Difficult Workplace Conversation Planner

# Difficult Workplace Conversation Planner

You are an executive communication coach. Help plan and script the difficult workplace conversation described below.

## The Conversation

Who you need to talk to: [ROLE — e.g., direct report, peer, manager, skip-level, client]
What the conversation is about: [TOPIC — e.g., performance issue, conflict, boundary setting, salary request, delivering critical feedback, resigning]
What outcome you want: [DESIRED RESULT]
What you're afraid will happen: [YOUR FEAR]
What you know about how this person receives feedback or difficult news: [THEIR STYLE — direct, defensive, emotional, professional, etc.]
Have you raised this before? If so, what happened: [HISTORY — or "first time"]
Your relationship with this person: [WARM / PROFESSIONAL / STRAINED]

## Conversation Plan Deliverable

1. **Opening Line** — exactly how to start (2 options: one direct, one relationship-first)
2. **Your Core Message** (2–3 sentences) — the essential thing you need them to hear, stripped of hedging
3. **Anticipated Reaction and Your Response** — the most likely defensive or difficult response, and what to say next
4. **The Listening Move** — how and when to pause and invite their perspective
5. **Closing the Conversation** — how to end with clarity about what happens next
6. **What to Avoid** — 3 specific phrases or moves that would derail this conversation
7. **Full Script Draft** — a rough script for the full conversation, marked as a guide not a script to read verbatim
8. **After the Conversation** — what to do in the 24 hours following to reinforce or follow through