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 Generation Gap

You head to work on a Monday morning knowing you’re about to meet the new boss. Is your stomach doing flip-flops? No? What about learning that your new boss is named Heather and that she is barely 30? Welcome to the brave new world of working for a younger boss — sometimes much younger — just as we’re hitting our career stride.

As a generation, we owned the turf of being the first and the youngest. A lot of us found it addictive; I know I did. At 21, I was the youngest woman in my university’s administration; at 32, the youngest head of advertising for Avon. At 39, I was one of the youngest women ever named CEO of a national ad agency. I still live in a bubble of disbelief that I’m no longer the prodigy, even though my business partners max out at 32. But Generation X, and now Y, are hot on our heels, and inevitably, we find ourselves reporting to them. Does this mean we’ve lost our brash edge, or worse, hit the top of our curve?

I asked MORE readers to weigh in and learned that the issue is more complex than it looks. The big question seems to be, how much younger is the boss? Too close to our own age for comfort (why don’t I have the job?) or so young that we don’t understand the watercooler chat? Is the problem the up-and-coming "them," or is it our own hang-ups or our fear that we’ve peaked? The answers lie in asking who we’ve grown to be and what our goals are now.

What We Know That They Don’t

JoAnn Peroutka, 46, a marketing consultant in Baltimore, Maryland, was caught in the same time warp I was. At 29, she had been one of the youngest VPs in her financial services firm. "Being the youngest means different things for different women," she says. "Some play up the ingenue role, while others — like me — want to catch up to what the big kids are doing. I enjoyed being a prodigy. But that doesn’t last forever."

When Peroutka joined a new firm at 41, her boss and peers were a few years younger than she, and initially she was fine with it. But she hit a glitch when they all started worrying about turning 40. "There was lots of hoopla and angst about their ‘big’ birthday," she says, "and I was uncomfortable because I felt out of the loop, even though I don’t think they gave a hoot about my age."

Then her wisdom kicked in. "I just sat back and thought, ‘They have no idea how good things are about to get,’" Peroutka says. "Forty was when my confidence finally caught up with my mouth. I was expressing the same opinions, but I had the experience to back them up."

Now a consultant, Peroutka often serves clients in their 20s and 30s. "I’ve found younger managers to be very open to information, as long as it’s relayed in a peer-to-peer way and not doled out with an attitude of been there, done that," she says. "There comes a point when all the ages run together, and you don’t care if you’re going through boot-cut jeans and platforms for the first or the second time."

The Dinosaur Syndrome

Working for a slightly younger boss is one thing; working for someone who was in diapers when you were in college is another. When Lee Weal, 52, of Philadelphia, interviewed for a job as an administrative assistant, she met with a supervisor about her age. She assumed her boss would be too, but on her first day of work, she learned that not only was she expected to support five people instead of the promised three, nearly all of them, including her supervisor, were in their 20s or early 30s.

More than the workload, Weal hated being the oldest in the office. "Nearly everyone spoke in that Valley Girl manner, where every sentence is a question: ‘You put the files here? And then you make copies? And then you distribute them to the partners?’ It drove me mad," she recalls.

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."

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.

First Published Mon, 2009-04-06 17:02

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