WEEK 4 · THINK BIGGER · 10 min

Stress-Test a Decision

Put a real decision in front of four people who'd push back — your CFO, a skeptical employee, your customer, your competitor — and let AI argue as each one.

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I'm weighing this decision:

[describe the decision and the context]

Pressure-test it from four points of view. Argue hard as each of these people, in their voice, with their real objections — don't soften it:
1. My CFO — what's the financial risk, what am I underpricing or hand-waving?
2. A skeptical employee who has to execute this — what breaks in practice, what am I missing from the ground?
3. My customer — why might this annoy, confuse, or lose them?
4. My toughest competitor — how do they use this against me, or where do they hope I go?

Then tell me: which objection is the most dangerous, and what would I have to believe for this decision to still be right?

Claude

Deciding whether to kill our lowest-tier plan and push everyone to the mid tier. Argue as my CFO, a skeptical employee, my customer, and my competitor.

CFO: Low tier is 40% of logos but 8% of revenue — fine. But model the churn from forced migration, not just the upsell.

Skeptical employee: Sales has been closing low-tier all quarter and support eats every angry downgrade. Who tells them?

Customer: 'Upgrade or leave' reads as a price hike with extra steps — I'll price-shop now.

Compet...

The point isn't to win the arguments. It's to finally hear the objection you've been talking yourself out of.

"What would I have to believe for this to still be right?" — if you can't name it, the decision isn't ready.

TODAY'S INSIGHT

A decision you can defend from four angles is a decision. Everything else is a hope.

COMING NEXT

Continue to Day 17: The Brief Only You Get →