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Management

Difficult conversation prep

Official

Official · updated Nov 4, 2026 · v1.0.1

Prepares a hard conversation: goal, facts vs interpretation, a neutral opening, listening prompts, likely reactions, next steps, and HR flags.

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A one-page prep with the opening words, listening prompts, responses to likely reactions, next steps, and HR flags checked.

The SKILL.md

---
name: difficult-conversation-prep
description: Prepares a manager for a hard conversation - performance that isn't improving, conflict between teammates, or bad news like a lost promotion or a role change - with the goal, facts separated from interpretation, a neutral opening line, listening prompts, likely reactions with responses, next steps, and flags for when HR must be involved. Use when someone asks how to have a difficult conversation, deliver bad news, address a performance problem, handle conflict, or prepare for a tough talk.
---

# Difficult conversation prep

> HR-sensitive. This is preparation, not HR or legal advice. If any flag in step 7 applies, talk to HR before the conversation.

Hard conversations go wrong when the opener is a verdict and the person spends the rest of the meeting defending themselves. The prep separates what happened from the story you've built about it, opens with a neutral description of the difference (what Stone, Patton and Heen call the "third story"), and plans to listen before problem-solving.

## When to use

- A performance problem that one round of feedback didn't fix.
- Conflict between two teammates, or between you and a report.
- Delivering bad news: no promotion, a role change, a project cancelled, a denied request.
- Not for routine feedback (use feedback-sbi) or a first mention of a small issue.

## What you need

- What the conversation is about and who it's with.
- The facts: dates, what was said or done, documents, previous conversations.
- What you want to be true after the conversation.
- Any HR involvement so far. If unknown, ask once; the HR flags in step 7 depend on it.

## Steps

1. **Set one goal.** What should be true when the meeting ends: "Sam understands the deadline problem is serious and we agree on a plan." Not "Sam admits fault." If the goal is to inform (a decision already made), say so; don't pretend it's open.
2. **Split facts from story.** Facts: what a camera would have recorded, with dates. Story: your interpretation of why ("they don't care"). Keep facts, label the story as a guess, and list your own possible contribution (unclear expectations, late feedback).
3. **Write the opening in 2 to 3 sentences.** State the topic and purpose plainly, describe the difference neutrally, and invite their view: "I want to talk about the last 3 deadlines. I see them as a problem for the client; I'd like to understand how you see them." For bad news, deliver it in the first 2 sentences, then pause.
4. **Plan the listening.** 3 to 4 open questions ("What's getting in the way?", "How did that look from your side?"). Plan to paraphrase what you hear before you respond. You can't move forward until they feel heard.
5. **Prepare for likely reactions.** For 3 to 4 reactions (denial, anger, tears, silence, blaming others, "is my job at risk?"), write one calm response each. Acknowledge the feeling, restate the facts, and don't argue about intent.
6. **Define next steps.** What happens after: an agreed plan with dates, a follow-up meeting, a written summary within 24 hours. For performance, name the specific change expected and when you'll review it.
7. **Check the HR flags.** Our default list; your company's policy wins. Talk to HR first if any apply: possible discrimination, harassment, or retaliation; a disability, health condition, leave, or pregnancy is involved; a formal warning, PIP, demotion, or termination may follow; the person has raised a complaint; pay or legal terms change; safety is involved. Mark "[check: company policy]" for anything about process.

## Output format

```markdown
# Conversation prep — [topic] with [name]
*Preparation, not HR or legal advice. HR flags: [none / list → talk to HR first]*

## Goal
[What is true when the meeting ends]

## Facts (observable, dated)
- [date]: [what happened]

## My story (labelled as interpretation)
- [What I assume] — could also be: [alternative explanation]
- My possible contribution: [e.g., unclear expectations]

## Opening (2–3 sentences)
> [Exact words]

## Listening prompts
- [Open question]

## Likely reactions
| If they... | I'll say... |
|---|---|

## Next steps
- [Agreed action, owner, date]
- Written summary sent by [date]

## HR flags
- [ ] [Flag] — [applies / doesn't]
```

## Example

**Input:** "Need to talk to Priya (senior analyst). Missed the last 3 client report deadlines (2 Oct, 16 Oct, 30 Oct) by 1–2 days each. Client complained on 31 Oct. I gave feedback after the first miss. I think she's checked out since she didn't get promoted in September. No HR involvement yet."

**Output:**

```markdown
# Conversation prep — missed report deadlines with Priya
*Preparation, not HR or legal advice. HR flags: none known; check before any formal step.*

## Goal
Priya understands the client impact, we find what's causing the delays, and agree on a plan for the 13 Nov report.

## Facts (observable, dated)
- 2 Oct, 16 Oct, 30 Oct: client reports delivered 1–2 days after the deadline.
- After 2 Oct: I gave feedback about the miss.
- 31 Oct: the client complained about the delays.

## My story (labelled as interpretation)
- She's disengaged since the September promotion decision — could also be: workload, unclear data handoffs, something personal.
- My possible contribution: I haven't checked her workload since September.

## Opening (2–3 sentences)
> I want to talk about the client reports. The last 3 went out a day or two late, and the client raised it with me on 31 October. I'd like to understand what's been happening from your side.

## Listening prompts
- What's been getting in the way of those deadlines?
- How does your workload look right now compared with the summer?
- What would help you hit the 13 Nov date?

## Likely reactions
| If they... | I'll say... |
|---|---|
| Blame late data from engineering | "That's useful. Let's look at when the data arrived for each report." |
| Bring up the promotion | "I'm glad you raised it. Let's give it its own conversation this week; today I want to fix the client deadlines." |
| Get upset | "I can see this is hard to hear. Take a minute; there's no rush." |
| Ask if their job is at risk | "This conversation is about solving the deadlines. I'll always tell you directly if it becomes more serious." |

## Next steps
- Agree a plan for the 13 Nov report, with a check-in on 10 Nov.
- Written summary to Priya within 24 hours.
- Separate conversation about promotion criteria, this week.

## HR flags
- [ ] Discrimination, harassment, or retaliation — not indicated
- [ ] Health, disability, leave — not indicated; if raised, pause and involve HR
- [ ] Formal warning or PIP likely to follow — not yet; talk to HR if the 13 Nov date is missed
```

## Checks before you send

- [ ] The goal is one sentence and doesn't require the other person to admit anything.
- [ ] Every fact has a date and is observable; interpretations are labelled.
- [ ] The opening is neutral, 3 sentences or fewer, and invites their view (or delivers bad news in the first 2 sentences).
- [ ] Each likely reaction has a calm response that doesn't argue about intent.
- [ ] HR flags were checked, and any that apply say "talk to HR first".

## Common mistakes

- Opening with small talk, then the hit. Get to the point within the first minute.
- Arguing about why they did it. Agree on what happened and what changes next.
- Promising things outside your authority ("you'll get the promotion next round").

Download SKILL.md

Changelog

Sources

  1. Summary of "Difficult Conversations: How to Discuss What Matters Most" | Beyond Intractability (2026-11-04)
  2. Use SBI (Situation-Behavior-Impact) to Inquire About Intent | CCL (2026-11-04)

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