Keil Hubert: High Plains Grifter

Keil Hubert: High Plains Grifter

Evil mangers are consistently evil; that’s how they earn the title. Business Technology’s resident U.S. blogger Keil Hubert wonders why otherwise intelligent executives foolishly expect that they can hire evil managers to clean up messy departments and somehow not have their selections turn on them.

Y’all may have noticed that I’m partial to American Western stories. That was probably pretty obvious, since I spent the last three weeks discussing the movie series that helped vault Clint Eastwood to stardom back in the early 1960s. As a sort of postscript to that series, here’s a fun fact: by the time the 1970s rolled around, Eastwood was an established big screen actor. He tried to break out of being typecast as a cowboy with 1971’s police story Dirty Harry, but he didn’t give up on westerns. In 1973, Eastwood directed and stared in a cowboy story with a supernatural bent called High Plains Drifter. The short version of the story is as follows: a frontier town hiding a terrible secret hires a vile stranger to protect them against the imminent return of a trio of vile bandits.

It had been a darned long time since I’d seen the film, but the plot and characters came back to me in a rush while I writing those three consulting columns. Not because the 1973 movie stylistically fit with its Spaghetti Western predecessors (it did!), but because of how closely HPD mirrored a real-world event that I’d gotten involved in that also touched on the topic of working with vile and untrustworthy people in order to mitigate the problem of other vile and untrustworthy people.

The setting for my story was a large government-run industrial complex located on the U.S. Great Plains. I was running IT for one of the large tenants: an outfit with 1,200 workers when running at maximum capacity. The organisation was large enough that it couldn’t all operate out of one office complex, so certain workgroups were scattered across the complex intermixed with other agencies’ workers. Certain specialty shops were isolated a long ways away from the main production arm.

This is actually a lot nicer than the old crap-shack that the group worked out of. Much nicer condition, and a balcony to boot!
This is actually a lot nicer than the old crap-shack that the group worked out of. Much nicer condition, and a balcony to boot!

The organisation’s industrial health group was set off on its own, away from the rest of the outfit. It was also ridiculously small. The section was only authorized three full-time employees and one junior supervisor. Work studies justified the low staffing on the grounds that three people could administer all of the hearing tests, track all of the workplace injuries and pregnancies, test all of the drinking water and so on based on the lazy post-Cold War 1990s standards. Unfortunately, in the post-9/11 environment, the team was inundated with work and couldn’t hope to catch up. Making things worse, the health techs had earned a reputation around the organisation for being annoyingly slow and for making lots of simple mistakes. Records got lost. Appointments weren’t scheduled. Hurt workers were idled, unable to get cleared to return to work. Managers all across the complex were furious with the industrial health people and the wanted Something To Be Done.

The organisation’s Big Boss agreed and decided to impose his will on the underperforming group. He removed the junior Public Health Officer that had been serving as the team’s supervisor, and used a little-known bureaucratic loophole to replace the PHO with a crusty old shop chief. Instead of going for another bright eyed and immature youngster, the Big Boss chose a tough old bird who wasn’t inclined to take any guff from anyone. I heard second-hand that the Big Boss felt strongly that the health techs needed a harsh enforcer to bring them to heel, and that a junior supervisor simply lacked the confidence and forcefulness to effectively clean house.

Honestly, I understood the man’s logic. A strong supervisor who was willing to crack the whip seemed like just the thing to get the errant team back on track. That being said, there were better options… you can be tough and still do things by the book. The crusty old shop chief that the Big Boss picked – let’s call her Bob – wasn’t that sort of leader.

As you’d probably guessed, mean old Bob didn’t actually fix any of the shop’s problems. A year after she started her assignment, the group’s basic processes were still taking too darned long to complete. Paperwork kept getting lost. Managers that depended on the health techs still couldn’t get straight answers. Everyone affected by the group’s recurring performance problems was still ticked off.

The people responsible for keeping workers healthy were significantly increasing the likelihood and severity of bleeding ulcers throughout the management tier.
The people responsible for keeping workers healthy were significantly increasing the likelihood and severity of bleeding ulcers throughout the management tier.

The Big Boss turned to his VP and demanded that things get fixed. The VP called down to Bob and demanded that she get things fixed. Bob, in turn, claimed that she was steadily making progress, and that the workload was simply overwhelming. Cracking the whip wasn’t enough; they had to have more people. Satisfied that that Bob wouldn’t steer him wrong, and confident that Bob was touch enough to solve any problems that were easily solvable, the VP authorized HR to hire Bob a couple of short-term contractors. Bob got her resources… and still nothing changed.

The managers complained once more to the Big Boss, who complained once more to his VP, who complained to Bob in turn. ‘It’s not just a matter of personnel,’ Bob reportedly whinged. ‘The junior contractors aren’t experienced enough, so I have to spend all my time correcting their mistakes. There aren’t enough hours in the day to correct all of the work products. I need more hours.’ The VP thought about it, assumed that Bob was perfectly loyal and therefore wouldn’t lie to him, and asked the Big Boss for extra payroll funds. The Big Boss assumed that his VP knew what he was doing and had done some sort of due diligence. Bob got her hours, and could now work weekends in order to clear her team’s backlog.

It’s important to note that Bob wasn’t an overtime-eligible employee. If she wanted to work ‘extra’ beyond normal banker’s hours, she had to submit a supplemental work request and get pre-authorized for an additional full day’s pay. She was required to work for a minimum of eight hours, and in return would be paid out an additional eight hours of base pay plus some additional dosh for having to travel to and from the office. Bob acted like a holy martyr, grudgingly enduring the new six-day weeks as her painful sacrifice for a noble cause. But did things get fixed? No. Of course they didn’t.

Eventually, the Big Boss got suspicious. He realized that he was pouring payroll into what seemed to be a bottomless pit, and wasn’t seeing any substantive improvements on his investment. This seemed to fly in the face of conventional wisdom; in most of the organisation’s under-staffed shops, throwing more labourers at a problem delivered a commensurate improvement in output. In the case of this one peculiar shop, it seemed like the Big Boss was shoveling pound notes into a locomotive’s furnace without so much as a trace of propulsion.

His next idea was probably to tell everyone to get out and push. Completely missed the plot, that one.
His next idea was probably to tell everyone to get out and push. Completely missed the plot, that one.

The Big Boss wasn’t a fool. One Saturday afternoon, he dropped by the complex to check on his ‘busy’ industrial health supervisor. He brought a photocopy of the supplemental work authorization that he’d signed for Bob to work that day. He pulled up to the clinic and didn’t see any parked cars. He tried all the doors and found them all locked. He peeked in the windows and couldn’t see any lights on. So, he pulled out his mobile and called Bob’s. When she picked up, the Big Boss asked her how things were going at the office. Bob complained that she was just swamped. She claimed that she was slaving away on a mountain of paperwork with no one to help. She was definitely going to need more supplemental pay authorizations if she was ever going to catch up on the backlog…

The Big Boss was furious. After he rang off, his next call was to me. ‘How,’ he asked, ‘can the IT department prove whether or not an employee is physically in the office?’ I asked him to give me an hour to figure it out, and then scrambled my voice and data teams to start gathering evidence. When the Big Boss came to work the following week, he found our written report in a sealed envelope on his desk.

All in all, the data that we presented suggested that if Bob had come to work on Saturday, then she hadn’t logged into the network and hadn’t made or received any phone calls from outside the complex. Since the ‘paperwork’ Bob was supposed to be working on all involved computerized data entry, it was very difficult to believe that she’d been ‘working’ for eight straight hours in the office. Combine that with the facts that her car hadn’t been in the car park, [1] the doors had all been shut and locked, the lights had been off and there had been no signs of movement inside the building, and the only reasonable conclusion that anyone could draw was that Bob hadn’t come to work that day. Circumstantial evidence? Maybe, but there was an awful lot of it.

The Big Boss presented Bob with his findings and gave her a choice: retire on the spot, or face a formal prosecution for fraud. Bob did the sensible thing (for once) and took the clean kill option.

Bob was evil and a bit arrogant, but not stupid. She made a half-hearted effort to weasel out of the consequences, then ejected once it was clear that her usual stunts weren’t going to save her.
Bob was evil and a bit arrogant, but not stupid. She made a half-hearted effort to weasel out of the consequences, then ejected once it was clear that her usual stunts weren’t going to save her.

You’d think that the problem was solved, and now the defection workgroup could get back on track. That would be incorrect. I said that Big Boss wasn’t a fool. Unfortunately, he had some pretty big blind spots that did him in. He made the exact same mistake a second time. After the scandal died down, the Big Boss hired a new junior PHOs to supervise the crew. For reasons that I’ll never understand, the man chose a near duplicate of the recently departed Bob. To make matters worse, he chose a supervisor that Bob herself had mentored. Oy.

As you might expect, this choice also turned out to be a disaster. The ‘new’ supervisor was just as feckless and even more corrupt and useless than crusty old Bob had ever been. The Big Boss wound up leaving a few years later and never managed to solve the problem. All five of his successors tried to solve the problem in the exact same fashion, and they all failed in exactly the same way, for exactly the same reasons: every time they went to ‘clean house,’ they invested their faith, trust and cash into a vile and untrustworthy person, thinking that their choice of bad guy would somehow be loyal to upper management and ‘correct’ the antics of all the other vile and untrustworthy employees in the isolated and unmonitored show. Each of the new Big Bosses were betrayed in turn when their choice for supervisor cheated them… and they absolutely should have seen it coming.

That’s the message that Eastwood was trying to convey in High Plains Drifter: in the movie, the townsfolk had betrayed their sheriff to a group of bandits (who then killed the layman). After that dastardly deed, the townsfolk betrayed the bandits to other laymen. They tried to have it both ways. When it came time for the angry bandits to be released from prison, the townsfolk tried to hire a clearly evil-as-sin wandering gunfighter to protect them from the revenge-seeking bandits. The craven, weak and feckless townsfolk irrationally trusted their mercenary to clean up their mess, and to not betray them afterwards. Things worked out in the film about as well as you’d expect… That is to say not at all.

I think that Clint Eastwood was channeling a universal human problem in this movie. He used a blood-soaked ghost story as a vehicle to explore the idea, and it worked. The fundamental point he was making was and still is fundamentally sound: You cannot effectively solve a rabid dog problem by sending a second pack of rabid dogs after the first pack. That sort of enemy-of-my-enemy logic simply doesn’t freaking work.

Remember: everyone that you work with believes that he or she is the protagonist of an adventure story and that everyone else is just a supporting actor that’s only around to advance their story. Most people can’t accept the idea that other people are just as complex, as motivated, and as complicated as they are.
Remember: everyone that you work with believes that he or she is the protagonist of an adventure story and that everyone else is just a supporting actor that’s only around to advance their story. Most people can’t accept the idea that other people are just as complex, as motivated and as complicated as they are.

That approach only works in fiction because a writer can bend reality to suit the needs of the story. The writer can make all of the baddies perish through contrivance and coincidence, because he or she knows that the audience wants to see the baddies get their comeuppance. That approach doesn’t work in business. If you have a problem with a group of bad employees, putting a different bad employee into a position of power over the malfunctioning group won’t magically fix whatever is broken. The new supervisor will inevitably take advantage of the situation for his or her own personal gain. They may even co-opt the junior troublemakers as allies. The one thing they’re guaranteed not to do, however, is to ever discipline or rehabilitate anyone under them. That sort of conduct runs counter to their essential nature because it’s diametrically opposed to their own self-interest. Real people aren’t self-destructively compliant the way fictional characters so often are.

Clint Eastwood understood that, and told a classic ‘weird west’ ghost story to drive the point home. If you truck with evil men – even in the pursuit of good ends – you’re likely to get yourself burned. The obvious business corollary to take away would be this: If you want to fix broken workgroups, you have to install men and women of character and integrity into leadership positions and then empower them to take all necessary corrective action.

Then again, if you hire men and women of character and integrity at all levels of your organisation, you won’t have broken workgroups to fix in the first place.


[1] There was no public transport onto the complex; everyone had to drive there.

[2] But that’s another story.

Title Allusion: Ernest Tidyman, High Plains Drifter (1973 Film)


POC is Keil Hubert, keil.hubert@gmail.com
Follow him on Twitter at @keilhubert.
You can buy his books on IT leadershipIT interviewing, and Horrible Bosses 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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