Not sure if it fits your bill, but I found "I Sing The Body Electronic" by Fred Moody a very interesting read. Moody was able to get some pretty intimate insig

Not sure if it fits your bill, but I found "I Sing The Body Electronic" by Fred Moody a very interesting read. Moody was able to get some pretty intimate insights into the development of a software product at Microsoft at the beginning of the 1990s (1992-1993, I think). I was surprised to learn afterwards that Moody had (has?) a reputation for being very pro-Microsoft; this book does not embellish the problems the people on the project team face, nor their conflicts.