Page 39 · Module 01, Think Like a Strategist · this screen continues that page

All 108 frameworks
1.8BeginnerModule 01 · Think Like a Strategist

Inversion Thinking

ou want to stress-test a plan before committing to it. Forward thinking hasn't revealed the

The prompt

Copy & paste ready
1.8Inversion Thinking
Act as a strategic risk advisor using inversion thinking. Goal : [WHAT I AM TRYING TO ACHIEVE be specific] Context : [SITUATION, INDUSTRY, STAGE, TEAM] Step 1 : List everything that would guarantee I fail. Think broadly - execution, market, team, timing, assumptions, behaviour. Step 2 : Rank these failure causes by probability. Step 3 : For the top 5, give one specific prevention action I can take before moving forward. STRESS-TEST PLANS WITH INVERSION THINKING Review and Mitigate List Failure Causes Cross off already Ask AI for failure addressed risks guarantees Build Prevention Inversion Thinking Define Goal Actions Be specific about Create actions to achievement avoid failure Unrevealed Plan Problems Stress-Tested Plan Forward thinking misses risks Risks are identified and avoided
LabelsReplace theseSwap the role below

LabelsReplace theseSwap the role below

Pro tip, from the book

Share the failure list with your team before launch. Ask each person to add one item you missed. The combined list will contain at least one thing that would have actually stopped you and now it won't.

Who should run this prompt

Module role profile

Who should reason through this problem? The quality of your thinking is shaped by whose lens you borrow. A strategist and a risk analyst look at the same problem and see completely different things — both useful, both necessary. Before you prompt, choose who you need in the room. These profiles give you six internal perspectives and four outside views that challenge your assumptions before you commit to them.

Choose any role to drop it into the prompt above. Only the highlighted opening clause changes — the rest of the prompt stays exactly as printed.

Internal rolesThink from inside the organisation
Outside perspectivesChallenge your blind spots

◆◆◆◆◆ → ◆ seniority, board level down to specialist outside the organisation

How to make any role sharper

  1. Add years of experience: "...with 15 years in enterprise SaaS" produces different depth than just the title.
  2. Add what they care most about: "You care most about [X]" shapes every word of the output.
  3. Add their communication style: "Be direct. Flag risks first. No jargon." changes the tone entirely.
See also: 1.3 Role Prompting - The Expert Chair

Use this when

The problem it solves

problems. You need a completely different angle of attack.

How the framework works

From the printed page

Inversion means solving a problem backwards. Instead of 'how do I succeed?' you ask 'what would guarantee I fail?' Then systematically avoid everything on that list. Charlie Munger called it one of the most useful thinking tools he knew. It surfaces risks that positive thinking consistently misses. Listing paths to failure is concrete and finite, while listing paths to success is easy to fool yourself with. The founders who last usually wrote the failure list first and took it seriously.

The method, in four moves

Do these in order
1

Define what you're trying to achieve be specific.

2

Ask AI to list everything that would guarantee you fail at that goal.

3

Review honestly. Cross off what you've already mitigated.

4

For everything remaining, build one prevention action each. What would guarantee failure? Now avoid that. Charlie Munger built Berkshire Hathaway's risk culture around inversion. Before every major investment, the team asked: 'What would guarantee we lose money here?' That list of failure conditions became the due diligence checklist. Not pessimism precision. Most investors ask 'why will this work?' Munger asked 'what would make this fail?' first. IN PRACTICE

Where the framework comes from

Charlie Munger, Poor Charlie's Almanack, 2005

When this page changes, your copy of the book does not have to.

The book prints the framework. This page keeps it — and keeps the prompt current, because prompting technique moves faster than print does. When it moves, this page is rewritten and the code in your copy keeps pointing at it. No second edition, no replacement purchase, no account.

If something here looks wrong — a prompt that does not match its framework, a figure that reads oddly — tell Raphy. That correction reaches every printed copy at once.

Framework1.8 of 108
Printed onPages 3839
Prompt extracted18 Sept 2026
Costs to readNothing, no account

Copying is free. An account keeps them.

Nothing on this page is behind a login and nothing ever will be. Save any prompt to your own list, pick up on another device, and send a colleague a link with your name on it. No card, no trial, no paywall on the prompts themselves.

See how it works
Save this framework to your own list
Pick up where you left off on another device
Send a colleague a link with your name on it