The Hardest Skill: How to Fire Someone Without Losing Your Soul

There is no task in business that causes more sleepless nights than the act of firing someone.

It is the absolute nadir of the founder experience.

You can handle a lost client. You can handle a server crash. You can handle a lawsuit. But sitting across from a human being, someone you likely hired and trained, and telling them their livelihood is being taken away? That is a visceral, physical weight.

Most business advice glosses over this. They use antiseptic terms like “downsizing” or “right-sizing” or “parting ways.”

We need to look at this directly. We need to talk about the mechanics of the termination because if you are going to build a company of any significant size, you will have to do this. And you will have to do it more than once.

The goal is not to make it feel good. It will never feel good. The goal is to do it with enough decency that the person leaves with their dignity intact, and you leave with your conscience clear.

The single biggest mistake founders make regarding termination is waiting too long.

We wait because we are nice. We wait because we are optimistic. We hope that one more coaching session or one more week might turn things around.

While this feels like empathy, it is actually a form of selfishness. We are delaying the inevitable because we want to avoid the discomfort of the confrontation.

When you keep a person in a role they are failing at, you are doing damage to three distinct entities.

First, you are damaging the business. Resources are being wasted and opportunities are being missed.

Second, you are damaging the team. High performers know who the low performers are. If they see you tolerating mediocrity, they lose respect for your leadership. They start to wonder why they are working so hard when there are no consequences for not working hard.

Third, and most importantly, you are damaging the employee. Most people know when they are failing. Keeping them in a state of professional limbo creates anxiety. It prevents them from finding a role where they can actually succeed.

Clarity is kindness. Ambiguity is torture.

If an employee is shocked when they are fired, you have failed as a manager.

Termination should be the final step in a long, documented process of feedback. The conversation in the dismissal meeting should almost be a formality, a confirmation of what everyone already knows is coming.

This requires a culture of radical candor.

When performance dips, it must be addressed immediately. Not in the annual review. In the moment.

“Hey, this deliverable wasn’t up to our standard. Here is why.”

If the behavior continues, you move to a formal Performance Improvement Plan (PIP). Many people view PIPs as just a legal checkbox to avoid lawsuits. While that is true, they serve a more important psychological function.

A PIP draws a line in the sand. It says, “If X does not happen by Y date, employment will end.”

When that date arrives and X has not happened, there is no debate. The data made the decision. You are simply the messenger delivering the news that the data has generated.

This removes the personal element. It is not that you don’t like them. It is that the agreement was broken.

If done well, a PIP should also clearly offer an early choice to the employee: “Ship up” or “Ship out”. The internet is filled with PIP-receivers coasting for a few weeks waiting to get fired. You’ll see this happen. But if they put in the effort, so should you.

How do you actually say the words?

Brevity is your friend here.

• Nerves will make you want to ramble.
• You will want to small talk about the weather to ease the tension.
• You will want to apologize.
• You will want to over-explain.

Do not do any of these things.

Schedule the meeting. Do not make it on a Friday afternoon. Friday firings are an old corporate relic that leaves the person stewing over the weekend with no one to call. Fire on a Tuesday or Wednesday morning. Let them start their job hunt immediately.

When they sit down, get to the point in the first sentence.

• “I have some bad news. Today is your last day at the company.”
• “We have decided to terminate your employment.”

Use the past tense.

If you use the present tense or conditional phrases like “I think it’s not working out,” you invite a negotiation. The employee will try to argue their case. They will promise to do better.

This is not a negotiation. The decision has been made. The time for debate was during the PIP period.

Your role in this meeting is to be a broken record.

“I understand you are upset, but the decision is final.”

It sounds cold, but it is actually the most compassionate way to handle it. It provides a hard wall of reality that allows them to start processing the grief immediately, rather than clinging to false hope.

Remember the unfairness in the meeting. You know what is happening and can prepare. They have a good idea, but it is surrounded by uncertainty. They might get angry. Upset. Cry. Shout. This is unfiltered human emotion. Do not take it personally. Do not take it as a representation of that person’s fundamental character. It sucks. Don’t offer false hope. Don’t be mean.

Once the sentence is delivered, the dynamic shifts from management to logistics.

How you handle the next twenty minutes determines how this person remembers you for the rest of their life.

The tree remembers but the axe forgets.

Do not have security march them out of the building like a criminal unless there is a genuine safety threat. That is a humiliation ritual that serves no purpose.

Give them a choice.

• “Do you want to say goodbye to the team, or would you prefer to leave now and have us communicate it later?”
• “Do you want to pack your things now, or come back on the weekend/after-work/tomorrow when the office is empty?”

Giving them agency in a moment of powerlessness restores a small piece of their control.

Furthermore, be generous with severance if you can afford it.

Severance almost always comes with a separation agreement. That can be helpful to clear any legal liabilities in the future. It can help with future acquirers. It can help with trade secrets. Consult a lawyer but if you can afford it, a severance and a separation agreement can be worth every penny.

The law might require two weeks. If you can give four weeks or eight weeks, do it. You are buying two things with that money. You are buying them a runway to find a new job, which reduces their panic. And you are buying your company’s reputation.

Ex-employees talk. A fired employee who feels they were treated fairly is neutral. A fired employee who feels they were treated poorly is a saboteur.

After the person has left, you have to talk to the team.

The rumor mill moves faster than Slack. You need to address it immediately.

Gather the team. Be brief. Be respectful.

“As of today, John is no longer with the company. We wish him the best in his next steps. We are going to distribute his workload in the following way…”

Do not explain why.

Even if John stole from the register, you do not say that.

Saying “It wasn’t a good fit” is enough. The team usually knows why. They worked with him. They saw the missed deadlines.

If you trash the person who just left, everyone in the room will instantly think, “Is that what he will say about me when I leave?”

Maintain the confidentiality of the employment agreement. It builds trust with the survivors.

Do not trash them employee later either. Bosses who trash previous employees show that they don’t care about the team except for when they’re on the team. It’s a bad look and looses you loyalty. The only exception to this is egregious behavior to other employees. Where you are seen to be defending the team. Tread carefully though.

Finally, we need to talk about you.

After you fire someone, you are going to feel terrible. You might feel a mix of relief and guilt. You might question if you made the right call.

This is normal. It means you are human.

Do not numb this feeling. Sit with it. Let it inform your hiring process next time.

Every firing is ultimately a hiring failure. Somewhere upstream, you missed a signal. You ignored a red flag. You didn’t onboard them correctly.

Use the pain of the firing to sharpen your filter for the next candidate.

Business is an engine of value creation. Sometimes, parts of that engine stop working. Replacing them is not an act of malice. It is an act of maintenance.

It never gets easy. But it does get clearer.

Keep building.