February 24, 2026

The Biggest Firing Mistake I’ve Made

The biggest firing mistake I’ve made is having the tough conversation on the day I fire them.

Do this instead.

Early Warning

6-8 weeks before:

“Something needs to change or the role will change. Let’s fix it together. I’ll do everything I can to help you succeed, but if this doesn’t improve, we’ll need to have a more serious conversation about whether this role is the right fit.”

Clear Checkpoints

Here’s our plan for the next [X weeks]:

Week 1-2:

  • [Specific action or process to implement]

  • Weekly 30-min check-ins to review progress

  • [Specific deliverable or milestone]

Week 3-4:

  • [Measurable milestone]

  • Continue check-ins, potentially shift to every-other-week

Success looks like: [Clear, measurable outcomes]

If we’re not seeing this improvement by [specific date], we’ll need to have a more serious conversation about whether the role is the right fit.

Make It Collaborative

I believe you can do this. [Acknowledge their strengths/value]. But I need you to [describe the shift needed].

What support do you need from me? What would help you [achieve expected outcome]? Is there a process or tool that would make this easier?

End With Clarity

To be really direct: This is critical. [Explain why it matters to the business/team]. I’m committed to helping you succeed in this, but I need to see you meeting this standard consistently.

Any questions or concerns?

After The Conversation

  • Send a recap email or Slack message with what you discussed to have it documented

  • Clearly outline the action items, timeline, and success criteria

  • Schedule follow-up check-ins

Key Takeaways

The biggest mistake is waiting until firing day to have the tough conversation. Instead, give your team member 6-8 weeks of warning, clear checkpoints, and genuine support to improve. Make it collaborative, end with clarity, and document everything after the conversation.

This approach gives people a real chance to succeed while protecting both you and your team. If you’re testing your hiring process, you’ll make fewer of these mistakes in the first place. And as you learn what to do sooner as CEO, handling tough conversations early becomes second nature.

Start the conversation before it’s too late.