Home · Jobs & career · Rehearse a tough conversation with your boss out loud

Just ask 10 min

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.

Updated 17 Oct 2026

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.

Loading the outline…