IT Management Must-Read Books: Managing Risk on Software Projects

By Bruce F. Webster  |  Posted 2008-11-17 Print this article Print

Post-mortem meetings are important, but they will only get you so far. Baseline columnist and senior IT project lead Bruce F. Webster reinforces one of the most overlooked aspects of IT management: Reading books. Webster outlines 5 books that are easy to read but chock full of real, practical project information and strategies for making IT management a better, less risky and more successful, less stress-inducing process.

Waltzing with Bears: Managing Risk on Software Projects by Tom DeMarco and Timothy Lister. I cited this book in an earlier column on risk management, but it’s worth citing again. As with the other authors named in this column, DeMarco and Lister have been writing on IT project management and software engineering for a long time; I had a hard time choosing between this book and Peopleware, their book on IT team management, which should provide you with a hint to go read Peopleware as well.

What is useful -- and in fact critical -- about Waltzing with Bears is that it takes you step-by-step through the process of identifying, analyzing and, where possible, quantifying the risks your IT project currently faces. DeMarco and Lister then discuss how best to mitigate those risks, either up front or as they arise. Their simplest answer is the most obvious, yet the one most often ignored: start earlier and build cushions into the schedule.

After all, as they point out, when we travel to another city for a critical business meeting, we usually leave lots of safeguards into our travel plans to account for traffic jams on the way to the airport, delays in getting through security, flight delays or cancellations, and so on.  Yet when we plan an IT project, we tend to rely upon highly optimistic assumptions for every aspect of the project – and then get upset when those assumptions turn out to be wrong.

Facts and Fallacies of Software Engineering by Robert L. Glass. Having spent decades both in the software engineering trenches and writing about his experiences, Glass now summarizes much of what he has learned in a highly readable and well-documented list of , well, facts and fallacies about software engineering. He gives 55 facts and 10 fallacies, each following the same format: he states the fact (or fallacy), discusses it, identifies controversies regarding it, then gives sources (with specific references). The facts are group into four major categories – management, life cycle, quality, and research – and the fallacies into three – management, lifecycle, and education.

My personal favorite is Fact #14: “The answer to a feasibility study is almost always ‘yes.’” Billions upon billions of dollars have been lost in major failed IT projects for just that reason alone.

I would say that many of Glass’s facts are obvious, except that I repeatedly see IT projects where they were clearly ignored. As an IT manager, you may find that the best use of this book is to quote sections of it wholesale into memos for upper management. Keep this book handy and review it often.

Webster is Principal and Founder at at Bruce F. Webster & Associates LLC. He works with organizations to help them evaluate troubled or failed information technology (IT) projects, or to assess IT systems and products for possible investment/acquisition. He has also worked in several dozen legal cases as a consultant and as a testifying expert, both in the United States and Japan.

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