5 things prison taught me about real leadership

What do prison and business have in common? At first glance, nothing. One is a place where hope and trust are scarce, and every decision you make is a matter of survival. The other is a world built on innovation and collaboration, full of opportunities. But when you strip them both down to their core, you’ll find the same thing: leadership. And not the kind of leadership you read about in glossy books. I’m talking about real-life, earned leadership.

My name is Andre Norman, and I was once sentenced to more than 100 years in prison. That kind of time breaks most men. But I worked day in and day out to earn my freedom and, after 14 years, I reentered the world as a completely different man. While I was behind bars, before I realized my life didn’t have to end in prison, I rose through the ranks of the gang system. As a prison boss, I managed gang activities from within the maximum-security walls, one of the toughest environments on the planet. But I soon realized that, even though I had a sense of leadership, I was the King of Nowhere.

During two years of solitary confinement, I made a decision that changed everything. I set my sights on Harvard University. It was a big goal for someone in my position, but I knew if I wanted it badly enough, I could make it happen. From that moment, I worked backward, using the same skills that had helped me survive in prison: reading people, networking, communicating. And in 2015, my dream became a reality: I earned a fellowship at Harvard Law School.

In prison, leadership wasn’t a title—it was survival. You had to know how to read people. If you make the wrong call, it could cost you your life. I didn’t have the luxury of guessing. I had to know. Is this person going to kill me today, or are they someone I can work with? Behind bars, you learn quickly that loyalty isn’t given, it’s earned. And trust? Trust is the most valuable currency of all.

When I got out and started working with CEOs and leaders, I realized that the business world is not so different from the world I left behind—besides the fact that nobody is coming to the table with a knife. Still, the principles of leadership don’t change. In prison, nobody cares about your title. They don’t follow you because you say you’re in charge. They follow you because you’ve proven you can lead. It’s the same in business. Your people aren’t going to trust you just because of your org chart. They’ll trust you because you’ve shown them that you’re worth trusting.

If I’ve learned one thing, it’s that leadership is universal. Whether you’re behind bars or behind a desk, the same rules apply. Here are a few of the rules I’ve picked up along the way:

Comfort is the enemy of success

Comfort is a trap. In prison, getting comfortable meant letting your guard down. And letting your guard down could mean losing everything. The same applies to leadership. When you and your team settle into a rhythm that feels “safe,” you stop growing. The best leaders embrace discomfort because it’s a sign of growth and progress. 

Make better people, not just better businesses

Prison taught me that the strength of your crew determines the strength of your leadership. If you’re only focused on hitting numbers or meeting deadlines, you’re missing the bigger picture. In business, just like in life, better relationships build better outcomes. As a leader, your job isn’t just to make sure the work gets done, it’s to help your team to grow into the best versions of themselves. When you invest in your people, the results take care of themselves.

Accountability isn’t punishment

Holding people accountable doesn’t make you the bad guy. Accountability is love. It means you care enough to challenge your team to be better, just like you challenge yourself to be a better leader. In prison, accountability was life or death. In business, it’s the difference between mediocrity and greatness. When you hold people accountable, you’re not punishing them—you’re showing them you believe in their potential.

Communication is everything

In prison, a single misstep in communication could lead to chaos. The same goes for business. Effective communication isn’t just about what you say but how you say it. Even more importantly, it’s about how you listen. Great leaders read between the lines and notice what’s been left unsaid. Their goal isn’t to be the loudest voice in the room, but to create space for people to speak up. Communication is the glue that holds your team together.

Golden handcuffs are still handcuffs

Handcuffs trap leaders, too. The question is: Are you in your position because you’re passionate about the work, or because of the allure of money, status, and power? Leadership can feel like a cage, even when it’s lined with perks. If you feel constrained, it’s time for a change. You can walk away. Or you can simply break free from monotony by seeking out fresh challenges that inspire and stretch you.

Leadership isn’t a position—it’s a practice. It’s something you work at each and every day. Leadership is earned through action and proven in the moments when you step up, even when it’s hard. So, you have a choice: to lead with purpose or to go through the motions. The leaders who make the biggest impact are the ones who never stop doing the work.

What does your leadership look like?

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