.

Not a one-and-done cycle

It’s not a one-and-done cycle. You don’t unlearn once. It’s really a system that you need to continuously adapt your behavior too. That was a really exciting moment for me because then I started to realize, well, if this is a system, that means we can define it and then we can start to teach people how to use it.

I’ve been coaching now senior executives from Fortune 500 companies right through to scaling startups here in San Francisco, this program and process for the last three or four years. Now I’ve started to build an application where people can actually use this software to teach them how to continuously innovate their behavior to changing circumstances.

It’s been amazing to see the impact of this system. As you say, in the book there are lots of case studies from Capital One and NASA and the National Health Service in the UK where they’ve had these exponential business results as a result of adopting this process. It’s been a pleasure to be a part of it.

What are the key characteristics of unlearning?

Barry O’Reilly: I’ve noticed that there’s a number of characteristics that you’ve got to cultivate within yourself if you want to unlearn.


The first one is a sort of curiosity. The reason I say curiosity is because it’s about getting new information, new information to challenge your existing perspective and mental model of the world.

My example of, well everyone tells me they’re curious, but the challenge I put to people is, when’s the last time you gave someone on your team who is maybe less experienced than you or new to the group, a problem to work on that you knew how to solve and then they started to solve it in a different way than you would?

What was your initial reaction? Did you stop them and tell them, no, you need to do it this way or were you curious enough to understand why they’re solving problems in a different way?

You know, one of the executives I worked with at when the world’s largest banks, he used to go and sit with graduates when they were hired in the company and he would pair with them and get them to sort of ask questions like, what new technologies are you using? How can we solve problems that I thought that you might do in a different way before?

He used to role model this curiosity in the company. This is a someone who’s running a multibillion-dollar portfolio sitting down with graduates who are starting on their first day so he could both learn and unlearn with them. So how curious are you really?


The second one is ownership. This is more about owning the outcomes of your efforts. Often what I find is when people are trying to do innovation and are struggling and it’s not working out, they often will say, well, we would’ve been successful if it wasn’t for that person or another team.

Really, if you want to be serious about unlearning, you’ve got to own the results. You’ve got to recognize that the only behavior you can change is your own. Whatever results you’re getting, you’ve got to own them and adapt your behavior to start to succeed.


Then the third part is about commitment. It’s like you’re going to try things that you’re not good at. You have to really commit to sucking at it for a while and deliberately practicing getting better and taking on more challenging steps as you go, which means you need to be comfortable with being uncomfortable, and none of your growth is going to happen inside your comfort zone.

It’s just going to be on the edge where your feet are sort of just touching the ground as you’re floating in the water. The way you get people comfortable with not being uncomfortable as you create safety.

Safety is about thinking big and starting small, so you learn fast what works and what doesn’t.

Starting small also makes it safe to fail. You have high psychological safety because you can try out new steps and not feel foolish and working in small steps so that as you to sort of learning quickly what works and what doesn’t.

Recap of the key characteristics to master unlearning

Small steps also have small risks. So you invest in getting information to inform what you’re going to do next and iterate. These are sort of the key characteristics I often say to people, and I sort of summarize it in thinking big, starting small and learning fast, but being aware that you need to be curious, you’ve got to own the results, be committed to be comfortable with being uncomfortable and create safety to succeed.

What’s status quo leadership and why it might be damgerous?

Barry O’Reilly: The danger is when people are successful in one company or context, they sometimes believe that they can sort of copy and paste the same behaviors that made them successful in that context and company into another.

You’ll often see when people move companies that they start implementing all the same practices they had in their last company because it’s comfortable for them. They know how to manage that type of system. They know how it works, they know how to manipulate it.

But often those systems aren’t the ones that are going to be most successful for an organization. You really have to adapt your behaviors to the context and the company that you’re in to be successful.

Avoid to just copy and paste frameworks

This is one of the dangers we see a lot at the moment with these huge scaling frameworks.

You have organizations that are just copying these massive frameworks from books and trying to just print them onto these complex systems that companies are, and you’re never going to get the same performance improvements that you expect when you do that you’ll cause a lot of activity, but does it actually drive any business outcomes?

Define the outcomes

A lot of what I focus on, especially when I’m coaching leaders, is they need to get good at defining outcomes, what they’re aiming for. Recognize where their behaviors or existing behaviors are not living up to those outcomes, and then start to relearn new behaviors to try and drive the outcomes that they want and get the breakthroughs as they need.

Build a system to continuous innovation through unlearning

As you start to teach people how to continuously innovate and adapt their behavior, then it starts to be less of concern what the problems are because they have a system to continuously innovate based on the problems are given.

What I’ve seen when working with teams like that is that they have exponential benefits and extraordinary results because you’re teaching to team both how to learn but unlearn, recognize when behaviors are working and not working and innovate and adapt.

I think based in the world that we’re in, the pace of change that we’re facing, I think teams that are able to adapt capability, they are going to be outperformed teams that are copying processes and trying to execute processes out of books or scaling frameworks or templates.

How to use the Three Cultures Model to build a successful company?


Credit: excella.com 

Barry O’Reilly: A lot of this is done by the work of Ron Westrum, and Ron is basically studying behavior sort of economics in organizations, specifically in health care. He sort of categorizes organizations into three types:

  • pathological: Pathological environments are where people use knowledge as power and they seek to blame people when there are failures.
  • bureaucratic: Bureaucratic organizations create lots of processes to ensure that failure never happens, and if a failure does happen, they look to see who didn’t follow the process.
  • and generative: In generative organizations, it’s about seeing knowledge and information as free that everybody can access it, and if everyone has good information, they’re gonna make good decisions. But they also recognize that nobody can often anticipate when failures are going to occur, so when failures do happen, they’re seen as new information to help the system get better.

And that’s why you find with these organizations that are powering ahead like Amazon and so forth, is they’re making it safe for people to gather new information. They build these platforms where they can safely experiment with customers to find out what works and what doesn’t roll back changes that don’t work and double down on changes that do.

They’re going to find out things, unexpected things, things they thought were true, maybe validate them, but the concept of failure is seen as a step on the way to progress. That you figured out something that doesn’t work and you’ll progress.

Not that it was somebody’s fault and they should be brought out and fired or reprimanded for trying to learn a lot of customers might potentially want. then there are systems in place to allow them to learn that safely and cheaply.

What are unlearning prompts? And why they matter?

Barry O’Reilly: A lot of people get quite upset when I say you need to unlearn because they feel like I’m saying that everything they know is wrong. That’s not correct. As I said, it’s a system. It’s about recognizing when you need to change the behaviors to drive the outcomes that you want. You don’t forget them.

I described it as unlearning is moving away from once useful mindsets and acquired behaviors that were successful in the past, but now might be limiting your success. It’s the conscious act of letting go of outdated information and actively engaging in taking in new information to inform your decision making and action.

It’s a system of both learning and unlearning, recognizing what works and doesn’t.

How do you know you need to unlearn?

Well, the simple thing is to say this a situation where you’re not living up to the expectations you have for yourself, or maybe you’ve defined some outcomes that you’re not achieving.

Maybe you’re struggling to resolve a problem. You’ve tried everything that you know and you’re still not getting the results you want, or there’s an area that you’re just totally avoiding altogether because you’re struggling with how you can solve that problem.

They’re all signals that you probably need to unlearn, that you’re existing behaviors are not driving the outcomes that you want and therefore you’re going to have to relearn new behaviors to try and get you there.

This is why this idea of unlearning is an essential but sort of over overlooked step of being able to learn, and what I’ve figured out over time is that unlearning is just as important as learning, and recognizing when you can identify those limiting behaviors, not achieving the outcomes that you want, relearn and breakthrough, that’s what leads to extraordinary results.

Is there a number one reason people don’t unlearn?

Barry O’Reilly: I think what happens is it’s hard for people to recognize our own that their behaviors are not driving the results they want. Often when people don’t get the outcomes that they want, very rarely do they look at themselves to say, what could I have done differently?

They often sort of focus on factors that they mightn’t be in control that led to failure. Really the problem there is you’ve got to really flip that mindset that needs to be unlearned.

You have to recognize that the only way and only person you can really change is yourself. By constantly trying to adapt your behaviors to get the results you want, eventually you’ll get the breakthrough that you need, and as your team and your peers see you start to constantly change your behavior, they’ll get inspired and they’ll be willing to try and change their behaviors, too.

Getting good at defining outcomes that you’re aiming for together, so you have a clear sense of what success is and where you’re trying to go, would be the other key part that I recommend is sort of a minimum requirement if you’re going to try and tackle this stuff.

Build a growth mindset

And I guess probably a key step is really to actually build up a growth mindset, which enables you to actually understand that you can improve in the process of unlearning. What are some of the key conditions to actually go through these unlearn, relearn and breakthrough processes? What are some probably a few key conditions for those things to happen?

You know what I’ve definitely learned when I ask anyone, do they have a growth mindset or a fixed mindset, nobody tells me they’ve got a fixed mindset. But the interesting thing is a lot of people do, and what happens is when you’re very successful at what you do, you’re used to getting great results.

Fixed vs. growth mindset

You’re used to being given problems that you like. You have great processes to solve those problems, and then you get the results and you get confident that you’re great at getting results.

Say you’re a product manager and you’re great at building products, all your products get launched and they’re successful. Now when you start to ask people than to do different things, so say you were a product manager for an e-commerce website, but now you’re going to ask somebody to move into a new role.

Can you be a product manager for, let’s just say a hardware device and a hardware device that has to connect to lots of other different pieces of hardware and software to make sure that it’s delivered on time. That is sometimes a tougher or more complex problem, and maybe a problem you don’t like.

The processes that you’ve used previously mightn’t actually be the best processes to solve that problem. Now you’re in an environment where it’s a difficult problem that’s unknown and unstructured for you. You don’t really have a clear process of how you’re going to use it.

The results that you’re used to getting are in jeopardy, and then people really start to react to that. They start to get concerned because they’re used to getting good results. Really one of the big shifts in learning and unlearning or growth mindsets versus fixed mindsets is you have to recognize and reward the effort.

Switch the focus from the person to the process

If you focus on results, people won’t do things that they won’t get good results in. That’s a fixed mindset. You see this with your children. If your children do swimming and you constantly tell them you’re great at swimming, anything that they do that might jeopardize them from not being great at swimming makes them nervous

Rather than rewarding him for saying, wow, that was a great effort. You dived into the pool, you looked like you were having fun. Brilliant. I wonder what else you can do. And the same is true with people.

I think recognizing as you change your roles, as you start giving bigger, harder problems to solve, often your first pass through a problem and the process and the results won’t be what you expect. You’re going to have to do things that you’ve never maybe done before that don’t work for you or new skills and recognize that the result isn’t about success or failure anymore.

It’s about new information and using that information to inform how you redefine your problem, how you try a new process and get another result to see if it moves you in the direction or the outcome that you’re aiming for.

Recap about growth vs. fixed mindset

That, again, is a huge shift for a lot of people. But this is sort of the real point of growth versus fixed mindset. Learning and unlearning, getting comfortable with being uncomfortable and sort of choosing a different path, courage over comfort, to tackle uncertainty and grow yourself as a result of taking on those challenges.

What suggestions do you have for executives to bring this process in their organizations?

Barry O’Reilly: Think big, start small, learn fast.

Thinking big is about trying to transform your organization. It’s really tough. But you can start small and start transforming yourself. What I always say to senior leaders is think about a place where you’re not living up to your expectations, not achieving the outcomes you want.

You’re struggling, don’t have an idea how to solve a problem, and then go and write that challenge down, and then go and find someone you trust, and ask them, on a scale of one to 10, how well do they think your existing behaviors are driving results towards solving that challenge? Let’s say that person gives you a six.

Then I want you to ask them, well how can I just get half a point better? What ideas would you have that I could go from a six to a six and a half? Get them to brainstorm a few ideas with you.

Then I want you to pick the one that’s a little uncomfortable. Not totally uncomfortable, just one that feels a little outside your comfort zone. Try that behavior for a week, and then go back and check in with the person again and ask them, hey, this is the challenge I was trying, here’s some new behavior I tried.

On a scale of one to 10, how would you think that that’s impacted most trying to solve that challenge? Then ask them again how to get half a point better. I guarantee you if you get into that process, that system, you’ll be amazed at some of the results you achieve.

Key takeaways

  • While knowledge grows, it sort of becomes obsolete as reality changes. Thus unlearning stand for learning new knowledge but discarding obsolete or misleading knowledge.
  • Disruption doesn’t happen to organizations but it applies to individuals. Because organizations are led by individuals.
  • Just like a product has features which you need to continuously innovate to stay relevant in the market, humans have behaviors, which needs to be continuously innovated to stay relevant in the market
  • You need to be curious, you’ve got to own the results, and be committed to being comfortable with being uncomfortable and create safety to succeed.
  • You have to adapt your behaviors to the context and the company.
  • You need to build a generative organization
  • Master a growth mindset, which enables you to understand you can improve in the process of unlearning.

And most of all think big, start small, learn fast!

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