Understanding the crazy boss

There is no shortage of crazy bosses, as many in the IT industry will attest. For the majority of IT staffers, however, there’s often a buffer between themselves and that tyrannical CEO or company president: the CIO.

Everyone can likely identify a "crazy" boss—they display severe personality glitches, such as neurotic behavior, an overbearing presence, and peculiar insecurities. They often also have few good management skills.

Yet having a tyrannical boss isn’t all bad, claims Brian Stern, president of Shaker Consulting Group, a management consulting firm in Cleveland. The good news is that CIOs and VPs of technology can actually learn more from a tyrannical boss than from a more rational, sedate executive.

“You learn how to deal with frustration, navigate a war zone, and how to manage upwards,” explains Stern.

That’s partly due to the fact that the crazy boss type is unlikely to change.

“These are people who spent their entire career getting to where they are,” Stern says. “They’re veterans of the career game. They see no reason to change, nor do they feel they have to. Often, their tyrannical behavior helped them get where they are.“

In short, working for a crazy boss—someone who emotionally explodes, yells, makes near-impossible demands, and rarely stops to consider his subordinates' feelings—can offer unique skills-building opportunities. When CIOs work with such a despot, they have to learn to be flexible to deal with the boss's frequent mood changes. Observing the behavior of off-kilter bosses can also boost tech leaders' nontechnical skills, such as diplomacy and salesmanship—skills that can’t be taught in a class or absorbed from a book.

Not all crazy bosses are stupid
While it’s difficult to accept that the crazy boss won’t change, it’s also sometimes hard to not view them as incompetent. It’s an assumption easily made, as these bosses make work life miserable most of the time.

But if it’s any consolation, most tyrannical bosses don’t intentionally cause harm, Stern insists, because they have little self-awareness.

Yet management consultant Harvey Hornstein, author of Brutal Bosses and Their Prey: How to Identify and Overcome Abuse in the Workplace, disagrees with Stern’s contention. Hornstein has identified three species of tyrannical bosses: “The Conqueror,” “The Performer," and “The Manipulator.”

According to Hornstein, Conquerors prey on employees who show signs of weakness. Once these bosses uncover a person’s Achilles' heel, they attack with a vengeance and zoom in on the weakness to create embarrassment and humiliation.

Performers have a penchant for belittling workers, but unlike Conquerors, they undermine employees to mask their own incompetence. Hornstein says attempts to reason with Conquerors will backfire and draw more wrath, as these bosses are known to have uncontrollable temper tantrums. The best defense is to stay out of their way, he adds.

The Manipulators are the smoothest of the tyrannical bosses. These types of bosses are afraid they’ll become less valued if subordinates step into the limelight or receive recognition. They’ll go to any end to retain power—such as stealing someone’s ideas and taking credit. Yet they’ll always appear to be the subordinate’s ally. Hornstein says manipulator bosses can be deadly to a person’s career aspirations within an enterprise.

More categories of crazy bosses
Yet, as other experts point out, Hornstein’s types of tyrannical bosses do not cover all of the varieties. Many are just neurotic, and only a small percentage are psychotic, says Bob Lambert, managing director of technology and venture capital at Christian & Timbers, an executive search firm.

The big issue when dealing with a crazy boss, explains Lambert, is whether a tech leader can effectively work with him or her.

“Tyrannical bosses come in different packages but fall into two categories,” Lambert said. “The first decision is deciding whether there is any chance of coping with the situation.

“The first are hard-nosed, tough, demanding perfectionists who can be hard to work with, but they will listen to reason because they’re all about doing the best job they can,” says Lambert. "These kinds of bosses also know that great people make things happen but can drive tech leaders nuts trying to achieve goals.”

The second type of boss is completely impossible to deal with, says Lambert. “They’re control freaks, unreasonable, and they have a total disregard for the facts. They want things done only their way. There isn’t a whole lot you can do about it.”

What to do if your boss is crazy
Lambert worked for a few CEOs who fall into the second category. He left the firms as soon as he found better opportunities, he recalls. While working beside a lunatic CEO or president is often an intolerable situation, Lambert advises not leaving the job until the right opportunity surfaces.

Stern suggests first trying to tactfully talk to a tyrant CEO or boss. Be aware that this approach can backfire—making extreme care and diplomacy essential, advises the consultant.

“Don’t take an accusatory tone,” he explains. “Instead, put the burden on yourself. Start by presenting the problem and suggesting ways you and the CEO can work together to achieve company goals. Begin with, ‘How can we work together?’”

Lastly, Lambert suggests taking a close look at your relationship with your boss. While a supervisor’s tyrannical behavior is transparent, and although the reasons may be obvious, there could be some responsibility on the subordinate’s end.

“Ask yourself, ‘Is my negative attitude heightening the bad situation?’ and ‘Am I doing everything possible to improve the situation?’ If you’re honest, you may learn something from the exercise, especially if your answers are not what you thought they would be,” says Lambert.

In many cases, the tyrannical boss presents an impossible working situation, and there’s little point in staying if there’s no way to rectify the situation. Stern and Lambert agree that no job is worth tolerating daily misery and angst.