Skills that have mattered to me as a CTO/CIO

This time on a more personal note: I’ve been reflecting lately about the various specific skills that helped propel me in my career, and how I picked those up. These are mostly metaskills, rather than specific technical capabilities. A number of technologies that I spent a long time becoming expert in are not listed, for example, in the interest of emphasizing the broader lessons, the mindsets, the “core understandings” that have molded my outlook. Are these skills applicable to you and to your path? Only you can be the judge. I offer them up simply as a catalog of things that I feel have boosted my career.

  • Writing. The ability to express one’s thoughts and plans in clear, logical, well-formed language is, I feel, the single most valuable skill to bring to the workplace, particularly in an executive role. Writing is not easy, and the result is by no means always perfect. But this skill is definitely top of the list.

  • Typing. Yes, believe it or not. The skill that I first learned during the summer after sixth grade, following along on my own in the typing course my older sister was taking, has been a surprising boon to me. Later, I honed this skill by necessity, as I jockeyed for mere 15-minute slots of computer time in our school’s computer lab, and I had to maximize my productivity during that time. The result is that I can type far faster than I can write by hand, meaning that thoughts flow out and get captured (and adjusted) far more readily.
  • Assembly language. Bare-metal programming. There’s nothing quite so instructive. I would have little hope of understanding things like network protocols, caching algorithms, and software in general, as deeply as I do, if I had not spent quite so many hours with the PDP-8 and NOVA instruction sets, way way way before the advent of the personal computer.
  • Public speaking. In another life, I was a teacher for several years, but it didn’t come easily. I had to get over the all-consuming sense of nausea that would hit me before (and after) I taught. After years of teaching, though, this “stage fright” phenomenon simply disappeared. Executives need to be able to present. If you don’t feel comfortable talking to groups, I’d recommend that you hone this skill.
  • SQL. I’m not putting specific computer languages on this list, although each language tends to expand one’s mind in a slightly different direction from before. SQL, though, is a non-procedural, data-driven, very different way of thinking, and I believe that it is so crucial to today’s systems that anyone in IT should understand the basics of how it works.
  • Unix piping. It’s not the syntax, it’s not the specific OS, it’s the mindset that matters here: simple, small, single-purpose, independent tools, chained together, creating magic.
  • Also-rans: source code control; object-oriented programming, and (yes, a specific language, the best “Swiss Army chainsaw” around) Perl.

So what skills do I wish I had that I haven’t been able to acquire? A couple of key ones come to mind:

  • Visual thinking. The old cliche about a picture being worth a thousand words? That just doesn’t work for me, although I certainly recognize that I’m in the minority on this one. Give me quality prose over often incomprehensible diagrams any day. But when diagrams and pictures do work, they elicit a kind of startling clarity and focus that I wish came to me more naturally. See the Lagniappe section for a couple of references.
  • Glib persuasiveness. I’m not great at “selling” in situations where I can’t feel a deep personal conviction. I’ve met people over the years whose powers of persuasion stunned me. Without any tinge of prevarication, these people were able to “spin” difficult situations or product aspects into total non-issues. Some call it “selling ice to Eskimos”. Me? At the extreme, it’s kind of like the old joke that HP would tend to market sushi as “cold dead fish”. Some days I feel that I could have worked for HP.


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