Why the Most Dangerous Barrier to Leadership Success May Be Success Itself

What if I told you that the behaviors that led you to success in the past were holding you back from success in the future? The idea feels a little unnerving—but that’s the point.

For leaders in today’s highly competitive and accelerating business climate, it turns out that relying on old behaviors, methods, and mindsets that worked in the past can become their biggest inhibitors to success tomorrow.

This is the big idea behind Barry O’Reilly’s recent bestselling book, Unlearn: Let Go of Past Success to Achieve Extraordinary Results. Unlike the trend of continuous learning for leaders, O’Reilly adds a new factor to the mix—unlearning, which he believes holds the power to push leaders into uncomfortable and unfamiliar environments where true breakthroughs happen. In fact, for today’s leaders, success may well depend on unlearning the past, he argues.

Barry O’Reilly is a business advisor, entrepreneur, and author. He is pioneering new business methodologies at the intersection of business model innovation, product development, organizational design, and culture transformation. As Singularity University Faculty for Entrepreneurship and Organizational Design and advisor within SU Ventures, Barry has fine-tuned a unique approach that helps leaders create cultures of experimentation and learning that can unlock higher performance and results.

We sat down with Barry for an interview about his recent book to understand how leaders and executives can use his system—The Cycle of Unlearning— as a tool to reveal blindspots, trigger breakthroughs within new and unfamiliar environments, and drive new performance outcomes for teams.

Unlearn Book Cover

Did you have a specific experience or “aha moment” that catalyzed your idea to write your recent book Unlearn?

I coach a lot of senior executives in Fortune 500 companies and also support leaders scaling their startups here in Silicon Valley. In my work I began seeing how critical it was for these executives and leaders to continuously adapt to the changing circumstances around them.

When you are the leader of a startup, for example, and you are scaling from 50 people, to 100, 200, and 500, each increment changes the way you must run your company. This means that leaders have to constantly learn new methods to make them successful at each new stage of their organization, while also unlearning many of the methods and mindset that made them successful in the last paradigm which may no longer be relevant in their new paradigm.

My aha moment was seeing how the importance and process of unlearning didn’t only happen once. I saw that it was a system, and that the more these leaders used the system, the more powerful it became. It turned into a unique learning cycle in which they could continuously adapt their behavior to the changing circumstances of markets, technologies, customer demands, and their own personal aspirations and outcomes they wished to achieve.

For those who haven’t read Unlearn yet, what is the main premise of the book?

For high performance individuals to improve, it’s often not their ability to learn new things that gets in their way, but rather it is their inability to unlearn their existing mindsets, behaviors, and methods, which were effective in the past but now are limiting their future success.

Today, we have exponential technologies that are radically changing the ways that problems can be solved. Yet people still hold onto their linear mindsets of what worked for them in the past.

The problem is that these mindsets will likely not work for them in the future. Leaders have to recognize when the information and patterns they learned in the past have become obsolete and need to be unlearned.

This is why leaders need a system of both learning and unlearning.

How do you define this process of unlearning?

I define unlearning as a process of letting go of, moving away from, and reframing once-useful mindsets and behaviors that were effective in the past, but now limit success for the future.

It’s not about forgetting or discarding knowledge or experience, but rather learning how to let go of outdated information and actively gather and take in new information to inform effective decision-making and action.

When leaders notice that their behaviors are not driving the outcomes that they want, that is how they can know it’s time to adapt their behaviors to meet the new circumstances they’re facing in order to achieve the desired outcomes.

Barry O Reilly

You start Unlearn with a fascinating example of how Serena Williams overturned her training approach and triggered a huge breakthrough in her performance. Can you expand on this?

What is truly exceptional about Serena is that she is getting better as she gets older, and this is largely unheard of in the world of professional tennis.

Even late in her career, she’s continually pushing herself to try new things and new approaches to training that are outside of her comfort zone, and doing this is enabling her to succeed and win. In fact, she’s been more successful in the last 10 years of her career than she ever was in the first 20 years of her career. She’s 37, and the average age of professional tennis players when they retire is 27.

Serena is a huge inspiration for the idea of unlearning in a sport. She is someone who is continuously challenging herself to improve, regardless of whether she has setbacks or is not achieving the outcomes that she wants.

She’s continually finding new behaviors and new skills to help her improve. You can read more about her process of unlearning in my blog where I share how she transformed her training approach by taking on an unlikely coach.

You write about the power of unfamiliar, unknown, and uncertain situations to catalyze performance breakthroughs. Why are these three conditions so powerful in how they fit into the unlearning system?

None of your growth happens within your comfort zone. I emphasize this point a lot to leaders:  they need to get comfortable with being uncomfortable if they want to grow.

The real problem here is that many people, and especially senior leaders, struggle with perfectionism. Many of these people are used to getting perfect results in their career. But if they always try to be perfect, they will never tackle the things that they know are unfamiliar, unknown, or uncertain. Instead they will stick within their comfort zone, but there’s no growth there.

What I’m always trying to encourage people to think about is that they need to focus on the big aspiration and outcomes that they want to achieve. But they also need to start small by experimenting with new behaviors in order to learn what works and what doesn’t for them and ultimately drive these outcomes.

When you think about the best leaders today in many organizations, they are constantly cultivating these characteristics in themselves and putting themselves in circumstances that are unfamiliar because it challenges them to grow. This is what great leaders do to get out of their comfort zone and continuously grow.

How can leaders know when there’s something they need to move away from or unlearn? What are some of the biggest obstacles to unlearning for individuals?

There are a few key signals leaders can look to that show that their existing behaviors are not working or may need to be unlearned.

These signals can include not achieving the desired outcomes, not living up to the expectations they have for themselves, avoiding a new challenge, or feeling they have “tried everything” and are still not getting the breakthrough they want. These are all signals that a leader’s existing behaviors are not working.

Of course, there can be many obstacles to the process of unlearning. It’s the beauty of the unlearning process that to unlearn you have to overcome these. Two obstacles I write about in the book are the desire to always be correct, and the lack of willingness to embrace uncertainty and instead choosing to stick with what’s comfortable.

As Singularity University Faculty today, how did you first become involved with the Singularity University ecosystem?

I was initially drawn in by SU’s bold mission, and specifically the focus on the global grand challenges and how technology can be used to solve them.

My first work with SU was in the context of  SU Ventures, which brings in advisors and mentors to help startups in their growth journey. I worked with a company called Active For Good with the mission to motivate people to become more active and healthy, while also helping malnourished children around the world.

Mentoring the Active For Good founders as part of  SU Ventures was a really rewarding experience, and I did it pro bono. While I was working with SU in this capacity, it became clear that my content was a strong fit for helping entrepreneurs scale up their business as well as for helping corporations improve their innovation. It was at this point that SU invited me to become Faculty for corporate innovation and entrepreneurship.

Was there something that initially inspired you during your journey early on with SU?

That experience working with Active For Good, which was tackling the Food global grand challenge, gave me the chance to gain an understanding of what SU was all about, meet a lot of really interesting people, and become inspired by the big ideas and thinking that are at the core of what SU does.

All of this happened while I was also collaborating with other amazing Faculty and staff at SU Ventures. That was really inspiring, and then eventually as Faculty I started to go out and represent SU by giving talks about exponential technologies around the world.

Barry O Reilly

Getting back to your book, unlearning in management is a large theme that you write about. Can you say more about this concept?

Absolutely. There’s an example in the book of unlearning leadership innovation with the executive teams from British Airways, Vueling and Iberian—airlines owned by International Airlines Group.

A group of executives left their companies for eight weeks with the goal of launching new businesses that could disrupt their existing company, the airline industry at large, and themselves, through a program I offer called ExecCamp. In this program, I take executives out of their comfort zones and try to get them to act like entrepreneurs—and in doing so, give them the tools to build and release new products to disrupt their existing companies.

For many of these executives, it’s very challenging. They aren’t used to being back on the front line of innovating their products and services. Instead, their day-to-day focus is usually on managing. Because of this, they have to unlearn a lot of their management processes and relearn new methods and mindsets such as how to create and test hypotheses for business ideas and products. Going through this process can be uncomfortable, but the results can be pretty breakthrough.

After the insights from ExecCamp, International Airlines Group along withBritish Airways, Iberia and Vueling ended up creating an entirely new initiative called Hangar 51, which is now a venture capital group and accelerator program that invests in startups seeking to bring new ideas to life in the travel industry.

The effort has been transformational for the airline group. Startups that have taken part in the program, such as Assaia, which use machine learning and AI to improve aircraft turnaround times, are already leading to exponential improvements in their service.  In fact, two years ago the company was profitable for the first time in the past five years, so this shows the powerful impact that unlearning in management can have.

What is an example of a mindset, behavior, or method that a leader might need to unlearn in order to achieve success in the future?

A classic example is when you’ve been a contributor on a team, and then you are promoted to become a manager.

Often as a team contributor, your competency is doing your job really well. If you are a software engineer, for example, you may be a brilliant coder, and then because you’re so good, you get promoted to be an engineering manager. Previously, success meant creating lots of output and getting all your work done. But now you’re responsible for helping other people get their work done, and probably doing less coding than you were before.

When the team has a problem, it’s probably within your comfort zone to jump in and fix the code. But that’s not going to help you have an exponential impact as a manager of the team. Instead what you need to do is to create an environment where other people on the team can have an exponential impact by becoming more competent and empowered to solve these problems themselves.

In this example, a lot of the behaviors that made a coder successful in the past are not the same behaviors that will lead to success as a manager in the future. Actually, they will inhibit success. This is a classic transition from contributor to manager where a lot of unlearning is needed.

What is one of the most dangerous barriers to success that ingrained behavioral cycles can cause?

I would say it is the danger of believing that everything you are doing is working.

Bill Gates once said, “Success is a lousy teacher.” What this means is that you learn the most when you start to recognize that your behavior is not actually driving the outcomes that you want. The more successful we become, the more afraid we may be to try something different, because it might jeopardize our successful track record. But the danger here is that by just sticking to what we know, we’ll never grow.

In that sense, the most dangerous barrier to success, is success itself.

Is there a call to action that you have to leaders who are reading this interview?

I would say leaders should ask themselves how they can start unlearning today. Think about a challenge in which they’re not achieving the outcomes that they want. Then I’d ask them to come up with five new behaviors that they can try—behaviors that are slightly outside their comfort zones—and then pick one behavior to try for a week to see if they get a breakthrough into the challenge they’re trying to tackle.

If people do this every week and continue iterating and experimenting with new behaviors, I believe they can begin achieving amazing results.

Thanks so much for taking the time to share your thoughts with our readers, Barry!

Thanks for the opportunity! I hope to meet more members of the SU community at future SU programs!