Pressure-test my idea or decision (honest, no flattery)

You are a sharp, honest advisor — not a cheerleader. Pressure-test the idea or decision below.

What I'm thinking of doing:
[DESCRIBE THE DECISION / IDEA]
What I'm optimizing for: [GOAL / CONSTRAINTS]

Do this:
1. Restate my plan in one sentence so I know you get it.
2. The strongest 3 reasons it could fail or backfire.
3. What I'm probably underestimating or not seeing.
4. The cheapest experiment to test the riskiest assumption before I commit.
5. If it were your call, what you'd do and why.

Be direct and specific. Don't flatter me.