Difficult Personal Email or Message

Write the message you have been putting off — declining, apologising, setting a boundary, or asking for something — in a tone you can stand behind.

The Prompt — replace [BRACKETS] with your details

Act as a thoughtful friend who writes well and will tell me if I am being unreasonable.

The situation:
- Who this is to and our relationship: [PERSON, RELATIONSHIP, HISTORY]
- What I need to say: [DECLINE / APOLOGISE / SET A BOUNDARY / ASK FOR SOMETHING / RAISE A PROBLEM / END SOMETHING]
- What actually happened: [FACTS]
- What I am feeling: [HONESTLY — the message should not say all of it, but you should know]
- What I want to happen after this message: [THE OUTCOME]
- What I want to protect: [THE RELATIONSHIP / MY TIME / MY POSITION / NOTHING]
- Channel and length: [EMAIL / TEXT / MESSAGE, HOW LONG]

Deliver:
1. A gut check first: is what I am asking for reasonable, and is there anything in what I told you that suggests I am missing something? Say it plainly, briefly
2. Three versions of the message:
   - WARM: preserves the relationship, still says the thing
   - PLAIN: clear and brief, minimal cushioning
   - FIRM: for when this has already been raised and ignored
3. For each: what it risks and what it protects
4. The sentences most likely to be misread, and safer phrasings
5. What to leave out entirely — the lines that would feel good to send and cost me later
6. If they respond badly, one calm reply I can send without escalating
7. Whether this should be a message at all, or a conversation

Rules: no passive aggression, no over-apologising, no paragraph of justification. If a boundary needs no explanation, do not write one.

How to use this prompt

Read the gut check even when you disagree with it — it is the part a friend would say and an AI usually will not unless asked.
Draft it, then wait a few hours before sending. The version you send after the pause is almost always the right one.
Take section 5 seriously; the satisfying line is usually the expensive one.

Why this prompt works

These messages get stuck between two bad drafts: too soft to land, or written from the feeling rather than the goal. Producing three tones with their costs makes the trade-off explicit, and asking for the gut check first catches the case where the message is not the real problem.

Variations to try

Add "we have had this conversation twice already" for a version that references the pattern without relitigating it.
Ask for a short text version and a longer email version of the same message.
Ask what a fair reply from them would look like, so you know what you are hoping for.

Common mistakes to avoid

Sending the FIRM version first, before the plain one has ever been tried.
Explaining a boundary at length, which invites negotiation of the boundary.
Sending immediately while still angry, which is what the three-version structure exists to prevent.

Works well with

Claude

ChatGPT

Gemini

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