Why Great Leaders Are Built, Not Born

I’ve heard it a thousand times. “Some people are just natural leaders.”

I don’t buy it. Not for a second.

After nearly 30 years in the construction industry, after building companies from the ground up, after leading teams of 180 people across four markets, I can tell you this with certainty: great leaders are built. Every single one of them. The ones who look “natural” just started building earlier.

TL;DR: Research from Exec.com shows only about 10% of people are natural leaders, with another 20% showing high potential that requires development. The global leadership development market hit $366 billion in 2025, yet 77% of organizations still report a leadership gap (DDI, 2025). Leadership isn’t genetic. It’s built through discomfort, failure, feedback, and intentional practice. These are the five experiences that shaped mine.

Why is the “born leader” myth so persistent?

A 2025 Chartered Management Institute study found that 82% of managers in leadership positions had no formal management training, what they call “accidental managers” (CMI, 2025). The “born leader” myth is comfortable. It lets people off the hook. If leadership is genetic, then you either have it or you don’t. No need to put in the work. No need to face the uncomfortable growth that real leadership demands.

But that’s not how it works. Leadership is a skill. Like any skill, it’s developed through practice, failure, and intentional effort. I wasn’t born knowing how to run a $35M operation. I learned it one painful lesson at a time.

What did my own building process look like?

Organizations that invest in leadership development see a $7 return for every $1 spent, according to the Center for Creative Leadership (CCL, 2025). My returns came the hard way. When I started in construction in 1996, I wasn’t leading anyone. I was learning the trade. Showing up. Doing the work. Watching how the people above me handled pressure, conflict, and decisions.

When I founded Penebaker Enterprises in 2002, I thought I was ready to lead. I wasn’t. Growing that company from $1.5M to $15M taught me that knowing the work and leading the people who do the work are two completely different things.

I made every mistake in the book. I micromanaged. I avoided hard conversations. I hired for skill and ignored character. Every one of those failures taught me something I couldn’t have learned from a book or a seminar.

The five experiences that built me as a leader

DDI’s 2025 Global Leadership Forecast surveyed over 13,000 leaders worldwide and found that 77% of organizations report a leadership gap, the highest rate in a decade (DDI, 2025). The gap isn’t because of genetics. It’s because not enough leaders are getting the experiences that build them. Looking back, five specific experiences shaped my leadership more than anything else.

1. Firing someone I liked. Early in my career, I had a crew member who was a great person but consistently underperformed. I kept him on for months because I liked him. The rest of the team noticed. Morale dropped. Accountability disappeared. The day I finally made the call was the day I learned that leadership isn’t about being liked. It’s about doing what’s right for everyone.

2. Losing a major contract. We lost a bid that I was sure we’d win. I spent weeks blaming the client, the competition, the economy. Then I sat down and actually looked at our proposal. It was sloppy. We’d gotten comfortable. That loss taught me that complacency is the enemy of excellence.

3. Having a team member call me out. A foreman once told me, straight to my face, that I was making promises to clients that the crews couldn’t deliver. He was right. I was selling timelines that ignored reality. That conversation taught me to listen to the people closest to the work.

4. Scaling across multiple markets. When I helped scale Roofed Right America to over $35M in annual revenue across four Upper Midwest markets with 180 employees, I had to learn a completely new style of leadership. You can’t be in every room. You have to build systems and trust people to run them. That’s a different muscle than managing a single crew.

5. My advocacy work. Fighting for gun violence prevention taught me about leading with purpose. In business, the stakes are revenue and reputation. In advocacy, the stakes are lives. That perspective changed how I show up in every room.

What actually builds a leader?

Gallup’s 2025 data shows that managers account for 70% of the variance in team engagement, yet only 30% of managers are engaged themselves (Gallup, 2025). That gap points to a development problem, not a talent shortage. Based on my experience, none of what builds leaders is genetic.

Discomfort. You don’t grow in your comfort zone. Every leap I’ve made as a leader came after a period of being deeply uncomfortable. Starting a company. Entering a new market. Having a conversation I’d been avoiding. Growth lives on the other side of discomfort.

Failure. Not the kind you read about in motivational posts. Real failure. The kind that costs you money, relationships, and sleep. The leaders I respect most aren’t the ones who never failed. They’re the ones who failed and came back smarter.

Feedback. You need people around you who will tell you the truth. Not what you want to hear. The truth. If everyone around you agrees with everything you say, that’s not leadership. That’s an echo chamber.

Repetition. Leadership is daily. It’s how you handle the Monday morning crisis. The Friday afternoon conflict. The Tuesday meeting where nothing exciting happens but your team needs to see you showing up. Consistency builds trust. Trust builds teams.

Self-awareness. The best leaders know their weaknesses. They don’t pretend to have all the answers. They hire people who are smarter than them in specific areas and get out of the way. I wrote about this in How I Build High-Performing Teams Across 4 Markets.

Does the research back this up?

Google’s Project Oxygen analyzed thousands of internal performance reviews and found that the best managers practiced specific behaviors: coaching, communicating, and empowering (Google re:Work, 2025). None of those are innate traits. Research consistently shows that leadership effectiveness is more strongly predicted by experience and deliberate practice than by personality traits.

The U.S. military, which has one of the most sophisticated leadership development systems in the world, operates on the fundamental premise that leaders are made through training, mentorship, and progressive responsibility. Internal promotions reach full competence about 20% faster than external hires, further supporting the “built, not born” model. If the institution that produces more leaders than any other believes leadership is built, maybe we should listen.

The bottom line

If you’re waiting to feel ready to lead, stop waiting. You’ll never feel ready. Leadership is built in the doing.

Take on the project nobody wants. Have the conversation you’ve been avoiding. Ask for honest feedback and actually listen to it. Volunteer for something that scares you. These are the reps that build leaders.

You weren’t born a leader. Neither was I. But you can build yourself into one. I’m proof of that.

Want to connect on leadership? Find me on LinkedIn or check out my Experience page to see the full journey.

Last updated: March 9, 2026