WEEK 2 · MAKE IT USEFUL · 10 min

Find What You'd Miss

Hand AI something you're too close to — a plan, a deal, a decision — and ask the one question you can't ask yourself: what am I not seeing?

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COPY THIS PROMPT

Here's something I'm working on or deciding:

[paste the plan / deal / strategy / situation]

I'm too close to this. Act as a sharp outside advisor who does NOT share my assumptions. Tell me:
1. What am I not seeing because of my role, my incentives, or what I want to be true?
2. What's the strongest case against this that I've been avoiding?
3. What would a smart competitor or a skeptical board member notice immediately?
4. What am I treating as fixed that's actually a choice?
5. The question I should be asking that I'm not.

Claude

We're about to raise prices 15% across the board next quarter. Pretty confident it's the right call — margins are tight and we haven't raised in two years. What...

A few things you may be too close to see:

• What you want to be true: that loyalty absorbs the increase — but your longest customers are the most price-anchored.

• The case against: a flat 15% treats a $200 and a $20K account the same; small accounts churn loudly, big ones renegotiate quietly.

• What a competitor notices: a single list...

The blind spot that's hardest to accept is usually the one worth the most.

Seeing the blind spot is step one. Closing it is the leadership move.

TODAY'S INSIGHT

Your blind spots are invisible to you by definition. That's exactly the job AI is built for.

COMING NEXT

Continue to Day 8: Your AI Chief of Staff →