The perils of a new CTO position

No matter how experienced or battle-scarred you may be as a senior information technology executive, starting a new IT executive job is laden with not only what are politely called “opportunities”, but also an intoxicating amount of mass euphoria. Here’s what you’re almost invariably walking into, no matter what the company is and what the history has been:

• You’re suddenly the anointed savior of a situation that it seems everyone was frustrated with. Thank God you’re here.
• All the “sins of the past”, however major they are in impact, are (consensus would seem to have it) nonetheless able to be cleaned up (yes, by you), in a jiffy (say within the first three months or so, unless of course you can do it faster). Get to work.
• You’re an “ear”, a new source of hope. People will want to explain things to you so that you “get it” as early and as fully as possible.
• You can’t believe, as you listen to people describe process and products and performance, etc., that things have really been this crazy, this non-standard, this out of norm. It’s great to be somewhere where you can make a quick difference.

It’s a heady time. Not to be macabre, but perhaps you can recapture a dose of humility by recognizing a key and depressing reality: this same euphoria will almost certainly greet your successor, notwithstanding whatever you happen to achieve in your tenure. It’s part of the territory.

So, what to do? Step back, listen carefully to all input, and then proceed to divide and conquer. Recognize that you will never clean up everything all at once, even though everything seems equally urgent. But you’re not new to this game: you know that some things may take a long time before you even can turn your attention to them, and you need to operate in triage mode at all times. To use the hackneyed adage: focus on how to WIN. WIN = What’s Important Now.

All that is no doubt fairly obvious to the seasoned IT executive. Yet, I’ve found myself falling into one of two diametrically opposed and perhaps less obvious traps in these situations. The perils are profuse.

The first trap is to assume that the situations you see (entangled systems, strange processes) are simply crazy and that people had no idea what they were doing. This is sometimes the case, but usually not. As you listen and learn, you often discover that in at least some of the examples, there’s actually a plausible and defensible reason that things were built that way. Things that appear at first glance to be crazy sometimes aren’t.

The second trap is to assume that people (long-standing veterans, key contributors, articulate spokespeople of the status quo) do know what they’re doing. Often they do, but quite often, and with all due respect for these individuals, they really don’t. Sometimes you’ll discover that they’ve been operating without much coaching, without full training or experience, without even a solid definition of success, and that they’re justifiably (and usually fiercely) proud of all they’ve accomplished despite these odds. Things that at first glance appear to make sense sometimes don’t.

All you have to do is figure out which situation is which. Simple, eh? Your closest (perhaps only) friend in this endeavor will be facts. I worked for a while with Jim Barksdale. I still remember him drawling, to a roomful of ornery regional executives for our company, the following: “If we’re going on opinion, then mine is the one that counts. On the other hand, if anyone has any facts, that’s a different story.” You’ll be presented with a lot of opinions during this heady honeymoon period.

Expect people’s expectations to be completely unrealistic. Your job is to play whack-a-mole with those expectations, without coming across as an Eeyore. That tap dance, that balancing act, is by far the most important thing you can do in your first 100 days. Here are some specific approaches you can and should take while juggling:

• Define, publicly, how you intend to measure success, rather than have it be defined for you by instinct, supposition, and that old stalwart, hope.
• Set up incremental, achievable milestones, rather than go for the whole enchilada on your important projects
• Get especially close to IT’s most prominent and/or influential critics in your new company. This is usually sales and marketing, and sometimes customer support. They need the ear, and you will need them as an ally as much as possible.
• You will be pushed (and you will be tempted) to abandon many current projects and start from square one. Sometimes doing so will in fact be appropriate, but keep in mind that you’re thereby eliminating any head start on actual delivery that you may have had. Don’t be rash.

Above all, don’t succumb. Don’t let the euphoria and sense of acclaim cajole you into the dangerous and adjacent emotions of machismo and chutzpah, where you start to believe early on that you’ll be able to accomplish just about anything in six months. It’s highly unlikely that it’s that simple, and you’ll only be hurting yourself by signing up for too much.

But you’re a seasoned professional. You already know that, right?

Lagniappe:

• John Kuypers, What’s Important Now