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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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, 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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“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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Mending Wall: Matches and mismatches in IT stakeholder expectations

Oil and water? Some days, the disconnect between stakeholder expectations and IT capabilities (and sensibilities) seems staggering.

Case in point: I was shown an astounding list of generic stakeholder expectations a while back, drawn up by an obviously frustrated group and titled “USER REQUIREMENTS FOR IT”.  The list is most interesting in what the items reveal between the lines. Let’s examine what probably caused this group to write down these specific but very abstract needs.

User requirements for IT

  • Must be adaptable to business situation
  • Must be able to employ multiple SDLC (Software Development Lifecycle) techniques as the situation dictates
  • Must be able to work in a highly parallized (sic!) environment
  • Must be able to accept and adapt to last minute scope
  • Should have multiple channels for functionality development both in terms of large releases and off cycle enhancements that occur in parallel.
  • Must provide the ability to externalize functionality to external teams to quickly develop new functionality
To most IT professionals, these come off as “unreasonable” demands at first examination. But they’re both understandable and revealing, if you take the stakeholder point of view, and if you remember the oft-cited adage that all progress depends on the unreasonable man.

Yes we can, yes we must: the ongoing case for IT/Business alignment

How do we (IT executives) get away from being typecast as technologists, unconsulted on core business issues and approaches? Face it, that’s a common situation and dilemma that we all encounter, early and often, and it’s the grist for a constant mill of articles and blog posts and books on business/IT alignment.

Lately, though, a part of that mill has started insisting that focus on technology should be avoided altogether by what they usually cast as the “next generation” of CIO.  So I’m going to (again) be a bit of a contrarian here: it’s possible for the pendulum to swing too far in the wrong direction. I think that we can at times go overboard in our desire to avoid being seen as the geek with the pocket protector.  Examples: some preach outright denial that there might be such a perception problem: don’t even think of using the terms “IT” and “business”, they urge, and they recommend against ever discussing “alignment” as a goal.  Stop referring to the “business” as something separate, they recommend; IT is just as much part of the business as anything else! Similarly, their advice is “avoid discussing the technology itself.” As if a mere shift in language could solve the perception problem and automatically propel the CIO into the inner circle of decision-makers.

Here’s the gist of how I see it, though: in many (I daresay most) companies, the path of IT from high priesthood to strategic key playerdom has not really been fully traversed: in other words, greater alignment IS still needed of IT with “the business.”

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

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 in order to provide input and executive-level decision participation, but left it to the director to actually run the meeting and present the topics.

Unfortunately, immediately before one of these weekly meetings, that director was given bad news (in a brief hallway conversation, no less) about a major bug that had just been discovered in the software for our highest profile project, which was currently in testing and due to launch in just a couple of weeks.  This project, with its strategic and revenue-enhancing potential, was foremost in the minds of everyone in the company.  Stakes were high, in other words.

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Conventional wisdom that fails for IT

I’ve done several posts featuring what I call “Peterisms”, which are basically aphorisms I’ve adopted that encapsulate hard-earned IT lessons. Let’s turn it around this time, and talk about two sayings that sound equally folksy-sensible, and that I hear again and again, but which I feel are actually dangerous to apply to information technology work. And, of course, I’ll discuss why that’s so.

  • If it ain’t broke, don’t fix it
I know of very few aphorisms that tend to be repeated as smugly as this one, particularly by scared people. The implication is that action is generally to be avoided, that the status quo is probably just fine, and that one should wait for a true crisis before intervening. And, of course, that it’s your fault if you’ve ignored this sage advice and intervened anyway. It’s ironic, then, how IT departments themselves end up complaining endlessly about how they’re always in fire-fighting mode.  This prevailing attitude evolves among (and is a telling symptom of) burned-out sysadmins and developers, especially those who are stuck maintaining systems they didn’t themselves write or engineer. It can be equally summed up as a “don’t touch it, don’t breathe on it” kind of superstition. Or, perhaps, it’s akin to the proud but defensive statement that “we’ve always done it that way.”
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The Practical CIO: Difficulties in project prioritization & selection, part 2

OK, let’s assume you’ve gotten great at picking the right projects to do to benefit the company. How do you know you can actually accomplish the ones you’ve picked with the resources you have? If you’re like most companies I’ve seen, it’s done on a wing and a prayer. But there’s a better way.

Last time, I wrote about ways to pick projects that satisfy the company’s “SHOULD do” dimension: ones that are strategic, financially beneficial, risk mitigating, or legally mandated, for example. I set out practical guidelines for the process of selection in that dimension, to ensure as level a playing field as is possible.  And I left it for this follow-on post to discuss the other dimension, the “CAN do” dimension, which needs to calibrate the list of chosen projects to what can actually be accomplished by the available resources.

Both dimensions inform each other, of course; they’re not independent or sequential. In other words, the company might be able to tackle five smaller projects rather than one huge project, and figuring out if it’s a good idea to actually make that trade-off will be based on executive judgment of the benefits in both scenarios.
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