I spent most of my thirties performing confidence. Board meetings, investor pitches, jobsite walkthroughs. I had a posture and a tone for each one. Different versions of the same act: the guy who always knew what to do next.
It worked, for a while. I built a roofing company from $1.5 million to $15 million. I hired 50 people. I stood on stages and told other people how to succeed. The whole time I was running on a combination of adrenaline and fear that someone would figure out I was making half of it up as I went.
The moment it cracked
There was a pre-construction meeting I remember clearly. We had underbid a project by a significant margin. I knew the numbers were wrong. My project manager knew the numbers were wrong. But I sat in that room and talked about execution timelines like everything was fine.
After the meeting, my PM pulled me aside. He said we were going to lose money on this one. I said I knew. He asked why I had not said that in the room.
I did not have a good answer. The honest one was that I was afraid. Afraid that admitting a mistake would make me look incompetent. Afraid my team would lose faith in me.
So I kept performing. We lost money on that project, and the trust of a project manager who had been trying to help me.
What I changed
I wish I could tell you there was a clean turning point. There was not. It was more like erosion. Slowly wearing down the need to appear perfect until what was left was just the truth.
The first time I told a team, “I am not sure what to do here, and I need your input,” I expected silence. I expected doubt. What I got was the opposite. Two people who had been quiet in meetings for months suddenly had ideas. Good ones. The kind of ideas that only come from people who feel safe enough to share them.
That taught me something I wish I had learned ten years earlier: my team was not waiting for my answers. They were waiting for permission to share theirs.
Why this matters for advocacy work
I carry this into my advocacy work now too. When I stand in front of a room and talk about losing my mother to gun violence, I cannot perform that. It is real or it is nothing.
Same thing on a jobsite or in a one-on-one with a struggling employee. People can tell when you are performing. They might not call you on it, but they adjust. They hold back. They cover mistakes. They start performing too.
Before you know it, you are leading a team of actors instead of a team that trusts each other enough to tell the truth.
What I tell new leaders now
You do not have to have every answer. You have to be honest about which ones you are still working on.
The performance gets exhausting anyway. I know because I did it for years.
If you are reading this and recognizing yourself in the old version of me, here is what I would say: your team already knows you do not have it all figured out. They are just waiting for you to admit it so they can help.
About Khary Penebaker
Khary Penebaker is Division President at MetalMaster-RoofMaster, the Upper Midwest division of Wolkow Braker Roofing Corp. He previously built Roofed Right America from startup to $35M+ in revenue with 180 employees (2014-2025) and founded Penebaker Enterprises, growing it from $1.5M to $15M. A gun violence prevention advocate and former Everytown for Gun Safety Fellow, Khary brings two decades of leadership in commercial roofing, architectural sheet metal, and civic engagement.
Common questions
Why is authenticity important in leadership?
People follow leaders they trust. Trust comes from honesty, not perfection. When you admit what you do not know, your team fills the gap instead of hiding their own uncertainty.
How do you show vulnerability without losing authority?
You share what you learned from the struggle, not just the struggle itself. Vulnerability without resolution is venting. Vulnerability with a lesson is leadership.
Can being too honest hurt your career?
Context matters. Sharing a mistake you fixed builds credibility. Sharing one you have not fixed yet can erode confidence. Know your audience and your timing.
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Last updated: June 28, 2026