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

The worst part for Weal was being perceived as "the dinosaur, who couldn’t relate to anything they were going through because I was so old," she says. Weal left that job after three months and, rather than risk a repeat situation, she started her own virtual assistant business. "Given a choice," she says, "I would not work for a younger boss again or work where I was the only baby boomer. Now thatI’m in the second half of my life, if I’m going to struggle to make ends meet, I’d rather work for myself, especially when I realize that I have shoes older than my former supervisors."

Youth — or Inexperience?

A close friend of mine who’s 53 and lives in San Diego, California, just survived a four-month nightmare as president of a startup where the CEO was 15 years younger than she. She’s still feeling the scars. And I’m feeling guilty I didn’t talk her out of taking the job, since I could have predicted what happened. When her recruiter called for a reference, she kept pressing me on whether I thought my friend could handle working for a younger, less experienced guy. I answered, "She’ll be a good mentor to him if he respects what she knows and listens." Silence on the other end of the line. I guess the writing was on the wall.

Because the job offer was her first presidency after many years as a senior vice president, and because the CEO came across as a charming, willing partner, my friend accepted the job. But his immaturity quickly revealed itself through emotional outbursts in the office. Worse, he was paralyzed by decision making, fatal in a fast-paced startup. "Until I worked for him, I didn’t realize that he wasn’t fully formed as an adult or as a leader," she says. "He was wasting valuable time developing his decision-making skills in an environment that screamed for action."

Realizing her mistake, she tried to quit at the end of her first week. He promised he’d listen more and convinced her to stay, only to fire her four months later. My friend believes she made two critical mistakes. "I should have approached the job with my eyes wide open, knowing that while he had a lot of charisma, he really didn’t have the experience," she says. Her other mistake was not fighting for equal footing with the board of directors, as a hedge against his inexperience and to protect herself. "Next time I’ll make sure there’s a management structure in place that allows for true partnership, no matter what the age gap," she says.

Thanks to smart financial negotiations up front, my friend is solidly set, and she has returned to the consulting practice she had set aside to go after the senior title she had craved.

Not Just a New Generation, But a Different One

Lynne C. Lancaster, 48, is the cofounder of BridgeWorks, a Sonoma, California-based consulting practice dedicated to bridging the generation gap in the workplace and marketplace. One reason that boomer/Gen X work relationships fail, she says, is that a younger boss may seem to be interested only in what’s next and not want to know what’s gone before. This bugs older staffers who’ve worked hard to make the business successful.

The hallway management style of a Gen X boss ("Hey, can you redo that report and zap it to me?") can come off as too flip or informal to someone raised on sit-down meetings and prepared appraisals. But style is just style. "It’s all about the person," Lancaster says. "Ask yourself, ‘Is this the kind of person I want to work with, who has the integrity and skills to be a good boss?’"

And don’t forget that, thanks to the next generation with their stronger priorities for family and personal time, the workplace is actually starting to adopt some of the flexibility we’ve craved all along. "Midlife women grew up with 80 million of us competing for the same jobs," Lancaster says, "so we focused on playing by the rules to keep the jobs we had snagged. With just 46 million Gen Xers in the workplace, they can afford to be more demanding."

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