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Rock and a hard place: why estimating turns into a squeeze play

I wasn’t ever a very good bridge player, and it’s been decades since I played. Hence, using this analogy may be stretching matters, but as is typical, I took away some key metaphors from my time with the game. One is the squeeze play, where you force your opponent to discard a vital card. It’s similar in a way to what’s called Zugzwang in chess, which describes a situation where one player is put at a disadvantage because he has to make a move, and by doing so (any move, in other words) will force himself into a weaker position.

How does all this relate to CTOs and CIOs? Consider the case of having to estimate how long a specific project will take, particularly early on, usually before any kind of detailed requirements are even remotely fathomed. Note that this kind of estimating is among the most critical activities that you and your organization will do, because it feeds into the organization’s whole prioritization and costing process as a whole. Unfortunately, it gets you into exactly this kind of squeeze situation. If you say a project is going to take what’s considered to be “too long”, you’ll get beaten down about why you can’t do it faster. If you blithely “sign up” for doing it too fast (say, as fast as they want it), there’s a huge risk that you won’t be able to deliver.

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Filed Under: Estimating, Pillars of Purview, Process
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The agony and the agony: firing an employee

This may be the hardest posting to write so far, but it is a necessary bookend to my other recent posts about hiring. It’s hard to write because actually firing anyone is hard: it’s emotional and full of moments of self-doubt, before and after. And I can only scratch the surface of the subject here in a normal-length post.

Terminating people is, of course, a necessary part of any senior manager’s responsibilities, but it never gets easier. It affects people’s lives, families, careers, self-esteem. I’m going to focus here on performance-related terminations, not on general staff layoffs (“RIFs”, or “Reductions in Force”, as they now seem to be universally called). And I won’t be talking too much about the nuts and bolts of how to do it most effectively or kindly; see the Lagniappe section below for some helpful tips from others on that subject.

Donald Trump aside, concluding that you’re going to terminate someone because of his or her performance is never a snap decision (or at least it shouldn’t be). Being a manager is primarily a people job, and people are, well, difficult at times. Technical people may be especially so: extremely bright, specialized, independent, resistant to coaching. Nearly everyone in a technology role has the ability to contribute in some form, otherwise they wouldn’t be in the job in the first place, or (at least) your decision wouldn’t involve quite as much anguish. Determining, conclusively, that the downsides of dealing with a problem employee outweigh the upsides of his or her contribution: that, in my experience, is the tough part.

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Filed Under: People, Pillars of Purview
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A team-oriented approach to making good hires

I made two really bad hiring decisions in a row a few years back, and I have to admit that it shook me for a while. I won’t go into details about why these two hires were horrendous (although I should note that the problem was not because the requisite technical skills were lacking), but the most important thing I can say about them is that both hires happened when, with all good intentions, I departed from the general hiring process and practice that I’ve evolved to over the years.

This process doesn’t always work out exactly as described below, for scheduling reasons, but here’s what I strive for and what I’ve found tends to get great results:

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Filed Under: People, Pillars of Purview, Process
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Hiring and firing: an example of a stellar employee

I plan to make a couple of posts surrounding the very thorny issue of hiring (and firing) IT staff. To start off, here’s a recommendation letter I wrote a couple of years ago, at the request of a former employee. It shows at least one executive’s (i.e., my own) view of what matters in a job candidate most of all, and how certain characteristics can (sometimes, not always) make up for lack of background or experience. I’ll call him Harry. What I sought (and found) in Harry doesn’t necessarily pertain equally to all IT positions, but I offer it for consideration:

I have known Harry for over four years, ever since I hired him into the role of Project Manager at XYZ, where I was the VP of Information Technology.

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Filed Under: People, Pillars of Purview, Top 25 posts
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Career tips for the CTO/CIO path

One of the most frequent questions I’ve gotten after starting this blog pertains to how one can work up to the CTO or CIO role in IT. This isn’t all that easy to answer, other than with some platitudes. Every career is different; every individual takes a separate path. I can’t exactly recommend to people that they take the path that I took, because there were certainly some odd stutter steps and digressions along my route. That said, I do indeed have some biases and thoughts about how a motivated, talented IT professional can position herself or himself for a top management role in IT.

  • Get broad. Strive to understand ALL of IT: development, quality assurance, operations, project management, architecture, user experience, PC help issues. And, of course, there’s no better way to understand those areas than to do some kind of rotation into each and every one of them, formally or informally. Diversify yourself. Doing so fully may require moving companies. One of my favorite Tom Peters’ quotes is “‘Repot’ yourself every ten years.” With respect to high tech, it needs to be more frequently than that.

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Filed Under: People, Role definition, Top 25 posts
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Einstein and the care and feeding of upper management

One area where I feel I’ve learned and grown in my career is achieving a much clearer understanding on how to communicate with upper management. Most advice along these lines tends towards simply warning against overuse of technobabble, and I can’t disagree with that. But there’s a lot more to successful communication than simply that, and I’d like to describe here a few ways to avoid the pitfalls that I’ve seen IT people (including myself) fall into in these situations. None of these ideas is especially new or difficult, but they don’t always seem to come intuitively to IT folks.

When presenting a problem and/or proposal to upper management, keep in mind the following:

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Filed Under: Communication, People
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tanstaafl: An Introduction to IT Portfolio Management

I’ve already written about how the most important task of management is the proper allocation of resources.

By that, I don’t just mean figuring out that Joe and Bob need to work on Project X this week. At a higher, macro level, the issue of resource assignment deals with how the company, as a whole, plans and spawns its suite of projects.

Much of what I’ll have to say in this post will perhaps seem to be intuitive, even obvious. Yet once again, for all its obviousness, it has been astonishingly controversial at many companies. Better said, these concepts seem to be intellectually understood and accepted, yet then resisted, perhaps due to the old adage of “everyone wants to get into heaven, but no one wants to do what it’ll take to get there.”

What does it take to get there, then? You need to plan and schedule projects holistically, not one by one. This approach is commonly known as Project Portfolio Management (PPM), although that term often is used more to describe the aspect of selecting and prioritizing IT Projects based upon corporate strategic and tactical objectives, and then optimizing the whole set to ensure maximum utility. All of that is both valid and critical, of course. I’ll have more to say about project selection criteria later, and in the meantime would point you to some of the references contained in my Lagniappe section.

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Filed Under: Pillars of Purview, Process
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Guest appearance on E-commerce Consulting blog

Sally McKenzie, with whom I worked when I was CTO at Classmates Online, writes a fine e-commerce-oriented blog that I read regularly. So I was especially pleased when Sally asked me to guest-contribute, via a back-and-forth interview format, on the subject of how IT folks and Marketing people can work better together. Not only is this topic especially close to my heart, but Sally’s also one of the sharpest executives I’ve worked with. She especially stands out in her ability to collaborate, forge agreements, and foster teamwork at senior executive levels, so this was a great conversation. Check it out here.

Filed Under: People, Pillars of Purview
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