How Do I Have a Difficult Conversation With an Employee?

What’s the best way to lead through a difficult conversation?


Celeste Headlee, author of We Need to Talk: How to Have Conversations That Matter, shares simple steps leaders can take to prepare for a difficult conversation with an employee.

“Make sure you've chosen a time of day that's not when not only you're at your best, but when the other person is gonna be clear,” she shares.

Watch the video to hear all of Celeste’s tips for navigating a difficult conversation.

If you have a difficult conversation coming up, there are some pretty simple things that you can do to prepare. Make sure you've chosen a time of day that's not when not only you're at your best, but when the other person is gonna be clear. Make sure you've chosen a venue that is quiet and allows for maybe perhaps emotions to run high if they need to, but still allows for privacy. Set it up so that they're comfortable. Give them some coffee or tea or whatever it is that they need.

The other thing I would say is don't wind up. For example, I had to reprimand someone in my team and I brought him in. He knew something, obviously, was wrong 'cause he'd been called into the boss' office and he sat down and I said, "Hey, listen, you're not fired. Nothing negative is gonna happen to you except there's some things going wrong and we need to work together to fix them." You could see his whole body go (exhales). If I'd done a long lead-up and just started talking about how bad things were, he would have been completely anxious and stressed and we would not have had a good conversation.
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Celeste Headlee

Celeste Headlee is an award-winning journalist, professional speaker and author of the book We Need To Talk – How To Have Conversations That Matter. After four years as the executive producer of On Second Thought at Georgia Public Rad...

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