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Barry O'Reilly

Why Great Leaders Must Unlearn to Succeed in Today’s Exponential World

There’s a learning curve to leading any successful venture. But when leaders begin to rely on past achievements or get stuck in outdated thinking and practices that no longer work, they need to take a step back ― and unlearn.

This innovative and actionable framework from Barry O’Reilly shows leaders how to break the cycle of once-useful but now limiting mindsets and behaviors that were effective in the past but are no longer relevant in the current business climate and may now stand in the way of your success.

Unlearn: Let go of past success to achieve extraordinary results is a transformative system that shows leaders how to rethink their strategies, retool their capabilities, and revitalize their businesses for stronger, longer-lasting success.

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Barry O'Reilly, Business Advisor and Entrepreneur, Author, and Pioneer of the intersection of business model innovation, product development, organizational design, and cultural transformation.

Jason Turner, Lead Product Designer, Kin + Carta (moderator)

Setting the Scene



The 1918 influenza pandemic, known as the Spanish Flu, was one of the most severe pandemics in human history. It's estimated that about 500 million people, about 30% of the world's population, actually became infected by the virus. The total number of deaths was estimated at 50 million worldwide.

At the time, there were no vaccines to protect against the influenza infection. There were no antibiotics. People had to come up with very simple, modern, innovative approaches to isolation and quarantine and good personal hygiene to get over the pandemic.

The Spanish Flu is really a product of its time. In 1916, we were still in the grips of world war one and there was actually a lot of censorship between Germany, UK, France, and the United States. However, Spain was a neutral country, and their press was open. They were sharing data about what was happening, and the King of Spain was one of the first sort of well known people to become infected by the virus. That's how it became known as the Spanish flu, even though it had been everywhere throughout the world, but the information was suppressed and people weren't sharing it.

Most people will say that we're probably experiencing some sort of a disruption at the moment, but, in reality, this is not actually a disruption. COVID-19 has actually been an accelerant of change.

Now, organizations must build platforms that can learn rapidly about how their customers work with them and unlearn what didn't work. They will need to build new products and services that meet the moment. However, most leaders live in a very linear mindset. We believe the things that made us successful in the past will be the things that make us successful in the future. We think our businesses will just keep propagating the way they always have and our skills remain relevant.

Unfortunately, innovation happens a lot more like this: You have new technologies or services that somewhat look deceptive and then suddenly they gain traction, leading to massive acceleration. You can even look at the S&P 500 and the centralization of value that’s happening right now. The organizations that have invested in technology to scale their business are centralizing that wealth. For example, Shell, who's primary, a commodity is oil, has actually gone to zero.

This moment is an accelerant to a digital world, something that is especially relevant to individuals. Just like products have features that need to be updated routinely, people have behaviors that need to be adapted to market trends. Many people are actually experiencing that for the first time, and it's uncomfortable. Therefore, organizations that have invested in and cultivate the capability to explore uncertainty are the ones that are accelerating.

I've coached hundreds of executives and leaders all over the world, and I've learned that it's important to develop a system for recognizing your limiting behaviors and beliefs. It’s possible to take small and somewhat uncomfortable steps to explore new behaviors, and to find out what might give you the breakthroughs that you need.

The Process of Improvement 



To begin, I'd get you to think about focusing on yourself. Maybe an aspect of your own work or your life. Whatever you're more comfortable with. There's a couple of characteristics that are really key for leaders. If you're actually going to truly unlearn.

The first one is curiosity. I coach the leadership team at HSBC, and, when the heads of global markets would go down and sit with the graduates when they came in every year, and he'd give them problems to work on that he was working on. Because he wanted to see how they would try to solve those problems. He opened himself up to new learning experiences, and you can imagine the cultural artifact that creates in a very large organization like that when you have the most senior people sitting with the most junior people, actively learning from them.

The next value is ownership. If you’re not getting the results you need or you want, what's your natural reaction. If you're blaming someone else or blaming the team, you simply can't improve. You've got to own the results. Considering what you can do differently is a super powerful, unique commitment to actually do things that you're going to struggle with. You're going to be developing new skills that are not your competencies, so you need to commit to that and recognize that you're going to have to get comfortable with being uncomfortable. We help you do this by creating safety to succeed and starting small, making it safer to fail.

Examples From Today’s Businesses



I want to give you a few good examples of companies that I've collaborated with over the last few years. I want to give you a sense of why they're succeeding right now. They're doing something that's different from what most organizations are doing or what most people have been conditioned to do.

First, you need to act to succeed in uncertainty. For many, our natural reaction when there is some sort of disruption or change or an unanticipated event is to freeze. We cut the budgets and pull everything back and wait and see what happens. Unfortunately, waiting and seeing is the way to failure. In chaos and uncertainty, the only way that you can get new information to understand how your business may operate is you have to take action. The way to fail is to stop, to pause, to wait and see. The way to succeed is to act and learn your way through the uncertainty. I think what you've seen of some of the organizations that have really powered ahead have done this.

The classic example, probably everybody understands at the moment, is what Eric Yuan is doing at Zoom. They've literally gone from 10 million to 200 million people in 12 weeks. In many ways, it exposed a lot of the vulnerabilities of their platforms. Their business was not designed to cope with that demand to scale. They've had frailties, and it has broken, but I think the thing that has really shown and stood out about Eric's leadership style is that he's owned it. He hasn't hid behind anybody else. He hasn't pointed at other people about what was wrong and whose fault it was, and they've actually owned the issues. They’ve been doing this from the moment that their platform started to scale way back. Even in March, he's been actively out in front, talking to customers, recognizing the ability that they're having failures and that they're having security issues. Most importantly, they've responded.

You can see even just from this simple example, throughout March, every week, every few days, they've been rapidly making small changes to try and improve their product in the face of uncertainty and usage that they could never have anticipated. And this is what great leadership is about. It's not about hiding behind failures. It's actually owning them being more authentic and actually getting out in front of them. Eric now is doing weekly CEO webinars where he's out in front talking to people about the challenges that they're also facing in their platform, owning us being open and honest, and actually building more goodwill through the community because they're actually responding to feedback as best that they possibly can.

How can you really be at your best in a crisis, and what are those outcomes that really matter to you?

One of the things that they've done about transparency and openness is they've had to really lean into their values. They're not just words painted on a wall. By owning the results, both the positive and the negative and continuously responding, they're making progress. They're striving for excellence rather than trying to be perfect. And I think this is a really powerful trait as you build this capability to rapidly respond to uncertainty and then lead with authenticity and honesty.

In contrast, many organizations are sort of trapped in a legacy world. They're still holding on to the notions of output in terms of what they measure of success instead of evaluating outcomes that are extremely hard to measure. And yet that's the direction you want to aim for.

Rewarding Innovation



Much of our existing organizational design is still based upon the Industrial Age. This is a very simple model around the principal agent problem, which involves paying for performance. We have this notion that the principal and agent is essentially the idea that a principal hires an agent to perform a task for them, and, if the agent performs the task, the principal offers a reward.

This arrangement is common, but it’s wrong. It's based on a contingent relationship. and once you offer people a contingent relationship, they just look at the “get” side of the equation. It's a real challenge.

High performance organizations focus on measuring outcomes because they're hard to measure. Output is easy to measure, and this is one of the reasons why most organizations actually fall and fail in a lot of their transformations. Most people are measuring lagging indicators that are outputs, user story points, burn down charts, velocity, revenue, but they're all lagging indicators based on outputs. They're not talking about outcomes, which are real changes in human behavior. Leading indicators to tell you people are potentially using your product that you want. And yet organizations are rolling out these ridiculous frameworks and capability models that just are copying and pasting a fixed set of behaviors onto complex systems and expecting them to win.

I work with the leadership team of Capital One, and I think one of the things at the top of the organization is Rick Fairbank got really clear about defining the outcomes that they were aiming for as a business. They wanted to increase the percentage of customer investments and our rates of product innovation. They also wanted to be a place where people can do the best work of their lives.

These are all objectives that he set at the top of the company. When you start to work in that organization, depending what part of the bank, you've got a lot of rope, your efforts to tie into these outcomes and ask questions like, well, how, if we're going to increase the customer investment with the bank, what kind of new products and services are we going to have to bring to market? And if we're bringing them to market, how are we going to be able to do that faster? This spins up a whole different type of conversation.

They realized that digital transformation is really talent transformation, but you need to define the outcomes that you're aiming for to know that you have digitally transformed. When you start to define outcomes, it starts to open up a lot more experimentation.

One of the things that we discovered, particularly at Capital One and with a ton of transformation, they knew that they were going to have to adopt cloud innovation to get there. Typically, most organizations were building cloud maturity models and explaining this journey to get there. Unfortunately, that needs to be unlearned. It's just a pure narrative. It's a sales tool. What we actually developed really at Capital One is understanding that once we defined how much of the infrastructure we wanted to have in the cloud and what was the actual cost savings that we wanted to have in terms of percentages, then we could really start to actually use data to understand what percentage of infrastructure was in the cloud, how much of a cost reduction that was having and how fast and more frequent we were seeing changes go into production.

Outputs are just a fallacy to try and justify your work. When you're talking about outputs, people are just ticking off tasks lists.I think that's one of the big challenges that most organizations are sort of struggling with. Some of the things for you to think about include “how could you unlearn if there were no real incentives or no financial incentives?”.

A Personal Application



One additional thing I just wanted to talk about was one small personal sort of story. Four weeks ago, my son was born here in San Francisco. I had never been to the hospital in over nine months due to the issues around COVID, but we also signed up to a tele-health pilot as part of the process. This has given me a real glimpse into the future of healthcare. The hospital sent us loads of devices that we could record all the telemetry at home, take measurements about his growth size, his weight, my wife's weight, healthcare measurements, and provide all that data to doctors in advance.

Our checkup times dropped by 75% because we were providing them so much data in real time. Even now that he's come home, we're continuing to send that data to the hospital in real time and they're synthesizing and processing it. They’re actually making better, more efficient decisions.

This is a real glimpse into the future of what healthcare is going to actually look like. However, nobody would have embraced tele-health because they were too scared. It was uncertain. How could we provide good care? In reality, we're providing higher quality of data on a regular frequency, both qualitative and quantitative to let doctors make better decisions and actually deal with more patients.

It’s truly interesting to see that pattern start to happen. So again, what can you sort of do to think big and start small and unlearn today? What I would say to you is this is quite simple to find someone you know and trust, write down and share the challenge that you wrote down at the start of this talk, explain to them what you're trying to unlearn and ask them to score you on a scale of one to 10.

Maybe they'll give you a six and maybe you could just ask them to get half a point better and they might give you a few new behaviors you could try. Why don't you just pick the most uncomfortable one, try it for a week and then go back and ask them “how do you think I've progressed based on trying that new behavior?”. You might be amazed at the results you get as you start to do that.

It's been a real pleasure to start coaching people to unlearn sort of all over the world. Pandemics are only going to increase the rate of technology. Innovation is only going to increase, and, if we're going to actually solve some of the bigger challenges that we're trying to face, not necessarily just solving for this pandemic but actually thinking about how we're going to think big about real societal problems we're facing right now, we need to start small so we can learn fast and really start to challenge some of the much bigger challenges we're facing at both to be social challenges that we're facing today in the United States or these global grand challenges that we've all got to solve together.




CEOs have a deep rooted investment in their own principles. If you work under a CEO who has that kind of deep rooting principles, is it a waste of time to think about trying to change?


Yeah, absolutely. I've a bunch of stories like you can imagine most of the people I coach are like fortune 50 CEOs. And when I walk in, they're sort of like, well, what the hell can you teach me about my domain? My job is not to teach a banker how to be a better banker. They're great bankers. What I teach them is to get better information, to make better decisions and actually create a better bank. I think one of the things that are really important if you're going to try and shift people's mindset is they have to experience a situation where their assumptions are unclear, so I coached a leadership team of a very well known phone manufacturer here in California. And they've been releasing their phone for over a decade and they really understand how to push it out into the market and what works and what doesn't so what I did with them is I got five of them. I gave them a credit card with a thousand dollars on it, and I told them they have to go out and sign up to buy their own phone within two hours which is like the KPI they'd set themselves. So this is really small. It's just five of them. The whole company doesn't know it's a sort of safe little experiment. So five of them went out, and only one of them was able to actually complete the task.

Another one nearly did and three failed. Initially, when they came back, they were angry. They were blaming the tellers. They were blaming the card. But actually, when they started to sit down and reflect on it, they realized that these were gifts like failures in the system, as they thought it operated as signals that it was not operating as they planned. That was actually a gift, a new insight for them about how they could improve their systems, build better systems and build better products. I think creating these small little experiences that are safe for leaders to actually unlearn that their assumptions are incorrect and that there's a potentially better way to do things and is key, I'm letting people experience that. Don't talk to them about it, let them experience it. That's the kind of scenario I'm always trying to create for leaders to create what I call an “unlearning moment.”


What's it like for you seeing people on that journey, you must get quite a broad range of reactions out of people at that level?


Yeah, it's absolutely a privilege. One of my key KPIs is like a lead time to aha moment. I often describe it when my consulting work is how quickly can I help these leaders have an aha moment? Or I never thought of it like that before. And like what's really powerful with the great leaders is they don't get upset. They don't think I'm trying to make them look foolish or trick them. They realize that I'm showing them signals that their assumptions are incorrect. I'm teaching them a system to rapidly test their assumptions, to find out which are true or which are invalid and then respond with a better solution, a better product, a better system. And that lets them accelerate. Great leaders understand that, but the old archetypes who think are no dolls and struggle to have humility and vulnerability, they struggle. And I tend not to work well with them or not work with them at all. So it's interesting cause you're, when you're doing those experiments, you're basically in a very kind of quick way forcing them to get on the unlearn relearn breakthrough wheel.


During the COVID-19 pandemic. How can we all embrace new and exciting ideas from neuro diverse thinkers who might have the answer to our challenges right now?


What we know is that the more options you spin up in an innovation it's called optionality and rapidly test those options as quickly as possible, you'll ultimately win. And that's why I think these sorts of examples where people are thinking about cross-discipline, they're trying to open up these problems and solve them in innovative, interesting ways. This is where we're going to have these massive breakthroughs and leaps forward and in both our thinking and our behavior and what we think actually success can be.


Do you have any tips or inspiration of how we can empower and inspire managers from the senior level up? Are there any examples or activities you could think of that people would use?


I think obviously if you want to do it, there's tons of them in this book, actual examples of and you'll see here, like I work with executives at Vanguard, at Hilton, at NASA, at Amazon, like these are organizations and leaders that are actively putting themselves outside their comfort zone. One of my favorite examples at the moment was actually the head, the CIO for Volkswagen and everybody in the company was like, “Oh, it's easy to be an executive. You just sit around and go to meetings all day. You just started hanging out.” And so he did something quite bold. He decided to let someone be CIO for the day so anyone in the whole company could sort of pitch it, like put their hand up to be the CIO for the day. And a two year graduate was the one who won it and he didn't even own a suit. He had to actually go out and buy a shirt to pretend to be the CIO for a day. And he went to every single meeting that the CIO would have had to be. He had to play that role. The actual real CIO just sat in the back of the room and observed what was happening. Unlearning happened on both sides. The whole organization going, wow, this two year old graduate just reported back. Like what a day in the life for a CIO is actually like, and the CIO themselves got to watching his own job. These are the leaders that are going to be successful because they are leading from the front by showing up and being authentic. It's the reason why people like Eric are firing ahead because they're leading with humility and vulnerability and authenticity. If you're not willing to be humble and test your assumptions, I think you're going to find out where you're going to end up in that curve pretty quickly.

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