How to end a difficult conversation at work

Short answer: say “Let's check in next Friday to see how the new approach is going.”

DON'T SAY
“So… we're good, right?”
after a tough talk
SAY THIS
“Let's check in next Friday to see how the new approach is going.”
A follow-up date shows you're invested in their success.

When to use it

Use it at the end of a tough feedback conversation. Agreeing on a follow-up date shows you care how things go next and gives you both a natural time to check in. It moves on from the hard part without pretending it didn't happen.

Example

You: “Let's check in next Friday to see how the new approach is going.”

Teammate: “Sounds good. I'll have the first week's numbers by then.”

In an email or Slack message

Send a short note afterward: “Thanks for the conversation today. I've put 15 minutes on Friday to check in on how the new approach is going.” Then keep that meeting.

Quick drill

When you notice the same problem happening more than once, like late reports or missed handoffs.

Which sounds more confident?

Practice 10 more →

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