Confessions of an IT Director

The “Right” Fit.

IT Executives tend to wear out their welcome after a little while. I’ve explored this before, but the premise is that with a new IT exec, there tend to be massive changes that accompany the arrival of the person. A new system, an implementation, organization, practices, etc… but as time moves on you get a regression toward the mean — or more simply put (in the article) “extreme performance tends to get less extreme the next time” Why is this? SImply put – you run out of projects to do, and eventually you go into maintenance mode. Right or not, the organization judges IT Executives (Directors) on a “What have you done for me lately” style – and so when the changes become less extreme, the (wrong) thought process is that the IT Executive is doing less, and so therefore the organization begins the process of replacing that executive, which starts the whole process over again. The new person will bring with them a stash of projects and ideas that the company will implement out of excitement, and then eventually that person will wear out as well. 

I don’t have any real stats to prove this, but I had a previous IT Director that I reported to once tell me that the lifespan of an IT Director is 3-5 years. I believe it.

Thus – companies are always on this cycle of looking for new IT executives, depending on where on the “bell curve” the current IT executive is in their lifespan. 

In my career I’ve changed jobs a few times for one reason or another. Better opportunities, better pay, closer to home, increase in title, etc. As I reflect on my career journey to this point, I notice that there have been some similarities as to how IT executives, and even standard IT technical people are recruited, but I’m not sure that’s the best way to do it…. And it has to do with the right fit.

Recruiters are usually given a technical “checklist” of attributes that an organization is looking for in a potential new person. If you’re looking for someone who makes a widget, you usually start by listing a request for someone who has that particular “widget-making” experience. The recruiter very often has no idea what it takes to make said widget, only that the candidate has to meet the “widget-making” requirement on the checklist before the candidate would even be admitted to a hiring manager. 

In the IT world, I find that this backfires quite often. I had a recruiter once tell me, “it sounds like you really know your stuff, but this client is looking for someone with RDP experience, and you don’t have that on your resume.” After assuring the recruiter that I was quite proficient in RDP, he then asked that I revamp my resume to mention it a few times so that the hiring manager can see it. So I did… uneasily, but I did.

This began a snowball effect in my mind about how to go about looking for a job. Does one make a specific resume that hits specific listed points so that you can get through the door? I suppose that’s the way to play the game, but I can’t help but think that organizations are short-changing themselves out of perfectly viable and perhaps better candidates by insisting they have arbitrary attributes that some job description has listed, versus gauging a technical candidate on their intangibles? Is too much importance put on specific acumen as opposed to how a particular person reacts, handles, or adapts to a situation? Can a weighted system where a technical baseline is pitted against a candidates intangibles make for a better choice in candidate?

I had a job interview for an organization once where the “wrong” answer on a technical question cost me the ability to procure the job. I had gotten along swimmingly in my initial video interview with the panel, and all looked very good for a second interview. The premise of this particular job was that this IT Executive was to bring management of IT resources in-house. Things looked good. It was for an exciting, well funded company, and the benefits were great. There was no current executive, but the firm had been using a consultancy to manage their IT needs.

Therein lay the problem. During the second interview, the firm asked the consultant to ask technical questions. Besides the fact that it was a conflict of interest (why would the consultant sign off on a candidate that would potentially lower the consultant’s footprint in the organization), I couldn’t remember an oddly specific question about a feature of Microsoft Exchange. I answered the question, with the caveat that I’d have to look it up (trying to prove that I have the resources necessary to adapt and find the answers that I didn’t know off the top of my head) but it was too late. The nail was in the coffin, and they didn’t hire me, despite the recruiter telling me that I was their first choice. 

Conversely, I worked for another organization that had me interview with a technical person, but then with a non-technical person for “mission fit.” I thought this was a pretty smart approach. There were no “gotchas” in the technical interview, only an establishing of a baseline to prove that I could handle the level of technology that I’d be managing at that organization, and then I was passed on to another executive to determine if I was a “mission fit” (also referred to as “cultural fit”) to the organization. 

The interview went well, and at the end when I was asked if I had any questions, I inquired about the “mission/cultural fit” interview as I hadn’t been part of that to that point in my career. The person I interviewed with told me, “the tangible, we can teach, but we want to make sure you have the intangible.”  

Somewhat recently, I had met with another organization who was looking for an IT executive. After a couple minutes, I could tell that they didn’t really know what they were looking for. There was someone in that role before, they had left, and for 8 months the role was vacant. They quizzed me incessantly about their particular ERP, the different applications they used, everything from their hardware purchases to data consolidation to worldwide collaboration between different ROBOs (remote office branch offices). I flew through everything, not hiccuping once, answering all their questions. I explained that someone to keep up the status-quo wasn’t exactly what the organization needed, and explained my spiel about bridging the gap between the organization and IT, aligning the business priorities with IT, and helping drive top-line revenue. Same story, the recruiter told me I was far and away their first choice. 

I didn’t get the position. “The other person was a better fit,” the recruiter told me. 

Now, giving that organization the benefit of the doubt, maybe the other candidate did blow them away. Maybe they were charismatic, knowledgeable, and motivated. More likely, they probably fit within their budget better, but it doesn’t change my point. There’s a vicious cycle where a request for an IT executive is put out by an organization that really isn’t sure what they need, but rather, are choosing an IT executive based on a checklist that someone, somewhere put together. A few years later frustration grows (due to regression towards the mean), the IT department is looked at as a cost center that needs to be reduced (instead of helping drive top-line growth), and the IT executive is replaced, with the company looking again for someone with (likely) the same checklist for “skills” that will get the next person through the door. Wash, rinse, repeat.

This is why it’s so important for IT leaders, executives, and directors to change the conversation. To help organizations understand that the intangible is much more important than the tangible. It doesn’t matter how proficient your candidate is in your particular ERP system, if they can’t align themselves with the overall direction of the organization and adapt to help the organization grow. “We all wear different hats” is a common phrase (especially where I work). Organizations need to look for the person who can change hats quickly and wear lots of them, not the person who has a specific set of hats. 

When you’re looking for “the right fit”, you need to be looking for someone who can buy in and further the goals of the company. Someone who is hungry and eager to prove their worth through their intangible skills is much more valuable than that person who has worked with all the technologies you’ve put on your candidate checklist. 

One thought on “The “Right” Fit.”

  1. Excellent topic Brigham. Companies rarely know what they’re looking for – at least in the introductory part of bringing someone on board.
    When I was working on switching careers and just trying to get my foot in the door SOMEWHERE in the IT industry, my first phone screen was with a company HR recruiter who asked about my experience. I had none. When I mentioned that I could set up an in-home wireless network, he got all excited and I immediately knew I’d stumbled onto one of his check boxes. The kicker? I did get the job, turns out it was in an environment where wi-fi wasn’t even allowed to be used. Turns out, I did well there anyway because of my ability to wear a bunch of different hats, even if they didn’t fit at the time I had to wear them.


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