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Rehearse a tough conversation with your boss out loud
Pay, workload, a complaint, a no. Practise the real conversation with an assistant playing your boss, so you've heard the hard replies before you're in the room.
The prompt · ChatGPT
Role-play a difficult conversation with my boss so I can practise out loud. What it's about: [e.g. a pay rise, too much work, a complaint, saying no] What I want to happen: [outcome] My opening line: [what I plan to say first] What my boss is like: [e.g. busy, defensive, kind but vague] What they're likely to say: [e.g. "there's no budget"] What I'm most worried about: [e.g. crying, going blank, backing down] Ask me up to 3 short questions first if anything important is missing. Wait for my answers. Then: 1. Play my boss. Keep each reply short, push back realistically and wait for me to answer. 2. After 5 or 6 exchanges, stop and tell me: where I was clear, where I backed down, and how I came across. 3. Give me a stronger opening and two lines to use when I'm under pressure. 4. Run it once more, a little harder. Only use what I've told you, leave blanks for anything I haven't given, and don't invent facts, dates or results. UK English. Stay in this ChatGPT chat. Do not turn on apps or connectors, and do not use memory from another chat.
A short example
Fill the blanks, then paste. e.g. a pay rise, too much work, a complaint, saying no: a short note you already have. outcome: a short note you already have. Leave the rest of the prompt as written.
The prompt · Copilot
Role-play a difficult conversation with my boss so I can practise out loud. What it's about: [e.g. a pay rise, too much work, a complaint, saying no] What I want to happen: [outcome] My opening line: [what I plan to say first] What my boss is like: [e.g. busy, defensive, kind but vague] What they're likely to say: [e.g. "there's no budget"] What I'm most worried about: [e.g. crying, going blank, backing down] Ask me up to 3 short questions first if anything important is missing. Wait for my answers. Then: 1. Play my boss. Keep each reply short, push back realistically and wait for me to answer. 2. After 5 or 6 exchanges, stop and tell me: where I was clear, where I backed down, and how I came across. 3. Give me a stronger opening and two lines to use when I'm under pressure. 4. Run it once more, a little harder. Only use what I've told you, leave blanks for anything I haven't given, and don't invent facts, dates or results. UK English. Stay in this Copilot chat. Leave plugins off, and do not open a file from OneDrive.
A short example
Fill the blanks, then paste. e.g. a pay rise, too much work, a complaint, saying no: a short note you already have. outcome: a short note you already have. Leave the rest of the prompt as written.
You type what the conversation is about, what you want and what your boss is like.
The assistant asks what they're likely to say and what you're most worried about.
You get a spoken role-play with your boss, feedback on how you came across and a stronger opening.
What happens
Use Copilot to rehearse a tough conversation with your boss out loud
Pay, workload, a complaint, a no. Practise the real conversation with an assistant playing your boss, so you've heard the hard replies before you're in the room.
Tools
Paste the prompt, fill the blanks, copy the draft.
- Microsoft Copilot — required. Drafts from the text you paste. Nothing is sent.
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