Beyond the Bugs

Beyond the Bugs

Playbooks

When Your Engineer Wants to Quit: The Retention Conversation

What to say (and not say) when someone tells you they're thinking of leaving

Feb 20, 2026
∙ Paid

When a good engineer tells you they’re thinking about leaving, your immediate reaction matters. This conversation is delicate. Handle it well and you might keep them. Handle it poorly and you’ll accelerate their exit.

This playbook walks you through the retention conversation: what to ask, what to offer, and when to let go.

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Photo by Javier Allegue Barros on Unsplash

The First Five Minutes

When someone tells you they’re considering other opportunities, your first job is to not panic. Take a breath. Thank them for telling you. Then listen.

“Thanks for sharing this with me. I want to understand what’s going on. Can you walk me through what you’re thinking?”

That’s it. Don’t jump to solutions. Don’t make promises. Don’t try to talk them out of it. Just listen.

What you’re listening for:

  • Is this about compensation, growth, work, team dynamics, or something else?

  • How far along are they? Casually browsing or actively interviewing?

  • Is this fixable, or have they already made up their mind?

  • What’s driving…

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