A difficult message that stays professional

Say the hard thing clearly, without softening it into mush or sharpening it into a fight.

Pushing back, declining, delivering bad news, raising a problem with someone senior.communicationfeedbackworkplace

Help me write a difficult message at work.

The situation: <what happened, specifically>
Who it's to, and the power dynamic: <peer / my manager / my client / someone I manage>
What I need to say: <the hard part, in your own words>
What I want to happen after: <the outcome>
What I'm afraid of: <how it could land badly>
Channel: <email / Slack / message before a call>

Write 2 versions:
1. Direct and warm: the hard thing in the first two sentences, facts not judgements, what I need, and one sentence that keeps the relationship intact. Under 150 words.
2. Shorter: for chat, under 60 words, that opens the conversation rather than finishing it.

Rules: no passive aggression, no sarcasm, no "per my last email". Describe behaviour and impact, not character. No apology for raising it. If I'm asking for something, one clear request.

Then: the two most likely reactions and a calm one-line response to each, and one sentence on whether this should be a call instead.

Replace every <placeholder> with your own details before you send it.

How to use it

1Write down what you're afraid will happen if you send it. The model uses that to calibrate.
2Sleep on it if you can. Ask for the version to send tomorrow, not tonight.
3One issue per message. Bundling grievances turns a message into an indictment.

Reviewed 2026-09-20

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