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Draft a difficult message with care

Turn a sensitive update into a clear, kind message that says the hard thing without sounding cold or vague.

Stage: Copilot Chat · For: End user, Manager · Level: Starter · Time: 5 min

When to use this

You need to decline a request, give direct feedback, or share disappointing news, and the first draft in your head sounds either too blunt or too apologetic. Use Copilot Chat to shape the message before you send it, so the decision is clear, the tone is humane, and the next step is obvious.

What you'll need

  • M365 Copilot license with Microsoft 365 Copilot Chat in Teams, Outlook, Word, or the Microsoft 365 Copilot app
  • The facts you can share, the decision or ask, and any constraints you cannot change
  • The recipient's role, relationship to you, and likely concern

Try it now — the prompt

Open Microsoft 365 Copilot Chat and paste:

Draft a sensitive [email/chat message/Teams post] to [recipient or audience].

Context:
- Situation: [what happened]
- Decision or ask: [state the decision, request, or feedback]
- Reason I can share: [brief reason]
- What I cannot say: [private or uncertain details to avoid]
- Desired next step: [meeting, acknowledgement, revised plan, no action]

Write it in a clear, kind, professional tone. Put the decision or ask in the
first two sentences, avoid blame, do not over-apologise, and keep it under
[length]. Give me two versions: direct and warmer.

Why this works: it gives Copilot the decision, the boundaries, and the relationship. That keeps the message grounded in facts while letting Copilot help with wording, tone, and structure.

Step by step

  1. Open Copilot Chat where you are already working. Use Teams, Outlook, Word, or the Microsoft 365 Copilot app. No agent or setup is needed; this is just a prompt in chat.
  2. Paste the prompt and fill the brackets. Be explicit about the decision or ask, even if it feels uncomfortable. Copilot should return two polished options.
  3. Check for truth and ownership. Make sure the draft does not invent reasons, soften the decision past recognition, or promise a follow-up you cannot deliver.
  4. Pick a version and refine it in the same chat. For example: 
    Make the opening more direct, keep the warmer closing, and remove any wording
that sounds like the decision is still open.

Screenshots

We deliberately don't ship screenshots that go stale — the Microsoft Copilot UI changes often. Follow the numbered steps above, which we keep current. Maintainers can regenerate fresh captures with the Playwright tool in tooling/screenshots/.

Make it better

  • Give me a version for a senior leader and a version for a close peer, using the same facts.
  • Highlight any sentence that could sound defensive, vague, or legally risky.
  • Create a short follow-up if the recipient pushes back or asks for an exception.
  • Make it easier to skim: subject line, first sentence, three short paragraphs.

Watch out for

  • Do not outsource the judgement. Copilot can improve tone, but you own whether the message is fair, accurate, and appropriate to send.
  • Keep private details out. Do not paste sensitive information the recipient should not see unless you are allowed to use it in Copilot Chat.
  • Check for false softness. Kind does not mean unclear. If the decision is final, say that.

Where this leads (the ramp)

When you find yourself drafting the same sensitive update every week, move the repetitive version to Stage 2 and let a first-party agent assemble the context for your review before you send.

Next: First-Party Agents → Delegate repetitive message prep

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