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When you come to the decision to remove someone from your team, how you handle it has far-reaching implications.

Before we get to that, let’s address the elephant in the room: firing someone sucks, and no one wants to do it—except malevolent sociopaths.

If you’ve ever been on either side of this conversation, you know it’s one of the worst and most traumatic experiences you can have as a professional.

When you’re the person being fired, you may feel angry, ashamed, and question everything—from your self-worth to your willingness to trust others. It’s devastating.

How could this happen to me?!

When you’re the person doing the firing, you may feel heartbroken, scared, and question if you’re even cut out to be a leader in the first place. It’s devastating.

How could I let this happen?!

It feels like a losing situation no matter what side you’re on.

Today, let’s talk about how to handle the unfortunate situation where you need to let someone go from your team.

Difficult and Necessary

There are different reasons why you may need to let someone go:

  • Cash flow problems
  • Performance issues
  • Culture or safety concerns
  • Changing needs of the business

Everyone might really like the person being let go, or maybe they’ve become toxic and are negatively impacting those around them.

Make sure this is something you need to do, and not a situation where you’d be better served by changing their role.

No matter the circumstances, there are all sorts of potential problems that could follow the decision to remove someone from your team. This can include the loss of specialized knowledge, gaps in coverage or productivity for critical roles, and even potential legal risks for wrongful termination, discrimination, or retaliation.

In short, you need to get this part right.

Difficult and Unprepared

The most common reason why a staffing change goes wrong is insufficient preparation. The three biggest pitfalls are:

  1. Thinking only about the business, and not the human being fired.
  2. Making the decision without talking to the team.
  3. Scrambling to fire someone quickly because you didn’t address the issues leading to it ahead of time: cash flow, performance, etc.

If this firing feels like it’s coming out of nowhere for the team or for the employee being fired, you haven’t done your job as a leader beforehand. If you run into a mountain of issues after they’re gone, you didn’t do enough to prepare.

On top of all this, you still have to tell the person their employment has come to an end. Out of everything, this might be the hardest part for leaders.

Luckily, the same principle can help you prepare for all of this.

Difficult and Kind

If you adopt the mindset of a Lovable Leader, then Care, Trust, and Safe Travels are your guiding lights. That requires preparation to become a habit.

When you center the people on your team, you are constantly analyzing how to put them in positions to win. This transparent and ongoing dialogue with them and the team means fewer surprises when it’s not working out.

With that said, here’s the process of firing someone as a Lovable Leader:

Step 1: Check-In

1a. First, check in with yourself.
Get clear on why this is necessary. Reflect on whether this decision is truly fair and in line with your values as a leader. Focus on the issues that led to this moment.

Write it all down so you can process it externally.

1b. Next, check in with your team.
This helps you find blind spots and potential biases.

Meet privately with the team members who will be most directly impacted. Be careful not to “lead the witness” by putting ideas in their heads about why this person needs to go. Be curious and let them share their thoughts.

This helps ensure this isn’t just about making it easier for you, but about doing it in a way that leaves everyone involved better off.

Step 2: Prep for the Conversation

2a. Write out your script or outline.
Make a clear case focused on the issue, not the person.

If you need help with this part, try my custom Sitting on the Same Side of the Table GPT— it’s only $10, and you keep it forever.

2b. Anticipate their reactions.
Anger, sadness, or confusion are normal. Prepare yourself to meet those reactions with empathy.

2c. Pick the right time.
Be considerate about when and where the conversation takes place.

Avoid high-stress times or public settings. Schedule the conversation privately and at a time when they can process (e.g., not at the end of a workday).

Step 3: Have the Best Conversation You Can

There’s a 99% chance this isn’t going to be a great conversation. How could it be? The point isn’t that everyone walks away smiling but that you did the best you could.

Here’s how to do that:

3a. Be Consistent. Don’t go halfway.
You mustn’t waver or backtrack. The decision has been made. Now is not the time to second-guess yourself. All that preparation was so you could focus on how you show up—not whether or not this is happening.

3b. Be Kind.
Kindness starts with being transparent and direct. Don’t keep them in suspense.

You might start with:

“This is going to be a difficult conversation for both of us. We’ve made the decision that we can’t keep you on the team anymore. This was not an easy decision. We want to do everything we can to support you through this transition and minimize the difficulty it causes you, to the best of our ability. I imagine it’s hard to hear this, and you probably have a lot of questions. I’m going to explain why we’ve made this decision and then give you the floor to ask questions.”

Don’t sugarcoat or drag it out. Be clear and kind.

Being kind also requires empathy. Talk to them like a person rather than a (former) employee. Even though they will no longer be part of your team, help them maintain their dignity by not attacking them. Acknowledge their strengths and contributions, and ensure the decision is anchored in the unmet business needs.

3c. Be Proactive.
Help them transition. If possible, provide a severance package. Offer a recommendation, connections in your network, or resume-building advice.

Offer whatever resources or guidance you can. Try to minimize the harm this causes them to the best of your ability.

The Necessity of Change

Firing someone is never easy, but it’s one of the most important ways we demonstrate who we are as leaders.

How we handle it speaks volumes—not just to the person leaving, but to the team that stays. Make sure to meet with your team and think about how to maintain morale. Be careful not to breach confidentiality or risk diminishing trust with those who remain.

If you handle these unfortunate moments with love, care, and respect, you’ll never have to look back with regret, no matter what happens next.

The Critical Last Steps: Reflection & Rebuilding

Once it’s all behind you, don’t miss the opportunity to grow through careful reflection.

Think about what you could have done differently as their leader to prevent this situation.

Give yourself space to process the emotional toll, and let it inspire you to do whatever you can to avoid it in the future.


I hope you enjoyed this post!

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