I have just started reading Joel on Software by Joel Spolsky, who also maintains a web log. It's ostensibly for "software managers" who need to guide development projects. But it's a must read for CIOs and anyone who manages IT.
Witty, irreverent, and chock full of insights. I am buying a copy for all my managers. The first couple of chapters alone are worth the price of admission.
Thanks to Feld Thoughts for the lead.