difficult-conversations

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Prepare for challenging conversations using Prepare-Listen-Empathize-Clarify-Solve framework.

itseffi By itseffi schedule Updated 1/23/2026

name: difficult-conversations description: Prepare for challenging conversations using Prepare-Listen-Empathize-Clarify-Solve framework.

Difficult Conversation Prep

Prepare for challenging work conversations using a structured framework.

When to Use

Before any conversation you're dreading or that has conflict potential.

The Framework: Prepare-Listen-Empathize-Clarify-Solve

1. Preparation Notes

Document:

  • Your intent (what you want to achieve)
  • Non-negotiables (what you won't compromise on)
  • Specific facts/examples (concrete, not accusations)
  • Language traps to avoid
  • Desired outcome
  • Success criteria
  • Medium choice (in-person/video/async)

2. Opening Lines (3-5 options)

Create openers that are:

  • Neutral, non-accusatory
  • Reference concrete impact
  • Invite their perspective

Examples:

  • "I wanted to talk about [situation] because I've noticed [impact]..."
  • "I'd like to understand your perspective on [issue]..."
  • "Can we discuss [topic]? I want to make sure we're aligned..."

3. Questions to Ask (5-7)

Use open questions (what/how/when):

  • Avoid "why" framing (feels accusatory)
  • Include one perspective-taking question
  • Include one constraints question

4. Anticipate Reactions

Prepare responses for:

  • Denial: [De-escalating response]
  • Deflection: [Redirect response]
  • Emotional reaction: [Calming response]
  • Counter-accusation: [Non-defensive response]

5. Clarify and Solve

  • State shared goals
  • Present options with trade-offs
  • Agree on commitments
  • Assign owner and timeline
  • Schedule follow-up

Self-Management Checklist

  • Deep breaths before starting
  • Slow speaking pace
  • Use pauses deliberately
  • Notice body tension
  • Stay curious, not defensive

Output

  • 1-page prep doc
  • Opening lines (3-5)
  • Questions list
  • Reactions/responses table
  • Close and next steps
  • Escalation flags (if HR/compliance needed)

When Not to Use

Do not use this skill when the request is unrelated, low-stakes, or better handled by a simpler direct response.

Install via CLI
npx skills add https://github.com/itseffi/agentic-os --skill difficult-conversations
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