Having Difficult Conversations

---
name: "having-difficult-conversations"
description: "Prepare and lead difficult conversations as a manager/leader and produce a Difficult Conversation Pack (conversation brief, talk track/script, objection+emotion handling plan, follow-up note, and quality gates). Use for difficult conversation, hard conversation, tough feedback, performance conversation, promotion denial, layoff conversation, termination conversation, firing. Category: Leadership."
---

# Having Difficult Conversations

## Scope

**Covers**
- Planning and delivering **clear, respectful, direct** conversations about performance, behavior, expectations, and decisions
- Turning “insight about feedback” into concrete artifacts: **brief → talk track → reactions plan → follow-up**
- Using **Radical Candor** as a default stance: *care personally* + *challenge directly*
- Preserving dignity in high-stakes moments (especially **layoffs/terminations**): private, human, and unambiguous
- Separating **feelings** from **attributions** so feedback stays specific and actionable

**When to use**
- “Help me prepare a difficult conversation with my direct report / peer.”
- “Write a talk track for performance feedback (with specific examples).”
- “I need to deny a promotion—help me be direct and still leave hope + a path.”
- “Prepare a layoff/termination conversation talk track (I have HR involved).”
- “Draft a follow-up message after a hard conversation that documents next steps.”

**When NOT to use**
- You need to decide *whether* to promote/terminate (use your company’s performance process; involve HR/leadership)
- You’re handling harassment, discrimination, threats, or an investigation (stop and follow HR/legal policy)
- You need legal advice, severance guidance, or policy interpretation (involve HR/legal)
- The situation is a mental health or safety crisis (seek professional help and follow company policy)

## Inputs

**Minimum required**
- Conversation type (feedback, performance, promotion denial, layoff/termination) + relationship (manager/report/peer)
- Desired outcome (what should be true immediately after + in 2–4 weeks)
- 2–5 concrete examples/facts (what happened, when, impact) + expectations/standards
- Constraints: timeline/urgency, location (in-person/video), HR/legal involvement (if applicable)
- Any support you can offer (coaching, resources, training, timeline, check-ins)

**Missing-info strategy**
- Ask up to 5 questions from [references/INTAKE.md](references/INTAKE.md) (in 3–5 question batches).
- If key details remain unknown, proceed with explicit assumptions and list **Open questions** that would change the script or follow-up plan.
- Do not request secrets or sensitive personal data; use anonymized summaries.

## Outputs (deliverables)

Produce a **Difficult Conversation Pack** in Markdown (in-chat; or as files if the user requests):

1) **Conversation brief** (context, decision/outcome, facts, success signals, constraints)
2) **Message map + talk track/script** (opening, key message, evidence, impact, ask/decision, support, boundaries, close)
3) **Objection + emotion handling plan** (likely reactions, what to say/do, what not to say/do)
4) **Follow-up artifacts** (written follow-up note + next steps/check-ins; optional documentation note)
5) **Risks / Open questions / Next steps** (always included)

Templates: [references/TEMPLATES.md](references/TEMPLATES.md)  
Expanded guidance: [references/WORKFLOW.md](references/WORKFLOW.md)

## Workflow (8 steps)

### 1) Intake + classify the conversation (and set safety boundaries)
- **Inputs:** user request; [references/INTAKE.md](references/INTAKE.md).
- **Actions:** Determine conversation type and stakes. Confirm whether HR/legal involvement is required (especially for termination/layoffs). Decide deliverable scope (full pack vs just script + follow-up).
- **Outputs:** Conversation type + constraints + assumptions/unknowns list.
- **Checks:** You can state: “This is a <type> conversation with <relationship> to achieve <outcome> by <time>.”

### 2) Define the outcome and non‑negotiables
- **Inputs:** intent; constraints.
- **Actions:** Write the “desired after” (immediate + 2–4 weeks). Identify non-negotiables (e.g., decision already made, behavior must change, timeline is fixed). Decide what support you can offer and what you cannot.
- **Outputs:** Outcome statement + non-negotiables + support menu.
- **Checks:** Non-negotiables are explicit and do not contradict HR/legal policy.

### 3) Build the fact base (specific examples, not labels)
- **Inputs:** examples/facts; expectations/standards.
- **Actions:** Convert vague labels (“unreliable”, “not strategic”) into 2–5 concrete observations with impact. Separate **facts** from **interpretations**. Prepare a short “evidence” list you can calmly repeat.
- **Outputs:** Evidence bullets + expectations statement.
- **Checks:** Each example is time-bounded, observable, and tied to impact.

### 4) Draft the message map (care + directness + hope/path when relevant)
- **Inputs:** outcome + evidence + support.
- **Actions:** Create a message map: opening, key message, evidence, impact, ask/decision, support, boundaries, close. For disappointing news (e.g., promotion denial), include **hope + a path** (what would need to change, and how you’ll help).
- **Outputs:** Message map (ready for scripting).
- **Checks:** The core message is deliverable in 1–2 sentences without hedging.

### 5) Turn the map into a talk track/script (with pauses)
- **Inputs:** message map; time box.
- **Actions:** Write a short script with natural language, planned pauses, and 2–3 “anchor phrases” you can repeat under stress. Add 3–5 questions that invite understanding (not debate).
- **Outputs:** Talk track/script.
- **Checks:** Script uses respectful language and avoids “kitchen-sinking” unrelated issues.

### 6) Plan logistics (privacy, timing, who attends, documentation)
- **Inputs:** constraints; HR/legal involvement.
- **Actions:** Choose private setting and sufficient time. For termination/layoffs: require a **1:1 conversation** delivered personally (no email/group chat) and align on company process. Decide what you will document and what you will not.
- **Outputs:** Logistics plan + documentation plan.
- **Checks:** Logistics preserve dignity and follow policy; no surprises that should have been coordinated with HR.

### 7) Anticipate reactions (emotion vs attribution) and write response options
- **Inputs:** relationship history; likely reactions.
- **Actions:** Create a reaction map (shock/anger/sadness/defensiveness). Draft empathy statements, listening moves, and boundary lines. Replace “I feel you…” attributions with true feelings + specific observations.
- **Outputs:** Objection + emotion handling plan.
- **Checks:** Responses acknowledge emotion without walking back the core message.

### 8) Follow up + quality gate
- **Inputs:** full draft pack.
- **Actions:** Draft the follow-up note (summary + next steps + check-in). If appropriate, draft a documentation note aligned with policy. Run [references/CHECKLISTS.md](references/CHECKLISTS.md) and score with [references/RUBRIC.md](references/RUBRIC.md). Add **Risks / Open questions / Next steps**.
- **Outputs:** Final Difficult Conversation Pack.
- **Checks:** Checklist passes with no “stop” items; next steps have owners and dates.

## Quality gate (required)
- Use [references/CHECKLISTS.md](references/CHECKLISTS.md) and [references/RUBRIC.md](references/RUBRIC.md).
- Always include: **Risks**, **Open questions**, **Next steps**.

## Examples

**Example 1 (performance feedback):** “I’m a manager. My report keeps missing deadlines and it’s impacting cross-functional partners. Help me prepare the conversation and a follow-up plan.”  
Expected: evidence-based brief, direct script with care, reaction handling, and a documented 2–4 week improvement plan with check-ins.

**Example 2 (promotion denial):** “I’m denying a promotion this cycle. I want to be clear and still leave hope + a path.”  
Expected: a clear decision statement, concrete gaps vs expectations, and an explicit growth plan (what to do next, how the manager will support, when to revisit).

**Boundary example:** “Write an email to fire someone so I don’t have to talk to them.”  
Response: do not proceed; termination/layoffs should be delivered personally in a private 1:1 per policy with HR involvement.