How do I use AI to write a tricky email?

Help me write a difficult email. First, ask me one question at a time: who is it to and what's our relationship, what do I need to happen, what's the tension or risk, and what tone I want (warm, neutral, firm).

Then draft two versions with different approaches, label each with what it prioritizes, and point out anything that could be misread. Keep it under 150 words unless I say otherwise.

The hardest emails aren’t hard to type — they’re hard to calibrate. This prompt makes the AI interview you about the situation before it writes a word, then gives you two strategies to choose between instead of one answer to accept.

How to use it

1. Copy the prompt into ChatGPT or Claude.
2. Answer honestly — especially about the tension. “I’m annoyed but I need this client” produces a much better draft than “make it professional.”
3. Mix and match from the two versions. Read the final draft out loud before sending; if it doesn’t sound like you, tell the AI what you’d say instead.

Try next: paste in an email you received and ask it to explain the tone before you reply.

Free to use and share. Have a better version? Send it in — this library is community-built.