A simple technique for having tough conversations at work

Executive overview

Tough conversations — especially letting someone go — often become cold, case-building exercises that leave both parties worse off. The fix is a single mental shift before the meeting.

Ask yourself: have I ever done the same thing? Find that story and share it. It changes your own mindset and reframes the moment for the other person from failure to lesson.

Shared experience — not empathy as a performance — is what makes hard news land well.

The one technique that changes everything

• Before the conversation, search your own history for a time you made the same mistake
• If you can't find one, look for someone close to you who did
• Opening with that story signals "we are the same" rather than "I am judging you"
• It shifts your internal stance: you can't build a legal case against someone when you've been there yourself
• It gives the other person an exit from shame — their identity is not the mistake

What this achieves for both sides

• Stops the post-firing spiral: the person kicking themselves and resenting you
• Reframes the moment as part of a normal growth process, not a verdict
• Creates a bond that helps the other person actually absorb and learn from the feedback
• The goal is not to make bad news feel good — it's to make it useful