| name | difficult-conversations |
| description | Use when preparing for or training on difficult conversations — performance issues, terminations, conflict, harassment reports, RIFs. |
Difficult Conversations
Structure
The structure of any difficult conversation:
- Prepare: rehearse with HR or peer
- Open clearly: don't bury the lede
- Listen: what are they hearing?
- Hold the decision: it's not a debate
- Cover practical next steps
- Close with humanity: acknowledge the difficulty
- Follow up: documentation, next conversation
Most failure is in preparation (or absence) and opening (waffling rather than naming the situation).
Specific Conversation Types
Termination (Performance)
"Thanks for coming. I have hard news. We're ending your employment with [Company], effective today. The reason is [specific, brief]. The decision is final. I want to walk you through what happens next."
Then: severance, final paycheck, benefits, equity, references, equipment, personal items, allow space.
Avoid:
- "I have no choice"
- "It's not personal"
- Detailed catalog of past failures
- "We'd love to keep you on as a contractor" (unless pre-cleared)
Layoff (Role Elimination)
"I have difficult news. As part of the changes we announced today, your role is being eliminated, effective [date]. This isn't about your performance — you've been [genuine recognition]. The decision is about [stated reason]."
Then: severance, outplacement, references, alumni network, logistics, Q&A.
PIP
"I want to talk about your performance. Over the last [period], I've raised concerns about [specific gaps — referencing prior conversations]. We're at a point where I want to be direct: if these gaps don't close in [30/60/90 days], we won't be able to keep you in this role. Here's a written plan of what I need to see, the support I'll provide, and how we'll measure success."
Then: walk through plan, confirm support, clarify check-ins, be clear about both outcomes.
The PIP must not be a surprise.
Demotion
"I want to talk with you about a change to your role. Based on [specific observations], I think you'd be more successful — and the team better served — if you moved into [new role]. Your title will be [X], and your comp will [stay / adjust over Y months / change]. Here's why I think this is the right call, and I want to hear what you think."
Avoid: pretending it's a great opportunity; vague language about "better fit."
Promotion Not Given
"I want to talk about your promotion. I appreciate the interest, and I want to be honest about where things stand. The calibration discussion concluded that you're not ready for [next level] yet, for these specific reasons: [evidence]. Here's what I think you'd need to demonstrate."
Comp Disappointment
"I want to walk you through your comp adjustment. Your increase is [X], which is [position relative to range]. Here's how it was decided. [Walk through inputs.] I know this may differ from what you were hoping for. Happy to talk through any of it."
Avoid: "It's all I could do"; comparing to peers; promising future raises that aren't yours to promise.
Preparation Checklist
What to Never Do
- Friday afternoon terminations
- Surprise low ratings or terminations
- Vague reasons ("it's just not working" without specifics)
- Decision-as-debate (opening as if open)
- Catalog of every past failure
- Performative empathy ("I know this is hard" with no warmth)
- Termination over Slack/email — always live (video at minimum)
- Forgetting practicalities (comp, benefits, references, equipment)
- No follow-up
Conflict Between Two People
When mediating:
- Each side states the issue (no interruption)
- Each side reflects what they heard the other say
- Identify underlying need (often different from stated issue)
- Agree on specific behavior changes
- Schedule follow-up
Avoid mediating when one party should be coached separately first, or when power asymmetry can't be resolved.
Harassment / Inappropriate Behavior Report
The manager's role is usually:
- Receive the report calmly
- Confirm investigation
- Don't promise specific outcomes
- Document
- Escalate to HR / counsel immediately
- Don't retaliate or appear to
- Communicate with reporter about process (without breaching confidentiality)
Investigation is HR / legal's job; response and escalation is the manager's.
Self-Care After
Difficult conversations cost emotional bandwidth. The cost of doing several poorly is greater than the cost of doing fewer well.
- Block time after difficult conversations (don't go straight to a customer call)
- Debrief with HR or peer
- Document while fresh
Cross-References
difficult-conversations-coach agent
dignity-in-transitions rule
feedback-frameworks skill
policy-writer agent (documentation)
offboarding-architect agent
Key References
- Stone, D., Patton, B., & Heen, S. (2010). Difficult Conversations.
- Scott, K. (2017). Radical Candor.
- Scott, S. (2002). Fierce Conversations.
- McCord, P. (2017). Powerful.