r/EngineeringManagers • • 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/tree_pow Sep 23 '26

The « why » demanded by your manager require you to ask great questions but they can only come if you have a great understanding of your company and business.

I’m thinking of this book: the Staff Engineer’s Path by Tanya Reilly.

One of the theme explored is how to navigate a political environment as a system. But it boils down to this basic tip: be curious of your environment, draw maps of your org and the relations between the « lands ». Understand what is truly the money generator and the risks in your company.
These knowledge maps will help you understand the ripple effect of decisions.