Keil Hubert: Fear and Loathing in the Boardroom

Keil Hubert: Fear and Loathing in the Boardroom

It’s accepted as general truth that it’s better to say nothing and be thought a fool than open your mouth and thereby remove all doubt. Business Technology’s resident U.S. blogger Keil Hubert turns to an American humourist to help understand why some heads of IT are so prone to making career-ending statements around their superiors.

Fans of Scott Adams’ Dilbert will no doubt be familiar with his character the ‘Pointy-Haired Boss’ (a.k.a. ‘the PHB’). This ignorant buffoon is a go-to source for humour that most everyone working in the IT sector will recognize from their own professional life: the technologically-illiterate person who holds great power over an IT team and who cannot admit that he or she is utterly unfit to make technical decisions. The character works, so much so that he may well be recognized centuries from now as the most recognizable stereotype of an early 21st Century human – the way modern folks imagine that all ancient Greeks must have looked like Jacque-Louis David’s rendition of Socrates.

The PHB resonates for us in the IT trenches because of his propensity to make stunningly-inept decisions about business and tech matters, often motivated by spite because of perceived threats to his authority. Anyone who has led an IT team in a non-tech organisation has experienced this pain. The thing is, this isn’t an IT problem so much as it is a general human behaviour flaw. When threatened, people tend to reflexively lash out. Decisions that appear to be arbitrary, capricious, or even downright spiteful are often motivated by irrational fear. It seems to be more prevenient in IT, though, given the propensity of business leaders to place inept cronies into positions of power over the IT staff.

The idea for this column hit me out of the blue right before Christmas when I was following a link to one of my favourite new humourist’s posts over on cracked.com. Staff huourist C. S. Coville penned a short and snarky article on five authors’ ill-advised marketing stunts that featured this paragraph:

‘It’s not like he was trying to get a deal for a book called… My Life With Bad Impulse Control. If publishers gave out book deals on the basis of who happened to dramatically catch their attention during the working day, you could start a luminous career by simply visiting Random House’s headquarters in New York City and throwing cats at people. And, believe me, that doesn’t work. I know.’

I don’t know if it was just random timing, or possibly my abnormally high level of caffeination at the time, but Ms. Coville’s proposed book title in that passage made me tear up laughing. It also made me think about the many IT heads that I’ve worked for over the years whose biographies absolutely deserved to be titled ‘My Life With Staggeringly Poor Impulse Control.’

'All right, so the lesson to be learned from this experience is ... nothing. Because I'm brilliant and therefore everyting I choose to do will be successful.'
‘All right, so the lesson to be learned from this experience is… nothing. Because I’m brilliant and therefore everything I choose to do will be successful.’

As an aside, Ms. Coville’s regular byline at Cracked is called ‘C. Coville’s Unarmed Unicorn Combat’ (which makes me laugh every time I see it). Coincidentally, I first introduced Business Technology readers to the IT Director that Ms Coville’s column made me think of back in my 50th BT column in May of 2013… titled Left-Handed Unicorns. I don’t think that there’s any connection there, but it made me smile to imagine that we’d both arrived at the same rhetorical device at around the same general time.

Anyway… In my piece on how businesses tend to have unrealistic expectations as to what constitutes a ‘good’ IT leader, I introduced readers to this obliviot:

Back before the bubble burst, I was building a Dot Com outfit in Houston. I got into a nasty scrap one day with the IT director over ‘how many nines’ our department was going to guarantee. When I told her ‘none whatsoever,’ she went berserk. ‘We must,’ she said, ‘deliver either four or five nines of uptime to the business.’ I pointed out that she’d refused my original technical design to run the business with a UNIX solution because she was only ‘comfortable’ using Microsoft Exchange. When she blinked like a dog that had been shown a card trick, I suggested that we’d be lucky to keep downtime under 1-2 days per month. The director threw a public temper tantrum and demanded that we go ‘buy some more nines.’

That particular Bob [1] was notorious around the Dot Com for making spur-of-the-moment pronouncements and decisions that inevitably resulted in disastrous consequences, both for our users and for her own career. Bob was, I believe, the poster child for my argument:

  • She was utterly unqualified to run an IT organization of any size. She lacked both technology knowledge and leadership experience.
  • She held her employees in contempt, despite realizing that they all knew scads more about their areas of responsibility than she did. [2]
  • She wouldn’t accept any technical explanation offered to her by a member of ‘her’ staff, because (we suspected) she thought that we were all lying to her.
  • She honestly believed that she could get away with lying to her bosses indefinitely about systems, capabilities, and accomplishments.
  • Whenever she felt like she was in danger of being caught out for her bad decisions, she either lashed out at her perceived adversary or (more often) viciously blamed anything that might be perceived as wrong her staff.

To her credit, she was entirely predictable. Whenever she was confronted over a technical issue, Director Bob found it was much easier to simply lie her way out of the conversation than it was to simply get the correct information or to reveal an embarrassing truth. She felt threatened, so she made up stories to protect her professional reputation. Her own lack of planning was actually a subordinate’s incompetence, and so on. I believe that behaviour counted as catastrophic impulse control; whenever she was caught off-guard, she simply couldn’t walk away: she was compelled to evade blame on the spot, even when she knew that her evasion might only compound the problem. In the end, Bob would up getting dismissed for cause after she was caught lying to the company’s board of directors about having deployed redundant network circuits that never actually existed.

Here in Texas, we refer to the act of telling someone an outright lie as 'blowing smoke' at them. Director Bob's smoke-blowing antics were truly industrial grade.
Here in Texas, we refer to the act of telling someone an outright lie as ‘blowing smoke’ at them. Director Bob’s smoke-blowing antics were truly industrial grade.

In the broader sense, this sort of irrational decision-making is depressingly common in the tech world. In the majority of businesses where I’ve worked, there’s a distinct line drawn between leadership positions that can be filled by veteran technologists (typically, no higher than a manager or a branch supervisor role) and positions that are filled by political appointees or cronies of upper management (typically director roles and above). [3] This divergence within the organisation leads to a suicidal imbalance: the people that understand what’s happening have no power to influence their fate, and the people with that power don’t understand what’s happening (and, therefore, can’t make effective decisions).

In a mature organisation, this practice is entirely manageable: upper leaders mentor their junior appointees to seek out and value the considered positions of their key staff members. Unqualified heads of IT are conditioned to honestly admit when they’re out of their depth, and to eagerly search out the people who have the answers. They develop trusted advisors within their team to discuss and refine ideas before taking them public. These appointed IT heads refuse to be baited – if they suspect that they don’t have enough facts to make a sound decision, they politely disengage rather than risk making a misstep. We love these sorts of bosses, and will usually be fanatically loyal to them. They are, unfortunately, rather rare…

Contrast that with the typical mid-career appointee: someone that’s eager to reach their next rung on the career ladder. They’re ambitious, but overextended. They view their appointment as head of IT as nothing more than a stepping-stone towards what they really want (usually, that’s the C-suite). Therefore, their strategic objective is usually to take as much credit as possible for the technologists’ accomplishments while obsequiously cozying up to more powerful people, all while trying to distance themselves from blame.

Some of these people can be managed (and even tolerated), so long as they treat their technical staff as allies rather than as adversaries. Truth be told, a decent corporate climber is often indistinguishable from an actual competent technical head to upper management, because their staff arms them up with all the right answers and hip, trendy phrases. When us techs are treated decently, we’re pretty eager to give out bosses the boost that they desire. They get to move up, and we get to get on with things. It’s a fair exchange, so long as we’re treated with respect.

Unfortunately for everyone, it’s the most common sort of appointed IT head that gives the PHB his eternal resonance within the community: the know-nothing/learn-nothing contemptuous git. Dilbert’s unnamed boss and my aforementioned Bob both fall into this category. These are people (only in the strictest sense of the word) that view their staff the way a prison guard views inmates – as dangerous deviants who will shiv them the moment they get the chance. These IT heads know – consciously or unconsciously – they’re out of their depth, and that they don’t measure up. They want to move out of IT before something happens to tarnish their personal brand, but they don’t dare trust anyone to help make a break for it. So, they posture. They make grandiose statements. They over-promise. They flat-out lie when asked a question. Worst of all, they lash out at anyone that dares to challenge them.

I have some small measure of empathy for these folks; I agree that they should never have been placed into a position where they lack the minimum skills needed to succeed. I can understand the dread that they feel about their future, especially given the dismal state of the world economy. My empathy runs out when these folks decide to abuse their people as a means of addressing their situation, however. Burn me when I’m trying to help you, and I won’t make any effort to help you again in the future. That, too, is human nature – the vindictive side of it. Loyalty is earned, not automatic; once you’ve expended it, it doesn’t come back.

Loyalty doesn't come back. Vengeance, on the other hand...
Loyalty doesn’t come back. Vengeance, on the other hand…

Further, this attitude isn’t exclusive to the downtrodden masses in the data centre: executives feel exactly the same way. The suits in upper management are struggling to stay productive just like everyone else in the company. They have objectives and deadlines. They depend on tools, infrastructure, and critical information to get things done. They want to be sure that the IT department has their back. The first time that the head of IT ‘burns’ them, it triggers their vindictive instincts. They can’t afford to suffer betrayers in the ranks, so they too lash out – often catching all of IT in the blast radius.

You’d expect, then, that any IT head who finds him- or herself out of their depth and under pressure to perform would recognize the dark truth of their circumstances and would rationally ally with their critical support personnel for survival’s sake. Most everyone has seen when happens when a mouthy director or VP tries to BS their way through a crisis and gets caught – mayhem ensures. Logically and pragmatically, the overwhelmed head would realize that it’s in their enlightened self-interest to keep their extremities out of all the allegorical bear traps – and the simplest way to achieve that goal is to decline to engage when provoked.

That’s not what people do, though. Some people never learned the fundamentals of impulse control. If you put a biscuit within their reach, they can’t resist the urge to pop it into their mouth. If you ask them a question about how many data circuits or ‘nines’ of uptime they’re providing to the company, they can’t resist the urge to answer. Even when they appreciate that it’s bad for them to do so, they can’t help themselves. They open their mouth. Bad things happen.

It’s a darned shame for the Bobs of this world and for everyone that serves under them. The Bobs are only good for pundits like me and for humourists like Ms Corville in that they give us ridiculous examples to share with the world about what not to do in pursuit of one’s dreams. Speaking only for me, I appreciate having the material… but not having to live through the making of the stories. [4]


[1] For new readers: most all of the anonymized people that appear in my columns are rechristened ‘Bob,’ both for their protection and for fine.

[2] Then again, so did the custodial staff.

[3] I have experienced exceptions to this rule in my working life, and those exceptions have been wonderful. It’s liberating to work for a leadership chain that knows what the heck they’re doing, and also values your contributions.

[4] Speaking of stories, I’m almost finished reading Ms Corville’s new book One Star Reviews. If you’re not up for kicking off the new year with one of my books, then I recommend you consider picking up hers. OSR isn’t exactly IT-related, but it is funny. In our line of work, we all desperately need a laugh.


POC is Keil Hubert, keil.hubert@gmail.com
Follow him on twitter at @keilhubert.
You can buy his books on IT leadership and IT interviewing at the Amazon Kindle Store.

Keil-Hubert-featuredKeil 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 Technology’s resident U.S. blogger.

Keil Hubert

Keil Hubert

POC is Keil Hubert, keil.hubert@gmail.com Follow him on Twitter at @keilhubert. You can buy his books on IT leadership, IT interviewing, horrible bosses and understanding workplace culture at the Amazon Kindle Store. Keil Hubert is the head of Security Training and Awareness for OCC, the world’s largest equity derivatives clearing organization, headquartered in Chicago, Illinois. Prior to joining OCC, Keil has been a U.S. Army medical IT officer, a U.S.A.F. Cyberspace Operations officer, a small businessman, an author, and several different variations of commercial sector IT consultant. Keil deconstructed a cybersecurity breach in his presentation at TEISS 2014, and has served as Business Reporter’s resident U.S. ‘blogger since 2012. His books on applied leadership, business culture, and talent management are available on Amazon.com. Keil is based out of Dallas, Texas.

© Business Reporter 2021

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