The Importance of Learning and Unlearning: A Q&A with Barry O'Reilly

04/29/20205 min read
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Barry O'Reilly
Chief Incubation Officer
verified iconExpert in Business Transformation
Nobody Studios
As founder of Outlier Venture Partners and ExecCamp, Barry O'Reilly generates higher growth and efficiency for start-ups and Fortune 500 companies alike.
  • Organizational Design
  • Business Strategy
  • Employee Productivity
The Importance of Learning and Unlearning: A Q&A with Barry O'Reilly

Join me–Paul Estes, editor-in-chief of–and Dean Bosche, head of partnerships from Toptal, for a new episode of Rise of Remote Live each Wednesday at 4:30 pm ET on LinkedIn.

This Week’s Guest: Barry O'Reilly is a business adviser, entrepreneur, and best-selling author of  Unlearn: Let Go of Past Success to Achieve Extraordinary Results and Lean Enterprise: How High Performance Organizations Innovate at Scale. Every day, O’Reilly helps the world's leading companies develop a culture of experimentation and learning. The following is an edited version of the conversation.

Q: In your book, you talk about leadership conditioning—the idea that we are byproducts of our parents, our first manager, and first work environments. How do you tell people who have spent 10 or 15 years working a certain way: Hey, it's time to change?

A: We are a byproduct of our environment, whether it's the leadership or personal role models we have. Every time we have been told, “This is the right way to work,” we incorporate that into ourselves.

How do you know what good is when you've only seen a fixed set of things? People who are serious about unlearning and relearning have to stay curious and actively put themselves outside their comfort zones.

For example, one of the most senior executives at HSBC had a practice of meeting with the new college graduates recently hired to the company. He’d give them problems he was working on to see how they would solve them. Now, when a senior person gives a junior person work and they start solving it in a different way, we typically say the junior person is wrong and the senior person is right. We shut ourselves down from learning.

Instead, at one of the largest banks in the world, the most senior people sit down with the most junior people to learn and unlearn how to tackle problems in a different way. You can imagine not only the cultural artifact that creates in the company but the curiosity that leader is role modeling. He’s conditioning the person he's collaborating with and the rest of the company about what good looks like.

When I work with these amazing leaders, the characteristics that stand out are curiosity, a willingness to get comfortable with being uncomfortable, and a commitment to try new things even when they know they'll struggle.

Q: How do you trust people that you can't see and empower them to help solve the company's problems?

A: One of the stories in the book is about the CIO of one of the largest hotel chains in the world. When she took over the role, everyone kept coming into her office asking her to make a decision—everything from what the company strategy was to what Sharpies they should order. After a while, she realized there's a problem with decisions here.

The employees had been conditioned that leaders make all the decisions for them. They had forgotten how to make decisions, or they were afraid to make decisions. One of the things we do with Unlearning is to write an unlearning statement, describing the outcomes that will demonstrate what you have unlearned. She wrote down:

  • 100% of my team will demonstrate no learned helplessness about making decisions.
  • 100% of my direction will demonstrate what success is and why it matters, never how.

That sounds big, but we started small. For one day, anytime somebody came into the office, she would not make a decision. Instead, she asked, "What do you think we should do?" She consistently got one of two responses:

  • I don't know. You're the CIO, you need to tell me what to do.
  • We have three options: A, B, C. Here are the pros and cons of A, and here are the pros and cons of B. I think we should do C.

Of those two experiences, who do you think she would trust to make decisions? She learned a huge amount by changing one small behavior on one day.

Q: A lot of people don't feel empowered to make decisions because they might be wrong—and because that mistake would end up on their performance review.

A:  You can't just give people empowerment. You have to create systems to allow people to make decisions. That helps you to build confidence in their ability and for them to build the capability to make those decisions. It's a two-way street.

You don't offer radical trust to someone you met that same day. You build that by taking small collaboration opportunities. It's not just about empowering people. It's about leaders having confidence in their team that they're making great decisions. It’s a series of small steps toward unlearning this learned helplessness.

Q: The optionality of now having a remote workforce seems like it makes complete business sense. How do you look at managers that don't understand optionality?

A: It's an interesting contrast. For businesses, people are designed to optimize processes. The danger is when you make something so streamlined and so efficient, people are locked into a very fixed set of behaviors that they use to solve solutions. When invariability comes in—it may be a pandemic, or a new technology, or a social shift—you only know how to work with a very small, fixed set of skills. Yet we know now the world is continuously evolving. You have to be able to adapt your skills.

I think this is why the Unlearning system has been powerful for so many leaders, from Fortune 500 executives to startups in Silicon Valley. I'm teaching people how to continuously adapt to changing circumstances. Really that's the skill to have: to be able to respond to uncertainty, to opportunity, and to unplanned events like we're in right now. That's what unlearning is all about.

As remote work becomes the new normal, has created a dedicated space to offer insights and tips. On our Rise of Remote pages, you’ll find The Suddenly Remote Playbook, articles, podcasts, and live streaming videos with experts in the world of remote work. Watch new Rise of Remote Live episodes each Wednesday at 4:30 ET on our LinkedIn page. Visit and subscribe to stay connected.

Barry O'Reilly
Chief Incubation Officer
verified iconExpert in Business Transformation
Nobody Studios
As founder of Outlier Venture Partners and ExecCamp, Barry O'Reilly generates higher growth and efficiency for start-ups and Fortune 500 companies alike.