The problem
Hard conversations get avoided or go badly because we only get one try and nerves take over.
Step by step
- Write what you want to say and the outcome you hope for.
- Ask the AI to play the other person, realistically, not as a pushover.
- Practise your opening line until it feels natural.
- Ask for feedback on tone and clarity.
- Have the real conversation in person or on a call, not by text.
The prompt
Help me rehearse a conversation. I need to {what you need to say} with {their role}.
The outcome I want: {outcome}
Play that person realistically, including pushback they might give. Reply one turn at a time and wait for me. After 6 turns, give me feedback on my clarity and tone and suggest a better opening line.
Replace the {highlighted} parts with your details, or fill them in with the prompt builder.
Check before you use it
- Your opening line is short and clear.
- You have a calm answer to the likely pushback.
Privacy
- Use roles, not names. Leave out private details about the other person.
Do’s and don’ts
Do
- Lead with the outcome you want.
- Listen as much as you talk.
- Agree on a next step.
Don’t
- Read a script in the real conversation.
- Have the conversation by text to avoid it.
- Rehearse winning instead of solving the problem.
When not to use AI for this
If the conversation involves harassment, safety or legal issues, talk to HR, a union, a lawyer or another qualified person first.
Tools that can help
ChatGPTOpenAI’s general assistant for drafting, summarising, analysing files and brainstorming.
ClaudeAnthropic’s general assistant, good with long documents, writing and analysis.
Goblin.toolsSmall free tools that break tasks into steps, estimate time and adjust the tone of a message.
We are not paid by any of these companies, and we list well-known options, not a ranking. Features and plans change; check the provider’s site and its data terms before you sign up. See all AI tools by category.
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