Seems like the first thing a new Head of IT does on taking office is outsource an ambitious new technology initiative. Business Reporter’s resident U.S. ‘blogger Keil Hubert suggests that this is a cagey survival strategy for what’s essentially a no-win scenario.
Once you reach the upper ranks in the IT leadership game, CV buzzwords become your very best friend. Many times, buzzwords are your only friend. More often than not, they’re your only reward for your hard work. You come into a mess, you make things marginally better, and you leave a slightly different mess for the next guy. Those CV-bolstering buzzwords are often all that you have to show for your investment, since those same buzzwords are what get you your next job. Not your past titles. Not your education. Not your certifications. Just the nonsense works (like ‘cloud’ and ‘mobile’) that executive head-hunters are actively searching for.
No surprise, then, that one of the first initiatives that a new Head of IT  launches is the implementation of a trendy new product or service. Why? Because the new Head needs an early win – specifically, a ‘paper win.’ That is, the new Head needs to get the trendy industry buzzword on his or her CV quickly in order to remain competitive. It doesn’t actually matter if the company needed the trendy new thing or not; what matters is that the Head gets ‘credit’ for having implementing it. Actual reforms addressing long-term problems have to wait until the new Head has secured his or her escape route for when the job goes sour. Because the job always goes sour.
Here’s the thing: being the Head of IT is a thankless, exhausting, never-ending slog. As the critical intersection between business needs, cost control, and security, the Head of IT’s primary function is to keep all of the crucial senior leaders and stakeholders happy. The problem is, it’s impossible to build a trouble-free information environment … on the cheap … that’s invulnerable to both insider threats and external hackers. Realistically, it’s impossible to build a network with any one of those characteristics, let alone all three. It’s fundamentally impossible for any Head of IT anywhere to build a perfect IT plant. Good? Yes. Acceptable? Absolutely! Satisfying for all stakeholders? Not a chance.
Old-school tech executives secretly dream of creating the ‘perfect network’ and, in doing so, being adored by all the company’s users. The reality is, you rarely get adored (or even liked) for building a network that’s ‘just good enough’ and ‘under budget.’
Understand that taking on a Head of IT role is like shouldering a massive yoke built from years of accumulated resentment, frustration, and failure. Taking the role involves inheriting the blame for all of your predecessor’s failures. The new Head not only has to make his or her own mark, but also has to make up for years of bad blood that saturate institutional memory. That puts the new Head in a precarious position: either dig in and fix the fundamental issues that have made the IT department ineffective or else allow the legacy problems to fester while securing one’s own future survival. There are rarely enough free resources to attack both options simultaneously … which means that option #2 is almost always the option chosen. It’s a matter of pragmatism over professionalism.
For contrast, when I took over as Head of IT for an organisation that had only ever had one Head (for more than a decade!), I inherited a staggering array of legacy gripes and grudges. I’d actually been one of the angry customers under my predecessor’s reign, so I was quite cross with how fouled-up the IT department was. My first objective when I took it over was to get the core functions up to industry standards. Playing against conventional expectations, I put a moratorium on major new technology deployments and focused on comprehensive internal reforms: I implemented new professional performance standards, drafted our pre-ITIL service catalogue, streamlined critical processes and services, replaced under-performing workers, and sent everyone in the IT department to extensive technical training. We kept our focus limited to internal rehabilitation for two years … until the reforms stuck. We waited until we were ready to take on more advanced projects.
So, do I recommend my approach – dedicated comprehensive rehabilitation – over, say, the industry norm of securing one’s own future first? Well, no … If I’m honest, I’d recommend that you follow established conventions. Ensure that you’ll still have a career after your current assignment fizzles out. Make sure that you can still feed your family. Be practical … if you’re compatible with the idea.
By ‘practical,’ I mean following the formula: research hot-and-trendy industry buzzwords, find a gap between what your new company is doing and what the industry is ga-ga over, then outsource an implementation to a disposable third-party. If the project succeeds, you get to take credit for being a bold visionary. Your predecessor didn’t or couldn’t implement [thingy], but you did! So visionary and decisive! Whereas, if your expendable third party fails to deliver the project, that’s okay too. It wasn’t your fault that your outside partner botched the job; your vision was brilliant, but your partner couldn’t pull it off. It still goes on your CV as a ‘win’ which makes you attractive to future suitors.
In Hollywood, no one confuses auditioning for a part to be the same as getting the part. In IT, however, it’s near enough as makes no difference. IT is weird
Let’s be clear: by ‘attractive’ I mean ‘economically competitive.’ When you have some hot-and-trendy buzzwords on your CV, you appear to have what companies want and are willing to pay for. By ‘suitors,’ I mean executive search committees, corporate head-hunters, etc. The people willing and able to give you an office and pay your bills.
Does this mean that you’re essentially taking advantage of your people and your employer? Yes. Yes, of course it does. You’re using your newly-acquired resources to secure your own future economic success (and, maybe, to gain some credibility with upper management) instead of fixing the problems that your new organisation hired you to fix. Hopefully you’ll be able to get around to actually doing your real job once you’ve taken care of your own future needs. If not … well …
This isn’t an IT sector thing. It’s a very old problem that’s rooted in economic and social viability. Consider Marilyn Monroe’s performance in the 1953 musical Gentlemen Prefer Blondes.  The story is straightforward: two ambitious young showgirls pursue romantic relationships; one woman (played by Jane Russell) seeks physically attractive mates while her companion (played by Monroe) exclusively seeks rich mates that will shower her with expensive gifts. The interplay between the two women’s perspectives provides the comedy and the underlying dark theme of the story: is it better women whose beauty, youth, and desirability are ephemeral to spend their limited competitive window opportunity pursuing fleeting satisfaction (that can’t be ‘spent’ later) or else pursue financially exploitative relationships (the spoils of which can be spent later) to ensure self-sufficiency?
Monroe’s musical number – Diamonds are a Girl’s Best Friend – makes her character’s positon clear. She trades intimacy for portable wealth – jewellery, primarily. When she delivers the line ‘Get that ice or else no dice,’ the audience understands that her character views interpersonal relationships as a purely-mercenary transaction. She’s selling what she has (sexual vivaciousness) at a competitive price (jewellery) to secure her economic independence while she’s still able to do so. Russel meanwhile walks away from her own relationships with little more than fond memories. It’s suggested that Russell’s character will be economically ruined if she fails to ensnare a rich partner before her beauty fades. Monroe’s character’s attitude is shockingly cynical … but not necessarily wrong. Even today.
Offered as counterpoint: ‘All true wealth is biological.’ – Lois McMaster Bujold
This analysis isn’t mine, by the way. Back when I was in university, I dated a mathematician who adored musicals and had very strong opinions about the sociology of gender relations. She held up Monroe’s character from GPB as a positive role model. A woman, she argued, must pursue her own economic self-sufficiency above all other considerations. Personal fulfilment, pride, and self-actualization were all nice-to-have goals in her world-view; the acquisition of wealth had to come first. She insisted that her would-be paramours gift her jewellery. No matter how fulfilling our relationship might be, she wanted to be able to walk away from it having made a profit. 
While I objected to her position on principle, I understood her position. Her thinking wasn’t clouded by romantic notions like ‘love conquers all’ or ‘being happy is good enough.’ She was also up-front about her expectations. For our first anniversary, she picked out the most expensive ring that I could afford to buy her on an officer cadet’s meagre stipend. Six months later, she took that ring with her when she left me to take up with an old high school flame.
I see that same sangfroid in many successful IT leaders. Whatever their personal beliefs or principles may be, their ideals take a backseat to cold pragmatism. As soon as these people step into a new Head of IT role, their first major initiative is always to spend their new company’s money on an outsourced trendy-buzzword initiative. That’s their price: whether they actually intend to follow through on their promise to provide good service as Head of IT or not (and most do, I’ve found), that faithful service doesn’t begin until after they’ve secured the résumé fodder that they’ll need to make their next professional jump. Self-before-service as a core principle. I understand.
Why do many IT leaders feel that they have to live this way? Because, to be fair, running IT means that you’re screwed no matter what you do. Fixing an underperforming IT department is a huge undertaking; it consumes all of your time and energy to establish and enforce new performance standards. Bringing a group up to par will yield sustainable long-term results … but they’re usually results that your replacement gets to enjoy. Why? Because all of political capital investment required to fix a broken IT department inevitably causes the team members to resist rehabilitation. Productivity drops as your necessary corrective action inspires resistance, provokes, mistakes, and exposes embarrassing failures. Worse, you can’t purge your troublemakers without airing your department’s dirty laundry (so to speak) with legal, HR, and upper management.
You know you’re making good progress when the mere mention of your name gives your top executives a migraine.
All of that drama in IT slows production down and inflicts discomfort on the other senior leaders They all have their own dramas to worry about; they don’t want yours. Non-IT executives already resent being dependent on IT for their own core processes. They’d prefer that IT be inoffensive. Quiet. Bland, even. A silent utility that doesn’t make waves. When IT starts tearing itself apart (in order to rebuild), that resulting metaphorical sparks make everyone else upset … which often leads to a very short tenure for the new IT guy. I understand that, too. I’ve lived that. Several times.
Therefore, even the most diligent and conscientious Head of IT needs to get his or her own future sorted immediately … before they start trying to pursue any meaningful systemic change. This is why pragmatic IT leaders launch their trendy-buzzword projects first, before taking on legacy problems. Get your metaphorical diamonds up front, as Marilyn might say it. Look out for your own future, because you can’t trust anyone else to. I don’t like it, but I understand it.
That being said, would I – if appointed as a Head of IT again – follow my own advice and do the practical thing rather than the Quixotic principles thing? *£&*$ no!
I understand this strategy. I can even recommend it for other people … people who aren’t like me. That’s because I don’t agree with it. In the same vein, I understood and grudgingly tolerated my uni girlfriend’s mercenary relationship philosophy but I never agreed with her and I wouldn’t treat any partner of mine the way she treated me. Call idealism a character flaw if you like: I don’t mind. I don’t take it as an insult. For me, it’s a defining characteristic borne from ethical principles.
This comes up for me at every senior leader interview. I was a soldier long before I became a Head of IT; When a hiring authority asks me in an interview what my ‘greatest weakness’ is, I don’t have to invent a humble-brag. I know me. My greatest weakness is also one of my greatest strengths: a strong streak of tested idealism. I believe – thanks to the commanders that I served under – that leadership is supposed to be a sacred trust; a leader’s authority is supposed to be used to create a fair, just, and honourable work environment. My primary goal in any leadership position is to optimize the group’s culture straightaway in order to deliver on the group’s assigned mission before taking on any other projects. Make the group worthy of its stakeholders’ and its superiors’ trust and confidence. Glory will come in due course once the group has proven itself. Loyalty to one’s people first, to one’s organisation second, to one’s own career last. Service before self.
My first job as a young squaddie was to carry the wounded to and from ambulances. That was it. No authority, just life-and-death responsibility. It cemented my perspective on what is and isn’t important when it comes to work.
I understand and accept that this approach often means mortgaging one’s future to secure one’s present. I concede that it probably is smarter to grab all you can get for yourself up-front. Smarter .,.. but not morally defensible. If I’m hired to do a job, then I’ll do the damned job. Yes, I realize that I’ll piss off a lot of influential people in the process of getting the organisation fixed. I know that attacking the thorny problems up front will be unpopular. I accept that I’ll run the risk of getting cut loose before I can finish implementing my reforms and that I may wind up with little résumé fodder to show for my efforts. On the other hand, I argue, introducing justice and stability where there wasn’t any before is its own reward … that is, if you have a conscience. I do.
If you prefer metaphorical diamonds over abstract principles, well, suit yourself. You’ll probably be more successful in your career than I’ll be over the same period. Good luck to you, and enjoy your diamonds (metaphorical and otherwise). I’m not trying to smugly insult you; quite the contrary. I appreciate the crap hand that we’ve all been dealt by our industry and how our choice of careers had warped since IT became a thing. When it comes to choosing between feeding your family and satisfying your ego … yeah. Your family should always come first. Needs must when the devil drives.
So, if you’re offered a chance to take over a Head of IT billet, do what you have to and good luck. I may disagree with your choices, but I won’t judge you. I’ve fought enough unwinnable battles to know that a man’s principles make a lousy shield against incoming fire. Secure your diamonds or pursue reform as you see fit. Just be aware that most executives are predisposed to reward blandness and punish boldness. I advocate for bold myself, but I appreciate that it’s a … risky … strategy.
 In large corporations, the ‘Head of IT’ can be the classic Chief Information Officer, Chief Technology Officer, or Chief Information Security Officer. In smaller outfits, the Head can be a Vice President, Director, or even just an IT manager. Title isn’t nearly as important as level of responsibility; the Head of IT is the ultimate top decision maker for his or her company’s technology operations, infrastructure, support, and defence.
 I’m sticking with the movie version here, since the original faux-diary novel treats the characters a bit differently.
 Things did not end well between us. As soon as it became cost-ineffective for her to maintain a long-distance relationship following graduation, she broke things off. While I was deployed to Korea, no less. Not that I didn’t see it coming …
Title Allusion: Anita Loos, Gentlemen Prefer Blondes: The Intimate Diary of a Professional Lady (1925 book); Anita Loos and Joseph Fields, Gentlemen Prefer Blondes (1949 Broadway musical); Anita Loos, Joseph Fielder, and Charles Lederer, Gentlemen Prefer Blondes (1953 film)
Photographs under licence from thinkstockphotos.co.uk, copyright: Surprised cowboy, CREATISTA; doll and dork, Feverpitched; cabaret artiste, Merydolla; woman in red corset, Anetlanda; helicopter evacuation, Stocktrek Images
POC is Keil Hubert, firstname.lastname@example.org
Follow him on Twitter at @keilhubert.
Keil Hubert is a retired U.S. Air Force ‘Cyberspace Operations’ officer, with over ten years of military command experience. He currently consults on business, security and technology issues in Texas. He’s built dot-com start-ups for KPMG Consulting, created an in-house consulting practice for Yahoo!, and helped to launch four small businesses (including his own).
Keil’s experience creating and leading IT teams in the defense, healthcare, media, government and non-profit sectors has afforded him an eclectic perspective on the integration of business needs, technical services and creative employee development… This serves him well as Business Reporter’s resident U.S. blogger.