Management & Thinking
ProInversion
逆向思考 · Source: Charlie Munger / Carl Jacobi
Finding "how to guarantee failure" in order to reverse-engineer "how to guarantee success"
Core Concept
Flip the question. Instead of "how do I succeed?", ask "how do I guarantee failure?" List every way to ruin this — then avoid them. Munger: "Tell me where I'm going to die, so I'll never go there."
✓ When to use this
When stuck on "how do I succeed," flipping to "how do I guarantee failure" is often easier to answer. Great for strategy review too — avoiding obvious disasters is more reliable than chasing the optimal path.
✗ When not to use this
Skip pure creative ideation (art, product imagination) — inversion pulls focus back to avoiding mistakes and kills exploration. In the optimistic brainstorming phase, let positive ideas grow first.
Questions you will be asked
Using this framework, you will work through —
- 1.What is your goal?
- 2.Now invert it: how would you guarantee this fails completely?
- 3.Which items from your failure list are you currently doing?
- …and 3 more
Worked example
Expand to see what a filled-in run looks like
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Worked example
Expand to see what a filled-in run looks like
Situation
想當一個好的軟體公司技術主管。問「怎麼當好主管」很抽象、答案太多元；倒過來問「怎麼當爛主管」答案明顯且具體得多。
1. What is your goal?
我想成為團隊真正信任的技術主管。但不知從哪些行為開始。
2. Now invert it: how would you guarantee this fails completely?
把「成功」反轉：要當爛主管，做這些事——不替屬下擋風、為了好看搶功、否決下面的判斷只因「我比較有經驗」、給模糊回饋、把責任往上踢。
3. Which items from your failure list are you currently doing?
盲點：「為了好看搶功」這件事我自己沒意識——上次 demo 我講得很流暢，但其實 80% 是 A 工程師做的，我沒明確點名她。
4. Which failure modes are you most prone to? Why?
只要避開上述爛主管行為，就已經比 70% 的主管好——這個基準率比我想的低。
5. To avoid the most dangerous failure modes, what will you do differently?
反推回正向：明確點名功勞、給具體（不是「再加油」）的回饋、被質疑時用「我看的是…，你的視角是？」對話、出事第一個扛下。
6. After inversion, has your original plan changed?
今天起每週一次「我有沒有犯爛主管行為」自檢，三個月後再評估正向行為是否足夠。
Use it inside ChatGPT / Claude
Paste the prompt below and the AI will walk you through this framework, one question at a time.
你現在是引導使用者用「逆向思考」的教練（Munger / Jacobi）。 依序問： 1) 你正在追求的目標或正面結果是什麼？ 2) 反過來問：要徹底失敗、做爛這件事，會做哪些事？列 5 條具體行為。 3) 在你目前的做法中，哪幾條已經中招了？誠實回答。 4) 光是避開這些「爛行為」就能達到什麼水準？這比你想的高還是低？ 5) 從反面再翻回正面——避開後該做的事是什麼？ 6) 接下來一個月最該避免的「爛行為」是什麼？ 提醒：「避開明顯的災難」往往比「追求最佳解」更可靠。 互動規則： 1. 一次只問一題，等使用者回答後再進入下一題。 2. 使用者答完所有題目前，不要做總結或下結論。 3. 若答案太抽象、太籠統，請追問一次具體例子或數字後再繼續。 4. 全部答完後，輸出三段：(a) 摘要使用者的關鍵判斷；(b) 你看到的盲點或張力；(c) 一個具體下一步行動建議。 5. 不要替使用者做決定，只把判斷攤開讓他自己決定。
Related Frameworks
Management & Thinking
Pre-mortem
Stress-testing a plan before committing — finding failure paths you haven't seen yet
Investment & Finance
Munger's Decision Checklist
Running a major decision through Munger's multi-mental-model filter before committing
Management & Thinking
First Principles Thinking
Breaking "we've always done it this way" inertia — rebuilding solutions from the ground up
FAQ
How is inversion different from a pre-mortem?
A pre-mortem is one specific application of inversion — assuming a particular plan has already failed and finding why. Inversion is broader: you can flip any question — "how would I guarantee failure?" "how would I make customers hate us?" Put simply: pre-mortem = inversion + a concrete plan + a team doing it together.
Won't constantly thinking about the negative make me too pessimistic?
No, because inversion doesn't stop at the negative. The full move is "list every failure path → then avoid each one" — negative thinking is just the middle step, success is the goal. After listing the problems you must convert them into "so what do I do now"; otherwise you've only done half the exercise.
Which decisions benefit most from inversion?
It's most effective when the goal is clear but the path is fuzzy, or when everyone is fixated on the upside and ignoring risk. When "how to succeed" is too diffuse to act on, asking "how would I guarantee a disaster" is often more concrete and easier to list out. Munger's line: "All I want to know is where I'm going to die, so I'll never go there."
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