In early 2004, I compiled a recommended reading list for program managers. I started with a list of my own -- a handful of favorites -- then emailed all of the Group Program Managers in the Developer Division to ask them for their recommendations, then put some structure on it and emailed it to a variety of internal Microsoft aliases. I still get requests for it periodically, so I thought I would share it. (Now I can link to it here rather than search my email archives :-)
I haven't read all of the books, so I have made no attempt to rank or rate them.