WEEK 1 · GET MOVING · 8 min

The Tough Reply

The reply you keep rewriting in your head. Let AI help you decide what to concede, where you have leverage, and what your response signals — before you write a word.

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COPY THIS PROMPT

I need to respond to this, and the stakes are high:

[paste the message + context: what's at stake, the relationship, what I actually want]

Before you draft anything, help me think it through:
1. What do I actually want out of this exchange — the real outcome, not just 'a good reply'?
2. What can I concede that costs me little but matters to them?
3. Where do I have leverage that I'm not using?
4. What will each tone — warm, firm, neutral — signal about where I stand?
5. Now draft a version that gets me what I want while protecting the relationship.

Claude

Delicate email: telling a long-time vendor we're ending the relationship...

Hey Michael,

I want to be straight with you because our relationship matters to me.

We've decided to move in a different direction for our Q4 fulfillment. This isn't about the quality of your work — your team has been excellent. It's a strategic shift on our end.

I'd like to handle the transition in a way that works for both of us. Can...

Half of hard replies feel hard because you haven't decided what you actually want yet.

The strategy is the gift here. The words are easy once the strategy is clear.

TODAY'S INSIGHT

The hard replies aren't a writing problem. They're a strategy problem. Solve the strategy first.

COMING NEXT

Continue to Day 6: Brief Yourself Like a CEO →