I once had to tell someone their project wasn’t going ahead. I’d thought about what I wanted to say, and I had it straight in my head on the walk to the meeting room.
Then they asked a question I hadn’t seen coming: “So what would it take to get it back on?” I lost my thread. I waffled, softened the message far too much, and they left thinking it was still a maybe. Which meant a second, harder conversation a week later.
The message wasn’t the problem. I just hadn’t practised hearing the hard bits out loud. These days, when I’ve got a tricky conversation coming up, I spend ten minutes rehearsing it with AI first. Here’s how.
Step 1: Write the situation in five lines
Keep it short. What the conversation is about, what you need the other person to understand, what outcome you’re hoping for, and how you think they’ll feel about it. One line on your relationship helps too, such as “a colleague I get on with” or “someone senior I don’t know well”.
Leave out names and anything confidential. You don’t need them for a rehearsal. For work conversations, only use the AI tool your company has approved.
Step 2: Ask AI to play the other person
This is the bit that feels odd the first time, and the bit that helps most. Here’s the prompt I use:
“I have a difficult conversation coming up. Here’s the situation: [your five lines]. Please play the other person. Respond the way they realistically might, including pushback, awkward questions and some emotion, but don’t make them a cartoon villain. Keep each reply short. I’ll start. After five or six exchanges, stop and tell me: where I was unclear, where I softened the message too much, and where I sounded defensive.”
Then type what you’d actually say, as if you were in the room. Don’t polish it. The point is to hear how your first instinct lands.
Step 3: Ask for the questions you’re least ready for
Once the role play is done, ask: “What are the three questions or reactions I seemed least prepared for?”
For me it’s nearly always some version of “why now?”, “what happens to me?” or “is this definitely final?”. Knowing they’re coming takes most of the sting out of them.
Step 4: Write your three sentences yourself
Don’t walk in with a script. Walk in with three sentences in your own words:
- What I need to say. The message, plainly, in one sentence.
- Why. The real reason, without a long build-up.
- What happens next. The next step, so the conversation has somewhere to go.
You can ask AI to tighten them, but rewrite anything that doesn’t sound like you. People can tell when you’re reading lines.
Step 5: Run it once more, then stop
Do one last quick rehearsal using your three sentences. If the hard questions no longer throw you, you’re ready. More practice than that tends to make you sound rehearsed rather than prepared.
Where AI stops
AI doesn’t know the person in front of you. It won’t pick up on their mood, the history between you, or what’s going on in their life that day. Use the rehearsal to get past the moment where you freeze, then listen properly in the real conversation. And if the rehearsal makes you realise the message itself is wrong, that’s worth more than any script.
Quick questions
Isn't it weird to role play with AI?
A little, the first time. It gets easier fast, and hearing the awkward question once in private makes it much less likely to throw you in the real conversation.
Should I use AI to write a script?
No. Use it to practise and to spot the questions you're not ready for. Then write three sentences in your own words so you still sound like yourself.
What should I leave out?
Names and anything confidential. For work conversations, only use the AI tool your company has approved.