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AI automation to prepare a difficult conversation

Drafts an opening line, the one change you are asking for, and a calm reply to the pushback you expect. You practise before you say any of it.

Level: Assist.

Trigger

Before a conversation you have been putting off

Setup

about 20 min (estimate)

Before you start

Steps

  1. Write the situation in a few lines

    Say who the other person is, what happened, and what you have already tried. Leave out full names if you can.

  2. Name the one change you want

    One sentence. If you have three requests, pick the one that matters this week.

  3. Ask for the card

    Paste the situation and the one change. Custom instructions: https://help.openai.com/en/articles/6825453-chatgpt-custom-instructions

    Help me prepare one conversation. Use only what I paste. Write four short parts: an opening line, the one ask, the pushback I should expect and a calm reply, and a stop line. The ask is one change. The stop line names what I will do if we cannot agree. Do not insult. Do not threaten. Do not tell me to send it.
  4. Let it play the other person

    Ask it to reply only in the other person's voice, twice. You answer as yourself. Stop if the reply becomes cruel, and delete that version.

    Reply only as the other person. One short objection. Do not give me advice in this turn.
  5. Ask for a clarity check

    Switch roles. Ask whether the ask is still one sentence, and what to cut.

    Now be a coach. Is my ask one sentence? Quote it. Cut anything that is a complaint rather than a change. Do not add a new demand.
  6. Keep a card, not a speech

    Copy the four lines you will actually use into a note. Save the instruction as a Gem if you prepare talks often. Gems: https://support.google.com/gemini/answer/15236321

Example output

Opening: I want ten minutes on the handover, and I want us to leave with one owner.
Ask: Please take the client update on Thursdays, starting next week.
Pushback: I am already full.
Reply: Then we move the status meeting, not the update. Which one can you drop?
Stop: If we cannot name an owner today, I will ask our manager to assign it.

Power move

When the card is written, ask the chat to answer only as the other person. Then switch and ask it to say whether your ask was a single sentence. If the app has a voice control, say your opening line aloud. You still choose the words you keep.

What to check

  • The ask is one concrete change, not a list of complaints.
  • The stop line does not threaten or insult.
  • You have not sent anything.

What it can't do

It does not send the message, and it is not counselling. Do not use it to pressure, threaten, or wear someone down. If you are unsafe, contact a local emergency service instead of practising a script. You decide whether the conversation happens.

Privacy

Paste only the text a chat tool needs. Leave out passwords, account numbers, and identity numbers. The steps link to each tool's own help page when a setting matters.

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