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Your Strategist Prompt Pack
You catch the tradeoff before the room commits. Hand AI the build; you own the check, the part with a standard and stakes it does not have. Judge the decision by the process, not the outcome, and use AI to argue the other side, not confirm the read you already have.
Before a plan review or a fast-moving decision.
Review this plan and name the weak assumption, the hidden tradeoff, the most likely failure, and one question I could raise without derailing the room. Plan: [paste]
When you are leaning one way and want to pressure-test it.
Make the strongest case against [decision I am leaning toward]. Then tell me what would have to be true for the opposite to be the right call. Context: [paste]
When the room is choosing between two or three paths.
Compare these options on what each one buys, spends, and puts at risk. Recommend one, and name the single condition that would change your answer. Options: [paste]
Before committing to a plan everyone likes.
It is six months from now and [plan] has failed. Write the three most likely reasons, and the early signal I could have seen for each. Plan: [paste]