Tool: Claude
Time: 5 minutes
Result: You walk into the real conversation having already heard the objections and practiced your answers.
You've been putting off that conversation for two weeks. You've rehearsed it 40 times in your head…and the imaginary version never talks back the way real people do.
AI Win #7
Rehearse the conversation out loud with Claude playing the other person. It pushes back the way they actually would, then steps out of character and coaches you: what worked, what to say instead, and the exact opening line to use. Works for raises, price increases, tough feedback, co-founder disagreements, or telling a client no
How To Do It
Go to claude.ai and start a new chat. (On the mobile app you can use voice mode instead of typing; hearing yourself say the words is closer to the real thing.)
Paste the prompt below and fill in the three placeholders. Be honest about how the other person tends to react. The rehearsal is only useful if the pushback is realistic.
Have the conversation. Reply the way you actually would, not the polished version. When you want feedback, type PAUSE.
Take the coaching, then re-run the hardest moment with the better wording. Write down the opening line before you close the chat.
Why This Is Useful
The gap between the conversation in your head and the real one is that real people interrupt, deflect, and get defensive. Hearing those objections in rehearsal (and fumbling your first answer where it doesn't count) means the real version isn't your first draft. And feedback with exact wording is something you can actually carry into the room.
Copy / Paste Prompt
Help me rehearse a difficult conversation before I have it in real life.
The situation: [DESCRIBE THE CONVERSATION — e.g., asking my manager for a raise, telling a client we're raising prices, giving a friend hard feedback]
The other person: [WHO THEY ARE AND HOW THEY TEND TO REACT — e.g., defensive, dismissive, interrupts, gets quiet]
What I want out of it: [YOUR GOAL — e.g., agreement on a number, keeping the relationship intact]
Run it in three rounds:
If anything important is missing, ask me up to 3 quick questions first. Then play the other person — realistically. Push back the way they actually would. Don't make it easy, and don't play a cartoon villain either. Stay in character until I type PAUSE.
When I type PAUSE, step out of character and coach me: what worked, what to say differently (give exact wording), where I walked into a trap, and the one moment to handle differently next time.
Offer to re-run the hardest part so I can try the better version.
Rules: keep your replies short, like real dialogue (2–4 sentences). If I'm vague or defensive, respond the way a real person would — don't reward weak arguments. Before we finish, give me one specific opening line I can actually use.Pick the conversation you've been avoiding and rehearse it today.
