Prepare for a Difficult Workplace Conversation
Prepare what you need to say, think through likely responses and rehearse a difficult workplace conversation before you have it.
Step 01
Prepare my talking points
Prepare Talking Points for a Difficult Workplace Conversation
Prepare clear talking points for a difficult workplace conversation so you can address the issue directly without turning it into a speech.
Help me prepare talking points for a difficult workplace conversation. Context: - Who I need to speak with: [ROLE / RELATIONSHIP] - What has happened: [FACTS] - What outcome I want from the conversation: [OUTCOME] - What I want to avoid: [OPTIONAL] First separate: - facts I can state confidently; - my interpretation or concern; - assumptions I should not present as facts. Then create talking points in this order: 1. A clear, neutral opening. 2. The specific issue or behaviour I need to discuss. 3. Why it matters or what impact it is having. 4. Questions I should ask rather than assume. 5. What change, decision or agreement I am seeking. 6. A constructive way to close and confirm next steps. Keep the points concise enough to use in a real conversation. Do not write a long script for me to memorise. Avoid manipulative language, threats or diagnosing the other person's motives. If the situation appears to involve serious HR, safety, discrimination or legal concerns, keep the preparation general and suggest using the appropriate workplace process rather than presenting legal advice. Situation: [PASTE DETAILS]
Step 02
Anticipate likely responses
Anticipate How the Other Person Might Respond
Think through several plausible ways the other person may respond in a difficult conversation so you can prepare without pretending to predict them.
Help me anticipate how the other person might respond in this workplace conversation. I will provide the situation, my intended talking points and what I know about the context. Do not claim to know what the person will think or say. Instead, give me a small set of plausible response patterns, for example: - they agree; - they disagree with the facts; - they agree with the facts but disagree with the impact; - they become defensive; - they raise information I did not know; - they ask for time; - they propose a different solution. For each plausible response: 1. Explain what I should listen for. 2. Suggest a calm question I could ask next. 3. Show what I should avoid saying if it would escalate or close down the discussion. Prioritise curiosity and clarity over "winning" the conversation. Situation and talking points: [PASTE] Relevant context: [OPTIONAL]
Step 03
Rehearse the conversation
Rehearse a Difficult Workplace Conversation
Rehearse a difficult workplace conversation interactively, with realistic responses and feedback on whether your wording is clear, fair and constructive.
Rehearse this difficult workplace conversation with me. You will play the other person using only the context I provide. Do not make them unrealistically hostile or agreeable. How to run the rehearsal: 1. Ask me to open the conversation in my own words. 2. Respond as the other person with one plausible reaction. 3. Wait for my reply. 4. Continue for a few exchanges, introducing a realistic question or disagreement where useful. 5. Do not coach me during the role-play unless I ask to pause. When I say "stop rehearsal", give feedback on: - clarity; - whether I separated facts from assumptions; - tone; - listening/questions; - whether I made the desired outcome clear; - wording that could unnecessarily escalate the discussion. Then let me retry the part that was hardest. Context: [PASTE SITUATION] What I want to achieve: [OUTCOME] Anything the other person is likely to know: [OPTIONAL]
Pack details
- Prompts
- 3
- Category
- Work & Communication
- Use case
- Difficult Conversations
- Updated
- 26 Aug 2026