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Automation Squad
You run thisWritten for ChatGPT or Claude

Rehearse a difficult conversation before I have it

Robert MacKelfresh

By Robert MacKelfresh

Founder, Automation Squad

Preparing what you'll say is a different skill from saying it under mild stress while someone reacts, and only the second one is what happens in the room. The rules constraining the roleplay matter more than the prompt itself — a model that folds after one good argument teaches you nothing, because the real person won't.

The prompt

I have a conversation coming up that I'm not looking forward to. I want to practise it, not plan it.

Who I'm talking to: [THEIR ROLE AND YOUR RELATIONSHIP]
What it's about: [THE SUBJECT]
What I want out of it: [YOUR ACTUAL GOAL — not the diplomatic version]
What they probably want: [YOUR HONEST GUESS]
What I'm worried they'll say: [THE THING YOU'RE DREADING]

You're going to play them. Rules for you:
- Be realistic, not difficult for the sake of it. Real people are mostly reasonable and occasionally not.
- Don't concede quickly. If I make a weak argument, push on it the way they would.
- Stay in character until I type STOP.
- If I say something that would genuinely land badly, react the way a person would — don't be a good sport about it.

Start with their opening line. Not a summary of their position — the actual first thing they'd say.

When I type STOP, come out of character and tell me:
1. Where I lost them, if I did, and the exact moment
2. The thing I said that I should cut entirely
3. The strongest point I made, so I keep it
4. What I never got to, and whether it mattered
5. One sentence that would have made the whole thing easier, and where it should have gone

Don't reassure me. If I handled it badly, I'd rather find out here.

Copy it, paste it, run it. Nothing here is gated.

More for the same job

Written for ChatGPT or Claude as of August 2026. Models change — if this stops working the way it should, that is worth telling us about.