Anyone ever tell you that a simpler approach can often work better than a more complex one? Whoever it was, it probably wasn’t a project management software vendor.  But simplicity has its merits, and I’d like to point out a few of these when it comes to resource allocation.

Project management, at its core, is largely about resource allocation, and this gets tricky when you have multiple projects going on, as most organizations do. Almost as much as I’ve seen organizations drop the ball entirely on cross-project resource allocation (essentially, simply pretending that there will be no contention issues), I’ve seen organizations go to the other extreme: they dive into the depths of intense Project Management, in capital letters: taken too far too fast, this approach can spin up to a high level of rigor and overhead, involving often-expensive software packages, precise low-level estimates, diligent collection of actuals, and ornate project calculations of hours burned and hours earned.  At the end, there you stand, like Goethe’s Faust, “no wiser than before.”

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What is it that sets apart a top-notch IT executive from others of his calling? To my mind, one mark of today’s true professional, especially at the senior executive level, is to be deeply familiar with the seminal books in his or her field. The dilemma for an IT professional, though, comes from the ongoing and increasing flood of books to choose from, and trying to figure out how to walk the fine line between focus on the intensely tactical and focus on higher-level concepts and ideas.

The tactical books do have their place on your shelf, actually, and it would be a mistake to ignore them simply because you’ve moved beyond daily application of your development, configuration, and technical trouble-shooting skills: judicious selection and absorbing of nuts-and-bolts techniques and new approaches will keep your insight into technology and its possibilities fresh.

I started in IT as a developer, and I remain fascinated by the endless possibilities and techniques of the world of software. In the last decade or two, though, I’ve become even more intrigued by a metalayer above the more tactical concerns. True to my ongoing insistence that the biggest challenges in IT aren’t purely technical, I am ever more convinced that the greatest difficulties are presented by “psychology of IT” issues: the human factors in how software and systems are conceived, built, tested, deployed, maintained, and eventually decommissioned.  Here are just a smattering of the eternal, non-technical questions that go far beyond the computer language du jour or the latest hot methodology:

  • How do teams actually create and complete information technology projects? What works, what fails, and why?
  • Why are some software developers ten times as productive as others?
  • Why do some software teams gel and others don’t?
  • Why do small companies with very few resources often beat out large, well-funded efforts in the marketplace?
  • How technical should managers be?

So starting with this post, let’s embark on a multi-part survey of the groundbreaking, timeless books on such issues. I’m going to pick what I consider to be the top three books from each decade, starting with the 70s.  Each of them deserves not only a place on your bookshelf, but to be read and reread every few years. And contrary to what one might think, their insights remain not only valid after all these years, but have become all the stronger by having been confirmed by the history of the industry since their publication.

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No silver bullets. Really!

December 16, 2009

Fred Brooks wrote a seminal essay in 1986, “No Silver Bullet — Essence and Accidents of Software Engineering“, a model of clear and cogent thinking that I consider to be required regular reading for anyone involved in information technology.  Despite the essay’s brilliance, and despite its wide promulgation and deserved fame, the phenomenon it describes [...]

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The CIO and the fine art of vendor negotiation

December 10, 2009

“Don’t write about that,” I’ve been told by several colleagues, when I’ve mentioned that I was working on a post about how best, as the senior technology executive, to negotiate with vendors.  “You’ll give away all your tricks!” they’ve said.
Well, actually, no.  Here’s the main trick: this particular CIO doesn’t have any “tricks”, if by tricks [...]

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IT transparency is good. But how transparent should you be?

November 24, 2009

A few years back, I had an extremely surprising and unpleasant experience as CTO. The director of my Program Management Office ran a weekly status meeting for project stakeholders, where we’d all methodically go through the current project portfolio, in order to communicate on issues, gather necessary feedback, and align everyone’s expectations. I typically attended [...]

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Complexity isn’t simple: multiple causes of IT failure

November 16, 2009

Roger Sessions recently published a white paper on IT complexity and its role in IT project failure: “The IT Complexity Crisis: Danger and Opportunity”.  It’s certainly possible to quarrel with bits and pieces of his analysis, and thereby tweak his numbers, but the overall thrust remains undeniable: IT failures are costing the world incredible amounts [...]

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Fits and starts: staying “tech savvy” as a CIO

November 9, 2009

Just a quick, personal post this time: I was recently interviewed by CIO Magazine on the topic of “How CIOs Can Stay Tech-Savvy“.  Since (as is normal) only a portion of my conversation with the reporter actually made it into the article, I thought I’d expand briefly on the topic here.
My remarks were two-fold, consistent [...]

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“Refuse to lose”: how executive pressure contributes to IT failure

October 28, 2009

“We went live before the system was ready”.  It’s a common excuse/explanation that I hear from IT people when they tell war stories about system launches that failed miserably. Implicit (and sometimes explicit) is the add-on statement: “and we told them so beforehand, too.”
There are obviously many things (and many parts of the org chart) [...]

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