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Working for Someone Young Enough to Date Your Kid

Having a young boss is tricky, but these six rules will help the two of you get along

By Barbara Peters Smith

Being willing to work for a boss who's younger than you seems to be part of the workplace survival scenario for employees in their 50s and 60s. So don’t be surprised if you find yourself answering to someone who could easily be dating material for one of your kids. 
Here’s the good part: You can draw on all that practice you got as a parent, holding your tongue when a child embarked on what looked like a mistake and rooting for your kid to find his or her way no matter how long it takes.
Use Your Parenting Skills at Work
This tact and generosity (in small, office-appropriate doses) can actually help you become indispensable to your young boss.
(MORE: How to Get Along With Younger Co-Workers)
Rattled by the idea of having a performance review from a 20- or 30-something whose discretion resembles WikiLeaks? Be careful. “Status anxiety” can be scorching if you let it seep underneath that coat of arms you’ve been wearing to work every day since the Great Recession arrived.
Empathy Is Essential
Your wisest strategy is to instead begin from the standpoint of empathy for your new supervisor’s vulnerabilities and insecurities. Imagine your own adult child in the same situation. 
When reporting to someone half your age, the need for collaboration remains the same as when you work for an older boss, says economist Steven A. Sass, associate director of the Financial Security Project at Boston College.
“Try to manage the boss and make the relationship succeed,” Sass says. “It’s rare when you can win if the boss loses.”
6 Rules for Working With Younger Bosses
Career experts recommend following these six rules for building a workable alliance with your younger boss:
Don’t take the situation personally. As the number of older workers rises — the nation’s 78 million boomers are 49 to 67 today — it’s inevitable that promising young candidates will increasingly be groomed to glide into management positions.
Understand that the younger boss/older underling anxiety works both ways. Your employer is expecting the newbie boss to grow in the job — and that includes the uncomfortable challenge of supervising you, somebody as old as his or her parents.
(MORE: Why You Need a ‘Reverse Mentor’ at Work)
Prove that the stereotype of older workers doesn’t fit. Research has shown, Sass says, that younger supervisors tend to see older workers as stuck in their ways. So make it your business to surprise your boss with your enthusiasm and flexibility. Become what's sometimes known as a "Generation Flux" employee.
You could take an online tutorial about electronic spreadsheets, for example, and show off your new skills in a report or presentation.
If your boss seems enamored with a particular technology that’s new to you, ask intelligent questions and demonstrate a willingness to use it in your work. View your superior as a reverse mentor who can teach you valuable skills.
Greet your boss’ ideas as if you’ve never heard them before. This is the time to draw on your parenting skills and really pull for the new young adult in your life to succeed.
Don’t moan about how a similar initiative failed in the past. Take a fresh approach with the goal of making things work this time.
Try to be supportive, not condescending, just as you would if your adult children attempted something they’d never done before. Use phrases like, “This is really intriguing” or “I think you’ve hit on a way to make this work.”
Let your boss in on your career plans. If you hope to be with the company for 10 or 15 more years, say so. If your retirement cottage is nearing completion, be as open about it as you can.
(MORE: How Boomers Can Prove Their Value at Work)
Being upfront about your future will remove any doubts about the kind of contribution you intend to make and for how long. Your eventual retirement is a topic your boss will likely be uncomfortable bringing up. “Look for some way to get the issue on the table,” Sass says.
Be an employee, not a parent. Your boss wants to see you as a useful support system, not a stand-in mom or dad.
Mentioning your children as if they’re relevant to your boss’ situation can unravel the professional rapport you’ve carefully knitted together. It can even strike your boss as creepy and inappropriate.
Remember when you were 26, and older co-workers tried to relate to you by bragging about their kids’ marriages or law school degrees? Chances are, you didn’t like it. Neither will your young boss.
Barbara Peters Smith is the health and aging reporter for the Sarasota Herald-Tribune and the John A. Hartford/MetLife Foundation Journalism in Aging and Health Fellow.

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