When I Fired My Top Salesperson
When to Fire Your Top Salesperson by Keith Rosen

You love your top performers. But are you being held hostage by them to the point where they’re doing more damage than they’re worth?

The holy grail of leadership is building a team of self-motivated, highly accountable, top performers. But if you ask any manager if they’ve ever dealt with an underperformer, they’ll almost always say yes.

So, what actually defines one?

One of my clients recently asked for advice about whether or not to terminate someone on their team. They were stuck. After understanding their approach and thinking, I shared a story of my own.

Back in 1985, long before I started my coaching firm, I owned a different company. I was responsible for a team of sales managers and about 50 salespeople. And like any good leader, I followed the A.B.R.s of leadership, Always Be Recruiting.

One day, I hired someone who impressed me through our hiring process. He became our top salesperson. His name was Peter.

Over time, Peter and I got close. I went to his wedding. We socialized. I was there when his first child was born. We shared not just a professional relationship but a personal one.

He was so good that when he asked for a new company car, we got him a Lexus. We even promoted him to team leader to mentor new hires.

Then something changed.

Peter’s positive, humble energy disappeared. He became arrogant and self-centered. His attitude impacted morale and the performance of the rest of the team. Still, he was our top performer. He was making us a lot of money. So, we looked the other way.

Even when he refused to sign the employee agreement and non-compete, we didn’t push. We told ourselves it was fine. We tolerated it.

I found myself spending more time managing the wake of Peter’s behavior than acknowledging his sales results.

The team noticed too.

They’d say things like:

  • “Peter gets special treatment.”
  • “His ego is unbearable.”
  • “He skips sales meetings.”
  • “He insults other reps.”
  • “He’s using the Lexus for personal errands.”
  • “He takes over our accounts to pad his numbers.”
  • “You’re doing his paperwork for him.”

Peter had become a toxin inside the company. A cancer. But we were afraid to lose the revenue he brought in. We kept hoping he’d return to the version of himself we once knew. I had honest conversations with him, told him what the team was experiencing, and asked him how we could get back to the Peter who led with heart.

He didn’t care.

Then one day, it hit a breaking point. He started using my office without asking. One day, I walked in to grab something during one of his calls, and he yelled at me. In front of the whole team. For interrupting his call in my office.

Still, my partners tried to justify it.

Then his performance started slipping. He wasn’t coming into the office. Excuses followed: his wife needed help with the baby, he was sick, he could run appointments remotely. We gave him space.

Then came the day that changed everything.

We went on a ride-along together. He picked me up in the Lexus. The car was a disaster. I teased him about it. Then I opened the glove compartment. Total mess. I laughed. Then I opened the armrest—and froze.

Inside were business cards.

They weren’t ours.

They had Peter’s name on them—with the title “Owner/CEO.” And the company listed? Not mine.

Turns out, Peter had been taking the leads we gave him, using the car we paid for, and closing deals under his own company. Stealing leads. Stealing revenue. Stealing from us.

And I didn’t need a detective to piece it together.

I coach people not to take work personally. To remember their job isn’t who they are. It’s just what they do. But back then? I took it personally.

I was devastated. Hurt. Blindsided.

This man I had trusted, mentored, celebrated—betrayed all of it.

There were no more conversations. No more benefit of the doubt. We fired him on the spot. We scrambled to repair the damage—calling every customer we could to try to recapture what was lost.

The team wasn’t shocked. They were relieved. Almost celebratory.

“It’s about time,” they said.

Here’s the truth: We knew. We just didn’t want to see it.

We tolerated behavior we never should have. We rationalized. We ignored the signs because he was “producing.” But deep down, we were being held hostage.

So, why am I sharing this?

Because while Peter sold like a champion, he was an underperformer.

That story forced me to redefine the word.

It’s not just about hitting quota. It’s about how that person affects everyone around them.

So, look at your team.

Who’s hitting their numbers—but burning bridges behind them?

Who’s closing business—but creating churn and chaos with their ego, attitude, or entitlement?

Are you spending more time managing their wake than celebrating their wins?

If so, you may have a Peter.

And if you let it continue, the cost is greater than lost deals. You’re teaching your team that behavior is acceptable. That results matter more than respect. That trust is optional.

Eventually, your best people—the ones who are solid performers and good humans—will leave. And they won’t tell you it’s because of Peter. But it will be.

You’ll lose culture. Trust. Integrity.

And here’s the kicker: You’ll lose yourself—because when your standards fall, your credibility goes with it.

I know how hard it is to let go of a top performer. Especially one you care about. But you have to ask yourself a different question:

Not “What’s best for me?”

Not “What if we lose revenue?”

Ask: “What’s best for my team and my company?”

The answer will be crystal clear.

Don’t wait to feel betrayed to do the right thing. Lead now. Before someone else’s behavior burns down what you’ve worked so hard to build.