Good Boss, Bad Boss

Seven executives on the managers that made—or stalled—their careers

“My boss at a consulting company shaped my management philosophies, including ‘Play offense, not defense,’ so we’re forward-thinking and aggressive. Whenever I’m stuck, I remember how he challenged me to shift the rules.”—Charlie Young, president and chief executive officer, ERA Real Estate

“I like to say I received a master’s degree from B.C., which are the initials of the former COO of Starwood Hotels. I replicate many of his habits: I host regular outings at my home for my team and their families, and I hire team members who have very different skill sets from me.”—Hoyt Harper II, senior vice president for global brand management, Sheraton Hotels & Resorts Group

Illustration: Michael Willis

“She was so good that I worked with her twice. She was clear about the problems we had to solve and gave us the license to explore creative solutions. I did some of my best work with her, because she inspired innovation, not demanded it.”—Leslie Dukker Doty, chief marketing officer, Reader’s Digest Association

“I still remember a senior executive at a large bank barking, ‘Think!’ when she didn’t like my work. As a mother, she could have been a role model for young women in the finance industry. Instead, she made me feel unsure of my career.”—Jennifer Fleiss, co-founder, Rent the Runway

“I worked for an architectural firm and was asked to color drawings for clients. My pencil strokes went in all directions. The boss was furious and tore them all up.”—Chris Kormis, associate dean, McDonough School of Business at Georgetown University

“The head of a hedge fund recruited me. When we were negotiating salary, he asked how much of my previous salary I needed, and I answered, ‘Roughly half.’ I expected him to say, ‘That’s silly. You shouldn’t take a 50 percent cut.’ He didn’t—he gave me half. I resented that until I left.”—Douglas Merrill, CEO, ZestFinance

“My team of 20 was reorganized under a leader who knew little about our business and didn’t engage us. Support was never coming, so I learned to tell him what the team needed. It’s a lesson I’ve carried through my career.”—Catherine Courage, senior vice president for customer experience, Citrix Systems

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