Being a good boss

Democratic U.S. Senate candidate Cheryle Jackson waits for the start of a debate against Alexi Giannoulias and David Hoffman in the race for the Democratic nomination for U.S. Senate in 2010. (Chris Sweda, Chicago Tribune / October 12, 2009)

Good boss story:

While she was working at National Public Radio, then-CEO Kevin Klose called her into his office. Jackson thought she was going to be fired. Instead, he said he wanted her on his senior management team. But he told her to do some internal politicking first. She needed to win acceptance from those who would soon be her peers before he would promote her.

"He was the first one who showed me how to work internal politics," Jackson said. "He even laid out a plan. He found me a coach from my industry. … He helped me pull together a kitchen cabinet that was external to the organization. And he appointed someone who was very well respected in the newsroom to be my mentor. And he told me, 'This is your mentor. Your success is tied to her success.' ... I think back on that experience. He was so ahead of his time."

Her "good boss" mantra:

"Great bosses are excellent at taking talent and seeing potential in people."

Jason Fried

Co-founder and president, 37signals

Industry: Technology

Bad boss story:

Long before starting one of Chicago's most respected technology companies, Fried was a shoe salesman at a sporting goods store. "I don't remember her name, but she basically completely distrusted me from the start. She'd watch over me while talking to customers. She'd even hide at the end of the aisle and watch me. I could sense in her eyes that she was just shooting laser beams of distrust at me."

Good boss story:

In high school, Fried detailed cars at a Highland Park carwash, where his boss exhibited the opposite behavior. "Everyone in the past was always looking over my shoulder. I felt very watched over, compared with this guy, who, if I made a mistake, he would talk to me, but he operated on the assumption that I was doing it right and not wrong."

His "good boss" mantra:

A boss should trust his employees, a belief Fried has applied at 37signals. "I feel like the more rules there are, the less trust there is. So our employees work whenever and wherever they are most comfortable. At home, at the office, during the day or at night, it doesn't matter as long as they're doing good work. That's how we came to have people in 20 cities around the world working for us. That can only happen if you trust people."

Melissa Harris writes the Chicago Confidential column and can be reached at or 312-222-4582.

Twitter @chiconfidential