Inversion

Most product managers (myself included) naturally focus on achieving success. But inversion, thinking backward, can often be even more powerful. Rather than asking how to win, first ask how to guarantee failure.

Inversion challenges us to pause and ask:

• What would definitely cause users to abandon our product?
• What actions would guarantee failure in this initiative?

The Theory

Inversion means approaching problems from the opposite end, asking reverse questions to reveal hidden risks. Popularized by Charlie Munger, inversion helps uncover overlooked blind spots by focusing on what to avoid rather than just on what to do.

For example, instead of only thinking "How can we retain customers?" start with "What would drive our customers away?" It’s surprisingly easier to spot what to avoid than to define precisely how to succeed.

Product Management applications

Inversion can dramatically improve product management. We did this extensively when I worked at a fintech to mitigate potential risks:

• Conduct Pre-Mortems: Imagine your project failed. Work backward to identify what caused it, then take steps to mitigate those risks upfront.
• Expose Hidden Risks: By listing worst-case scenarios, your team becomes proactive rather than reactive, addressing potential pitfalls before they happen.
• Clarify Priorities: Identifying clear failure points helps teams prioritize the most impactful actions to prevent them.

My personal extension: Creating a culture that learns from failure

Inversion doesn't just mitigate risk, it reshapes organizational culture around continuous learning.

Great product leaders leverage inversion by:

• Rewarding teams for identifying critical flaws early rather than punishing mistakes.
• Promoting safe-to-fail experiments, allowing quick learning with minimal downside.

This approach transforms failure from something feared into an asset. A real world example is Google’s “moonshot factory” (X) where they celebrate teams discovering major flaws early, recognizing these moments as breakthroughs rather than setbacks. This mindset shift encourages bold decisions and accelerates innovation, helping teams outperform more cautious competitors.

Great Resources on Inversion

• Harvard Business Review - Performing a Project Premortem: Introduces pre-mortems as practical inversion exercises to spot risks before project launch.
• Tedx Talk - Invert, Always Invert: Engaging talk highlighting real-world examples of inversion across various fields.
• Using Inversion as a Mental Model for Product Management
  Explains inversion with a clear, practical example of improving user retention.
• Mental Models for Product Managers: The Inversion Principle
  Provides a simple three-step framework (define, invert, avoid) with a product conversion case study.
• Seeking Wisdom Episode #147 – “Invert, Always Invert”
  Short episode demonstrating practical uses of inversion in business and product challenges.
• Moonshots Podcast Episode 138 (Shane Parrish: Mental Models)
  Discusses inversion as a creative tool for solving tough product problems.