Confessions of a Kiss-Ass: How Being "Perfect" Almost Ruined My Career

There is a difference between sucking up and managing up.

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My boss Roberta smiled with her mouth, but not her eyes, as she unwrapped the Christmas present I'd bought her—a calendar filled with pictures of antique porcelain shoes. She collected the miniature shoes; they were scattered across her desk and the shelves in her office. It was the day before the holiday break at one of my first magazine jobs. "Thank you," she said, nodding at me. She turned back to her computer. I felt her waiting for me to leave.

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 "Is there anything else I can do before day's end?" I asked. She inhaled through her nose and looked at me with her mouth-only smile.

"Nope, all good!"

"Okay," I answered, as I backed out."But really, if you need anything, I'm right outside."

I am a bona fide, Grade A, certified, card-carrying, award-winning ass-kisser.

Confession: I am a bona fide, Grade A, certified, card-carrying, award-winning ass-kisser. I have been known far and wide as such, ever since I sat so close to my high school history teacher's desk that when I leaned forward to cup my chin in my hands, my elbows were on his desk and not my own. I laughed uproariously at my college fiction teacher's jokes. I complimented my academic advisor's ties. Still, I always had this sense that I annoyed them, and it was a mystery to me. How could they not love me? I was always there, ready to help or volunteer or pitch in. Seriously. I was pretty sure I was a dream.

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In school, I chalked it up to being a not-great student. But my intentions were never insincere; I was raised in a religious home where respect for my elders was paramount. So I was habitually agreeable and pathologically punctual. Yet boss after boss treated me the way Roberta did: wary, unimpressed.

And the worst part: Just when I thought I might be able to explain it away as my bosses being just plain sociopaths, I'd watch my co-workers roll their eyes and argue with management—even name-call and storm out, in some cases—and still gain favor. But why? I was creative! I had ideas! I even disagreed (respectfully, of course), but I was never rewarded for it. I watched everyone else get promoted while I felt like I was barely being tolerated.

You don't know me, so let me explain: I have friends. People like me. My co-workers liked me. I swear. It's just the bosses. It's not that they hated me. It's just that they seemed to dread me. And by the time I was 30, there had been too many bosses—all very different personality types—to ignore. The only common denominator was me.

It was only years later that I saw it clearly. A friend was confiding that she had the same issue. At her new law firm, where she knew she had been the second choice for the job, she was having a hard time getting the office culture down. She was plagued by a need to interact. Those were her words: "a need to interact." It was that minute that I saw myself.

That's what had been driving me all along. Are we okay? Are we cool?

According to Lois P. Frankel, PhD,author of Nice Girls Don't Get the Corner Office: 101 Unconscious Mistakes Women Make That Sabotage Their Careers, it wasn't the fact that I too-obviously liked my bosses that doomed me. It was all that door-knocking, head-poking, and helpful-suggestion-making that was alienating them. But we're supposed to offer ideas and check in, right? That's a normal part of being a worker. If I'm honest, though, I was often doing it not out of utility—"Hey, Sally! I have a genuinely good idea that will make things easier and more efficient!"—but as an anxious mechanism to compensate for what I felt were my own inabilities. I worried that I came up short in a lot of ways, even though I had a writing degree and was part of an actual business.

"You were kissing up, not managing up," Frankel explains. "Bosses like employees who manage up." Meaning they want you to interact with them in ways that help the business and make them look good. Yes, suggest your good ideas. But if you see yourself in my story at all, ask yourself with every check in, "Can this wait?" "Is this necessary?" And most importantly, "Why exactly am I doing this right now?" In other words, consider taking a pass—because if you aren't good, checking in won't help.    

I'd love to say that I became the perfect employee, but I didn't. I traded office life for freelance; I learned it meshed better with my personality, not to mention my approval-seeking proclivities. I still try to get approval (I won't lie), just not constantly and from the same people. And, slowly, I've found a way to let my work speak for itself—maybe that was the problem the whole time. Maybe I was trying to show how indispensible I was instead of doing great work and having faith that the people who needed to notice would.

The biggest difference now? When I find myself crafting unnecessary emails to editors, demonstrating how helpful I am or how on-top-of-things, I stop before hitting "send." Now, I click "delete draft" and go make a sandwich instead.

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