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.
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.
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.
Boundary example 2: “Help me set up a regular coaching cadence with my team.”
Response: this skill is for preparing specific difficult conversations, not designing ongoing coaching systems. Use running-effective-1-1s for 1:1 cadence and coaching toolkits, or coaching-pms for PM skill development.
Anti-patterns (common failure modes)
Kitchen-sinking: Piling every past frustration into one conversation instead of focusing on 2-3 specific, recent, observable examples. The recipient feels ambushed and shuts down.
The empathy sandwich gone wrong: Opening with excessive praise, burying the real message in the middle, and closing with more praise. The recipient walks away confused about what actually needs to change.
Label-based feedback: Using character judgments (“you’re not strategic”, “you’re unreliable”) instead of describing specific observable behaviors and their impact. Labels trigger defensiveness and are unfalsifiable.
Deferred decision delivery: Spending 10 minutes “setting context” before revealing that a decision has already been made (e.g., promotion denied, role change). The recipient feels manipulated. Lead with the decision.
Missing follow-up loop: Delivering the conversation well but failing to send a written follow-up with next steps, check-in dates, and documented expectations. Without a paper trail, accountability evaporates.