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I’ve kept people too long at Legiit. More than once. Each time, the damage wasn’t the person. It was every month I waited after I knew.
The most expensive employee in your business isn’t the highest paid one.
Think Big Minute #10
It’s the one you kept past the month you knew they weren’t it.
Every founder knows the month. You remember the call, the project, the thing they said in the meeting… the moment the picture snapped into focus and you knew.
And then you did nothing about it for 6 more months.
Sometimes 12.
Sometimes longer.
You told yourself they might turn it around. You told yourself the timing wasn’t right. You told yourself firing them would hurt the team. You told yourself you owed them another chance because they were loyal, or because you liked them, or because their kid was about to start college.
All of that is real. None of it is the job.
Here’s the actual cost of the month you knew vs. the month you acted.
The work they should be doing doesn’t get done. The work they are doing has to get redone. The team around them carries the weight and resents you for it. Your best people start looking around because they’re watching you tolerate mediocrity and wondering what else you tolerate. Your growth plan slips a quarter, then two, then a year.
And the person you’re “protecting” by not firing? They know. They’ve known since the month you knew. You’re not doing them a favor. You’re letting them waste their own career in a seat they shouldn’t be in.
Here’s how to stop doing this.
Write down the moment you knew. The second it hits, open a doc and log it. Date, what happened, what you felt. This kills the “maybe I’m overreacting” loop that costs you six months.
Give one honest conversation, one plan, one deadline. 30 days, 60 at most. Specific outcomes, not vibes. They either hit it or they don’t. No third meeting. No fourth chance. You already gave those when you waited 6 months to have the first one.
Stop confusing loyalty with fit. Someone being around a long time is not a reason to keep them. It’s a reason to owe them a clean exit. A severance. A good reference. A real goodbye. Not a slow death in a role they can’t do.
Fire on a Monday, not a Friday. Friday is for your comfort. Monday gives them the week to start looking. Do the harder thing, not the one that feels better for you.
Ask yourself the question every 90 days. “If I were hiring for this role today, would I hire this person?” If the answer is no, you already have your answer. You’re just deciding how long to pay for it.
Replace the seat before you replace the person when you can. Know who you’d hire next. Have the conversation with them. The reason most founders wait too long is they’re scared of the gap. Close the gap first.
I’ve been on both sides of this. I’ve kept people too long. I’ve also been kept too long in jobs where the person above me knew and didn’t say anything. Neither side is the mercy it looks like.
The kind thing and the clear thing are almost always the same thing.
You already know the month. Act in it.
Think Big
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