What I Learned From Having Not-So-Horrible Bosses

What I Learned From Having Not-So-Horrible Bosses

I saw The Devil Wears Prada when I was in middle school.

When I was 12, I used to play the Virtual Assistant game on Seventeen Magazine’s website (think Diner Dash, but instead of serving up the right burger, you’re scrambling to manage the editor’s schedule and put the right number of sugars in her coffee). Long before I was actually hired at my first job, I was primed to expect bosses (especially female bosses) would be caffeine-guzzling-stiletto-clad-dream-crushing villains.

As I read The Nanny Diaries and watched Ugly Betty, the image I had of a female boss solidified. She would be extraordinarily skilled but cruel, and would spend most of her time parading around in expensive footwear, all the while stomping all over her intern’s sense of self and sucking the post-grad joie de vivre right out of her.

Now, ten years after I watched Miranda Priestley school Andy Sachs for the first time, I have only ever worked for women — none of whom has been anything like the monster boss I anticipated.

We know, of course, that the way we treat working women is harmful. We expect them to have it all, to be authoritative without seeming “bossy,” to be kind without being pushovers. The way we depict female bosses is – unsurprisingly, then – unflattering and unfair, and it’s not indicative of the behaviors I think most high-powered women actually exhibit.

My bosses (and I know to count myself among the lucky ones; everyone goes through their share of awful bosses at some point) have each, with their compassion, drive, and humility, upended my expectations.

Time and time again, I have been astounded by bosses who have cared about me as a whole human being, not just as their employee. At my summer job, my boss quickly became the first person I turned to when I needed good advice — she guided me through arguments with my parents, helped me decide who to invite to Prom, and taught me what it feels like to be mentored. She was invested not only in my career path and in my work for her, but in my growing up. Another boss let me make an enormous pro/con list on her office floor when I needed help making decisions during the college process, and another scheduled a meeting just to ask how I was feeling about an impending move to a new city.

In caring not only about the work but also about the people doing it, and in their respect and generosity and commitment to leadership and to developing and nurturing their employees, my bosses have shown me what a disservice we are doing to each other all too often. We know that when we perpetuate the bitchy boss stereotype, we’re furthering a falsely gendered idea of success — but we’re also suggesting that abuse at work is at all tolerable.

When I watched The Devil Wears Prada, I came away with some inherent understanding that I was likely just going to have to grin and bear whatever mistreatment I might have to endure on the way to success, because, I guessed, offices were unkind places and being hardened was the only way you’d ever get to be in charge.

Luckily, I’ve worked for women who have shown me I was wrong. They’ve proven that we can make a little room for humanity at work, and, actually, that when we do, we make room, too, for the respect and diligence and ambition that will ultimately set us apart.