In context of software development these books (and other works by same people) might be interesting. I have not read them all yet but have been recommended by a colleague. My perspective is defined by being a developer in circa 100 people company.
* The Mythical Man-Month by Fred Brooks https://en.wikipedia.org/wiki/The_Mythical_Man-Month
* Facts and fallacies of software engineering by Robert L. Glass https://en.wikipedia.org/wiki/Robert_L._Glass
* Lessons learned from 25 years of process improvement: The Rise and Fall of the NASA Software Engineering Laboratory https://www.cs.umd.edu/users/basili/publications/proceedings...