AMA: Becoming an Executive

Jason asks:

Before asking my question I would like to say thank you for your contributions to the Powershell community. I’ve read several of your books particularly both lunches books and a few of your ebooks. Powershell has had a profound impact on my IT career especially in improving my productivity and effectiveness.
At this midpoint in my career I am evaluating pursuing an MBA. However I don’t want to make the financial and time commitment without a clear idea of how an MBA plays in to a career trajectory that lands at a CTO or equivalent position. What from your experience is required to make that transition executive management.

And here’s the list of everything asked so far. 

First, thank you! Second… I’m not sure how helpful I’ll be, as I’m not an executive myself, but let’s see what we can do.
First, the easiest way to answer this is to go ask an executive or two. Make it clear that you’re open to a very forthright answer from them, and be prepared for that. I find that with a lot of IT people, there can be a lot of personality issues that would keep a CEO from hiring them as a CIO/CTO. I don’t know you personally, but just understand that it might not be an MBA you need.
Also bear in mind that I don’t have a college degree of any kind. That may ultimately stop me from being in the C-suite, but I’ve made it to Vice President, based in part on my experience in running businesses. I was in my 20s when I got my first Director position, and was fortunate enough o work for companies where my leaders took an active interest in teaching me how to run the business. It’s possible an MBA can do something similar; I just have a deep distrust of college degrees in a lot of ways, because I’ve run into so many college-degreed people who couldn’t tell what from what.
Look at job posting sites for people hiring CIOs/CTOs – what are they asking for?
“CIO” and “CTO” aren’t used consistently, but generally, a CIO is the person in charge of the internal technology stuff, while a CTO is in charge of the technology the business sells to other people. That, in my mind, makes CTO a harder job. You’ve got to know a lot about your target market, you need to understand how products-for-sale are built and how they differ from products-for-internal-use, and so on.
I’ve noticed a few characteristics in executives over the years that are pretty constant, and they differ pretty sharply from the rank-and-file attitudes.
Executives are there for the business, which means they care about things like budget, triaging priorities, and so on. They have to make tough decisions that aren’t always popular. They’re not there to be friends, although in the right environment everyone can certainly be friendly. They’re the ones who tell you you’ve got to do X, Y, and Z, and no, you can’t have more headcount or buy expensive tools. Executives answer to their CEO, and to the company’s Board, and ultimately to its shareholders (whether those are public or private). They don’t answer to the team. The ones I’ve known have gotten their jobs by working up: they started as Directors, became a Vice President, and so on. That journey, probably more so than an MBA (the executive I currently work for, for example, does not have an MBA; only a couple of our executives do), is what taught them how to run real-world businesses.
As I’ve moved into senior leadership, I guess the one thing I’ve noticed is that you, and your peers, start making decisions less selfishly. By that, I mean that when I’m confronted with a business decision, sometimes the best decision for the business is one that will negatively impact my team the most. That’s a difficult thing for a lot of people to do, and I frankly suspect it’s at the root of why it can be difficult to move into leadership for many people. As a leader, you can “protect” your people, but you also have to lead them to where the business needs them to be. That can be hard. People can get very emotional when they feel they’re being impacted, or treated unfairly, and so on; you’ve got to have the strength of personality, the empathy, and the business acumen to steer a team through that. At an executive level, even more so. An MBA can help you understand how a business works, but I’m not sure it can create this kind of mental shift or not.
Another challenge I had moving into leadership was to let go. Nobody likes a micromanager, but as a leader, by definition, you’re responsible for outcomes that you often have very little control over. You can’t ride herd on your team all the time, though: you have to trust them to do their jobs and, again, lead, not just manage, to the outcomes you need. For those of us who’ve always had more or less full control over our destinies, relying on a team tome yours happen is kind of a big step. I’m not sure an MBA class teaches this or not, but it’s certainly a big emotional adjustment.
Poking around job listings for CIOs in my area, I’m seeing a lot of “Masters in Computer Science preferred,” but not seeing any specific requests for an MBA. I’m seeing a hell of a lot more soft skills requirements – team building, communications, ROI analysis (heck, maybe a CBAP would be better than an MBA), that kind of thing. Business-y stuff. This is pretty typical:

EDUCATION Requires a Bachelor’s or Master’s degree in Computer Science, Management / Computer Information Systems or a closely related field. A Master’s degree in Computer Science, Computer or Management Information Systems (MIS), Engineering, or a closely related field may be substituted for up two (2) years of the experience requirement.
EXPERIENCE At least twelve (12) years of experience of progressively responsible management roles for a department or enterprise IT environment that includes five (5) years managing a technology team.

I mean, to me, that’s saying, “we’d really rather have the experience, but you can defray that with some degrees if you’ve got ’em.” Progressively responsible is the key – you want to show, as you wrote, a trajectory of increasing responsibilities, which is likely going to mean changing companies a bit to find the next job on your personal ladder.
Hope that helps.

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