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 (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):
- Conversation brief (context, decision/outcome, facts, success signals, constraints)
- Message map + talk track/script (opening, key message, evidence, impact, ask/decision, support, boundaries, close)
- Objection + emotion handling plan (likely reactions, what to say/do, what not to say/do)
- Follow-up artifacts (written follow-up note + next steps/check-ins; optional documentation note)
- Risks / Open questions / Next steps (always included)
Templates: references/TEMPLATES.md Expanded guidance: references/WORKFLOW.md
Workflow (8 steps)
1) Intake + classify the conversation (and set safety boundaries)
- Inputs: user request; 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 conversation with to achieve by.”
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 and score with 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 and 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.