Nice Girls Lean Nowhere: How Embracing My Bossy Side Impacted My Career

Me talking about the value of assertiveness on live television. Photo credit: Alisa Bowman

When I was a little girl, my favorite Golden Book was Good Little Bad Little Girl by Eloise and Esther Wilkin. I asked my parents to read it to me over and over, always imagining myself as good. Every day, I modeled myself after the good girl, trying to be nice, agreeable, dependable, non-abrasive and complimentary.

When I was in junior high, I knew I could never compete with the girls who were naturally popular. These beautiful, funny, and gregarious girls were, at times, all about drama. They were high-maintenance and had high expectations. They were the girls the boys complained about and also put up with because they were worth the trouble.

I didn’t believe I was worth the trouble. I just couldn’t be the gregarious, sure-of-herself, bossy girl. But I could be the girl who excelled at the opposite of bossy. I could be the girl who laughed at dumb jokes and who listened to anyone’s story. I could be the girl who never complained.

The pleasant girl.

The nice girl.

When I graduated from eighth grade, my yearbook was filled with comments like, “I don’t know you that well, but you seem really nice.”

During my early 20s, if someone disagreed with me about anything, I immediately backed down and said, “Yeah, you’re right,” even if I thought they were wrong. I became the young woman with no opinions. During brainstorming meetings at work, I held back, letting others talk first. During a rare lull in the conversation, I might say, deferentially, “My idea isn’t as amazing as John’s, but for the sake of brainstorming I’ll voice it” or “This is probably a bad idea, but what about ….” I assumed that, by being deferential, I’d endear others to me. Instead, what I really did was cause others to doubt my ideas as soon as those ideas came out of my mouth.

Still, I came in early. I stayed late. I turned everything in on time. I wrote great copy. I did my best, and I didn’t call attention to myself. I didn’t boast or brag.

I assumed that good work was rewarded. Then my performance review came around. The big raise and promotion I was so sure I’d earned was not offered. Afterward, a close male friend counseled me, “Don’t you know that you have to tell your boss that you expect a promotion?”

The following year, I followed that friend’s advice. I got the promotion and decent salary bump.

Still it felt wrong to me. I wanted to get ahead based on the quality of my work, and not on how aggressively I campaigned for raises and promotions. Within a few years, I left corporate life and began working for myself.

I doubled my salary in just one year, but my legacy of niceness caused me problems in other ways. I worked with demanding clients who had busy schedules, and my niceness allowed them to invade every boundary. A client wanted me to do a call on Christmas Day? Sure! A client wanted me to drop everything so I can help you with a rush favor that the client wasn’t even willing to pay me for? Sure!

I was that nice.

One day I found myself standing outside a New York City business at 5:30 a.m. on a Saturday. I was supposed to meet a client. He’d told me that 5:30 a.m. on a Saturday was the only possible time he could fit me in. So I’d agreed. I kept pressing his buzzer. He kept not answering the buzzer.

It was pouring rain, and I didn’t have an umbrella.

There I stood pressing that buzzer for 45 minutes. Finally, around 6:15 a.m he let me in, and he didn’t apologize.

That’s when I knew something had to change. I no longer wanted to leave behind a legacy of niceness.

No one goes down in history as the world’s nicest person. No, people are remembered for their convictions — for standing up for what they believe. When I died, I didn’t want people to eulogize me by saying: “I didn’t really know her that well. She was really nice, though.” I wanted people to know me, understand me, and admire me for who I really was rather than for who I wasn’t: bossy.

Men didn’t worry about being perceived as bossy. No, bossy men were known as one thing: confident.

Wasn’t there a way for a woman to be confident and also kind, and not be thought of as bossy?

I wish I could tell you that I found the solution right away. I didn’t. It took many years, a baby, a nervous breakdown and the near break up of my marriage for me to find that not-bossy place where assertiveness and kindness meet. From my marital problems I learned that my husband needed me to tell him what I wanted. Otherwise, he wouldn’t deliver. It felt foreign to me at first, this telling him what I wanted and expected. But the results were amazing. Within months, my marriage was healing, and he and I were happy again.

My newfound assertiveness spilled over into everyday life. I learned how to ask for what I wanted at restaurants, at the bank, in my other relationships, and in my career. If I couldn’t talk to someone at 9 p.m. on a weeknight, I said so.

It also led to me develop skills I never before thought a shy, nice girl could possess. I began doing public speaking and appearing on TV. Thanks to the wonderful advice I received from communications coach Bill McGowan, author of Pitch Perfect, I learned not to start my sentences with “This is probably a dumb idea….” He taught me how to pitch ­myself, my ideas, and my opinions with confidence and grace.

If I didn’t think a client’s idea would work, I explained why.

And if I found someone too difficult, I stopped working with that person.

I thought all of this assertiveness would eventually mean I’d end up with fewer clients. It didn’t. It made me even more in demand.

These days I wish I could go back and talk to my eighth-grade self. I wish I could tell her that being nice is deceptively mean, both to yourself and to others. Most people don’t enjoy dealing with wishy-washiness. Having to second guess or walk on egg shells — never truly knowing if you are helping or making things worse — makes the vast majority of people absolutely uncomfortable. They’d prefer to know where you stand, what you enjoy, and what you don’t enjoy. For one, it’s a lot easier to buy the perfect gift when you know what someone actually likes and doesn’t like. More important, most people enjoy being kind and generous, and it’s hard to be either when you have no idea who someone really is.

Here’s more. Most people also feel the most relaxed when they know — without a doubt — that at least one person in the room is capable of leading everyone else in the room in the right direction. Leaders bring calm to every crowd.

That’s why it’s kind to let people know what to expect, where your boundaries are, what your opinions are, and what you do and do not stand for. It’s kind to let people know who you really are. It’s kind to lead them in the right direction.

Kindness and assertiveness really can and do meet, and it’s at that intersection where you’ll find success.

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Article Posted 3 years Ago

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