One CIO’s “lessons learned” in managing others

Here’s a shocker: none of us has failed to fail at times.

We’ve all screwed things up on occasion, and I’m no exception. And that’s especially true when it comes to managing others, which I believe is very much a learned skill. In that spirit, there are a number of things about people management (call them reminders, admonitions, lessons) that I’d especially want to tell my younger self if I had a time machine. Each one arises from a situation where I’ve learned a lesson the hard way over the years, either from mishandling something myself, or from watching a peer, colleague, or my own manager mishandle it.  As the saying goes, “Good judgment comes from experience; experience comes from bad judgment.”

So here are a few things to keep in mind when managing others.  These lessons have arisen from (largely) IT situations, but their scope and impact is hardly limited to IT.  They’ve become a capsule summary of how I want to manage, and how I like to see people around me manage others.  In fact, when I encounter an instance of “bad management”, or think back on my own missteps, I can almost always point to a deficiency in one or more of these specific areas as the underlying root cause.In no particular order:

“ASAP” considered harmful

When do you want it?  “As soon as possible”, comes the ready answer.

Everyone says it. Everyone knows what they mean by it, in essence, and it seems fairly harmless.  But more often than not, I’ve seen it overused as a substitute for real thought and real leadership.

Especially in this new era of “internet time”, the declaration of “I want it ASAP” has often turned into an excuse not to plan, a rejection of due diligence and careful preparation, or even an intentional ignoring of previous lessons learned.  Taken to an extreme, it can represent the triumph of pure testosterone over diligence and caution.

Meg Whitman, former CEO at eBay, writes in her recent book, The Power of Many: Values for Success in Business and in Life about how one positive performance differentiator of individuals at eBay was their sense of urgency.  “eBay never would have prospered as it did without a team with a strong bias for action,” she states.  Having worked in a couple of places that were unnecessarily and infuriatingly slow in their decision-making, I too tend to generally applaud a bias towards action in business.  It reflects a philosophy that an imperfect plan executed right now is usually better than a perfect plan executed next year.  Or, as Seth Godin puts it in his book Linchpin: Are You Indispensable: “Real artists ship.” Or, as a tweet I saw recently had it, “if you’re not embarrassed by the first launch of your product, that means you waited too long.”

However, one can take a bias towards action too far.

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Bears, hedgehogs, and Gladys Knight: parables of IT leadership

For years, I’ve had two framed items hung on my office wall throughout my various stints as CIO, CTO, etc.  I like to think of them, both individually and together, as reflecting certain truths or ironies I encounter as a technology executive, particularly in the realm of leading others.  They serve as cautions to me of leadership potentially gone awry.  So let’s talk about what they show.

The bear and the hedgehogThe bear and the hedgehog: “Vielleicht kannst du auch mal was machen”

The first is a decades-old cartoon taken from a German calendar, preserved from the years I lived in Berlin.
Two animals are playing on a seesaw. One is huge and bear-like, the other a small critter like a hedgehog.  As you’d expect, the bear outweighs the hedgehog, who dangles on the high end of the seesaw. The large one says to the small one, “Now make yourself heavy.”  The little one says “OK”, and voilà: the next panel shows the seesaw reversed, contrary to gravity and logic, where the hedgehog is now outweighing the bear.

The bear says, “You see? It really does work.  Now make yourself light again.” Whereupon the hedgehog quietly retorts, “How about you doing something once in a while?”

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We don’t like that estimate. Change it.

CIO: “We can’t go live in six weeks as you want.  It’s going to take at least three months.”

CEO: “That’s … unacceptable!

One of the most recurring memes in IT, for me, has to be hearing “we don’t like that estimate”, coming from stakeholders, senior management, etc. Depending on the mood and/or semi-intellectual rigor of the person saying it, the conversation then typically devolves into one or more of the following:

  1. identifying and removing any hint of schedule contingency (which is often viewed as padding just to make life easier for IT);
  2. mentioning repeatedly the idea of “what if we double the team size to get it done twice as fast” etc.;
  3. conducting a scrutiny, one by one, of the bottom-up estimates (”it won’t really take three days to test that feature”);
  4. volunteering resources (usually less than qualified) to “help”;
  5. insisting on scheduling full-time work for all remaining weekends and holidays between now and the desired launch;
  6. making frequent use of the phrase “why don’t you just …”
  7. declaring that system delivery must occur by a specific date, no matter what.

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The IT project failure dilemma: how to get early warnings

Thinking about how to prevent big system project failure has somehow always reminded me of the Will Rogers quote: “Don’t gamble; take all your savings and buy some good stock and hold it till it goes up, then sell it. If it don’t go up, don’t buy it.”

In other words, with big projects, by the time you realize it’s failed, it’s pretty much too late.  Let’s think a bit about the reasons why, and what we can do to change that.

First off, I’ve never seen a big project fail specifically because of technology. Ever. And few IT veterans will disagree with me. Instead, failures nearly always go back to poor communication, murky goals, inadequate management, or mismatched expectations.  People issues, in other words.

So much for that admittedly standard observation. But as the old saying goes, “everyone complains about the weather, but no one does anything about it.” What, then, can we actually do to mitigate project failure that occurs because of these commonplace gaps?

Of course, that’s actually a long-running theme of this blog and several other key blogs that cover similar topics. (see my Blogroll to the right of this post). Various “hot stove lessons” have taught most of us the value (indeed, necessity) of fundamental approaches and tools such as basic project management, stakeholder involvement and communication, executive sponsorship, and the like.  Those approaches provide some degree of early warning and an opportunity to regroup; they often prevent relatively minor glitches from escalating into real problems.

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Simple, more practical approaches to actual resource allocation

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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The CIO and the fine art of vendor negotiation

“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 you mean ways to outfox the opposition, or anything else that is best kept secret.  In fact, I’m not a natural avid negotiator. I’m not one of those people who looks forward to buying a new car because of the thrill of haggling with the salesperson.  But I’ve learned over the years how negotiations can best be structured for the optimal outcome.  Like cryptography, where greater obscurity isn’t equivalent to greater security, successful negotiation isn’t dependent on tricks or subterfuge.

I’m quite content to tell any vendor or salesman how I go about negotiating, because doing so doesn’t provide them any kind of advantage.  If anything, it’s beneficial to me and my company that all parties in the negotiation understand clearly the basic principles and approach that I’m using; it cuts a lot of the normal gamesmanship out of the equation.

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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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