My go-tos are the mythical man month and Peopleware:productive projects and teams. There’s the Peter principle too. On more technical (slightly) topics, I like the Pragmatic Programmer. I also like people to be aware of re-engineering concepts, so Hammer and Champy’s Re-engineering the Corporation is also good.
Arthur Bloch's Murphy's Law and Other Reasons Why Things go ƃuoɹʍ is a compendium of engineering and organisational dictums. Of itself it provides relatively little insight, but many of the principles themselves trace to more substantive works, including Parkinson's Laws, the Peter Principle, and many, many others:
Bloch himself was working off a number of earlier compilations, several already popular in the high-tech industry (programming, weapons design, biotech, etc.), as well as other fields. I'd tracked those down at one point but seem to have lost those references. Bloch cites some, though not all, his sources in this and subsequent "Murphy's Law" books.
"Gamesmanship" and "Systemantics" cover similar ground:
Charles Perrow explores organisational foundations of failure in Normal Accidents and The Next Catastrophe. To an extent Joseph Tainter and Jerard Diamond's books (particular each author's independent Collapse titles) look into the dynamic at much greater depth.
For programming, MMM (Brooks), PeopleWare (Demarco & Lister), The Psychology of Computer Programming (Weinberg), Code Complete (McConnell), and a substantial literature on quality assessment and practices emerged in the 1970s -- 1990s. The bibliographies of the above books, as well as citations of them, should provide an ample set of references for further reading.
