Towards a more balanced list of content about #NoEstimates

Both my readers will have noticed there’s been a fairly large gap between my posts here, as life (picnic, lightning, and all that) has intervened. Like J.D. Salinger, however, I have continued writing drafts on various topics, and I plan to post more in the coming months.

My past posts here have often delved into a favorite theme of mine: that IT people tend to go to extremes, often rejecting something useful (an approach, a technology, a tool) simply because it has downsides. Such rejection is at times emotional and even self-righteous; we can get so caught up in it that we fail to look at a topic at all evenhandedly, let alone dispassionately.

No better case example along these lines has come along in the past year than the active and contentious #NoEstimates debate on Twitter and in the blogosphere. I’ll have a much more detailed post soon about my objections to the #NoEstimates approach overall (full disclosure: I’m one of its most vocal critics), but right now, let’s focus on one aspect of the relentless advocacy I see in the hashtag’s proponents: its lack of evenhandedness.

Specifically, proponents of #NoEstimates insist repeatedly and proudly that they’re “exploring”; recently, one major advocate tweeted out a call for links to posts about the topic (“I’m gathering links to #NoEstimates content”) so that these could be collected and posted. Yet, it turned out that only posts advocating one side of the issue would be included, even though the resulting list of links was then touted to people who might be “interested in exploring some ideas about #NoEstimates.” When challenged on this dubious interpretation of the meaning of “exploring”, the advocate then defiantly attached a disclaimer: “Warning! There are no links to “Estimate-driven” posts”.

Advocates can use their own blog for whatever purposes they want, of course. Yet, there’s an interesting split going on here: staunchly claiming to be “exploring”, while rejecting the inclusion of any summarizing or critical posts, and then sneeringly labeling all such posts as “estimate-driven.” There couldn’t be a clearer case study of IT black-and-white-ism, them vs us. Explore all you want, this behavior says, as long as you’re doing it on my side of the issue and on my terms. What, there’s a post that attempts to summarize both sides of the argument? Not interested.

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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?


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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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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Novels of IT, Part 3: Adventures of an IT Leader

My long quest for an insightful, broad, and practically applicable “novel of IT” finally met with resounding success, once I got my hands on the outstanding book that is the subject of this post: Adventures of an IT Leader, by Robert D. Austin, Richard L. Nolan, and Shannon O’Donnell.

To recap: I was looking for a book that was both reasonably engaging as a novel and one that accurately portrayed 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. See my earlier posts on Chris Potts’ FruITion and John Hughes’ Haunting the CEO.  Again, my views aside, I should emphasize that all three of these “novels of IT” are worth reading and forming your own opinion.

Adventures of an IT Leader comes by far the closest to meeting the criteria I had outlined for a “novel of IT.”  It opens with an executive, Jim Barton, being unexpectedly tapped as CIO by the new CEO of his firm, after long and successful stints managing other areas of the company.  In short, Barton isn’t an IT person by training or experience. In fact, one reason for his selection as the new CIO is that he has long been the foremost critic of the IT function at his company. And now, unexpectedly, he has to walk a few miles in IT’s moccasins, so to speak. The novel then follows Barton and his numerous IT challenges and crises for about a year.

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Novels of IT, Part 2: Haunting the CEO

Last time, I introduced this series by pointing out that reading what I call “novels of IT” could serve a few very useful purposes for those of us who work in and around information technology.  In fact, I presented a number of criteria that come to mind when answering the implicit question of why anyone should bother to read a novel of IT.

Ideally, it’s because such novels, at their best, can do the following:

  • provide a degree of engagement and entertainment in making their points
  • provide a realistic insight, in a “show not tell” kind of way, into what motivates the typical players in these business scenarios,
  • help all factions (inside and outside IT) come to see the other side’s perspective and arrive at deeper understandings of common problems and disagreements.
  • allow the CIO to hand the novel to his or her CEO or CFO and trust that everyone’s reading of it will help reach common ground in how to collectively and collaboratively approach the company’s goals.
There are, of course, pitfalls involved in constructing such a novel, the foremost of which is falling into blatant stereotypes: most notably, the nerdy CIO who clings to technology and can’t see a larger role for himself or herself. The book I covered in my first post on IT novels, Chris Potts’ FruITion, not only fell into this trap in spades, but took it to a whole new dimension, painting IT in general as basically no longer needed as a separate discipline, and as having become so trivial as to not need an executive at all.
This time, I’ll discuss John Hughes’ recent and excellent contribution to this genre, Haunting the CEO.

Novels of IT, Part 1: Turtles All The Way Down

Novels are harder than most technology-oriented people typically realize. The backbone of a good novel is character development, meaning that the character learns and grows — which makes it easy for especially amateur novelists to start off with a character who is, frankly, little more than a one-dimensional dolt. This is an even more dangerous pitfall when it’s a “novel of IT”: the temptation is almost unavoidable for the author to create as protagonist a stereotypical technology leader, clueless as to what is really important or how to be effective, who is then gradually enlightened by wiser individuals as the novel progresses.

There are three IT-related novels I’m aware of, all relatively recent, that fall essentially along those lines.

All of them are worth reading, but I had majorly different reactions to each. While I’d intended to cover all three in one blog post, the complexities involved in discussing the first, very problematic example have led me to divide this discussion into more than one post.

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Must-read books on the human factors of IT — part 1, the 70s

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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