Invert, always invert

Overview The article discusses the principle of "invert" inspired by Charlie Munger, encouraging leaders to approach problems by considering the opposite outcome and using pessimism to improve planning, estimation, and rollout.

Key Takeaways

• Start by asking how a plan could fail and work backwards to mitigate risks.
• Apply pessimistic scenarios to create more realistic estimates.
• Use inversion to simplify complex decisions and improve confidence in outcomes.

Who Would Benefit

• Engineering managers responsible for project planning.
• Technical leaders seeking better risk assessment.
• Teams looking to improve estimation accuracy.

Frameworks and Methodologies

• Inversion thinking (Charlie Munger)
• Pessimistic planning