I suppose it is obvious that these two books are "must reads" for current or aspiring software CEOs, but I wanted to draw attention to them nonetheless. By pure coincidence (I swear) I went to the Naked Conversations home page and was surprised to see a post on The Tipping Point by Malcolm Gladwell which is one of the two books I just finished.
The other is Naked Conversations, by celebrity bloggers Robert Scoble and Shel Israel, is a must read because so many software CEOs are still not on the bandwagon to 1) understand the basics of the blogging phenomenon and 2) are not participating directly themselves (either as a blogger or a reader.) Much of it is obvious if you are aware of this blog revolution we are all living in and actually paying attention, but there are lots of interesting tidbits around the genesis of blogging, early vendors such as Six Apart, "how-to" checklists for aspiring bloggers, and even a blogger's "manifesto" which supposedly has been updated on the Naked Conversations blog but I didn't check.
Both of these books are important for CEOs to read; one to catch up with the blogging revolution, and the other to stimulate creative thinking in the corner office to break out of the typical processes typically used in defining and marketing great - truly great - software products. Whether in the software business or not you and your senior folks should make these two a must-read.
P.S. I also started reading Freakonomics and not sure I can recommend it yet but it is entertaining.