Draft a difficult email
Get a firm, fair first draft of an email you have been putting off: chasing, declining, apologising, or pushing back.
Yours to copy, change, and make your own.
Replace every [BRACKETED PLACEHOLDER] with your own material before you send it.
Help me draft a difficult email.
Situation: [DESCRIBE THE SITUATION]
Recipient and our relationship: [RECIPIENT]
What I need the email to achieve: [GOAL]
Tone I want: professional, warm but direct. Not grovelling, not aggressive.
Rules:
- Get to the point within the first two sentences.
- Acknowledge the other person's position once, briefly, without conceding things I have not conceded.
- Make the ask or the decision unambiguous. The reader should not have to infer it.
- No corporate filler ("I hope this email finds you well", "as per my previous email").
- Keep it under 200 words unless the situation genuinely needs more.
- Use British English.
Give me two versions: one firmer, one softer. Then tell me in one sentence what the riskiest line in each version is.- [DESCRIBE THE SITUATION]
- What happened, in a few sentences. Include dates and any commitments already made.
- [RECIPIENT]
- Who they are and the relationship, for example "long-standing client, senior to me".
- [GOAL]
- The one thing the email must achieve, for example "payment date agreed this week".
Where it shines, and where it falls over.
- Chasing overdue invoices or unanswered decisions
- Declining requests, proposals, or meeting invitations
- Apologising for a service failure without over-committing
- The "riskiest line" review at the end is the most useful part; read it before you read the drafts.
- If the thread matters, paste the last two or three emails so the draft matches the tone of the conversation.
The model only knows the situation as you describe it, and people describe their own disputes generously. If your summary is one-sided, the draft will be too, and it can escalate a situation that needed de-escalating. Reread your description as if the recipient wrote it before you trust the draft.
Do not use this for anything with legal or HR weight: grievances, dismissals, contract disputes, safeguarding. Those emails become evidence, and a plausible-sounding AI phrase ("we accept responsibility for the delay") can concede more than you intended.
AI output is a first draft, not a finished product. You are responsible for whatever you send, publish, or decide with it.
More prompts worth exploring.
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