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A model that agrees with you is worthless as a thinking partner. These prompts are built to argue: they attack the option you favour, hunt for the assumption you have not noticed you are making, and ask what would change your mind before you have committed to anything. Several deliberately refuse to give you a balanced list, because a balanced list is how a decision gets postponed. Use them before a choice you cannot easily reverse, during one you are making with less information than you would like, and afterwards when you want to know whether a good outcome came from a good decision or from luck.
36 prompts in 5 groups
Working out what is really being decided, how reversible it is, and whose call it should be.
Pre-mortems, arguing the other side, and following the consequences past the first order.
Digging out what you are taking for granted, including the sunk cost you keep not naming.
Making the call when time is short, information is missing, or your capacity is already full.
Calibrating how firmly to hold a view, recording the call, and judging it later on its merits.
Send a prompt you keep coming back to. A person reads every one.
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