Managing Up

10Difficult Bosses

“Happy families are all alike; every unhappy family is unhappy in its own way.”

—Leo Tolstoy, Anna Karenina

If you stay in the workforce long enough, at some point you are going to experience a difficult boss. Because most organizations still promote people based on their technical skills and not their managerial aptitude, you are more likely to experience mediocre or difficult bosses than great bosses. While this is unfortunate, it doesn't have to be the end of the world or a roadblock in your career. Learning to deal with a difficult boss is a great skill to develop. Learning to manage a difficult boss means being able to adapt a strategic perspective. Learning to manage a difficult boss requires you to work a little harder, reflect a little more, and make conscious choices.

Great bosses share lots of similar traits; they are trustworthy, encouraging, empathetic, engaged, supportive, knowledgeable, communicative, fair, respectful, and motivating, just to name a few. They make work rewarding, happy, and positive. We feel engaged and supported. The difficult boss, however, comes in many shades, flavors, and complexities. Most difficult and dysfunctional bosses are composed of multiple personality traits and behaviors, some good, some bad. Your boss may be kind, but controlling. He may be trustworthy, but not very smart. She may be loyal, but nitpicky. He might be motivational, but overbearing. She may be engaged, but not very decisive. He may be super knowledgeable, ...