How to fire the friend you hired

Jorge: You’ve fired six people in twelve years. The number that matters is how long each one took longer than it should have.

Sample Guest: Every one of them. The first one took eighteen months from the moment I knew. The most recent one took six weeks, and that was still too long.

Jorge: Walk me through the first one.

8:00 Skip to “Why founders avoid the conversation”

Sample Guest: It was someone I’d known since university. We started the company together, not as co-founders, but they were the first person I called when the seed money came in. The work that needed doing in year one was the work they were good at. The work that needed doing in year three was not.

Jorge: When did you know?

Sample Guest: Month fourteen. I remember the meeting. They presented a plan that was the same plan as the previous year, slightly rearranged. Everyone in the room had moved past it except them. I went home and didn’t sleep.

Jorge: And it took you four more months.

Sample Guest: Eighteen. I told myself I owed them. I told myself the company owed them. I told myself the team would be fine waiting. None of those things were true.

19:00 Skip to the framework, three questions

Jorge: What changed the next time around?

Sample Guest: I started writing down three questions every time I had that uneasy feeling about someone. The questions are simple. The discipline is asking them on a timeline, not when the discomfort gets too loud to ignore.

Jorge: Walk me through the questions in order.

Sample Guest: Question one, would you hire them again today, given everything you now know about the company and the bar? If the answer is no, you have your answer. People want question one to be more complicated than it is. It isn’t.

Jorge: Question two.

Sample Guest: What would have to change for the answer to question one to be yes? If you can name a specific, finite thing, like, they need to learn this skill, or they need to grow into this scope, and you’d genuinely invest six weeks of your time helping them get there, you have a coaching problem. If your list is everything, or you can’t name anything specific, you have a separation problem.

Jorge: Question three.

Sample Guest: Does the rest of the team already know what you know? Because if they’ve been carrying the work, or covering for the gap, or having sidebar conversations about it, every extra week you wait, you’re paying with their trust.

33:00 Skip to “What the conversation actually sounds like”

Jorge: Let’s get tactical. The conversation itself. What does it sound like?

Sample Guest: Short. Direct. No preamble. I start by naming the gap between the work and the bar, and I name it as my responsibility, I hired for one thing and the company now needs another. Then I say the decision, not as a question. Then I shut up and let them speak.

Jorge: And then.

Sample Guest: Severance is generous. References are real. The exit is on a timeline that lets them tell their own story. I’ve never had one of those people refuse to take a coffee with me a year later. That’s the test, I think. Did they walk out with their dignity.

47:00 Skip to “What the team sees afterward”

Jorge: What does the team see afterward?

Sample Guest: Two things. They see that the bar is real. And they see that you’ll act on it without making the person who didn’t clear it feel like a failure. Both of those things matter, and they have to be true at the same time.

Jorge: What did this cost you to learn?

Sample Guest: Three separations that took at least a year longer than they should have. And one person I really respected who quit because they were tired of carrying the work of someone I wasn’t willing to deal with. That’s the one that still bothers me.

Jorge: What’s the action for someone listening to this?

Sample Guest: Pick the one person on your team you’ve been quietly worried about. Don’t pick three. Don’t make a list. One. Sit down by Friday and answer the three questions on paper. Then decide if the next thing is a conversation or a coaching plan. Either is honest. The dishonest thing is doing neither.