It is one year from now, and my plan has failed. Completely.
The plan: {{describe your project or decision}}
As a premortem facilitator:
1. Write the failure story — a specific, plausible paragraph about HOW it most likely died. No lightning strikes; ordinary causes.
2. Extract the 3 biggest failure causes from that story, ranked by likelihood × damage.
3. For each: the cheapest insurance I could buy NOW (a conversation, a test, a deadline, a backup).
4. Tell me the one assumption I'm making that, if wrong, sinks everything — and how to test it this week.
Then write the success story version, so I know what I'm actually steering toward.
You are a decision analyst. Your job is clarity, not comfort.
My decision: {{what you're deciding}}
My options: {{list them — include "do nothing"}}
What actually matters to me: {{criteria, gut feelings welcome}}
My deadline: {{when}}
Build the one-pager:
1. Restate the decision sharper than I did.
2. Score each option against my criteria (simple table, 1–5). Add one criterion I forgot but clearly care about.
3. Name the reversible vs. irreversible parts — irreversible gets the scrutiny.
4. Your recommendation, in one paragraph, with the strongest argument AGAINST it stated fairly.
5. The tripwire: what early signal would tell me I chose wrong, and what I'd do then.
Do not hedge into "it depends". Commit.
I've been stuck deciding this for too long. Help me actually decide.
The decision: {{what it is}}
Why I'm stuck: {{too many options? fear of wrong choice? perfectionism?}}
My real deadline (or set one now): {{when}}
Force it: 1) IS THIS REVERSIBLE? If yes, the cost of a 'wrong' choice is small — decide fast and adjust. Tell me honestly which this is. 2) THE 'GOOD ENOUGH' BAR — what would make an option acceptable, not perfect? 3) NARROW to the top 2, kill the rest. 4) THE TIEBREAKER — one question that separates them (which do I regret NOT trying? which is easier to reverse?). 5) THE DECISION and the immediate first step to make it real. Done-and-adjusting beats perfect-and-paralyzed.
Help me apply the regret-minimization frame to a decision.
The decision: {{the big choice}}
What's holding me back: {{fear, comfort, others' opinions, money}}
Work it: 1) THE 80-YEAR-OLD VIEW — imagine me at 80 looking back. Which choice am I more likely to regret NOT making? Walk both futures. 2) SEPARATE the fears — which of my hesitations are about real, lasting downsides vs. temporary discomfort or others' judgment that won't matter in a decade? 3) THE REVERSIBILITY — if I try the scary thing and it fails, can I recover? Usually yes. 4) THE ASYMMETRY — is the upside life-changing and the downside survivable? 5) What the long view says, plainly. Optimize for a life without 'what if', not a year without discomfort.
I'm stuck. Help me reframe the problem itself.
How I currently state the problem: {{your framing}}
What I've tried: {{approaches that didn't work}}
Do this: 1) RESTATE it five different ways — as a different question, a different scale, from a different stakeholder's view, as an opportunity not a problem, and by questioning a hidden assumption in my framing. 2) THE HIDDEN ASSUMPTION — the thing I'm treating as fixed that might not be. 3) WHICH REFRAME opens the most new options, and what those options are. 4) THE REAL PROBLEM — after reframing, is the thing I've been solving even the right thing? Often the stuck-ness is the framing, not the problem.
Help me get clear on what I actually value, for a decision I'm facing.
The decision: {{the fork — job, move, relationship, path}}
The options: {{list them}}
Guide me: 1) Ask me 4-5 sharp questions that surface what I truly prioritize (not what I think I should) — about how I want to spend my days, what I'd regret, whose approval I'm chasing. Wait for my answers. 2) NAME THE PATTERN — from my answers, the 3 values that actually seem to drive me. 3) SCORE the options against THOSE values, not generic ones. 4) THE MISMATCH — where I'm tempted by an option that serves someone else's values, not mine. 5) The choice my own values point to, stated back to me. Help me choose my life, not the expected one.
Help me think through the downstream effects of a decision.
The decision/action: {{what you're considering}}
What I expect to happen (first-order): {{the obvious result}}
Go deeper: 1) SECOND-ORDER — 'and then what?' What happens as a result of the first result? People react, incentives shift, habits form. 2) THIRD-ORDER — and then what after that? 3) THE SLEEPER EFFECTS — the non-obvious ripples (on relationships, reputation, future options, my own behavior). 4) WHO ELSE is affected and how they'll respond. 5) THE REFRAME — knowing the full chain, is this still a good move, and what would I adjust? Most bad decisions look fine at first order.
You are a root-cause facilitator. I brought a problem; you suspect it's a symptom.
The problem as I see it: {{what keeps happening}}
What I've already tried: {{attempts that didn't stick}}
Facilitate:
1. Ask me "why does that happen?" — then WAIT for my answer. One why at a time, five levels deep. Push on vague answers ("it just does" isn't a cause).
2. At each level, note whether we've hit: a process cause, a people cause, or a structure/incentive cause.
3. When we reach bedrock, name THE REAL PROBLEM in one sentence and check: "if this were fixed, would the original symptom disappear?"
4. Flag the level where my previous fixes were aimed — and why they kept sliding off.
5. One fix at the root level: smallest change, biggest stick.
Rule: causes are things that can be changed. "People are lazy" is never bedrock — keep digging.
You are a philosophy professor who believes you don't hold a view until you can defend its opposite.
My position: {{what you believe about the issue}}
The context: {{debate at work? essay? family dinner? deciding something?}}
Run the exercise:
1. STEELMAN — the opposing view argued at full strength: its best evidence, its most reasonable version, the smart person's case for it. No strawmen, no "some people think".
2. THE STRONGEST POINT — the single opposing argument I most need an answer for.
3. MY POSITION, STRESS-TESTED — where my view held up, and where it needs repair or narrowing ("X is true, but only when Y").
4. THE SYNTHESIS — is there a version incorporating the best of both? Or is this a true either/or?
5. If I'm debating: the respectful acknowledgment line that makes my counterpart actually listen.
Do not just agree with me. If my position is weak, say so.
Help me use inversion on this.
What I'm trying to achieve: {{the goal}}
Where I'm stuck: {{context}}
Do this: 1) INVERT IT — instead of 'how do I succeed?', ask 'how would I GUARANTEE failure here?' List the surest ways to wreck this. 2) THE AVOID LIST — turn each failure mode into a thing to actively prevent. 3) THE ALREADY-HAPPENING ones — which of these failure behaviors am I unknowingly doing right now? Be direct. 4) THE HIGH-LEVERAGE FIX — the one avoidance that matters most. 5) NOW forward — with the traps cleared, the simplest positive path. Sometimes avoiding stupidity beats seeking brilliance.
Check my reasoning for bias.
What I believe / how I'm reasoning about it:
{{lay out your thinking on the topic or decision}}
Do this: 1) THE LIKELY BIASES — which cognitive biases might be distorting this (confirmation, sunk cost, recency, anchoring, motivated reasoning, overconfidence...) and WHERE specifically in my reasoning each shows up. 2) THE STEEL-MAN of the view I'm dismissing. 3) THE MISSING EVIDENCE — what would I look at if I actually wanted the truth vs. to be right? 4) THE CLEANER TAKE — how the reasoning looks with the biases corrected. Be direct — I asked for this because I want the blind spot, not comfort.
Help me think about this from first principles, not by analogy.
The problem or thing I want to rethink: {{describe it}}
How it's 'normally' done: {{the conventional approach}}
Strip it down: 1) THE FUNDAMENTALS — what do we know to be actually true here, beneath the conventions? Break it to the base facts. 2) THE INHERITED ASSUMPTIONS — which parts of the 'normal' way are physics/reality vs. just tradition, habit, or 'because that's how it's always been'? Separate them. 3) THE REBUILD — starting only from the fundamentals, what would I design if the conventions didn't exist? 4) THE REALITY CHECK — which conventions exist for good reasons I shouldn't discard, and which are just cruft. 5) THE INSIGHT — the non-obvious move first-principles reveals. Question the 'obviously' before accepting it.
You are a reflective coach running my annual review. Interview me — one question at a time, waiting for each answer.
Cover, in order:
1. THE ENERGY AUDIT — what gave me energy this year, what quietly drained it (people, projects, habits).
2. THE REAL WINS — including ones I haven't given myself credit for. Push me on this; humans under-count.
3. THE PATTERN — reading my answers, name one pattern I probably can't see (be direct).
4. THE SUBTRACTION — what to STOP in the new year. At least one thing, named specifically.
5. THREE COMMITMENTS — sized to survive February: one habit, one project, one relationship. Each with a first step scheduled in week one.
Then write "the letter" — 150 words from me-in-December-next-year, describing the year where the three commitments held. Present tense.
Help me do rough expected-value thinking on a risky decision.
The choice: {{option A vs option B, or do-it vs don't}}
The possible outcomes & my rough sense of their odds: {{describe, guesses are fine}}
Work it: 1) LAY OUT the outcomes for each option, with a rough probability and a value (money, time, happiness — whatever fits) for each. 2) THE NAPKIN EV — weight outcomes by odds to compare options, roughly. Show the math simply. 3) THE ASYMMETRY — is there a small-downside/huge-upside (or the reverse) that matters more than the average? 4) THE RUIN CHECK — any outcome so bad I can't recover, that I should avoid regardless of EV? 5) THE CALL, and the assumption most likely to flip it. Numbers to inform the gut, not replace it.