I Learned a Lot About Leadership When I Had to Fire Someone for the First Time

“Bobby, you’re going to have to fire Mark (pseudonym). None of his previous managers had the courage to give him feedback, so Mark thinks he’s performing well. But he’s been a cancer on the team, and you’ll need to let him go.”

That’s what my District Manager told me right after I accepted my first management job. Yowza.

The entire situation caught me off guard. I had just graduated with my MBA, and I had a rosy view of what my introduction to management would be like.

I envisioned myself mentoring team members, crushing company metrics, and garnering promotions. I had not envisioned having to fire someone—especially so soon.

After I composed myself, I asked my District Manager (DM) why no one else had given Mark feedback over the years. The DM explained that everyone else had been scared of Mark because he’d been at the company for five years and was a burly ex-football player.

Sounds about right,” I thought.

I didn’t love the hand I was dealt, but it didn’t make sense to complain. I wanted to make a good impression with the DM, and there’s nothing he or I could do about the fact that no one had given feedback to Mark.

So I spent the next few weeks diligently watching Mark’s performance. He knew the ins and outs of the business, but he treated people poorly and talked down to others. Colleagues were scared of him, and he frequently refused to help both employees and customers with their requests.

Week after week, I gave him feedback. Week after week, he still struggled.

So I did what I had to do: I fired Mark.

That was 13 years ago, but it remains one of the worst moments of my career. Not only was it agonizing to have to let someone go, but the entire situation went down about as poorly as one could imagine.

When I was preparing for the termination discussion, my manager was so worried about Mark’s anger problem that she posted a security guard outside my office door when I had “the talk” with Mark.

Sure enough, when I told Mark it was his last day, he started cussing me out. For a minute, I thought he might come across the table at me.

I tried to wrap up the conversation quickly, then our security guard literally had to drag Mark out of the building as Mark shouted warnings and obscenities at his (now former) colleagues.

Once he got out to the company parking lot, security watched him on the parking lot cameras to make sure he didn’t key my car. And when I left work that day, I took a few glances over my shoulder to make sure he wasn’t around (thankfully, he wasn’t).


As crazy as that situation was to deal with as a brand new manager, I’m glad it happened. It taught me a lot about leadership, and it gave me the confidence to deal with other tough situations I’ve faced later in my career.

Looking back, here are five lessons I learned from working with Mark:

1. Company messes are your messes

“When you are a leader, most things that go wrong are not directly your fault, but they are always your responsibility.” -Elena Botelho and Kim Powell

When you become a manager, you inherit the problems of past managers who filled that role. Those problems could be bad hires, unresolved team issues, broken processes, poor expectations set with clients, or a host of other messes.

Once you step into the role, it no longer matters who created the mess. It’s now yours to solve.

2. There’s no use complaining

“Don’t wish it were easier, wish you were better.” -Jim Rohn

I didn’t love the fact that I had Mark on my team and that no one else had dealt with his problems, but none of that mattered. If I were to complain to my DM or anyone else in upper management, it would have just made me look bad. Complaining solves nothing.

I quickly realized the only option was moving forward: I had to do the difficult work of performance-managing Mark, giving him feedback, dealing with his attitude, and (ultimately) firing him.

My DM didn’t want to hear that these tasks were hard. He just wanted to know that I’d handle them, so I did.

3. Every human contains multitudes

“Slapping a label on someone is a great way to render them invisible and destroy a hard conversation.” -David Brooks

When I’ve talked to friends about Mark through the years, their first reaction is usually, “Wow, what a horrible guy!”

But I don’t think he was horrible at all. Sure, he was aggressive and he treated people poorly at times, but he wasn’t a bad guy.

In fact, there were a lot of things he did well: he worked hard, had high standards, and drove strong numbers in multiple areas of the business. He wasn’t trying to be an asshole. He just hadn’t gotten feedback in a long time, so his personality flaws became more jagged and his demeanor became more ruthless.

This experience taught me that our brains rush to simple explanations: hero/villain, good/bad, just/unjust, industrious/lazy, etc.

But those labels are never 100 percent accurate. The world is never that clean, and adjudicating the cases of life is never that easy.

Mark was a good guy who was trying his best, and the system had let him down. We (and yes, I was now part of that “we”) had not given him the feedback he was due, and our failure prevented Mark from getting time to course-correct before it was too late.

4. Clear is kind, unclear is unkind

“One of the most important insights anyone in business can have is that it’s not cruel to tell people the truth respectfully and honestly.” -Patty McCord

For some reason, we’re all hardwired to believe that criticism is unkind because it could potentially hurt another person’s feelings.

But which option is more unkind: being honest with someone so they have the opportunity to improve or setting them up to fail because they don’t realize there’s a problem?

The author Brené Brown says, “Clear is kind. Unclear is unkind.” That phrase now pops into my head every time I deal with an employee who’s struggling.

If you can teach yourself to embrace feedback and redefine kindness to include candor, you can better care for your team and help them become the employees they want to be.

5. Don’t soften the blow

“The gap between what you’re really thinking and what you’re saying is part of what makes a conversation difficult.” -Douglas Stone, Bruce Patton, & Sheila Heen

I gave Mark feedback every week until I fired him. In the moment during each conversation, I thought my feedback was direct and forceful.

But as soon as I fired him, I reflected on the conversations I’d had with Mark and realized I wasn’t direct enough.

I sugarcoated a lot of my messages. I softened the blow over and over. I hedged with language like “maybe” and “kinda.” I refused to use phrases like, “If this behavior doesn’t change, you will lose your job.”

I didn’t want to be mean or unkind or aggressive.

That was a mistake. If I could do it over again, I would deliver each difficult message with greater candor — not for my sake, but for his. Mark deserved to know what was coming.


Thankfully, I’ve taken these lessons to heart and employed them in my life and leadership since that initial painful termination discussion.

With every struggling team member since Mark, I’ve been more direct — and also more kind. (Remember, clear is kind.) Due to that clarity, every person I’ve had to fire since Mark has been less surprised than the person before.

With every conversation, I’ve gotten better at embodying these five principles:

  1. Company messes are your messes
  2. There’s no use complaining
  3. Every human contains multitudes
  4. Clear is kind, unclear is unkind
  5. Don’t soften the blow

I hope you can incorporate these lessons into your team leadership without having to replicate my mistakes.

And when you do have to fire your first person, I hope you’ll sleep a bit better than I did because you’ll know you did everything possible to help the person course-correct before it was too late.

Want to become a stronger leader?

Sign up to get my exclusive
10-page guide
for leaders and learners.

Leave a Reply