Use AI to rehearse a difficult conversation by role-playing the other person's reactions.
Before a tough conversation — like asking for a deadline extension, addressing a performance issue, or negotiating a resource conflict — use AI to practice. Ask it to role-play the other person based on what you know about their concerns, style, or likely objections. This lets you test your approach, refine your wording, and prepare for pushback before the real conversation happens. You'll walk in calmer, clearer, and ready for whatever comes up. It's like having a rehearsal partner who helps you think through the angles you hadn't considered.
Try this prompt today
“I need to have a difficult conversation with a colleague who keeps missing deadlines on shared projects, which is affecting my own work. They tend to get defensive when criticized. Role-play this conversation with me — you play my colleague. I'll start by explaining the issue, and you respond how they realistically might. Then give me feedback on how I handled it and suggest better ways to phrase my concerns.”
February 27, 2026
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