Email for a difficult conversation

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

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Prompt template
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.
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.

Why it works

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

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