A bad leadership experience teaches you more than any great mentor ever will. I didn't become a coach because I had great mentors. I became a coach because I survived some of the worst leaders I've ever seen. And I had a front-row seat to every single one of them.
The lies. The ego so thick it suffocated everyone in the room. The tantrums. The manipulation. The backstabbing. The explosions.
I watched leaders destroy good people and call it management. I watched cultures rot from the inside while the person at the top blamed everyone else. I watched teams full of capable, motivated human beings slowly stop giving a damn. Not because they were lazy - but because leadership failed them so completely they ran out of reasons to try.
And then one day, something happened to me personally. A defining leadership experience earlier in my career forced me to confront what bad leadership really looks like up close. Not as an observer. As the person on the receiving end.
That experience broke something in me. I mean that more literally than you might think.
And then it built something better.
Bad Leadership Experience Lesson 1: Nobody Was Helping These Leaders
Here's the thing nobody talks about: most CEOs don't get honest feedback. Not from their team, who are afraid of losing their jobs. Not from their peers, who have their own egos to protect. Not from the people closest to them, who've learned that honesty has a cost.
So the leader lives in a bubble. And inside that bubble, ego grows unchecked. Blind spots calcify into character flaws. Bad behavior gets normalized because no one has the courage to call it out.
I've seen it happen over and over. A founder who responded to every challenge with aggression and genuinely believed he was "just passionate." An executive who took credit for everything and deflected blame onto his team and genuinely believed he was "protecting the culture." A CEO who hadn't heard an honest word from his leadership team in three years because every single person in that room had learned, through painful experience, that honesty wasn't safe.
None of those leaders thought they were the problem. And that's just what made them so dangerous.
This is exactly why CEO coaching matters - not because great leaders need cheerleaders, but because every leader needs someone in their corner who will tell them what their team won't.
The Culture Was a Costume
Some of the worst leaders I've been around had the best slogans. Values on the wall. Mission statements in the handbook. Mottos printed on t-shirts and repeated in all-hands meetings like a company prayer.
Good Vibes Only. Billion Dollar Standards. We Win Together.
Sounds great. Looks great on a careers page. Here's what those phrases actually meant in practice:
Good Vibes Only meant the entire organization operated around the emotional weather of one person. Nobody brought problems because problems were bad vibes. Nobody raised concerns because concern was negativity. The only vibe that was ever truly welcome was agreement. It wasn't a culture built on positivity. It was a culture built on fear dressed up in optimism.
Billion Dollar Standards meant the team was held to an exacting, unforgiving bar while the leader operated without one. Accountability flowed in one direction only. The standard wasn't about excellence. It was about control.
We Win Together meant the trophy belonged to the leader and the losses belonged to the team. Together was a word that lived in the all-hands presentation and disappeared the moment accountability entered the room.
Real culture doesn't need a slogan. It shows up in how a leader behaves when things go sideways.
When a leader's ego is running the show, the culture exists to serve them. The values are props. The mission is marketing. And the people who thrive aren't the most talented or the most committed - they're the most agreeable. That's not a culture. That's a controlled environment. And eventually, the best people always find their way out of it.
Bad Leadership Experience Lesson 2: What It Actually Costs
Think about the best person you've ever had on your team. Sharp. Motivated. Cared about the work. Now think about what it takes to make that person stop caring.
It's not one big moment. It's a thousand small ones. Unclear expectations that make them guess at what success looks like. Feedback that never comes until something goes wrong. A leader who takes the win and passes the blame. A culture where saying the truth out loud is career suicide.
In my book Build Kickass Teams, I wrote:
- "When people are left to guess long enough, they stop trying. Not because they don't care. But because they're tired of caring in the dark."
That's the real cost of bad leadership. Not just turnover. Not just performance metrics. It's the slow death of people who came in wanting to do great work and left with nothing left to give. And the worst part? The leaders responsible never saw it coming.
Because nobody told them.
Bad Leadership Experience Lesson 3: Empathy Is the Fix
After that defining experience, I went deep. I needed to understand: why do some leaders build people while others break them?
What I found wasn't complicated. But it was hard.
The leaders who build people lead with empathy. Not the soft, therapeutic version. The real version - the kind that says: I understand what you're dealing with, I see you as a human being, and I'm going to give you the clarity and direction you need to actually win.
In my book Lead With Empathy, I put it this way: empathy is the most strategic leadership skill on earth. Without it, leadership becomes control instead of connection. And control always breaks eventually.
That book wasn't written from theory. It was written from scar tissue.
Why I Coach the Way I Do
I'm not a business coach for founders who sits across from a client and asks how they feel about their goals. I'm the person in the room who tells you what your team is afraid to say.
I've earned that seat. Not through a certification or a course. Through two decades of operating at the highest levels of multiple businesses, watching leadership succeed and watching it fail, and living through enough of it personally to know the difference.
The best coaches aren't the ones who had perfect careers. They're the ones who've been tested and came out the other side with something real to offer.
I've hired the wrong people and paid the price. I've avoided hard conversations and watched problems grow. I've been in rooms where the culture was poisoned and no one had the guts to say it. And I've been on the receiving end of leadership so bad it forced me to rebuild from the ground up.
That's not a liability. That's the whole point.
Here's what I ask every leader I work with at some point: are you building people, or breaking them? Because every leader does one or the other. And the answer is rarely found in intentions.
It's found in what your team says about you when you leave the room. It's found in whether your best people are growing or quietly updating their resumes. It's found in whether you're the kind of leader someone looks back on ten years from now and says, "That person made me better."
The terrible leaders I had early in my career shaped me more than they'll ever know. Not because of anything they did right. Because of what they got so catastrophically wrong. And because of what I decided to do with it.