Email for a difficult conversation

Deliver hard news or feedback clearly and kindly, without burying the point or sounding cold.

Change note: Initial version

Prompt

Help me write a message about a difficult topic.

Situation: {{situation}}
Who I am writing to and my relationship with them: {{recipient}}
What I need them to understand or do: {{outcome}}
Things I must not say or promise: {{boundaries}}
Tone: {{tone}}

Write it so that:
- The main point appears in the first two sentences. No long warm-up.
- It states facts and the impact, not assumptions about their motives.
- It acknowledges how the person may feel in one sincere sentence, with no corporate language.
- It ends with a specific next step and, where useful, an invitation to talk.
- It is no longer than 200 words.

Output format:
1. The email, with subject line.
2. "Riskiest phrase": the one line the recipient is most likely to react badly to, and a softer alternative.
3. Whether this should be a call or in-person conversation instead, in one sentence.

Variables

• {{situation}}Situationlong

  Default: A colleague has missed the last three deadlines on shared reports, and it is delaying my team's work.

• {{recipient}}Recipienttext

  Default: A peer I get along with, Chris, from the analytics team

• {{outcome}}Desired outcometext

  Default: Agree a realistic delivery schedule this week

• {{boundaries}}Do not saytext

  Default: Do not mention performance reviews or escalate to his manager

• {{tone}}Toneselect

  Options: Warm and professional, Direct and concise, Friendly and casual, Formal, Confident and persuasive, Empathetic

  Default: Empathetic

Example output

Subject: Report timing and finding a schedule that works

Hi Chris,

I want to raise something directly: the last three shared reports have arrived after the agreed dates, and that has pushed back my team's analysis each time.

I know your plate is full, and I would rather solve this with you than around you. Could we agree on delivery dates that are realistic for you? I am flexible on format if that makes it easier.

Can we spend 20 minutes on Thursday to work it out? Tell me what time suits you.

Thanks,
Alex

Riskiest phrase: "have arrived after the agreed dates". Softer: "have landed later than we planned".

Call or email: A short call would likely land better; use this email only as a written follow-up to confirm the new dates.

Notes

The 'riskiest phrase' check catches wording that triggers defensiveness. Listing what you must not say keeps the draft clear of promises you cannot keep.