WEEK 5 · BUILD THE HABIT · 10 min

Let AI Challenge Your Strategy

Upload your most important document. Then ask AI to find the holes in it.

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Your business plan. Your pitch deck. Your Q3 roadmap. The document that's driving your biggest decisions.

COPY THIS PROMPT

Read this carefully. This is the strategic document driving my most important decisions right now.

Don't summarize it. Challenge it:

1. Where is the logic thin — what claims aren't backed by evidence?
2. What's the biggest assumption I'm making that could be wrong?
3. If my smartest competitor read this, what would they exploit?
4. What's missing that should be here but isn't?
5. Where am I being too conservative? Where am I being too aggressive?
6. If you were my strategic advisor, what's the one thing you'd tell me to change before presenting this to anyone?

Claude

📎 strategy doc — Don't summarize. Challenge it.

Where the logic is thin:

1. You claim "product-led growth" but your team structure is entirely sales-driven. There's a strategy-execution mismatch on slide 4 that your board will catch.

2. The TAM calculation on page 12 includes three market segments you've never sold into. That inflates your addressable market by roughly 40%.

What a c...

AI isn't always right. But it'll ask the questions your team is afraid to ask. The competitor question alone is usually worth the 10 minutes.

TODAY'S INSIGHT

A good advisor tells you what you want to hear. A great advisor tells you what your competitor would think. AI can be the second one.

COMING NEXT

Continue to Day 25: Rehearse the Hard Conversation →