Thinking prompts
120 prompts · A–Z
- 10/10/10See how you'll feel about this in 10 minutes, 10 months, 10 years.framework
- A completely different approachGet an approach you haven't considered.framework
- Advice I'd give a friendGet the clarity you'd offer someone else in your shoes.framework
- Am I anchoring?Check whether the first idea or number is dragging your judgment.analysis
- Am I over-deliberating?Check whether a decision deserves more thought or less.framework
- And then what?Walk a decision forward several steps.analysis
- Argue the oppositeHear the most convincing case against your conclusion.analysis
- Ask me questions, don't answerGet unstuck by being questioned instead of advised.framework
- Best, worst, most likelyMap the three cases for a plan.analysis
- Bet on the predictionPressure-test a prediction by imagining money on it.analysis
- Break it into smaller questionsSplit a big question into ones you can tackle one at a time.analysis
- Build a comparison matrixLay options against criteria in a clear matrix.framework
- Compare options in a tableCompare options across your criteria and get a verdict.framework
- Compounding over timeSee how a choice compounds over one year and five years.analysis
- Control vs notSort what you can control from what you can't.framework
- Cost of being wrongWeigh the cost of being wrong and whether it's recoverable.analysis
- Decide between two optionsGet questions, a case for each side, and a recommendation between two options.framework
- Decide what to dropChoose what to give up when you can't do both.framework
- Decision vs anxietySeparate the actual decision from the anxiety about making it.framework
- Decision-journal entryWalk through a structured decision-journal entry for a choice.framework
- Define 'good enough'Decide what 'solved' or 'good enough' looks like before you start.framework
- Design a testTurn a belief into an experiment you could actually run.analysis
- Do others see it as I do?Question the assumption that others share your view.analysis
- Do, defer, delegate, or dropSort a list into act now, schedule, delegate, or drop.framework
- Early warning signDecide what would tell you early that things are going wrong.analysis
- Efficiency vs effectivenessCheck whether you're doing the thing right or doing the right thing.analysis
- Estimate expected valueRoughly compare options by expected value.framework
- Facts vs interpretationsSeparate what actually happened from the story you're telling about it.framework
- Find the bottleneckIdentify the constraint that limits everything else.analysis
- Find the feedback loopsMap which loops reinforce the problem and which dampen it.analysis
- Find the goal underneathKeep asking why until you reach the root goal.framework
- Find the high-leverage optionFind the choice that makes other choices easier or unnecessary.framework
- Find the weakest linkLocate the weakest step in your chain of reasoning.analysis
- Generalizing from one example?Check whether one vivid case is doing too much work.analysis
- How confident should I be?Put a calibrated number on your confidence and justify it.analysis
- How reliable is my evidence?Weigh each piece of evidence you're leaning on.analysis
- How would they approach it?Borrow the approach of a specific person or role.framework
- If I weren't already convincedSee what you'd notice without your existing conviction.analysis
- If no one would knowStrip out reputation and see what you'd actually choose.framework
- Insure, plan, or accept?Sort risks into insure against, plan for, or simply accept.analysis
- InversionFind the path to failure so you can avoid it.framework
- Is my fear aimed right?Name the fear and check it's pointed at the real risk.framework
- Is sunk cost driving me?Test whether past investment is steering a present choice.analysis
- Keep only one thingFind the single most essential part of a plan.framework
- Key uncertaintiesIdentify the uncertainties that would swing your decision.analysis
- Know vs inferSeparate what you actually know from what you're inferring.analysis
- Know, think, guessSplit your claims into knowledge, belief, and guesswork.analysis
- List the assumptionsSurface the assumptions baked into a plan and flag the riskiest.analysis
- Map cause and effectLay out the cause-and-effect chain in a situation.analysis
- Motivated or objective?Spot where you're reasoning toward a wanted conclusion.analysis
- No-regrets versionDefine what 'no regrets' looks like regardless of outcome.framework
- One action, many problemsFind the move that makes several other problems easier.analysis
- One-way or two-way door?Tell whether a decision is reversible, and how that should change your approach.framework
- Optimize the systemSee what changes if you fix the system instead of the single problem.analysis
- Options I'm avoidingSurface the uncomfortable options you're stepping around.framework
- Outside my experienceSurface what you might miss because it's outside your own experience.analysis
- Plan for the median caseStop betting on the best case and plan for the middle.analysis
- Play devil's advocateGet the three strongest arguments against your plan or view.analysis
- Problems success createsAnticipate the new problems that come from things working.analysis
- Rank my prioritiesRank priorities against a limited resource and explain why.framework
- Real opportunity costSurface what you'd actually be giving up by choosing an option.framework
- Red-team this planAttack your plan the way someone trying to break it would.analysis
- Reframe this three waysSee the same problem from three different framings.framework
- Regret testSort what you'd regret skipping from what you'd barely remember.framework
- Right problem or obvious one?Test whether you're solving the right problem or just the most obvious one.framework
- Riskiest assumption to testFind the riskiest assumption and a cheap way to test it.analysis
- Run a pre-mortemImagine the plan failed badly and work out why.analysis
- Second- and third-order effectsTrace the ripple effects beyond the immediate result.analysis
- Set decision criteria firstDefine what matters before you look at any options.framework
- Short-term vs long-termWeigh the near-term and long-term trade-offs in a decision.framework
- Single points of failureFind where one failure brings the whole plan down.analysis
- Smallest sharpest versionFind the smallest, sharpest slice of the problem to start on.framework
- Solve once or manage forever?Tell whether this is a problem to solve or a tension to keep managing.framework
- Speed, cost, quality trade-offsMap the trade-offs between speed, cost, and quality on a project.framework
- Starting fresh todayDrop the history and decide as if starting now.framework
- State the real problemPin down the real problem in one sentence and check you're not chasing a symptom.framework
- Steelman the other sideGet the strongest, fairest version of the view you disagree with.analysis
- Strongest evidence against meConfront the best evidence opposing your view.analysis
- Summarize my thinking backHear your own reasoning reflected back to test if it holds.analysis
- The 20% that drives 80%Find the small share of effort that yields most of the result.analysis
- The advice I don't want to hearGet the strongest version of the hard truth.analysis
- The assumption that breaks itFind the assumption that would change everything if it were false.analysis
- The binding constraintName the constraint that matters most right now.analysis
- The clarifying questionFind the one question that would make everything clearer.framework
- The five-minute gut checkSee what you'd choose under time pressure and what it reveals.framework
- The next concrete actionCut to the one action that makes progress today.analysis
- The other person's viewSee the situation from the other side.framework
- The outsider's conclusionSee what a fair-minded outsider would conclude from the same facts.analysis
- The question that decides itFind the single question that would make the decision obvious.framework
- The system behind the symptomFind the larger system that would keep regenerating the problem.analysis
- Think it through step by stepWork a problem through in order before concluding.analysis
- Turn it into a decision treeConvert a messy situation into a clear decision tree.analysis
- Twice the resources, halfReframe by imagining double the resources, then half.framework
- Urgent or just loud?Separate what's genuinely urgent from what's just emotionally loud.framework
- Values conflict or info gap?Tell whether a dilemma is about values or missing information.framework
- Want it or should-want it?Tell whether you're chasing something for yourself or for the 'should'.framework
- Want-to-be-true vs is-trueCatch where wishful thinking is standing in for truth.analysis
- Weighted pros and consBuild a pros-and-cons list that weights what matters.analysis
- What am I optimizing for?Name your real target and check it's the right one.framework
- What biases are at play?Identify the cognitive biases most likely distorting your thinking.analysis
- What could go wrong?Surface the failure modes you're not planning for.analysis
- What do I actually want?Find what you truly want underneath what you think you should want.framework
- What if everyone did this?Test an action by universalizing it.analysis
- What incentives does this create?Surface the incentives a plan sets up, including unintended ones.analysis
- What info would change this?Find the information that would actually move your decision — and whether it's worth getting.framework
- What must be true?List what has to hold for the plan to work.analysis
- What to stop doingFind what you could stop doing to improve things.analysis
- What would a skeptic attack?Find what a smart skeptic would poke holes in first.analysis
- What would change my mind?Name the evidence that would genuinely shift your belief.analysis
- What would make me wrong?Find what would have to be true for you to be wrong.analysis
- What would my future self do?Decide through the eyes of the person you want to become.framework
- What would prove me wrong?Name the evidence that would disconfirm your view.analysis
- What's actually changeable?Find what you're treating as fixed that might actually move.framework
- What's the base rate?Ground your expectations in how these things usually go.analysis
- Where's the mistake hiding?Stress-test a conclusion for where it's most likely wrong.analysis
- Which value wins here?Decide which of your values matters most in this call.framework
- Who else is affected?Find the affected people you haven't considered.analysis
- Worst realistic outcomeName the worst realistic outcome and whether you could live with it.analysis
- Wrong or just uncomfortable?Tell whether you're avoiding an option for good reasons or just discomfort.analysis
- Zoom outCheck how much this will matter in a week, a year, ten years.framework