Hard conversations at work don’t get easier by avoiding them. Preparation helps.
Why Practice Leaders Put These Off
A conversation with an underperforming employee, a vendor who missed a deadline, or a patient who’s upset about a bill, all of these tend to get rehearsed in your head for days before they ever actually happen. The dread usually isn’t about the facts. It’s about not knowing how the other person will react, or saying something in the moment that makes things worse.
The Prompt To Copy And Paste
This week’s tip: before a difficult conversation, use this prompt to get organized, and to separate what you actually know from what you’re assuming.
“I need to have a difficult conversation with [an employee / a patient / a vendor] about [brief description of the situation]. Help me prepare by: 1. Separating what I actually know from what I’m assuming 2. Identifying the likely concerns from their side 3. Listing my strongest, most factual points 4. Flagging anything I should avoid saying that could make this worse 5. Suggesting how to open the conversation without putting them on the defensive right away.”
Fill in the brackets with your own details, then copy and paste directly into ChatGPT, Microsoft Copilot, or any AI tool.
What This Doesn’t Do
Use this to organize your thinking, not to decide who’s right. That part’s still on you. It won’t script your emotions, but it will help you walk in with a clear head.
Try It This Week
- Think of a conversation you’ve been putting off or needs to be addressed
- Run it through the prompt above before you have it
- Separate what you actually know from what you’re only assuming
- Walk in with your strongest, most factual points ready
Take a deep breath. Now you’re prepared.
For more AI tips, get our free guide here.

