Every boss deserves a second chance; some don’t deserve a third chance. Business Technology’s resident U.S. blogger Keil Hubert considers how our idealistic need as leaders to offer redemption to others can bite us in the tail.
How many second chances does a bad boss deserve before you write him or her off as being irredeemable? That’s often a tougher challenge than you’d expect… not because of the mysterious nature of bosses, but because most of us err on the side of granting people unwarranted charity. I’ve found that most people are far too willing to keep affording a crap boss the benefit of the doubt, long past the point where they should have given up and walked away. This is almost always a painful mistake, since a thoroughly crap boss will usually let you know that they’re a crap boss very early on if only you’re paying attention. I admit I can be just as guilty as anyone else of this over-extension of credit. I want people to be decent. I want things to work out for the best. Unfortunately the keyword in ‘irrational optimism’ isn’t ‘optimism’.
I suspect that a great deal of our misplaced charity probably stems from our constant exposure to pop culture stories that are structured around the principles of tolerance, compassion and redemption. Movies and television shows especially drive home the moral message that all men deserved a fair chance to try and change their ways and that even villains may be capable of goodness if only you afford them an opportunity. These are concepts that I struggle to believe in even though the preponderance of evidence suggests that it’s often a doomed effort.
Case in point: a tech sector vice president that we’ll call ‘Mongo’.  Why Mongo instead of our more traditional pseudonym Bob? Because just like the character from Mel Brooks’ classic cowboy movie farce Blazing Saddles, this Mongo was a larger-than-life caricature of a man. He was unyielding, deaf to argument and outrageously destructive. In the movie, Mongo (played by actor Alex Karras) was a dim-witted but immensely strong thug who eventually changes his allegiance from the villain’s side to the hero’s and abandons his evil, destructive ways.
In parallel with the movie, the real-life Mongo was a living legend in his company. He’d held the same senior leadership position in three previous incarnations of the company and had remained in charge of his business unit after each corporate acquisition. Along the way, he’d developed a reputation as an executive wunderkind. During my stint, the man’s name was used as a ward against evil. ‘Mongo wouldn’t like that,’ people whispered, and, ‘Mongo says that we have to get this finished!’ To hear him spoken of, you’d have thought the man was 30 stories tall and belched radioactive flame.
Mongo was so powerful in fact that I didn’t even get to meet him until a month after I joined the company. When I asked for an introduction, I was told that Mongo was just too busy… even though I worked right down the hall from his office. I was told that I’d be awarded the joy of his august presence eventually (assuming I lived a virtuous life and faithfully obeyed all of the man’s unwritten rules).
Hang on a minute… unwritten rules? Yep! I discovered – much to my dismay – that nearly all company policy was based on oral transmission. People avoided written records like the plague. All of the records explaining how the division was structured, what they did, why they did it, how they did it and what their function was supposed to be were years out of date, and were often obsolete.
The department’s strange lack of artifacts made me suspect that Mongo might not be all that he’d been hyped up to be. In my experience, a responsible leader never created mandatory performance expectations that weren’t clearly spelled out and explained. Disseminating critical operational and strategic guidance solely by conversation left the entire organisation vulnerable to compounding errors. Messages would get corrupted in the retelling, or lost entirely. Responsible leaders used verbal guidance to supplement their clear, written guidance.
I asked our department’s senior manager for copies of the Mongo’s strategic plan, performance standards, leadership philosophy and other records that would help me understand his vision and leadership style. My manager laughed and admitted that there weren’t any such artifacts. My co-workers warned me that Holy Bob never wrote such things down; you had to learn his desires through chance personal encounters and post-hoc interpretation. I was aghast – Mongo’s leadership more closely resembled a cult leader than a corporate executive. This revelation was pretty damning.
Nonetheless, I decided to give the fellow the benefit of the doubt. I didn’t want to go into my first encounter with him prematurely prejudiced. Maybe (I mused) the junior employees were simply wrong, and the man’s guidance was being shared directly with his subordinate leaders and staff. Maybe the man’s orders just weren’t trickling down coherently to the line like they should. At least… I hoped that was the case. 
After several weeks, I finally got to meet Bob face to face… sort of. Our team was filing out of a conference room at the conclusion of a work assignments meeting when the hallway door flew open and a very large man stormed in, swaggering like he owned the place. My co-workers swiftly melted away from the fellow like serfs fleeing before a feudal lord. Curious, I stood still and watched.
The large man – Mongo, obviously – went straight for our senior manager and dragged him into our conference room. Ten minutes later, the two of them emerged, and Mongo stormed right back out. Our boss assembled the team and directed several people to stop working on Project X (which he’d just told them during our team meeting was our highest priority), and directed them all to start work on Project Y instead. The workers shrugged, dropped everything and started researching Project Y.
I’ve worked in high-pressure environments. I’m comfortable being told to pivot unexpectedly to respond to an emergency situation.  The way that Mongo burst into the office and demanded immediate change certainly seemed like we were experiencing a crisis situation: his tense body language, his glower, his evident impatience and his sudden change to our team’s work priorities all suggested that one or more of our clients was having a Very Bad Day and that extra resources were required to get something sorted. I figured that we’d deal with Mongo’s emergency, get a post-facto explanation about the crisis and then get back to our regularly-scheduled work.
Later on that afternoon, I asked my boss what the ‘emergency’ had been about. My boss surprised me by saying that there hadn’t been a crisis; Mongo had stormed in to our area to announce an all-new initiative that had occurred to him on his drive in to work. Suddenly and without warning, Project Y was our team’s number one effort… even though Mongo had admonished our boss to finish Project X at all costs right before they both left the office the night before.
That revelation left me cold. Changing an entire team’s priorities in a boss’s prerogative, but it’s usually ill-advised for non-emergency work. The large inter-departmental projects that our group managed didn’t continue to ‘coast’ along when we stopped tending them; they often had dozens of moving parts and dependencies that needed constant (if low-level) attention to keep the project from derailing. I assessed that Mongo either didn’t understand enterprise-level project management, or didn’t care about the damage that he was doing to his own business initiatives. What the hell?
I hoped that the X-to-Y change had been an aberration. It wasn’t. Two days after the sudden reversal, Mongo stormed into our area (again) and interrupted our departmental meeting (again). This time, he didn’t take our senior manager away for a private convo – instead, he publicly demanded to know where we stood on completing Project X. Our boss respectfully reminded Bob that we’d redirected all of our workers off of Project X over to work on Project Y exactly as he’d ordered us to less than 48 hours before. Mongo snapped at him that it was ‘unacceptable’ to have stopped work on Project X. Mongo never acknowledged his own previous orders and didn’t make any effort to de-conflict the two contradictory demands. The team was shocked into silence.
I was horrified. This was the exact opposite of leadership playing out in a public forum. Mongo was proving that he had no idea how to plan, organize, monitor or support project work. Worse, the contempt that he displayed for his critical subordinate leaders completely undermined their authority. Insanely, though, cognitive dissonance kicked in among the junior workers – many of whom started apologizing to me for Mongo’s outlandish behaviour. Several of my peers admitted that Mongo always acted that way, but excused it because ‘he’s under a lot of pressure’.
I left the encounter convinced that Mongo was a dangerous fool. I figured that I’d just have to find ways to avoid him. Then, just like everyone else, doubt started to nibble away at my indignation. What if there were factors in play that I didn’t understand? What if Mongo had privately given our boss some clarifying orders and those orders hadn’t obeyed? Maybe (I thought) I should offer the fellow the benefit of the doubt until I was absolutely sure that I understood the complete context…
You can see where this is going, can’t you?
I finally gave up on trying to find some redeeming good in Mongo after he conclusively proved that he held me, too, in utter contempt. Mongo had placed me in charge of coordinating a huge international interdepartmental project. It was a job that I was eminently qualified to do. The problem wasn’t the job itself; it was how he brought me into it.
Specifically, Mongo called my boss on a Sunday afternoon and ordered him to have me attend a secret meeting of the senior staff first thing on Monday morning. My boss tried explaining that I wasn’t available, and was bluntly overruled. ‘Keil has to be there on Monday,’ Mongo said. So my boss called me on Sunday, woke me up, and ordered me to come in.
Why did my boss have to wake me up in the middle of the afternoon? Because I had just spent the Friday prior undergoing abdominal surgery. I’d suffered a hernia during military service, and it had finally gotten so bad I needed immediate surgery because it was about to become life-threatening. I went under the knife Friday. By late Sunday, I’d only recovered enough to stand unaided for a few minutes at a time. I wasn’t supposed to return to work for at least a week.
My boss told Mongo this. Mongo didn’t care. If I wanted to keep my job (he said) I’d better show up and sit through Mongo’s all-day-long senior leaders’ meeting. No excuses. I wanted to throttle the man. Nonetheless, I needed to keep my job.
I limped slowly into work on Monday. After four hours of sitting vaguely upright listening to pointless management banter, Mongo finally revealed I was going to take over coordinating a critical project effective immediately. A project, I discovered, that Mongo had known about and had been working on for months. Mongo haughtily told me to start drafting the project plan for a mass-termination and off-shoring operation that he’d already committed the company to, but hadn’t (in all that time) bothered to plan.
Maybe it was the pain that kept me silent. Maybe it was the exhaustion. I found that I couldn’t muster the energy to hate Mongo for what he was doing to me or to the 100+ loyal employees that he was about to fire. I saluted, took some notes and limped home at the end of the meeting, absolutely convinced that I was working for a fiend on loan from the seventh ring of hell.
I spent about a year and a half dealing with Mongo. Throughout that period, I constantly struggled to give him a fair hearing. I wanted to find some positive attribute(s) in him that would justify his awful behaviour. I tried to understand the quasi-religious awe that his people held him in. I kept searching, and I just couldn’t find evidence to justify the man’s grossly inflated hype. Mongo treated people horribly, led his operations haphazardly, kept his people in a constant, low-level state of paranoid anxiety, did nothing to grow his subordinates and was constantly angry with everyone. Mongo had the same net effect on office productivity as a blind and random mortar barrage.
What truly killed me though was the cult following that Mongo had in the company. His devotees believed that the man could do no wrong. ‘He’s harsh, but he’s brilliant!’ they crooned. ‘He’s so loyal and kind when nobody’s watching!’ they promised. ‘He cares for all of his people even though he never shows it!’ they whimpered. I eventually attributed all of the man’s appeal to a corrosive cocktail of desperation and Stockholm Syndrome.
The thing is, I knew that I’d worked out Mongo’s number the first time that I met him. Instinct warned me that Mongo was operating way out of his depth as a senior leader and was using overbearing bluster to mask his (conscious or unconscious) sense of inadequacy. By the time Mongo got around to proving just how awful a human being he was, I had no excuse left for not calling a spade a spade. Mongo had never tried to hide who and what he was. He’d been remarkably consistent from our first meeting through to our last.
Mongo also never showed the slightest interest in redemption. He didn’t try to become a better leader or a better person. He didn’t invest in his professional relationships. He didn’t care what people thought or felt about him. To Mongo, his subordinates weren’t even real people; we were just annoying plaything, fit only to be used, abused and discarded.
Take in too much cinema and you’ll start to believe that all people can change. If only a decent person creates the right conditions and offers a bad person who wants to change some support, the bad person will transform over time and through great personal effort into a good person. This a fundamental concept that resonates in religion, philosophy, justice, literature and pop culture. Unfortunately, when we focus on the theoretical possibilities of personal redemption, we blind ourselves to the practical realities of free-will and self-determination.
Put bluntly, fiction is misleading because of its essential nature. When you only have 22, 44 or 90 minutes to tell an entire story, you can’t afford to waste time showing the long, grueling and difficult process that a redeemed character had to go through in order to agree to seek redemption. Instead, we’re shown a brief glimpse of the character in their transitional state, get some spotty exposition regarding their previous state, spend a few tense moments watching others doubt their sincerity and then share a warm moment at the end where the hero’s faith in the former villain is vindicated.
In Blazing Saddles, the hulking Mongo forms a childlike bond with the story’s hero after the hero defeats him. From that point on, he transitions from implacable field to adorable companion. His transformation is so complete that a few lines of dialogue are all that we need to understand that Movie Mongo had completed a complex personal transformation. Personal redemption doesn’t work like that in the real world. It isn’t something that you can decide to do on a whim. It isn’t a guaranteed or fast process. And for men like real-world Mongo, it just isn’t possible.
It’s hard to accept, but some people just can’t be saved… especially someone like Mongo, who occupied the top of his professional pyramid. What possible interest would such a tyrant have in personal transformation when he already had everything that he ever wanted? He had power, dominion, scads of money and free reign to indulge his every whim without suffering any logical consequences. Trying to rehabilitate Mongo was pointless. May as well try and rehabilitate the mountain that he resembled.
I’ve had to learn this lesson many times over because the harsh truth of it conflicts with my leadership ideology. I desperately want to believe that the possibility for redemption exists in all people. Intellectually, I realize that it often isn’t achievable. That conflict between what is and what should be often causes me (and possibly you too) to keep irrationally investing our time, attention and forgiveness in terrible people long after it’s clear that they’re lost causes.
 It was not the case.
 My first professional job was serving as a combat medic in the US Army where the stakes were literally life and death.
Title Allusion: Mel Brooks (et al), Blazing Saddles (1974 Movie)
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 Technology’s resident U.S. blogger.