Crazy People: Are You the Bad Boss?

God Bless America, land of hope, promise and opportunity, where anyone can become the CEO of a Fortune 500 company. And that’s just one of the hazards of being a CIO.

A few weeks ago over beer and pretzels (too much beer, perhaps), I found myself sitting among a group of very senior executives from a variety of large companies playing a top-this-one competition of “the worst boss I ever had” stories. The competition raged for hours and careened wildly from the bizarre to the hilarious to the downright scary—like the story one contestant told about an intimate dinner out that he and his wife were treated to, hosted by his boss and his wife, a few weeks after he joined an East Coast consumer products company:

“They asked us to meet them outside the restaurant,” he said. “It was snowing, but we dutifully stood outside and waited for them to finally arrive 15 minutes late. We walked into a very crowded waiting area, whereupon I offered to take the ladies’ coats. The coat rack was jammed full, but I did managed to find one empty hanger and proceeded to hang both coats on it, one over the other. Seeing this, my new boss shouted, ’What the hell do you think you’re doing?’ in a voice so loud it brought all other conversations in the restaurant to an abrupt halt. Striding over and still shouting loudly enough for everyone to hear, he snatched the hanger from my hand and said, ’Don’t you ever hang your wife’s coat over my wife’s coat! Who do you think you are?’ and so on for what seemed like an eternity. Then, he yanked his wife’s coat off the hanger, causing my wife’s coat to fall on the wet floor, took his wife by the arm and stormed out of the restaurant, leaving us to slowly gather our things and slink out. I resigned the following week.”

And there was the one told by a CIO whose boss’s favorite routine was to summon him and others for impromptu meetings and then let them just sit in his office, for as much as an hour sometimes, while he talked on the phone. “It never seemed to embarrass him in the least that most of the conversations (at least the half that I could hear) were complete nonsense—personal calls about golf games and the like. Very late one Friday night, the CFO and I were rushed into his office in time to watch him dial up his real estate agent. After 20 minutes of listening to him negotiate the purchase of vacation property in Santa Barbara, the CFO reached into his pocket, pulled out a cell phone and dialed this guy’s direct number. The phone rang, our boss apologized to his real estate agent as he had to put her on hold, then picked up the ringing line. ’Hello,’ he said, to which the CFO replied, ’I quit,’ then hung up and calmly walked out.”

Refusing to be outdone and with such a rich assortment of possibilities in my own past, I related a bad-boss story from my days as an up-and-coming project manager. Adolph, as he was affectionately known around the office, was a bully of the first order, prone to talking nonstop until he could think of something to say and famous for pulling the wings off interns. In this tortured soul’s special brand of logic, the greater the level of humanity in managing a project, the lower the results and vice versa. In short, Adolph was a jerk. Among those things that he was most proud of, and something he liked to constantly remind us about, was that, because his personal standards of performance were so high, he had never awarded any of his direct reports an “excellent” rating in a performance evaluation. We, not wanting to disappoint him, rose to this challenge by turning in consistently mediocre performances. When Adolph got transferred, we threw the wildest going-away party anyone could remember. Adolph would have loved it, but he wasn’t invited.

So the evening went. And as the stories wore on, I wondered, as I looked around this circle of high-powered whiners, how many of us would eventually become the central characters of bad-boss story contests in the future, or already had?

How is it that everybody (and that’s a big number) has at least one or two bad-boss stories? In spite of the numerical imbalance, bad-boss stories even outnumber bad-coworker stories. Where do bad, nutty bosses come from? How do people this flawed come to positions of such enormous power in large, public, high-profile companies? Most of the really large corporations I’m familiar with have highly structured, aggressive “weeding out” programs that are pretty effective at filtering out the nutballs long before they ever reach the senior levels of the organization and yet, there they are

In my opinion (this is an opinion column after all), bad bosses are not born, they are made. If you leave out the true wackos—ones that, for instance, dispatch underlings to rummage through their competitor’s trash dumpster in the name of consumer protection—and you leave out the job hoppers who leap (or are pushed) from the upper rung of one company to that of another (and another and another), staying just long enough for their incompetence to peek through, you’re left with a collection of otherwise good people who have fallen victim to their insecurities or their ego or both. These people have, essentially, been driven quite nuts either by the pressures of their jobs or by the belief that the loftiness of their positions somehow implies superiority.

For the most part, insecurity comes in two flavors: insecurity about technical skills and insecurity about one’s general qualifications for the job. Concerns about technical skills is a natural worry (as it should be) for CIOs with little technical background to begin with. Even for those of us who came up through the ranks, it’s a constant challenge to keep up, especially when the effort necessarily gets relegated to an after-hours pursuit. The result is that we have to rely more and more on the technoids with the baby faces and poor communication skills. I’m not sure I’d want to order a pizza from some of these kids, but often you just have to hold your breath and hope for the best.

Fear of termination is still the main engine of organizational evolution, even in these heady times. That’s why the other type of insecurity, concern about one’s overall qualifications (and hence longevity), is far more common and insidious among managers of all stripes. Many of the executives I know, myself included, have enjoyed far more career success than they (and their mothers-in-law) could ever have imagined. For some, the altitude is so dizzying that career goals have shifted from climbing to just hanging on. When these people, who are by nature aggressive and tough, go into a bad patch and start to fear they’ll lose everything, it doesn’t make them any nicer.

Ego is a funny thing. On the one hand, it would be impossible for you to be an effective leader without a generous helping of it. On the other, too much (even a little too much) is a nightmare for everyone within the blast zone of your personality and will eventually undermine your effectiveness. Success is a kind of a trap, and after a while, power and influence can make you sour. It doesn’t help that just when you’re at your most successful and at highest risk of a runaway ego, a few well-meaning friends and a thousand not-so-well-meaning hangers-on will line up to tell you what a genius you are. This is thin gruel best set aside.

Big Egos have always been easy to spot in the companies I’ve worked at. Part and parcel to this character flaw is the need to constantly signal one’s importance. For instance, Big Egos do not place there own phone calls; their secretaries do it for them. Once the secretary reaches the person, she says, “Mr. Ego is calling for you. Please hold.” Then Mr. Ego keeps the callee waiting on the line for several minutes before he picks up. This is because executives sold on the notion of their own divinity are fond of manipulating time and its availability as a kind of negative status symbol. They believe that the more time one appears to have, the worse off one appears to be. Through a conspicuous absence of free time, Mr. Ego can signal the value of his time and thus himself. Wasting other people’s time without spending a moment of one’s own clearly establishes the pecking order, and no self-respecting senior executive would be caught dead with a hole in his or her schedule.

Does any of this sound familiar?

So, like it or not, here is some advice for victims of these aforementioned maladies. The rest of you may stop here.

If you wake up tomorrow morning feeling in any way insecure about holding onto your job, for God’s sake, get a grip on yourself! Holding onto your job ought to be the least of your worries. You are in the most highly sought after, highly portable profession in the world in an economy hotter than a check from a B2C startup. Hey, if Adam Sandler can keep getting movie contracts, anybody (especially you) can get a far better job than you’re sweating over today. If you insist on worrying about something, worry about your people and their insecurities. Worry about getting too complacent and timid. Worry about keeping your department excited and inventive. Be bold and, above all, trust.

If you wake up tomorrow morning thinking that, as CIO, you’re the most important IS person in the company, for God’s sake, get over it! You’re not. The most important person in your department at this very moment is the one who’s solving a user’s problem or making sure the network is up or monitoring the batch runs. If tomorrow you and your workstation tech both decide to take the day off, who do you think will be missed the most? In many respects, you are the departmental gopher, the guy or gal charged with keeping the playground clear of obstacles, making sure everyone plays nice and has what they need, and cleaning up the mess afterward. Embrace the bad news and the criticism for their ability to keep you centered and make you better. Disregard the praise, the executive trappings and the superficial friendships. They have a toxic effect on the character and will surely disappear one day without so much as a nod.

Trust me.