If you're interested in why software goes wrong - and anyone who uses a computer for anything more than reading the occasional e-mail should be - then there are a couple of classic books you should have read by, say, December 30.
The first, little-known but very accessible, is "Digital Woes: Why We Should Not Depend on Software" by Lauren Ruth Wiener. This is about 14 years old and hardly mentions the Internet (!), but it is extremely readable and gives a good insight into the organisational issues around software projects. Anyone who buys software or IT services, and especially anyone who is the business owner of an IT project, should have read this book thoroughly before the salesperson from EDS, CSC, or IBM drops by.
If you're in software development, you could then move on to the daddy of all books on writing software, "The Mythical Man-Month: Essays on Software Engineering" by Frederick P. Brooks. Although most people under 40 will struggle to understand some of the technical references, and some of the suggestions have been made obsolete by hardware improvements, the general principles of how software development works are still as valid as they were 32 years ago when the first edition of the book appeared. My favourite quote: "Adding people to a late project, makes it later". If you can get your pointy-haired boss to understand that, you're half-way there.