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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IT does the moonwalk: our endless search for absolutes

Scene: I was CTO at a high-traffic social networking site, circa ten years ago. It was one of those times when our site got crushed by unexpected sudden volume, due to being mentioned in an article in a prominent newspaper. My infrastructure manager walked into my office the next morning, ashen-faced. “We’re gonna get killed tomorrow unless we add ten front-end servers to our prod environment,” he proclaimed. A fairly common IT reaction: absolute, adamant, ominous.

Ten new servers? That was a nice round pulled-from-thin-air number, obviously, and by the time we talked through it, we actually found other, more practical, more feasible ways first to estimate and then handle the increased load. But to the infrastructure guy as he walked in, the situation was both dire and absolute, and he saw only one solution that should even be considered.

So now let’s look at another data point on IT psychology. Take the latest iPhone brouhaha: the quick “cracking” of the iPhone 5s Touch ID fingerprint scanning technology.  Amazingly, Touch ID has turned out to be less than perfect. Someone with $1,000 of equipment, plus lots of time, motivation, and patience, could conceivably fool the scanner. Meanwhile, what gets lost in the outrage over this turn of events is the notion that the technology might indeed be “good enough”, or “better than the alternative”. We forget the simple fact that the technology is primarily oriented to people who currently don’t use passcodes at all, and that it vastly improves general security for those sorts of users.  As one article pointed out, “The point of any security system isn’t to be unbreakable – there’s no such thing – but to be fit for purpose.”

My larger point: if there’s a problem or a difficulty or even a nuance to a particular approach’s applicability, a common IT practitioner’s instant reaction is that the approach or practice is absolute junk and should be completely avoided.

Similarly, we often reject fundamental improvements to a situation, simply because they are not perfect. We let “best get in the way of better.” On this general theme, an amusing tweet crossed my screen the other day. @rands wrote, “I find when an engineer says, ‘Less than ideal’, they often mean ‘Complete fucking catastrophe.’”  I laughed at this, of course, but partly because I’ve more often experienced that scenario in reverse: an engineer deciding, and then loudly and profanely proclaiming, that a situation was nothing short of a complete disaster, simply because it was less than ideal.

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Starting points for the quantitative CIO: downloadable basic tools

Much as in any field, IT executives constantly have to seek a balance between idealism and pragmatism. Given a particular problem and the range of possible solutions, do we insist on “doing it right”, or do we buckle down and “just get it done”, even with gaps?

There’s obviously no single right answer, which is what makes IT consistently so fun and frustrating at the same time. Over time, though, my own approach has typically been to focus on the continuous improvement aspect of “doing it right”: whenever possible, get something going as a start, then hone it over time as you learn more about the problem and your situation.

Using spreadsheets as a management tool definitely falls on the “just get it done” side of this spectrum of approaches. Spreadsheets are seductively easy, omnipresent, and usable by people with a variety of skill sets and technical savvy.

But there’s a host of downsides: spreadsheets are frail creatures. Errors can creep in fairly easily, even for experienced users, as data and circumstances change, and spreadsheets are especially prone to the incursion of silent errors and omissions when undergoing revision.  And once implemented, in all their imperfection, spreadsheet-based solutions can broaden and become large-scale, long-term systems (I’ve seen this happen again and again).

Yet, I feel that every technology executive should be maximally fluent in spreadsheeting: simple tracking, analyzing, modeling alternatives, understanding costs and risks. The technology provides a readily available, easy way to knock out quick and dirty models that can clarify one’s thinking and approach enormously. They work well, as long as you keep in mind that the spreadsheet is usually a stop-gap, for those times when you are faced with a glaring need and you don’t have time, budget, or staff to implement anything deeper right away.

In an early blog post, I listed the seven areas where a quantitative approach is especially necessary for the technology executive:

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CMOs outspending CIOs on technology: “so what?” Here’s what.

Rarely do I write targeted responses to specific blog posts, but last week, an article crossed my screen that I think is both representative of many people’s attitudes, and enormously flawed in its assumptions, logic, and conclusions. Esmeralda Swartz, writing for ReadWrite.com, titularly opines the following: “So What If Chief Marketing Officers Outspend CIOs On Enterprise Tech?” Even more grandiosely, the post’s subtitle is “Isn’t it possible that a technology buying process driven by marketers instead of technologists will make things better?

Well, I suppose I should allow that anything might be possible, but no, not by the unconvincing (yet not atypical) line of argument Swartz pursues, and not when you consider standard business realities. Here are a few representative quotes related to the backbone of her argument, namely that buying technology is like buying a new car:

  • “Let’s look at an everyday example. Prior to investing large sums of money in a new car, few people feel the need to master the inner workings of the internal combustion engine. “
  • “Despite all this blindness, for the most part, what we buy doesn’t let us down.”
  • “Ultimately, we’ve got a problem that buying a car solves, so we buy a car.”
  • “Buying software – wait for it – simply because it threatened to get the job done – will likely ruffle some feathers.”

Here’s the thing, though. IT systems are not cars. 

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IT conferences for the CIO: microcosms of industry trends

I’m back from attending ServiceNow’s Knowledge13 conference last month in Las Vegas, and have a grab bag of random thoughts and reactions to share as a result. As usual, these thoughts reach beyond any particular vendor or product niche.

For anyone not familiar with this company, ServiceNow is slowly and steadily developing a generalized platform (“ERP for IT”) for enterprise IT management, all the way from IT service management (ITSM) to (now, in a new offering) cloud orchestration and management of instances.

My attendance last year at this same conference broke a personal streak of almost 8 years of avoiding conferences altogether. My recap post from last year discusses how I discovered what I’d been missing: exposure to new approaches, new energy, and new perspectives that, like it or not, don’t just come from online.

In fact, it reminds me of the classic Woody Allen line about “I need the eggs”. Conferences are messy, chaotic, overwhelming, sipping from a firehose, and so on. But we keep going, because we need those eggs.

Here are some “eggs,” large and small, that I took away from this year’s experience.

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CDO: The Chief Déjà Vu Officer

Whac-a-mole. It’s my favorite of all metaphors, at least when it comes to applicability to IT. For those who don’t know the background: Whac-a-mole  is a commonly seen arcade game, where plastic moles pop up at random through holes in the game panel. The job of the player, of course, is to pound them down again with a mallet, accumulating points with each kinetic, mind-clearing, vigorous whack. And, of course, the game keeps speeding up. The moles never stop coming.

Any readers who don’t instantly get the clear analogy to IT are probably reading the wrong blog.

A career spent in IT feels like a constant bout of Whac-a-mole. But here, again, is one key recurring “mole” that I find especially irritating: the proliferation, against all logic, of articles and tweets about the demise of IT, the death of the CIO, and how technology is now so easy, so omnipresent, that experts are no longer required.

I wrote about this ever-repeated meme a year ago in a post titled “IT consumerization, the cloud, and the alleged death of the CIO”.  I railed against the meme, pointing out that “this frequent linking of cloud and IT consumerization to the looming demise of the CIO and IT is not just misguided, but actually gets it completely backwards. In fact, I argue that IT consumerization and the cloud will actually elevate the importance of IT within a company, as both a service and a strategic focus.

But IT moribundity is a meme that somehow refuses to, uh, die.

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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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