Essay: Bad Boss

Dec 27, 2019

He might have been the worst boss I ever had. I’ll call him Roy and he could have been a giftedleader. 


He was smart and experienced and wonderfully funny. But there was a dark side to Roy that emerged after he was hired. He didn’t work very hard and couldn’t deal with problems or conflict. Instead, he’d just leave the building—get in his car and drive around listening to country music. Overwhelmed by his own insecurities, Roy punished the people who worked for him—threatening to replace us, sometimes with himself. “I could do your job,” he said to me which wasn’t true because he would have had to work hard. Yet, on one occasion, when I was feeling misunderstood by the higher-ups, Roy stopped into my office. “Don’t worry,” he said. “They only know the answers.” What he meant was that the higher-ups thought they knew everything. But answers weren’t as valuable as questions and the best questions are asked by people in the trenches, including me. In this moment, I forgave Roy everything. I felt as if he appreciated me even if he couldn’t say so. Astonishing how one generous act can soften the heart. Roy was a bad boss and was finally fired. He could have been so much more.