How to start a difficult conversation

Image of Brian Kight
Brian Kight

Raise your hand if there’s a conversation you need to have with someone but haven’t had yet because you’re nervous about how it would go. If everyone reading this right now were together in a room, most of you would have your hand raised.

Here’s how to get permission to have a difficult conversation, especially when you’re anxious. Start with this:

“I’d like to share an observation (or perspective), but I’m concerned about how you would react. I believe it’s important and worth discussing. However, I’m unsure of your willingness to listen, consider it, and have an open discussion with me. So my question is, are you willing to have a discussion with me about something that might be sensitive, maybe even emotional, but also important?”

If the person says no, then you have your answer. Respect that. They’re not ready to have the conversation you want to have. Now you know and can adjust accordingly.

If the person says yes, then you have the permission you need. Consider starting the conversation with this:

“If you find out this isn’t something you’re willing to discuss with me, you can tell me at any time. I respect your boundaries. My intent is for your benefit, not to involve myself. Here’s what I’ve observed . . .”

Answer the call. Do the work.

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