Keil Hubert: Becoming Your Own Worst Enemy

It’s always jarring to learn that the world doesn’t work the way you thought it should. Business Technology’s resident U.S. blogger Keil Hubert relates the tragic tale of an executive who lost his mind over a simple misunderstood process.

One of the difficult aspects of growing up is having one’s illusions shatter – when you discover that most of what your parents had taught you about the world was utter crap. There is no Father Christmas. Your dog didn’t really go to live on a farm in the country after he got sick. There’s no such thing as a ‘permanent’ school record that will follow you your entire life. That was all nonsense designed and delivered to keep you temporarily docile while your beleaguered parents tried to get on with life.

For many kids, the first crack in the theatre façade came when mum and dad’s policy of ‘do unto others as you’d like them to do unto you’ morphed into ‘do what I say, not what I do’. Those first manifestations of hypocrisy from a trusted authority figure can leave life-long scars, thereby instilling in a kid an abiding distrust of other people’s motives.

You might think that these common formative experiences would leave us all a bit jaded and ever-so-slightly paranoid when we grow up and become bankers and bakers and businesspeople. It certainly seems reasonable to believe that the more one sees of the messy and morally ambiguous adult world, the less one would be willing to extend one’s trust to others. Further, because it’s a universal human experience, it should probably be expected that the other people that we meet feel and act exactly the same as us. I’ve met a great many people that fell in line with these expectations. I’ve also met several peculiar people over the years that seemed to be utterly oblivious to the idea that other people might also be as cynically distrustful of them as they are of their people.

Yes, I meant ‘of their people’; the overwhelming majority of such gormless folks that I’ve run into have been senior managers, directors, executives and other well-off decision makers. Somehow, these clueless people tend to rise to the top of immature or troubled organisations. As you’d expect, mayhem usually ensues.

As a practical example, I offer the following anonymized Bob Story: our company had recently lost the executive who managed the business operations support functions (e.g. human resources, the IT department, et al) to an ‘expedited’ early retirement. [1] For reasons beyond my ken, the CEO and the board of directors decided that their best option was to elevate a completely inexperienced division manager up to take over our vacant executive billet – right over the heads of all of his seasoned and better-qualified peers.

The new executive, Bob, initially tried to portray himself as laid-back, warm, and undemanding. ‘I’m one of you,’ he liked to say. ‘I came from the same place, and I know the troubles you’re dealing with. I’ll never abuse you the way the old boss abused us, rest assured!’

‘We’ll all be best friends for ever and ever,’ Bob said. ‘Don’t think of me as your boss; think of me as the chief party planner!'
‘We’ll all be best friends for ever and ever,’ Bob said. ‘Don’t think of me as your boss; think of me as the chief party planner!’


Bob’s honeymoon period went extremely well; the staff took to his laid-back style and devil-may-care approach to administrative activities with a sense of profound relief. It was a delightful respite from the days of brutal micromanagement. For about three months, division staff meetings were carefree gabfests. Morale started to climb. Workers all up and down the division started to relax. Then – as you’d expect in a Bob Story – something odd happened.

During one lazy autumn staff meeting, Bob announced that he’d been given a new paperwork drill to complete from the CEO himself. We – Bob’s managers – all had to generate a report on some silly personnel issue (I’ve forgotten what about). Our reports were due in Bob’s inbox no later than the start of the next week’s meeting. I dutifully wrote the task down, and got it hammered out that evening before I went home.

The next week, as I was getting my coffee brewed before the division staff meeting, Bob called my office and laid into me as soon as I answered. ‘I told you that I needed that personnel report before this week’s meeting,’ Bob hissed. ‘Why didn’t you file your report?’

‘I did, Bob.’ I said. ‘It’s in your inbox.’

‘No, it’s not!’ he growled. ‘I have Outlook open and there’s nothing here from you.’

‘Hmmm,’ I said. ‘I sent it to you a week ago, an hour after you gave us the task …’

I could hear Bob tapping the page down key on his laptop and he tried to scan though all of his unread and unfiled messages. ‘I don’t… you didn’t… oh, wait. There it is. Never mind.’

I’m not about to claim that this was a disillusioning experience for me. Rather, it confirmed what I’d already begun to suspect about the new boss: Bob was a disingenuous fellow. He’d actually needed his reports in two weeks, not in one. He only gave us managers one week to complete them and turn them in. He’d actually programmed time into his schedule to chew out everyone for not meeting his initial deadline. To be clear, Bob expected that most of his people wouldn’t meet his clearly-stated expectations – that’s why he gave himself a week’s grace to police up the reports.

While that behaviour demonstrated an appropriate level of cynicism for a company as poorly run as ours, it showed me more about Bob’s way of thinking than he realized. More important than catching him out as a cynic (to me, anyway) was the fact that I now knew for certain that Bob hadn’t actually read the email that I sent him. He’d had a week from the time I’d sent him his report until he called me to bitch about having not received it. A week. For that entire workweek, Bob had left unread a message from one of his top managers in his inbox without action. He hadn’t skimmed it, hadn’t read it, and hadn’t acted on it. I learned from that experience that Bob was one of those disengaged executives who preferred to ignore the majority of his official correspondence. [2]

‘You cannot seriously expect me to deal with all these messages; I’m an executive now. I shouldn’t have to make hard decisions or understand complicated issues anymore.'
‘You cannot seriously expect me to deal with all these messages; I’m an executive now. I shouldn’t have to make hard decisions or understand complicated issues anymore.’

I’d suspected as much for several weeks prior to this particular event. I’d already submitted several invoices, briefing papers, and read-ahead packages to Bob that he needed to consume in order to make sound decisions. We’d already had a few meetings where I’d wondered if Bob had actually prepared for our discussion or not (clearly, he hadn’t). This taught me that I couldn’t trust Bob to actually comply with our organisation’s policy that all business processing be done through email (rather than through old-school paper forms). Fine. Knowing that mitigated the problem… for me.

The personnel paper mishap caused me to change how I treated Bob. From that point on, I still responded to all of his tasks immediately after his staff meetings… but I also dropped by his office the next day to casually mention that I’d taken care of his previous day’s tasks. That cued him to actually search for my messages and set them aside to add to his other other managers’ submissions later on (when his actual deadline came around).

Per the start of this column, the disillusionment in this story wasn’t mine – it was Bob’s. See, Bob had ‘grown up’ in the company’s management program and had been thoroughly acculturated by it. He expected incompetence from his managers as a matter of course; that was the performance standard that he himself had been held to during his decades supervising a department. Blowing off deadlines was considered normal and acceptable; if you really wanted something from someone, the thinking went, you had to pressure them to comply with your instructions.

Further, Bob thought himself at the time to be a stud-muffin among managers – he knew that he could knock out most admin tasks in an afternoon if he set his mind to them. He figured that his superior management ability justified his rapid ascent to the executive caste; he was awesome, and his peers were all weak, craven, and inept.

Bob wasn’t prepared to deal with a manager who accomplished everything in a fraction of the time that it took him. It shook his worldview. Over the course of his first year on the job, Bob appeared to experience an epiphany: he realized that his managers didn’t actually need a week to accomplish most of his tasks. They could get things finished appropriately in a timely fashion if they wanted to. Bob wasn’t the administrative stud that he thought it was. That shook his confidence something fierce.

As did the time he mixed up the shredder and the fax machine.
As did the time he mixed up the shredder and the fax machine.

It only got worse for Bob from there as Bob began to cultivate grader ambitions. He began to lust after the CEO’s billet, but knew that his political position was precarious, and his staff’s reluctance to exalt him wasn’t helping any. Since the majority of his managers couldn’t be bothered to meet Bob’s deadlines, it must (he mused) be because they secretly wanted Bob to fail. Instead of being a bunch of inadequate fools, his managers were revealed by their inaction to be passive-aggressively ‘sandbagging’ their work specifically to set Bob up to miss his own deadlines – and, therefore, to lose face with the other executives.

It didn’t matter that Bob’s logical conclusions weren’t true. He perceived them to be true, and therefore let his fears warp him. Around six months after the aforementioned incident, it became pretty clear that Bob’s personality had changed. Bob in summer had been cheerful, relatively open, and accommodating of others. By winter, Bob had become slyly paranoid: he’d go to great lengths to avoid sharing information with us managers about what he was up to. He ‘played his cards close to his vest’, in Texan-speak. He grew more and more distrustful of people’s assumed motives. He crew cold and distant to his old friends from his former division. He began to make disparaging remarks about the competence and loyalty of managers that weren’t in the room. He grew shifty and distant. By the end of his first year leading the division, Bob had completely transitioned from a welcome presence in the division to a despised one.

The reality of the situation was more prosaic: the operating culture of the organisation was a ‘blue’ one. Per last week’s column, the company had evolved a culture of accepting non-compliance. Bob’s formative experiences had been accurate: managers weren’t held to account for missing deadline. Executives would bluster, but they weren’t really serious about enforcing their edicts unless and until they called you up to complain. Therefore, when Bob tossed around his assignments, he people treated them the way they’d already treated such work: as something that could be ignored until it was mentioned a second time.

Although Bob couldn’t accept it, his line managers weren’t actually out to undermine his position in the company. Most of them just wanted some relief from the sort of abusive, bullying environment they’d endured before Bob arrived. His subjects tolerated even his misguided ambitions of further ascendance. The line managers and workers were perfectly content to let Bob strut around in his executive digs as a little would-be god-emperor. He wasn’t respected necessarily, but he wasn’t despised either… at least, not at first.

In the end, this Bob’s tale is every bit as pointless and tragic as you’d expect. When Bob’s illusions about how the company really worked shattered, he didn’t grow and mature from learning the unpleasant truth. Like a child who insanely starts to believe that her parents were malevolently abusing her by lying about Father Christmas, Bob insanely began to suspect that all of his critical supporters were secretly plotting against him out of some weird alchemy of spite, jealousy, and schadenfreude.

The sad reality of that office was that no one had the energy to spare for something as petty as spite.
The sad reality of that office was that no one had the energy to spare for something as petty as spite.

Just as a homicidally-deranged tot might try to burn her house down in order to ‘punish’ her Christmas-ruining parents, Bob’s suspicion caused him to destructively overreact to threats that didn’t actually exist at the time. Over the course of the next two years he created the conditions that made his people grow to distrust and despise him, all because he thought that they already did. He squandered a perfectly good opportunity to turn around an inefficient work unit.

The moral of the story, such that there is one, should be this: part of growing up involves discovering that the world doesn’t actually work they way you thought it did. Sometimes that’s because you were lied to, other times it’s because there were factors in play that you couldn’t comprehend or put into context. The wise leader embraces the new information and strives to re-order his worldview to better deal with his environment as it actually exists – not as he’d prefer it to be. A good leader can admit when they’ve made a mistake and move out smartly; a damned fool tries futilely to lash back at the universe for having been more complicated then he’d previously appreciated.

[1] Also known as ‘caught one too many times undermining the CEO’s agenda’, which inevitably became an ‘invitation to pursue other career options’.

[2] Bob never corrected that bad behaviour over the time I knew him.

POC is Keil Hubert,
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, 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 Keil is based out of Dallas, Texas.

© Business Reporter 2021

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