Difficult Feedback Message Crafter

What it does

Helps you write feedback messages — emails, Slack messages, or speaking notes — for situations where you need to be direct about a problem without damaging the relationship. Covers performance concerns, missed expectations, behavioral issues, and project problems. The output is specific, uses concrete examples, and avoids both corporate softening and unnecessary harshness.

The Prompt

Help me craft a feedback message for a difficult situation.

Context:
- My role: [YOUR RELATIONSHIP TO THE RECIPIENT — "their manager" / "peer on the same team" / "client" / "stakeholder"]
- Recipient: [THEIR ROLE — no need for names]
- Delivery method: [EMAIL / SLACK / SPEAKING NOTES FOR 1:1 / WRITTEN PERFORMANCE REVIEW]

The situation:
[DESCRIBE WHAT HAPPENED — be specific. Include dates, examples, and observable behaviors. "They've been underperforming" is too vague. "They missed the March 5 deadline on the API migration and didn't flag it until I asked on March 8" is useful.]

What I want to achieve:
[YOUR GOAL — "I want them to understand the impact and commit to a plan" / "I want to set a clear boundary" / "I need to formally document a pattern" / "I want to course-correct without demoralizing them"]

Relationship context:
[IMPORTANT — "generally strong performer, first time this happened" / "this is a pattern, we've discussed it twice before" / "new hire still ramping" / "senior person who should know better"]

Write the message following these rules:

## Structure
1. **Open with the specific observation.** Not a compliment sandwich. Not "I've been thinking about..." Just state what you observed. Use facts and dates, not interpretations.
   - YES: "The API migration deadline was March 5. On March 8, when I asked for a status update, it was the first time the delay was flagged."
   - NO: "You don't seem committed to deadlines."

2. **State the impact.** Why this matters — to the project, the team, the client, or the person's own growth. Be specific about consequences, not hypotheticals.
   - YES: "This delayed the QA cycle by 3 days, which means we'll miss the client demo on March 15."
   - NO: "This could cause problems down the line."

3. **Acknowledge their perspective (briefly).** One sentence showing you're open to context you might not have. This is not a hedge — it's intellectual honesty.
   - YES: "There may be context I'm missing about what caused the delay."
   - NO: Three paragraphs of "I'm sure you're very busy and there are a lot of demands on your time and I completely understand..."

4. **State what you need going forward.** Specific, behavioral, measurable. Not "do better" or "be more proactive."
   - YES: "Going forward, if a deadline is at risk, I need to know at least 2 days before — even if the news is bad."
   - NO: "I need you to be more responsible with timelines."

5. **Close by inviting dialogue.** One sentence. Not optional — feedback is a conversation, not a broadcast.
   - YES: "I'd like to hear your take on this — can we discuss in our 1:1 Thursday?"

## Rules
- No compliment sandwich. It undermines the feedback and insults the recipient's intelligence.
- No hedging language: "sort of", "maybe", "a little bit", "I feel like." Be direct.
- No character judgments. Describe behaviors, not traits. "You missed X" not "You're unreliable."
- Match the tone to the severity. A first-time minor issue gets a lighter touch than a repeated pattern. Don't bring a cannon to a squirt gun fight, and don't bring a squirt gun to a cannon fight.
- If this is a pattern (discussed before), reference the prior conversations explicitly: "We discussed this on [date]. This is the third occurrence."
- If the delivery method is speaking notes, format as bullet points with key phrases, not a script to read verbatim.

Usage Notes

• The hardest part of writing feedback is being specific. “They have an attitude problem” isn’t feedback. Force yourself to write concrete examples before using this prompt — the AI can’t invent them for you.
• The compliment sandwich ban is intentional. Research shows recipients tune out the positive, wait for the “but,” then discount the critical feedback because it feels manipulative.
• For truly high-stakes feedback (termination, PIP, final warning), have HR or legal review the output before sending.
• Speaking notes format works better for 1:1s than a written message. You want the key points, not a script — reading from a script in a feedback conversation kills trust.
• After sending written feedback, always follow up verbally. Text-only feedback leaves too much room for misinterpretation.