Difficult conversations

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.