The Leader You Swore You’d Never Become

Jeff checked every box: right people, right calls, right outcomes. And then one question cracked the whole thing open.

The Zoom call started on time. Jeff appeared, fiddling with his headphones.

His smile was polite. Maybe too polite. The kind you could fold up like a receipt and forget in your jacket pocket.

His Zoom background was honest in a way most aren’t. No blur. No flickering beach. Just the real stuff: an uneven bookshelf, a framed map of a bike trail, and a photo tucked off to the right. Him and a kid, maybe twelve, mid-laugh in the stands of a baseball game.

You could almost hear the crack of a bat.
Summer, frozen in a frame.

"Thanks for making time," he said.

He was interviewing for an M2 role at Meta. Manager of managers. The kind of job where you don’t just lead, you absorb fire. You inherit scale, velocity, politics, and a salary that makes your friends quietly do the math.

Jeff wasn’t new. Three years leading other leaders. Recently let go from a Director role at a startup. His résumé read like a case study: led, scaled, delivered, transformed.

But under the words, I felt it. That tightness in the air. The tension of a man who played by the rules and still got benched.

“I want to work on my leadership stories,” he said. Like the stories just needed polishing. Like the cracks were cosmetic.

I’ve coached hundreds of leaders. Here’s what no one tells you:

Interviews are mirrors.

And if you’re not ready to see what’s staring back, you’ll spend the whole time adjusting your mask.

Startups reward velocity. Big tech rewards alignment. One teaches you to move fast; the other, to move well.

And somewhere between those worlds, most leaders collect scars that look like promotions. Jeff had a few. Still healing, just beneath the surface.

I already had a guess where the break was. But you can’t just hand someone the truth. You have to give them a flashlight, hang on tight, and walk them to the edge. Slowly.

The Question

“Tell me about a time when you saw an engineer who could do better,” I asked. “What did you do?”

He paused. Not long. Just long enough to show he already knew which one.

“When I joined the team, I started meeting with cross-functional partners—product, UX, ops. Everyone warned me about this one engineer.”

He gave a short laugh. No humor in it.

“They didn’t even wait for me to ask. Just… volunteered it.”

“What did they say?”

“That he called people incompetent. Said it directly. Once, in a team meeting, he told someone we should fire them and hire someone smarter.”

His tone was calm. Professional. The voice of a man reading facts from a file he’s already closed.

“I met with his manager. Asked what was being done. Manager was new. Said he was still observing. I told him we didn’t need to observe anymore.”

“And then?”

“I even offered to be in the meeting when he gave feedback. Just in case. He said he didn't need me to.”

That line came soft. Almost too soft.

I took a note.

“It didn’t work,” Jeff said. “So I met with the engineer myself. He doubled down. Said we should just replace a few people. Like he was doing us a favor.”

“Then what?”

“I pulled in HR. Started a PIP. But he quit before it landed.”

He stopped.

The story closed like a cabinet drawer.

“So,” I asked.

“What did you take away from it?”

Jeff exhaled. “He was a brilliant jerk. He didn’t want to change. I took the right steps.”

Wait. Let’s hit pause here.

Hi.

What do you think of Jeff’s story?

If you're nodding, you’re not the first.

Jeff checks every box on the Corporate Savior Checklist:

1. He protects the team. Names the villain. Slays the villain.

2. He’s emotionally aware but steady.

3. He doesn’t micromanage but knows when to step in.

4. He makes the hard calls early.

5. He follows the process like a badge-polishing boy scout.

Nice.
Neat.

Too neat.

Especially when I smell the buried bones.

I circled back to my note.

“You offered to sit in the room,” I said. “Why?”

His jaw tightened. There it was. The flicker.

“Because I don’t like brilliant jerks.”

Molars grinding. The sentence held back something heavier.

“Have you ever worked with someone like that before?”

Pause. Perhaps a bit too long.

“No,” he said, looking away. “Because I used to be that guy.”

There it was.

The fossil I was looking for.

Not the kind you frame. The kind you drop on your toes. The kind you find again every time you open the wrong closet.

Let’s check one.

“If that engineer had stopped calling people names,” I asked, “if he’d behaved better—would that have solved your problem?”

“Yes.”

“But would it have solved his problem?”

His brow shifted. A small storm gathering.

“What do you mean?”

“Look, Jeff. I get it. The guy was an asshole. Shame on him.”

“But contrary to the popular belief, most assholes don’t want to act like assholes. You know that well. Did he ever say why he was so angry?”

Jeff paused. Then his voice softened.

“He said people weren’t following technical standards. That they skipped docs, broke production. That he had to miss family events to clean things up.”

I let it hang in the air like smoke.

“So even if he’d changed how he said it, the why would still be there.”

Jeff nodded. Slower this time.

“Yeah… he was still alone in it.”

I said, “He didn’t know how to say what mattered without cutting people down.”

“You weren’t reacting to him,” I said.

“You were reacting to you. To who you used to be.”

Jeff looked up.

“You punished him because you haven’t forgiven yourself.”

He froze.

That kind of truth takes a minute. You let it bleed.

The Triangle

I checked the time. We had a few minutes left.

“We’re not done yet. I’m giving you the short version for now. I’ll send you something to go deeper after.”

Jeff leaned forward, nodding.

“Ever heard of the Drama Triangle?”

Shook his head. “Maybe. I don’t know.”

“That’s okay,” I said. “Honestly, it’s better that way. Less to unlearn.”

I shared my screen and pulled up the triangle.

Three corners. Three roles. One trap.

In 1968, Stephen Karpman, a psychiatrist, developed a model to describe how we unconsciously create and sustain conflict — at work, at home, everywhere humans bump into each other. He called it:

The Dreaded Drama Triangle (DDT).

The Victim.

Life is happening to them. They feel powerless.

“In your story? That’s UX. Product. The people your engineer burned.
And also… the people you hurt, back when you were that guy.”

His face didn’t move. But something behind it did.

The Villain.

The one to blame. Loud. Sharp. Maybe even right.

“Most villains were victims first,” I said. “They just didn’t know what to do with the pain. So they sharpened it.”

Jeff’s voice dropped. “So he was the villain. And… I was, too.”

“Yes. And now? You’ve turned the blame inward. You’ve made yourself the villain.”

He said it before I could.

“I’m a villain to myself.”

“And when someone reminds you of the version you haven’t forgiven?” I said. “You show up as the villain to them. Just like you did to him.”

Then, a pause.

“And here’s the funny part,” I said, leaning back. “The one people miss.”

The Hero.

Not the cape-wearing kind. The compensator. The former victim still trying to feel their power, says:

“I won’t let this happen again. Not on my watch!”

“The Hero thinks they’re fixing things. Protecting others. Making it right. But if you lead from pain, even your rescue becomes harm.”

Jeff blinked. “So I thought I was saving the team…”

“…but really, you were still fighting yourself.”

I smiled.

“And honestly? Most leadership material out there is sugar-coated ding-dong corporate peanut-safe fluff.”

He laughed. It came out tired, but honest.

“It took me years — embarrassment, self-coaching, a lot of awkward conversations to understand this triangle. And the Hero role is the hardest to step out of. Because it feels noble.”

He nodded.

I opened a new tab.

“This lesson is called “How to create ownership. It’s from my course, Top Tech Leader. It walks through the triangle and explains how to escape it. ”

Then I stopped sharing my screen.

And we just sat for a minute.

The window behind him caught a shift in light. And in the corner of the frame, that photo — the one of him and his son — came into view again.

“Jeff,” I said. “One more thing before we wrap.”

“If I had your exact life; same parents, same scars, same experiences, what are the odds I’d have done the exact same things?”

“High,” he said. No hesitation.

“And what are the odds I might still screw it up?”

He smiled. “Also high.”

“But you’re not choosing that anymore,” I said. “You’re choosing better. That’s the only thing that ever mattered.”

He sat up straighter.

I glanced again at the photo. The boy. The bat. A time when everything still feels simple.

“They say the apple never falls far from the tree,” I said.

“Tomorrow, it might be him, misunderstood. Frustrated. Trying to be heard. And if you’re still holding grudges against this old version of you…”

“You’ll correct him,” I said, “not from love but from guilt.”

Jeff looked at the photo. Just for a moment.

And that’s the thing about blind spots:

They don’t just shape how we lead. They shape who we protect. Who we punish. Who we allow to grow. And who we quietly hold back, because we’re still afraid of what we used to be.

Jeff didn’t get the role.

But that wasn’t the real test.

He came into the interview with a story about fixing someone.

He left with a story about finally facing himself.

And that’s where real leadership begins.

Not in what you build.

But in who you’re finally ready to stop hurting — even if that person is you.

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