Most famous general book would be Gall's Systematics https://en.wikipedia.org/wiki/John_Gall_(author) https://en.wikipedia.org/wiki/John_Gall_(author) He is th

Most famous general book would be Gall's Systematics https://en.wikipedia.org/wiki/John_Gall_(author) https://en.wikipedia.org/wiki/John_Gall_(author) He is the author of the famous Gall's Law: A complex system that works is invariably found to have evolved from a simple system that worked. A complex system designed from scratch never works and cannot be patched up to make it work. You have to start over with a working simple system But then you need to dive into the field you are asking questions about. So, for example, you'd need some knowledge about how software engineering organizations work to help answer the OS/bug question. Gall's law just takes a critical look at systems and tries to describe common patterns of human organization. It has a lot of insight. "The Mythical Man Month" is great for insights on software engineering. Other books have good insights on corporate culture, business, etc. Also Taleb, although I find him opinionated and annoying, does have useful insights on risk that are important to understand.