I Didn’t Fire Him for One Conversation. I Fired Him for Four.

September 25, 2026 • 5 min read

I didn’t let him go over one bad conversation. I let him go because we had too many of them. The fact it took four is on me, not him.

I’ll call him Bob, because that’s not his name. Bob was one of my favorite people on the team. Great personality, great track record. Just a great dude. We became friends. Great 1 on 1’s, texts, the whole deal. You guessed it, that’s where it started to go sideways. We got too comfortable. Not him, we. The more comfortable we got, the harder it became for me to have a hard conversation with him.

The Problem Wasn’t His Talent

I trusted Bob enough to hand him a lot of my clients. Other people on the team did too. He wasn’t putting notes in the system. His follow-up emails and action items weren’t getting tracked. He wasn’t sharing progress.

Others handing him clients had no idea where their clients stood. They couldn’t do their customer service. They couldn’t protect the long-term relationship, the residual income or the referrals that come from it. It was costing them money. Time. Energy. It was just all around frustrating. I was getting A LOT of communication and e-mails about it.

I kept putting it off.

Until I didn’t.

Four Conversations

First conversation: “Bob, we’ve got to start putting this in the system.” Yeah, yeah, I got it, I promise. He’d do it for a day or two, for a couple of clients, and then it would fall off.

Second conversation: I broke it all down. Set the expectation, gave clarity, showed him exactly what to write and what to send. Same result, a few days, never a few weeks.

Third conversation, now people were calling me asking what was going on with him. I shielded him. He’s a good dude. Means well. Has a family. He’s my guy.

We all need development. At least that’s what I kept telling myself.

Every time I let it slide, I was telling the rest of the team it was okay. If it’s okay for him, it’s okay for me. That’s how culture starts to crack.

The Question That Changed It

I finally talked it through with Jenny. How long has this been going on? What’s actually happening? Walk me through it. As the words came out of my mouth, the answer was obvious. It was time. (why you need a coach by the way)

I called him. No waiting, no dancing around it. “Bob, I have to let you go. I’ve asked you numerous times to put notes in the system. It’s hurting other people’s business, you haven’t done it. This isn’t about you and me as friends. It’s about the thing that has to happen to run the business.”

That fourth conversation lasted two, maybe three minutes. The first three took a month and a half.

Waiting Isn’t Kindness

I wish I’d done it sooner. Not because I didn’t like him or respect him. When someone’s performance is costing the people around you money, it’s time.

This isn’t about firing people. It’s about setting the expectation, give clarity, showing them exactly how. If it still isn’t getting done, it’s time. You’ve done your part You can look yourself in the mirror and respect it.

Every week you put it off you’re doing a disservice to that person, yourself, your team, your culture and your family. I was too weak of a leader to have that conversation when I should have. That’s where it has to stop.

Lean in. Have the conversation.

Ready to stop putting off the hard conversations?

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