Learning to Unlearn: Changing the Behaviors That Hold You Back

29 August, 2019 | 23 min 48 sec
Podcast Host Sam Massey | Podcast Guest Barry O’Reilly
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Brief Summary

Many of us are guilty of clinging to once-useful mindsets and behaviors, that were effective in the past, but no longer serve us in today’s rapidly evolving world. Executive coach, Barry O’Reilly shares how leaders can unlearn their outdated behaviors to take the next step forward for more effective leadership. If you are a business or tech leader, seeking practical approaches to evolving your organization into modern digital businesses, this is the podcast for you.


I’ve worked with amazing leaders all over the world. I came to realize that what was holding them back was not their ability to learn new things, but their ability to unlearn the existing behaviors- that had made them successful up until that point- but were no longer creating value. 

The world is changing. Customer demand is changing. Technology is changing. If you haven’t built the capability to react to these changes, at some point in the future, some of your behaviors will no longer work for you, or create the outcomes you want to achieve.

The biggest role of leadership is to role model the behaviors you want to see others in the team exhibit, which has a network effect. If leaders experiment and try new things, and share what worked and didn’t, others in the company will start doing that too. 

So, successful leaders are great experimenters. They are constantly looking for opportunities to get outside of their comfort zone. They think big, but start small to experiment and iterate their behaviours in an intentional way. 

Knowledge used to last a lifetime. Not anymore. If you think of knowledge as a cup, and keep pouring new knowledge into it, it starts overflowing. You need to empty some of it and re-fill it with new stuff.

You need to adopt a system that allows you to continually identify and adapt to changing circumstances- recognizing what behaviors are working- and doubling down on those- and what behaviors are holding you back- and unplugging those for now. 

One of the biggest obstacles for experienced leaders, is their own expertise, because they believe that their own assumptions are always correct, since they have usually been in the industry a long time. Listening to the customer and acknowledging what they tell you, is vital.

Trying to do too many experiments or changes on yourself in progress limits your ability to change. Choose one or two things to experiment with so that you are able to correlate outcomes with that change.

Sometimes leaders don’t believe that they need to change. Their feedback mechanisms tell them that they have been promoted for a reason, or their metrics are good. So they can be complacent about the need to change. But a disruption in the business world can happen overnight- so becoming comfortable with being uncomfortable to keep sharp and reducing learning anxiety is critical.

My biggest unlearning in working with leaders was recognizing that I don’t change companies; companies change themselves. I can give advice, support and counsel, but I needed to realize that the ones that transform are the ones that do the work themselves. 

Podcast Transcript

Sam: Many leaders are guilty of clinging to once useful mindsets and behaviors that were effective in the past, but no longer serve them in today's rapidly evolving world.

Marshall Goldsmith hit the nail on the head when he said, "What got you here won't get you there." So what needs to change to be an effective leader in our modern digital future?

Welcome to Pragmatism in Practice, a podcast from ThoughtWorks where we share stories of practical approaches to becoming a modern digital business.

I'm Sam Massey. I'm here with Barry O'Reilly at our executive event, ThoughtWorks Live UK. Barry is a business adviser, entrepreneur and author of Unlearn: Let Go of Past Success to Achieve Extraordinary Results and co-author of the international bestseller, Lean Enterprise. He's pioneered the intersection of business model innovation, product development, organizational design and culture transformation. A former ThoughtWorker and longtime friend of ThoughtWorks Barry is here to talk to us about how leaders can unlearn their outdated behaviors to take the next step forward for more effective leadership.

Barry O'Reilly: After we published Lean Enterprise, I was going all over the world and had opportunity to work with these amazing companies and leaders. What I constantly found is, although we were teaching them these sort of new behaviors, and that was hard. The thing that constantly held them back was not learning new things, but unlearning their existing behaviors and behaviors that had made them successful to that point.

It's hard when you're sitting down with like an executive, top of their discipline, chief product officer, chief technology officer. All their feedback mechanisms are telling them, I'm doing the right things. Look, I've been promoted to this role, so why would I change my behavior?

But I think this is the thing of recognizing that externally a customer's demand is changing, technology's changing, your environment is changing, even internally. The way that made your company successful when you were 10 people, 50 people, 500 people, 5,000 people. It's constantly changing.

So if you're not innovating your behaviors to adapt to those changing circumstances, that's where you can get into trouble. So you've got to learn. We've also got to unlearn. And that was the sort of real inspiration for me.

Sam: You made a really good point in your talk this morning, which was about not transforming the way that you think, but by transforming the way you act. Why must we unlearn what we've learned? We've been successful. People listening will be thinking, 'I don't need to change. The results look good. The line points up. Why do I need to change?'

Barry O'Reilly:I think the thing to recognize there is, that's a moment, and you might be there for a period of time, but you're not always going to be there. The world is going to change. Technology is going to change.

So if you've not built the capability to adapt to circumstances, if you're just holding on to this is the way I do things, at some point some of those behaviors are not going to work for you. So you'll be using a set of behaviors that won't drive the outcomes that you want. And then you'll start getting frustrated with people. 'This used to work here.'

Very simple example is often when startup founders come into companies. It's a couple of few people. They are getting stuff done. Then more people join the company and things get a little slower. It's harder to do. They always go around Carter's and go we used to get stuff done around here, but the company has changed. The way you operate probably has changed.

But those leaders are probably using the same behaviors they used when they were startup. When there's only three people everyone knew exactly what they're building. They're not communicating to people like what our vision and mission that we're trying to achieve. They value output in terms of success. And really what they need to do is they start need to unlearn themselves because at the start maybe shipping stuff was great, but now they've got people that are new to the company and won't know how the company operates. So they need to start thinking about what's the actual outcomes and they need to not measure their success in terms of how much stuff they've got done. It's how much stuff they've allowed other people to get done.

So these are like very subtle shifts in behavior that need to happen as a leader when you're sort of scaling up companies from startup to scale up to these enterprise organizations. And a lot of the behaviors that made you successful in one moment or one paradigm can actually limit your success as you move to new paradigms, new situations and new circumstances.

It's one of these reasons why you've got to get really good at identifying what's the outcomes you're trying to drive and are the behaviors you're using driving those outcomes? Because if they're not, it's not the other person's fault. It's not that team that needs to change. It's you that needs to change, you need to own that.

I think what I find with leaders who have that sort of aha moment of that insight that they start to recognize the way they change companies is role modeling the behaviors they want to see other exhibit. That starts to have this sort of network effect. People start copying what leaders do. So if leaders are constantly experimenting, trying new things, sharing what's worked or not worked for them, everyone in your company is going to start doing that.

Sam: Do you think that's the secret to success for when you see or when we see companies that are doing extremely well or they're the buzz company of the moment? Do you think it's because of the inherent leadership style that they've adapted? Is it because you think these types of leaders have learned how to unlearn, or is there a bit of luck in there, or is it the business model or is it the product? Do you think that the success of those businesses is actually on the shoulders of the leader?

Barry O'Reilly: I think when you're in a big company, we hold up these leaders as inspiration for us. What are their behaviors that they're doing that are making them successful as a leader, right? Everybody wants to codify everything. Everybody wants to small steps, sort of three things that I can do to be Jeff Bezos. Do you think there's only three things Jeff Bezos does to be who he is? But what these leaders really cultivate and what I'm noticing the more I work with them is they're great experimenters. They're constantly looking for opportunities to get outside their comfort zone. I sort of call it, they're comfortable with being uncomfortable. They're actively creating scenarios where they's sort of at the edge of their excellence. They're sort of pushing themselves to do something a little bit more tougher, a little bit new for them.

But the way they manage that is they're really good at designing sort of safe to fail experiments. They think big, but they start small and learn fast what works and what doesn't, so they can iterate very quickly.

So just like a product has features and you need to constantly innovate the features of your product for it to stay relevant in the market. I think great leaders are really good at iterating their behaviors to adapt to the market that they're in, trying things and seeing what works and what doesn't.

Often people think that it's just intuitive or it's magic. But what I've learned is it's actually very intentional and it's deliberate. When you start to make that system visible to people, then it can be system they can learn.

That's what sort of got me to this concept of unlearning and turning unlearning into a system that people could recognize when they need to unlearn when they weren't driving the outcomes that they wanted. Relearn with small new behaviors and experiment with what works for them to get the breakthroughs that they want in their performance, their behavior and results.

Sam: It's kind of scary, right? What you're asking here is for our leaders to take quite big leaps of faith at times on their own belief system. And then at the same time trying to relearn some things that are completely new to them when they may have 30, maybe 40 years of experience. We're asking a lot, right? We're asking a lot of our leaders when we do this. I'm interested in how do we get there? How do you get there when you embark on this journey with an individual?

This is a challenge for a lot of people, right? If you feel like you've invested all this time and energy into learning a discipline and then someone tells you, "Oh, you need to unlearn that." I get a lot of pushback. People get quite upset. They sort of have some learning fallacy of some description or they feel like knowledge used to last a lifetime. Why doesn't my knowledge last a lifetime?

Really the way I describe unlearning is it's not forgetting, throwing away. It's actually moving away from once useful mindsets and behaviors that were successful in the past, but now limit your performance. So it's the active part of taking in new information to inform decision making and action. It's not like your wall is just built as high as it can and you just keep building it as high and high and high. It's recognizing that this wall is going to need to change. I'm going to need to put some parts in. I'm going to need to take some parts out. It's an adaptive thing.

You don't just think of knowledge as a cup and just pour new knowledge into it. It starts overflowing, right? You've got to empty some of it and then refill it with new stuff. So, where you need the system to recognize what are the behaviors that are working, let's double down on those. What are the behaviors that are holding me back? Let's take those out for now. This is all knowledge and experience I have. I might need those behaviors in the future because circumstances might change.

So really what I need is a system to recognize what things to plug in and what things to unplug. If you can build this capability to like continuously adapt rather than be fixed on a set of behaviors you'll only ever use, that's the real power of the world we're in now. Like everything was going to change. Things that we think will be happening in two years time and will happen in a month. Things that we think will are 10 years away end up happening in a year. Right? So it's recognizing like how do I have a system to continuously adapt my behavior to changing circumstances? And that's a super capability to build.

Sam: I was going to say incredibly challenging, right? For the individual and there must be... You've got some great examples actually in your talk and in the book as well. As an individual, as a leader, when you come to work with these people, what are the obstacles that they're facing? What were challenges? How are they going to overcome those big leaps of faith that you're asking of them? What are the biggest obstacles for them?

Barry O'Reilly: I think one of the biggest obstacles for leaders, especially experienced leaders is their expertise because they believe a lot of their assumptions are correct because they've been in the industry for 20 years.

So one of the stories I was sharing at the talk today was from International Airlines Group. They own British Airways, Iberia, Vueling, Aer Lingus. They're the sixth largest airline group in the world. When we took their senior leaderships out of their business for a couple of weeks, one of the sort of first ideas when they came back to innovate the business was a CTO of one of the operating companies was like, "I have the perfect idea to build this new ticketing platform. I've been in the industry for 20 years. I know how it works. We just have to build it like this." The way we sort of help them sort of unlearn, instead of pushing their ideas onto people, how do they pull them from customers.

So they sat down and built a prototype, showed it to a customer. Customer thought it sucked. Their initial reaction was, "Well, this customer is wrong. I'm the expert here." And then we did it again. Same results and again and again. Then we sat down and reflected and we're like, "What do you think is the problem here?" And the exec was like, "The idea sucks."

That was their unlearning moment, right? They recognized that they were pushing their ideas onto people. And that's very typical for leaders, right? People are asking you, "Tell me the answer, tell me the answer, tell me the answer." You've probably become a leader because you've been used to telling people the answer. That's your competence. It feels good. But in this moment, it was recognizing that they actually needed to pull the ideas and that exec went on to be one of the best experimenters that I've ever worked with because it reactivated their curiosity.

They started to see a lot of their assumptions actually as hypotheses and how quickly they could test those hypotheses to find out what worked and what didn't. I led them to learn quickly what would work and what wouldn't. They went on to be phenomenal, right? They started setting up and testing all their business strategy and getting customers involved.

My favorite example was a couple of weeks after the camp that they sent me an email. Someone from their team had come in to their office and they were like, "Hey, we've just got this new product ready to launch, would you sign it off?" And the exec was like, "Why are you asking me to sign it off? It should be out in the airport and get customers to sign it off."

It just showed that sort of journey that they had gone on and how it did shift... That, those new behaviors, had actually shifted their mindset, which also shifted their behaviors when they went back into the company. So instead of signing stuff off, they were getting their teams to get customers to sign stuff off.

Sam: How do you go about maintaining that style of leadership, because I'm sure you've probably heard the success stories and then us human beings, we kind of fall back into a safe place often. How do we go about maintaining this constant iterative way of thinking to test and learn constantly? How do we keep going with that?

Barry O'Reilly: I think one of the tricks... First and foremost is you've got to get good at describing outcomes for people, not outputs. So not talking about what you're going to do, talk about what success is and then you can figure out things to do to try and get there. That's a very simple thing.

The other part is trying to do too many experiments or too many changes on yourself in progress actually limits your ability to change. It's better to have like maybe one or two things that you're working on. So when you try something new, you can actually correlate is a new behavior driving the outcome that they want?

If you're changing like 50 things about yourself, say you're trying to get healthier and you're running more, changing your diet, you're having a few cheeseburgers, you're probably having a few beers, whatever it is, there's so much stuff happening. It's very hard to correlate to say what's helping me go forward or holding me back.

So I think just getting very deliberate thinking big. Again, starting small, trying one or two things. Try it for a week, see what happens. Try a simple experiment.

For the listeners out there, think about something that you probably think you need to unlearn or somewhere where you're not living up to your expectations, right? Write it down and then go and find someone in your company and say, "I'm trying to improve in this area. On a scale of one to ten, how well do you think I'm doing there?" Say, they give you a six. Thank them and then ask them how could you just get like half a point better in the next week? What are some behaviors do they think you could try. Write them down together and maybe pick one that's just like a little uncomfortable and just try it for a week.

Maybe instead of telling people the answer, ask them, "What do you think?" Very simple behavior, but you'll learn a whole new lot of stuff and go back and then check in with that person in a week later and say, "Look, I've tried these new behaviors. What have you observed on a scale of one to ten, where am I now? How could I get half a point better?" Again, I guarantee you if you get into that cycle, you'll be amazed in the results that you get.

Sam: That was a great advice. I think we're all going to try that point system for ourselves. I think it's probably something that we are so wrapped up in everything else in our day to day, BAU, whatever you want to call it, that we forget to sometimes reflect. I'm sure there are a lot of people out there who do a lot of self reflection, but then are struggling to maybe put some practical things into place. I love that one of asking someone as if they were their customer, a real team member, how can I improve my on my six? I hope I'm more than six.

Barry O'Reilly: The question is, how can you get to a seven?

Sam: Right. Okay. Maybe you have a four, we'll see.

Barry O'Reilly: Yeah.

Sam: I mean, I love this practical advice as well. Your exec camp and that's something you've started, your CEO of, People have obviously taken that leap already. They know they want to change. How do people go about when they're not thinking like that already, where can they start to sort of change the way they're doing things, change their mindset of, "I don't think I need to change it. I think I'm good. I'm thinking I'm happy and everything's fine."

Barry O'Reilly: Yeah, I think it's tough, right? A lot of the feedback mechanisms for a lot of leaders is they're the chief something that head of something, right? So they're promoted to the highest level in the company. All their financial metrics and dash cards are green or growing.

Disruption in the business world as we've already seen can happen overnight. You could imagine if you were in a telco company five years ago, three years ago, WhatsApp only launched in less than four or five years ago and they've obliterated not only the SMS market, but the international calls market, right?

The industries can get commoditized overnight. I think a lot of those executives would have been sitting in those meetings, seeing their revenue from international phone calls as the world got more connected, their revenue from text messages just going up in to the right and complacency then sets in.

I think it goes back to the thing I've observed with these great leaders is that they recognize that it's only a matter of time until something changes. So I need to build a system that helps me adapt to change. And that's why they're always seeking out these sort of uncomfortable situations for themselves because it keeps them sharp. It peaks their survival anxiety, but it also reduces their learning anxiety because they're used to trying new things. So they're actively designing a system to sort of keep them match fit or ready to respond.

Sam: What about when as an individual, someone might take that step and say, I'm prepared to do it. I'm unlearning. I'm unlearning all the time. I really wished this person would, my team could also listen or maybe read some of the things that you've been talking about. How would you go about taking your team members on the same journey with you?

Barry O'Reilly: Well, I think the biggest role of leadership is to role model the behavior they wants to see other people in the team exhibit. One of my stories that we include in the book is the CEO of a massive bank in America. He's asking the company to digitally transform, to go agile. And then in most organizations, that means, right, you're all going to go agile. I'm just going to keep doing what I would always do. But him and his leadership team were like, well, if we're asking the team to go agile, we should start working in an agile way. We started coaching them about how to do everything from sprints to retrospectives and reflection.

So we did this for a month. I did the first retrospective and it was amazing. He goes up and never done a retro in his life. Puts a post it note in the wall and it says, "Agile is hard." The team, literally, were gasping. What does that mean? Are we in trouble? Do we not do right? He went on to share that and he thought that they were being agile, but he realized every week in their status meetings, they were just ticking off tasks. They weren't seeing where they were achieving any outcomes, like increasing customer retention by 5% or growing customer product purchasing of their own products by 10%. They weren't thinking and outcomes and that meant that they weren't being agile. And the team were sort of gasping in horror.

But then what he did is he went back to his desk and then he wrote an email with the title, agility is hard. And then he sent it to 50,000 people in the company and he's like, "Hey everybody, we're asking you to go agile or create business agility. We tried to do it as a team and guess what? We figured out it's really hard, but here's some of the experiments we're running. Here's the things are trying. Good luck everybody out there, keep trying hard. We know it's hard." And that immediately humanizes that leadership team that everyone who's done sort of in the guts of the company trying to make stuff happen. Who knows this is hard. It's like, "Wow, the leadership team are doing this? Maybe I'll try." It gives agency for people to not be afraid to try new things and some work, and some not work and adapt. I think that's the most powerful way to be. Just not tell people what to do, show them. I think that's one of the big differences.

Sam: Incredibly empowering for those 50,000 people to go on that journey with that leader and good for them for sending that email.

Barry O'Reilly: That's amazing, you know? They are like the poster child for technology innovation in the banking sector. Like Amazon, I want to speak about them all the time. They're killing it.

Sam: Before we wrap up, I want to know about you and your learnings in unlearning as you've gone on this journey through the examples that you've given in the book, obviously, are fantastic.

What for you, have you found is the biggest learning as you've been working with leaders and an organizations?

Barry O'Reilly: I think one of the big learnings for me was recognizing that I don't change companies. Companies change themselves. I work with leaders to give them information, give them advice, share experiences, counsel, advise. But the ones that really transform are the ones that do the work themselves. I think that's been very interesting for me is how I learned to step back and create the circumstances to let change happen and let change be owned by the people who need to lead it versus me trying to get in there and make it happen.

Sam: Right.

Barry O'Reilly: It's sort of my version of output. Me doing stuff, flipping to more outcomes is how can I make other people successful in the things they want to achieve. So that's been a good unlearning for me.

Sam: Enjoyable one probably as well.

Barry O'Reilly: I think all these things, right? I'm a big believer in putting yourself in these comfortable with being uncomfortable, right? I'm constantly trying new things. I'm doing podcasts now as well. I'm building software to help people to use this system of unlearning, which has been amazing, right? As you start to see people use software, you see their behaviors, you gather data about what works and what doesn't. And that helps me informed my thinking and build more stuff.

I'm just extremely excited to see where all this goes. I'm going to make mistakes, I'm going to learn, I'm going to unlearn, but hopefully I'll have some breakthroughs along the way that leads to some good results.

Sam: Barry, thank you so much for joining us on the Pragmatism in Practice podcast.

Barry O'Reilly: Oh, it's been a real pleasure and I'm looking forward to hearing people's stories of unlearning.

Sam: If you enjoyed listening to that interview, be sure to check out Barry O'Reilly's presentation from ThoughtWorks Live. Re-imagining the future organization. Driving perpetual evolution at

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