Recommended reading for the CTO/CIO

There are really only three fundamental ways for a senior technology executive to hone his or her abilities:

• networking with peers,
• on-the-job experience, and
• voracious reading

An astounding number of executives neglect the last one. Throughout the essays on this blog, you’ll see me cite seminal books in the field fairly regularly, across the spectrum of IT-related concerns. I’ll collect a list of the most important ones here.

A seasoned IT executive should be familiar with most, if not all, of the “Must Read” books.  The rest of the books on the various lists below are ones I’ve found particularly compelling from my reading over the course of my career.

Must-reads:

• Peopleware: Productive Projects and Teams, by Tom DeMarco and Timothy Lister
• Rapid Development, by Steve McConnell
• The Psychology of Computer Programming: Silver Anniversary Edition, by Gerald Weinberg
• The Mythical Man-Month: Essays on Software Engineering, 20th Anniversary Edition, by Frederick P. Brooks, Jr. See my brief discussion of this book here.
• Software Estimation: Demystifying the Black Art (Best Practices (Microsoft)), by Steve McConnell
• Testing Computer Software, 2nd Edition, by Cem Kaner et al.

Recommended for general background:

• Creating a Software Engineering Culture, by Karl Wiegers
• Quality Software Management: Anticipating Change (Quality Software Management), by Gerald Weinberg
• IT’s hidden face: Everything you always wanted to know about Information Technology. A look behind the scenes, by Claude Roeltgen
• IT Savvy, by Peter Weill and Jeanne W. Ross

Architecture and Technical:

• Scalable Internet Architectures, by Theo Schlossnagle
• Scalable Web Sites, by Cal Henderson
• Release It!: Design and Deploy Production-Ready Software (Pragmatic Programmers), by Michael Nygard

Business and IT:

• Competing on Analytics: The New Science of Winning, by Thomas H. Davenport and Jeanne G. Harris
• Eliminating “Us And Them”: Making IT and the Business One, by Steven Romero
• 8 Things We Hate About IT: How to Move Beyond the Frustrations to Form a New Partnership with IT, by Susan Cramm
• Does IT Matter? Information Technology and the Corrosion of Competitive Advantage, by Nicholas Carr
• The CIO Paradox: Battling the Contradictions of IT Leadership, by Martha Heller

Internet Sociology:

• Here Comes Everybody: The Power of Organizing Without Organizations, by Clay Shirky
• The Tipping Point: How Little Things Can Make a Big Difference, by Malcolm Gladwell
• The Long Tail: Why the Future of Business is Selling Less of More, by Chris Anderson
• The Big Switch: Rewiring the World, from Edison to Google, by Nicholas Carr

Operational and Financial:

• Reducing Risk and Maximizing Investment Through IT Asset Management: A Practitioner’s Perspective, by Richard L. Allen, Jennifer D. Doyle, Tory M. Lehr, and William B. Fisher. See my review of this book here.
• Achieving IT Service Quality: The Opposite of Luck, by Chris Oleson, Mike Hagan, and Christophe DeMoss.

General technology background:

• The Information: A History, a Theory, a Flood, by James Gleick

Also recommended:

• Growing Software: Proven Strategies for Managing Software Engineers, by Louis Testa
• The Shallows: What the Internet is Doing To Our Brains, by Nicholas Carr
• Cognitive Surplus: Creativity and Generosity in a Connected Age, by Clay Shirky
• You Are Not a Gadget: A Manifesto, by Jarod Lanier
• What Technology Wants, by Kevin Kelly
• The Filter Bubble: What the Internet Is Hiding from You, by Eli Pariser

Note: I’ve also started a series of posts on the most important “human factors in IT” books, picking what I consider the most important three such books from each decade, starting with the 1970s.

Additionally, I have a series of posts on four “Novels of IT,” as listed above.