How to Work With a Young Bossypants

It's simple – all you have to do is change who you are

Six months ago, when I learned our department would be restructuring, I was told that it meant Cherita was about to become my boss. Cherita was born in 1986 — the year after I gave birth to my son.

I'm not alone. According to a 2012 survey, 34 percent of workers report to a younger boss. The modern workplace, it seems, is fast becoming the Land of the Older Underling.

Cherita had to train me to take over her responsibilities as our company's website editor. She was starting her new gig the next day, so we barely had time for a half-day crash course. She was talking and demonstrating at hyper speed — there must have been 20 different windows open on her computer — while I frantically scribbled notes. At one point, she explained that she likes to pull photos from Creative Commons to avoid copyright complications.

"What's that?" I asked.

She said it again, "You know, Creative Commons."

"I don't," I said.

"On Flickr," she said.

"Show me," I suggested.

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She looked up from her monitor and took her fingers off the keyboard for the first time in three hours. "You don't do Flickr?" Her voice was practically dripping with disgust. You'd have thought I told her that I don't bathe.

The next few days sucked. I wore my resentment on my sleeve. I even considered quitting. After work one night, my son Jesse came over for our weekly mac-and-cheese Thursday and I took the opportunity to complain about reporting to someone young enough to date him. His reaction?

"Don't judge," he advised.

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Another weeknight, I went hiking with my friend Mindy, who had gone through the same thing a year before. During our climb, Mindy told me the toughest adjustment had been adapting to her boss's communication style. Gen Y's constant e-mails and instant messaging can be unsettling to someone who prefers an actual face-to-face conversation. Mindy learned the hard way that Me-Me-Me kids assume a missed call serves the same purpose as a voicemail message saying, "Call me back!"

On the flip side, Mindy discovered some unexpected benefits of the age gap. Her twentysomething boss, a man, was far more comfortable with women in leadership roles than most of Mindy's same-age male colleagues had ever been.

As the weeks went by, I made an effort to adjust my work style to accommodate Cherita's — the way I would for any other new boss. Meanwhile, in my new gig, there was always another deadline around the corner, so I just didn't have any bandwidth left for resentment. As I found myself learning a lot from her, it quickly became clear why she'd been promoted: the girl knows her shit.

One day, when I was about to pop over to Cherita's office to let her know I was leaving a few minutes early to catch an Iggy Pop concert, I decided to IM her instead. "No worries," she typed. On my way out, I passed her open door. "Have fun! she yelled. "Is Iggy Pop a new band? I never heard of them!" I must have reflexively shot her a look, because she immediately added, "Don't judge."