Insight The operator's journey
Letting a hire go, the right way
Keeping a hire who is not working hurts the business, the team, and the person too. Here is how to know when it is genuinely time to let someone go, and how to do it with decency.
Letting someone go is the part of building a team that almost nobody talks about and everybody dreads. It feels like a failure, it is emotionally heavy, and so founders postpone it, often for months, telling themselves the person will turn a corner. Usually the delay just prolongs the harm. Here is how to know when it is genuinely time to let a hire go, and how to do it with decency once you decide.
The test that cuts through the doubt
The hardest part is knowing whether you are giving up too early or holding on too long. The cleanest test is a single honest question: knowing what you now know, would you enthusiastically hire this person for this role again? Not reluctantly, not with caveats, enthusiastically. If the honest answer is no, some part of you has already made the decision and is waiting for permission to act on it.
That is not the whole story, of course. You owe the person clarity about what good looks like, honest feedback, and a real chance to close the gap before it gets to this. But if you have done those things and the gap is still there, the answer is usually clear, and the only question left is how long you let it drag.
The honest test is whether you would enthusiastically hire them again knowing what you now know. If the answer is no, you have already decided, you are just waiting for permission.
Keeping a bad fit harms everyone
Founders delay out of kindness, but keeping someone in a role they are failing is rarely kind. It harms everyone involved, including them.
Doing it with decency
Never let it be a surprise
If you have given honest feedback along the way, the conversation should not blindside them. The cruelty is not in the decision, it is in someone learning for the first time, on the day they are let go, that they were failing. Ongoing honesty is what makes the final conversation fair.
Be direct, then be kind
Deliver the decision clearly, without burying it in vague language that leaves them unsure what just happened. Then be as kind, respectful, and practically supportive as you can in how you do it. Decency lives in the honesty and the respect, not in softening the message until it is unclear.
Once decided, move
Drawing it out helps no one. When you have genuinely made the decision, act on it promptly and privately, with dignity. A slow, ambiguous exit is harder on everyone than a clear, respectful one.
Letting a hire go
- Use the test: would you enthusiastically hire them again?
- Confirm you gave clear expectations, feedback, and a real chance
- Recognize that keeping a bad fit harms the team and the person too
- Never let the decision be the first they hear of the problem
- Be direct and kind, not vague and soft
- Once decided, act promptly, privately, and with respect
The best way to face fewer of these conversations is to hire more deliberately in the first place: clear about the role, assessing properly rather than under pressure, and onboarding well so a promising person is set up to succeed. Many painful exits are really bad onboarding or bad fit that better hiring would have caught. You will never avoid it entirely, building a team means occasionally getting it wrong, but honesty early prevents most of the worst cases.
If team decisions like these are weighing on you and you want a clear-eyed read on what your operation actually needs from its people, that is exactly the kind of conversation a Growth Audit can open.