Thinking & decisions
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
Thinking & decisions21 categories
Framing the decision
Working out what is really being decided, how reversible it is, and whose call it should be.
- Is this reversible or not?LongDeciding how much deliberation a decision actually deserves.
- Find the real question behind the stated oneLongWhen the decision keeps stalling and the reasons given do not explain why.
- Who should actually make this call?LongA decision that has landed on your desk and may not belong there.
- What is the real question?ShortGoing in circles on a problem that keeps shifting shape.
- Is this reversible?ShortWorking out how much deliberation a decision deserves.
- Who should decide this?ShortA call that may not be yours to make.
- Urgent or just loud?ShortSomething demanding attention it may not deserve.
- Am I overthinking this?MediumA decision that has taken more time than it is worth.
Stress-testing a plan
Pre-mortems, arguing the other side, and following the consequences past the first order.
- Run a pre-mortem on this planLongBefore committing to a plan that people are already enthusiastic about.
- Argue hard against the option I pickedLongWhen you have already chosen and want the case against before you announce it.
- What happens after the thing I want happens?LongAny change where the first-order effect is obvious and everyone stopped thinking there.
- Map who this decision lands onLongA change that will affect people who are not in the room when it is made.
- Argue the other sideShortWhen you have already decided and want the decision tested.
- What is the worst case?ShortAnxiety about a decision you have not actually sized.
- What if I do nothing?ShortBefore acting because acting feels better than waiting.
- Quick pre-mortemMediumA plan you are about to commit to properly.
Assumptions and reasoning
Digging out what you are taking for granted, including the sunk cost you keep not naming.
- Invert the problemLongStuck on how to succeed at something, when it is easier to see how to fail.
- Rebuild this from first principlesLongWhen the reason for doing it this way is "that is how it is done".
- Surface my hidden assumptionsLongWhen the reasoning feels solid, which is usually when an assumption is buried in it.
- Am I continuing because of sunk cost?LongA project you have invested a lot in and keep not cancelling.
- What would I need to believe?ShortA choice that only makes sense under certain assumptions.
- What am I assuming?ShortAny plan that feels obviously right to you.
- What would I tell a friend?ShortStuck on something you would see clearly from outside.
- Ignore what I have already spentMediumDeciding whether to continue something you are deep into.
Deciding under pressure
Making the call when time is short, information is missing, or your capacity is already full.
- What am I giving up by doing this?LongSaying yes to something when your capacity is already full.
- Decide well under time pressureLongA real deadline, and not enough time for the analysis you would prefer.
- Decide with information I do not haveLongWhen the missing information may never arrive and the decision still has to be made.
- Break this into smaller betsLongA big commitment that could be a sequence of cheaper ones.
- Pick one of these twoMediumTwo options, roughly equal, and a decision that is overdue.
Confidence and hindsight
Calibrating how firmly to hold a view, recording the call, and judging it later on its merits.
- Separate the decision from the outcomeLongAfter something worked out, or did not, and you want to know whether to repeat it.
- What would change my mind?LongCommitting to a position, before the evidence starts arriving.
- Calibrate my confidenceLongWhen you notice you have said "definitely" about something you have not checked.
- Write a decision recordLongRight after a call is made, while the reasoning is still in your head.
- Retrospective on a past decisionLongMonths later, when you can finally see how a decision actually played out.
- How confident should I be?MediumA belief you are about to act on.
- Write this decision downMediumRecording a call so the reasoning survives the next six months.
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