The Hardest Conversation

Everyone tells you to hire slow and fire fast. The first part is easier to understand. The second is harder to do. Firing someone especially an early employee is one of the most painful jobs a founder has.

You feel like you failed them. You feel like you failed the company. You worry about their life their family and their reputation. So you wait. You hope things will get better. You make excuses. You tell yourself it is just a rough patch or that more training will fix it.

This is almost always a mistake. Delaying the inevitable doesn’t help the employee. It hurts the rest of your team and your company. The cost of keeping the wrong person is far higher than the discomfort of the conversation you need to have.

The Signs You Waited Too Long

You often know it is time long before you are willing to admit it. The signs are usually obvious if you look for them.

Your best people are frustrated. They either complain to you about the underperforming employee or worse they stop complaining and start quietly working around them. They pick up their slack and their resentment grows. This is poison for a small team.

You avoid giving the person important new work. When a critical project comes up your first thought is to give it to someone else because you can’t trust the underperformer to get it done right or on time. You are managing them out of the workflow before you have managed them out of the company.

You feel a sense of relief when they are on vacation. This is the clearest sign. If your immediate reaction to someone being out of the office is relief not a feeling of being shorthanded you have a serious problem. Their absence improves the team’s mood and productivity.

A Framework for the Decision

Emotion makes these decisions hard. A simple framework can bring clarity. Before you decide ask yourself three questions.

First is this a problem of skill or a problem of will? A skill problem can sometimes be fixed with training or mentorship. A will problem cannot. Is the person trying hard but failing or are they not trying hard enough? Is the issue a lack of capability or a lack of commitment? Be honest. Most of the time in a startup it is a fundamental mismatch of capability.

Second does this person’s presence drain or add energy to the team? Some people are competent but have a negative effect on morale. They might be cynical pessimistic or just not a good cultural fit. In a small company energy is everything. A single person who drains it can capsize the whole boat.

Third and most important is the simple direct question.

Knowing what you know today if this person were a candidate for the job would you enthusiastically hire them?

If the answer is anything less than an immediate yes you have your answer. You are not running a charity. You are building a team to do something hard. You cannot afford to have people on the bus you would not let on in the first place.

The Conversation Itself

Once you have made the decision you must act quickly. The conversation should be planned but not rehearsed to the point of sounding robotic. It should be in person if possible and always private.

Here is a simple structure.

1. Get to the point immediately. Do not start with small talk. It is cruel. Sit down and say “Thanks for meeting with me. I have some difficult news. We are letting you go and today is your last day.”

2. State the reason simply and finally. Do not get into a long debate or a performance review. The decision is made. The goal is not to convince them but to inform them. A simple explanation is best. “This is not working out because we need a different set of skills in this role for where the company is going.” This frames it as a role mismatch not a personal failure.

3. Explain the logistics. Immediately transition to the details. “We will pay you through the next two weeks and your health insurance will continue through the end of the month. Here is a document that explains everything. We will need you to return your laptop.” Have all this information ready in writing.

4. End the conversation. Do not let it drag on. It is an uncomfortable situation for both of you. Once you have delivered the message and the logistics you can say “I want to thank you for the contributions you made here. I wish you the best in your next role.” Then stand up. The conversation should take less than fifteen minutes.

What Comes After

Your team will know something is wrong. After the employee has left gather your team. Be direct and respectful.

Tell them “Today was [Name]'s last day with the company. I know this is difficult news. We wish them well.”

Do not share the specific reasons for the termination. It is unprofessional and creates a culture of fear. The team does not need to know the details. They need to know you are in command and that the company is moving forward. Reassure them and shift the focus back to the work. Let them know how the person’s responsibilities will be handled in the short term.

Firing someone is a sign that your hiring process failed. Each time it happens you must ask yourself what you could have done better. Did you define the role incorrectly? Did you miss red flags during the interviews? Improving your hiring is the only way to have these conversations less often. You can find some thoughts on that here https://journalofme.com/blog/minimalist_hiring_loop.

This is the hard work of building something. It never gets easy but it is necessary. Learning to do it cleanly and respectfully is one of the most important things you can do for the people who remain. Think about when you have put off a hard conversation and what the cost of that delay was.

— Rishi Banerjee
September 2025