Working for a Younger Boss

Can the generation gap be bridged when our jobs depend on it?

By Mary Lou Quinlan
Mary Lou Quinlan
Photograph: Photo courtesy of Mary Lou Quinlan

We’re in This Together

Pat Aylward, 51, an internal communications manager in a Chicago insurance company, is proof that the generations can learn from each other. At 49, after studying communications to move out of her career in human resources, Aylward decided to leave the small firm where she had worked for 18 years. Interviewing for a new job after all that time was nerve-racking. "I hadn’t slept the night before, and I was a zombie just praying to make it through," she says. "When David, who is 17 years younger than I am, casually slid into the chair and politely began asking questions, I was startled. I thought, ‘This guy could be my new boss!’ But he turned out to be smart, genuine, and totally disarming. Later I realized he was struggling with his own insecurities after being plucked from his peer group and promoted."

The two bonded quickly and have worked well together for nearly two years. Aylward attributes their success to their "shared lack of ego and a shared twisted sense of humor. He is generous and courteous in sharing his knowledge," she says, "but he will occasionally ask me how to handle tricky management situations, because of my background in human resources. I’m also amazed that this 33-year-old father of four has his work-life balance issues in good order. At his age, I was still caught up in proving I could conquer Corporate America!"

Are You Sure You Want to Be in Charge?

When I was offered the presidency of the ad agency, I left a job I loved because I wanted to be in a high-status role on my 40th birthday. But in the end, the five years I spent as agency president taught me more about what I didn’t need in my life: sleepless nights, unending pressure, and a daily agenda steeped in everyone else’s problems.

When I finally quit to start my own firm (yes, as the boss, but of a much more manageable and lovable company of my own design), I found joy in molding the job to the woman, instead of the other way around. Now I wonder whether the role of boss is sometimes better suited to the naive but energetic whippersnapper who’s blissfully ready to endure the good, the bad, and the ugly of calling the shots. The more we know about being the boss, the more we need to decide if it’s what we really want.

The whole concept of "the boss" may be overrated and, at this stage of our lives, outdated. When we began our working lives, we imagined the boss as a big, gray-haired, growling guy at a big desk — someone who was part parent, part school principal, part mysterious Oz behind the curtain. Then, as we climbed higher, the big cheese was one of us, a rebel who worked to rewrite the rules of women at the top. Tomorrow, or perhaps at this very moment, the woman settling into the corner office might be someone young enough to be…well, you, back then.

Now that I run my own company, I guess I’ll never know the agony or the ecstasy of working for a younger boss. But often, my clients are younger than I am. I’ve stopped risking the icebreaker of "Oh, did we graduate the same year?" Instead, I’m delighted when I discover that a once-fledgling assistant from a past life has morphed into today’s chief marketing officer, giving me a shot at a big consulting assignment. All I can think is, thank God I was nice to him or her, way back when. You never know who’s going to grow up to be your boss.

Mary Lou Quinlan is appearing in ABD TV’S American Inventor and is the author of Just Ask a Woman: Cracking the Code of What Women Want and How They Buy.

Originally published in MORE magazine, June 2006.

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