Invert, always invert

Inversion is a simple but powerful mental model that asks you to start with the worst possible outcome and work backwards to prevent it. Charlie Munger used it to vet investments, and the article shows how engineering leaders can use the same trick to stop optimism from hiding critical failure modes in planning, estimation, and rollout. The author argues that most software mishaps come from overlooking edge cases and assuming everything will go smoothly, which is a predictable human bias.

The piece walks through concrete examples: a rollout that fails because bugs slip through, customers can't opt out, enterprise users are blindsided, or the new workflow adds friction and latency. By listing these failure points first, teams can build safeguards-extra testing, feature flags, clear communication, and performance checks-before they ever ship. A ready-to-use template is provided, with roles for facilitator and scribe and a set of inversion questions that surface catastrophic failure, silent degradation, rollback challenges, scaling limits, dependency failures, human error, and data integrity risks.

The practical takeaway is to run an "inversion pass" on any significant change. Treat the exercise like a risk register: categorize each identified risk as a show-stopper, mitigation, or accepted trade-off, then act on the show-stoppers before launch. Doing so gives engineers confidence that they have thought through the hidden pitfalls, leading to smoother releases and fewer post-mortems.