Prepares one difficult conversation with a report, producing a prep sheet with a one-line purpose, dated facts and the first two sentences, likely reactions with replies, and the follow-up note you send afterwards. Use for "run mgr-difficult-conversation-prep", "prepare a difficult conversation", "how do I tell my report", "conversation I keep putting off", "how to start a hard conversation", "script for a tough talk with an employee", "what do I say when they get upset", "write the follow-up...
Scanned 10/4/2026
npx -y skills add polar-bear-org/claude-skills --skill mgr-difficult-conversation-prep --agent claude-codeInstalls into .claude/skills of the current project.
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---
name: mgr-difficult-conversation-prep
description: Prepares one difficult conversation with a report, producing a prep sheet with a one-line purpose, dated facts and the first two sentences, likely reactions with replies, and the follow-up note you send afterwards. Use for "run mgr-difficult-conversation-prep", "prepare a difficult conversation", "how do I tell my report", "conversation I keep putting off", "how to start a hard conversation", "script for a tough talk with an employee", "what do I say when they get upset", "write the follow-up after a hard conversation", part of the AI for Managers Pack by Polar Bear.
---
# Difficult Conversation Prep
## When To Use
It is the conversation you keep putting off, and every week it waits it gets closer to a grievance. Use it before one named conversation with one person, when you know something has to be said and not how to open it. It answers: what exactly do I want to be true afterwards, and what are the first two sentences out of my mouth?
## When Not To Use
If it is one piece of feedback on one behaviour, SBI Feedback Model is lighter and faster. If the informal talk has already happened and the gap persists, move to Performance Improvement Plan (PIP); if the issue may be serious misconduct, stop here and go to HR and a formal process.
## Inputs
- What is going wrong, in your notes, with dates where you have them
- What you have already said to the person, and when
- What you know of their situation, only as far as they have told you
If you have none of this, I start from one sentence about the issue and mark the output as a first draft with the facts still to find.
## Approach
This follows the Acas guide to challenging conversations and Acas "Problems with an employee's performance": talk informally first, separate capability from conduct, listen for causes, and keep a record the employee also gets. Each fact is written in the Situation, Behaviour, Impact form from the Center for Creative Leadership. The failure it prevents: a manager opens with three compliments, says "there have been some concerns", and the report leaves thinking the meeting was about something else.
## Workflow
1. Ask at most three questions: what you want to be true after the talk, what you have already said, and when the conversation is booked.
2. Sort the issue first: capability (they cannot yet do it) or conduct (behaviour). If conduct could be serious, I stop and say it goes to HR; this sheet is for the informal talk that comes first.
3. Write the purpose in one line, as an outcome ("deadlines are agreed and met or flagged early"), not as the speech you want to give.
4. Build the fact list: dated, observable, first-hand. I strike anything heard second-hand and rewrite labels like "lazy" or "negative" into what happened, or drop them.
5. Draft the opening as two sentences: the purpose, then the first fact. No compliment sandwich, no warm-up paragraph.
6. List the likely reactions (denial, tears, anger, silence, a reason you did not know about), each with a reply that goes back to listening for causes. If a health or disability cause comes up, the reply pauses the topic and I flag it for HR or a qualified adviser.
7. Draft the follow-up note: what was said, what was agreed, the next date. You read it, edit it after the real conversation and send it yourself.
## Output Format
```markdown
# Difficult Conversation Prep Sheet
## Purpose
[One line: what is true after this conversation]
## Facts
| Date | What happened (observable) | Impact on the work |
|---|---|---|
| [date] | [behaviour a camera would record] | [effect] |
## Opening
[Sentence 1: purpose] [Sentence 2: first fact]
## Likely Reactions
| If they... | I say... |
|---|---|
| [reaction] | [reply that returns to listening] |
## Follow-up Note (draft, edit after the talk)
[What was said, what was agreed, next date]
## Decision
[name] decides whether the informal route has worked, or whether to move to a written plan with HR, at the check-in on [date].
```
## Done When
- The purpose is one line and describes an outcome
- Every fact has a date and nothing in it is a label or hearsay
- The opening is two sentences and contains a fact
- The follow-up note is marked as a draft for you to edit and send
## Quality Bar
- Never guesses at motives, health or diagnoses; a possible health or disability cause goes to HR or a qualified adviser.
- No labels in the facts; every adjective about the person is rewritten or cut.
- Replies to reactions invite the person's account instead of arguing it down.
- Legal and disciplinary questions are marked "check with HR or a qualified adviser", never answered.
- Claude drafts the prep and the note; you have the conversation and nothing is sent until you have read it.
## Next
Run mgr-sbi-feedback (SBI Feedback Model) to turn each fact into a feedback statement that lands.
## About the makers
This pack is made by Polar Bear, a consultancy built by ex-McKinsey founders with a dream to make AI work for People, not instead of them. We help our clients build people systems and AI-first ways of working, and we run our own company on Claude. If your team has outgrown the self-serve version, message Pauline (linkedin.com/in/paulinebertry).
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