Rehearse a hard conversation before you have it
Ask the AI to play the tough stakeholder and push back on you. Practice your answers in private, then get feedback on how you did.
How do I tell a stakeholder their project is being delayed?
I need to tell the head of a partner team that the reporting dashboard they asked for will be six weeks late, because two of our analysts were moved to another project. They're under pressure from their own leadership and tend to push back hard. Play that person. Stay in character, be skeptical, interrupt with objections, and don't accept vague answers. Ask me one question or objection at a time and wait for my reply. When I type "pause", step out of character and tell me what I handled well, where I sounded defensive or unclear, and one better way to phrase my weakest answer.
Why it works
Reading advice about a hard conversation is not the same as practicing one. When the AI plays the other person, you hear the objections out loud and find the weak spots in your answers before they matter. Asking it to stay in character, go one step at a time and give feedback on request turns a chat into a short practice session.
Try it now
Click a highlighted part and type your own details. Press Enter to jump to the next one, then copy.
I need to tell [who] that [the hard news], because [the reason]. They tend to [how they usually react]. Play that person. Stay in character, be skeptical and push back. Ask me one question or objection at a time and wait for my reply. When I type "pause", step out of character and give me feedback: what worked, where I was unclear, and a better way to say my weakest answer.
Variations
Turn up the difficulty
Run it again, but this time be more difficult. Bring up the time we missed a deadline last quarter and ask why anyone should believe the new date.
Practice the other side
Now swap roles. You deliver the news to me the way a calm, experienced manager would, and I'll play the skeptical stakeholder.
Prepare before you practice
Before we role-play, list the five toughest questions this person is likely to ask, and for each one, the honest answer I should be ready to give.
Based on: One Useful Thing (Ethan Mollick), "The Machines of Mastery". Last checked October 3, 2026.
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