Book review: The CIO Paradox: Battling the Contradictions of IT Leadership

It’s a universal trait, it seems: we all want to be understood, want the world to see things through our eyes, want to watch the “aha” light go on when people finally realize just how tough we have it and how magnificently we still prevail.

IT people, and senior technology executives in particular, are anything but exceptions to this longing. In fact, it seems that very few other disciplines have to put up with a constant stream of articles and books questioning our very existence, approaches, purpose, and worth (Does IT Matter?, the death of the CIO , etc.). Even the acronym CIO is commonly and gleefully referred to as standing for “Career Is Over”. And you want a downer? Just try googling “average tenure of the CIO”.

A person could downright get a complex here. No one seems to get it! No one understands how tough a job this is! No one seems to perceive the “damned if we do, damned if we don’t” intrinsic nature of our role. I present this syndrome with all due humor (“against the assault of laughter nothing can stand”, said Mark Twain), but I also mean it: is it utter masochism that leads us to choose this “whipping boy” kind of career at this level?

The CIO Paradox, book cover
That’s why it’s so welcome when a book comes along that effectively presents insight and understanding into the “big picture” struggles of today’s CIO, even combined with empathy and warmth. Martha Heller’s The CIO Paradox: Battling the Contradictions of IT Leadership, just out late last year, brims with “been there seen that” deep insight into many of the standard CIO predicaments.

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Novels of IT: The Phoenix Project

Nerd alert: it’s an exciting day for me when someone releases a new “novel of IT”. I’ve made it my mission to find and review several of these (now four) over the past couple of years, and I may be one of the few people out there who has read and reviewed all of them.

To recap: what do I mean by a “novel of IT”? It’s a term I coined to describe a fictionalized depiction of life in a corporate IT environment, usually bearing a number of intended lessons in tow about IT best practices, approaches, pitfalls. They’re generally not works of serious fiction; their audience is usually the lot of IT professionals rather than the broad public. (For example, I don’t include in this category two fine and recommended works that in fact aspire more to literature than to IT didacticism: Douglas Coupland’s Microserfs and Ellen Ullman’s The Bug).

As I’ve traveled through the fictional scenarios depicted in these four books, I’ve evolved criteria for what makes them successful (or not) in my eyes. In a novel of IT, I’m looking for a book that is both reasonably engaging as a novel and one that accurately portrays a broad swath of the inner workings, nuances, and personality types that are typically part of the landscape of IT in today’s world. Reading the book should provide a window into common dilemmas and disagreements regarding IT issues, lending perspective and insight into all parties’ motivations and interests.

I looked forward for many months to the release last week of The Phoenix Project: A Novel about IT, DevOps, and Helping Your Business Win, by Gene Kim, Kevin Behr, and George Spafford,  after meeting and chatting with Gene Kim at a conference back in May of last year. I was greatly impressed at the time with Gene’s general demeanor, enthusiasm, and articulateness. He gave a rip-roaring presentation at the conference on “ITIL at Ludicrous Speeds: Rugged DevOps”: I recommend seeing him speak if you get the chance. I felt certain that his long-promised “novel of IT” would be a worthy addition to the collection of works in this category.

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The One True Way syndrome exemplified: the overstated case against code comments

I write frequently, and not without some exasperation, about the perennial search for the “silver bullet” in IT: the holy grail, the end-all, be-all solution to preventing IT failure.

The silver bullet has a very close and similarly pernicious internal twin cousin: the One True Way. That’s a technique or practice that is (usually) adopted by its IT aficionados as the key to overall success, with the important insistence that it will work as long as you follow it to the letter, in all cases, no matter what.

So this post will seemingly be about a specific (and low-level) development issue, but it’s only to serve as an example to illustrate this One True Way syndrome that is so prevalent in IT. At core, my takeaway boils down to the same old message I usually have when it comes to IT matters: be wary of something promising to fix all your problems. Be wary of absolutes. And be especially wary of the combination.

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The value of DOING for the CIO: test-driven development

“How technical are you?” This common challenge, almost playground-aggressive in nature, can turn into a sore spot for the CIO today. It’s inevitable (and actually desirable), you see: as you move up to executive rank, you lose your day-to-day involvement in the actual nuts-and-bolts implementation of technical details. Many executives respond by essentially abandoning all direct personal engagement with technology. But to do so across the board is a mistake.

Here, I seldom post directly about technologies or techniques, because, quite frankly, I’ve found in business situations that technology in and of itself is very rarely either the real problem or the real solution. Despite this, I still see technology as an ongoing crucial area of expertise for the CTO/CIO (contrary to the claims of some pundits that I’ve written about before). To maintain this vital expertise, the CIO’s dilemma is as follows: you have to keep your hand in, but you won’t ever have the time or focus to try out every technique, tool, or approach. You’re going to be, at best, a dilettante.

However, just because you’re doomed, as an executive, to be a dilettante doesn’t mean you should give up all efforts to stay current, or that such efforts won’t provide you with useful CIO-level insights. Even a little goes a long way. This post describes one example of that, as a case study.

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“No IT projects”? A practical take

If you follow the news, it’s quite clear that we’re in the “silly season” of politics, that time when people eagerly grab hold of any questionable statement of their opponent and use it to extrapolate rank incompetence or dastardly intentions (or worse). Language is frequently quoted out of context, definitions become blurred, things get inappropriately juxtaposed. We’ve all seen it.

That’s why they call it silly season. And that behavior isn’t just true of politics, but also can appear in normal business life, on Twitter, and (often) in IT matters as well. When I run across items I disagree with, though, I try to remember that rather than expressing categorical disagreement (let alone outrage), it’s far more useful to look first for common ground, then aim to identify the areas of contention or difference in perspective. That struck me recently when I read Todd Williams’ (@BackFromRed) recent blog post with the title “Stop All IT Projects!” and recalled that another esteemed colleague, Steve Romero (@itgEvangelist), has expressed views along the same lines.

Todd and Steve are both smart, experienced IT professionals whom I highly respect. In Todd’s case, we’ve met in person; in Steve’s, we’ve exchanged numerous emails and blog posts over recent years. Both of them unquestionably “get it” when it comes to IT matters. I generally agree with what they post or tweet; they’ve each written books that I recommend to others. In fact, I even agree with much of what Todd writes in this particular post. But still, with consummate respect, I think these colleagues (and others) are picking the wrong battle when they insist so staunchly on “no IT projects”. Here’s why.

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Valuable vs. fun: learning to love IT Asset Management

My attitude is that if you push me towards something that you think is a weakness, then I will turn that perceived weakness into a strength.

— Michael Jordan

As with so much in life, so it goes with IT: the parts that are fun aren’t always valuable, and the parts that are valuable aren’t always fun. Let’s talk about a hugely valuable side of IT that isn’t really much fun at all. And when it’s not fun, that means that it’s often neglected, and thus turns into a great weakness.

IT assets (hardware, software, systems, services) represent a major investment for most firms today. For “new economy” companies in particular, the cost of such resources (both bringing them on board and maintaining them as corporate assets) often exceeds expenditures in any area other than wages and benefits.

It’s astonishing, then, that firms (not to mention IT management specifically) don’t always embrace the ongoing hard work required to maximize the value of those expenditures and minimize the corporate risks involved. All too often, I see IT asset management (ITAM) neglected by IT executives because, well, it involves a discouraging amount of drudgery to do it right, especially over the long haul. This neglect occurs even more often when an executive succumbs to the latest faddish push for IT to focus on strategy and innovation to the detriment of fundamentals.

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More timeless, still-relevant information technology jokes

One of my most visited blog posts noted that certain IT jokes tend to come up again and again. That post covered four such familiar jokes, along with what I felt were some common themes uniting them: IT hubris, narrow perspective, self-righteousness. Each of those jokes contains a “grain of truth” to it that makes it funny, to IT and non-IT people alike.

Along those same lines, here are three more time-honored IT jokes, ones you’ve probably already heard if you’ve spent much time in the industry. Again, take a few moments to revisit them and consider what makes them timeless: how the common situations they describe seem to never quite go away. And then I’ll talk about what I think unites them thematically, and the resulting lessons for IT professionals.

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IT entropy in reverse: ITSM and integrated software

Why am I an IT professional? Here’s one major compelling reason: you simply can’t rest on your laurels. You can’t stop learning and growing and examining and improving, in all aspects, or you stagnate and die. The best IT professionals, I’m convinced, work energetically and on an ongoing basis, actively striving to push the scales from their own eyes at every juncture. It’s part of the job.

Last week I had the opportunity to attend what was my first industry conference in almost 8 years, Knowledge12, put on by ServiceNow, a software-as-a-service (SaaS) provider of IT service management (ITSM) software. (See my post explaining why I’ve tended to avoid industry conferences in recent years). And to my surprise and delight, I discovered that it was well worth the time. Let me share my thoughts on why.

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