WEEK 5 · BUILD THE HABIT · 10 min

Rehearse the Hard Conversation

Before you walk into the room, run the conversation with AI first.

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Performance feedback. Pushback on a decision. Setting a boundary. Renegotiating terms. The conversation where you keep rehearsing what to say in the shower.

COPY THIS PROMPT

I need to have a difficult conversation and I want to rehearse it with you.

Who: [person and your relationship to them]
What happened: [the situation — be specific and honest]
What I want: [the outcome — what does success look like?]
What I'm afraid of: [the relationship risk, their reaction, what could go wrong]

Help me prepare:
1. What's the opening line that sets the right tone — honest but not aggressive?
2. What's the one thing I need to say that I keep avoiding? Write it for me.
3. Play their role. How are they going to react? What are they going to say back?
4. When they push back, what's my response? Give me the exact words.
5. What's the line I should NOT cross, no matter how heated it gets?
6. How do I close this conversation so we both walk away feeling respected?

Claude

I need to give honest performance feedback to a long-time employee who's underperforming.

Opening line:
"I want to have an honest conversation because I respect you too much to let this go unsaid."

The thing you keep avoiding saying:
"Your output in Q2 didn't meet the bar we need at this level. I need to see [specific change] in the next 60 days."

Playing their reaction:
They'll get defensive first: "I've been here for 5 yea...

You're not using AI's words in the actual conversation. You're using AI to organize your thoughts, anticipate their reaction, and find the version of honest that preserves the relationship.

TODAY'S INSIGHT

The best leaders don't wing hard conversations. They rehearse them — just not out loud, and not with another person. AI is the safest rehearsal partner you'll ever have.

COMING NEXT

Continue to Day 26: The Org X-Ray →