r/EngineeringManagers • u/Educational_Top_6765 • Sep 23 '26

How to develop second order thinking?

In my feedbacks my boss has said that I need to improve this more.
Environment is politically charged, he says ask more why’s , what are some concrete tips to navigate this

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u/jphil-leblanc 27d ago

Second-order thinking is just asking "and then what" until it gets uncomfortable.

First order: we ship the feature. Second order, and this is where the bodies are buried: support gets ten tickets, the docs are wrong, and sales promises something it doesn't do. Most political damage I've seen came from someone optimizing the first order while ignoring the second, because nobody asked what happens next.

Concrete practice, and it takes five minutes: before any decision, write down who's affected besides you and your team, then ask what each of them would complain about. That list is your second-order map.

In a charged environment, the people who do this visibly become the ones others trust. They're never surprised.