Do You Ever Regret Firing An Employee?

Disappointed jobless cartoon businessman is carrying a cardboard box with personal belongings, leaving office after being fired. Use as unemployment, financial crisis and depression theme design

“What took you so long?”

Every single time I’ve fired someone as CEO, someone on my team has asked me that question. Every. Single. Time.

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And, there’s a good reason I was asked that question. You see..

You, the CEO, almost always wait too long to fire someone.

For example, I realized, about two months after we became operational, that “Randy,” one of my co-founders, wasn’t going to make it. He was causing too many problems, and he was pissing too many people off.

Yet, there he was, still wreaking havoc, still working with us three months later. That’s when I finally fired him.

So Randy lasted five months, and my regret was that I didn’t fire him a few months earlier.

The same thing happened again seven months later with “Ken,” one of my other co-founders. I knew Ken was struggling three months after we became operational.

Yet, there I was nine months later, trying to find a way to save Ken and get him motivated. Nothing seemed to work. In desperation, I had lunch with Ken and I pushed him really hard, knowing he might quit.

The next day, Ken quit. Again, I regretted not taking action months sooner.


You have an obligation to your team, to your investors, and to yourself to do the right thing.


I got better at moving quicker when I realized that someone had to be fired. However, there was always some latency between recognizing someone had to be fired and firing the person.

But, what I kept thinking about was the team. A bad senior employee can cause so much damage with the biggest damage being to your team.

For example, Ken’s replacement, “Tommy,” didn’t work out either. Before I fired him, two of the best people on the team quit.

That’s why you need to move fast. Yes, a bad employee hurts your company, so it hurts your investors. And yes, a bad employee hurts you.

But, I always thought of the human cost to the team. That’s what motivated me to move as fast as possible and take action.


An employee that doesn’t work out is always your fault. Always.


I was really disappointed in Randy. I was really frustrated with Ken. Tommy, well, what he did was beyond words. However, in every single case, it was my fault.

No one forced me to hire these people or make someone my co-founder. I made that choice all on my own.

That’s why it’s always your fault. You’re the CEO. You are responsible for every single hiring decision, especially the hiring decisions that don’t work out.


It’s always painful to fire someone.


As much as I wanted Randy, Ken, and Tommy out, it was always painful to actually let them go. And that’s as it should be.

You should feel bad when you fire someone because you are changing their lives forever. For most of the people you fire, it will be the first time they’ve ever truly been told they failed in their lives.

The person you fire is going to have to go home and face their spouse and their kids. I imagine what that must be like every time I fire someone.

However, you have a job to do. Your responsibility is to the company, your team, and your investors to do what’s necessary.


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