I’ve been called it. So have most women I know who are some combination of assertive/confident/ direct/ clear.  

It can feel like – and be intended as – an insult.

It can also be a compliment to be called the ‘B’ word.


Ask my younger sister Amy about my bossiness.  It’s become family lore, captured in a hand-scrawled message that still hangs on the wall of my childhood home, that she noted my ‘bosse-mouth’ tendencies when we shared a room for a spell.  I like to think she recognized my leadership skills that were budding at such a young age. She may reflect on the ‘sharp’ tone in my voice, and the urgency of my ‘requests’ regarding the use of our shared space. Over time I like to believe the sharpness and urgency have mellowed into something more Michelle Obama-esque.  A gal can dream.

A conversation about bossiness came up in a recent Sidecar Rally meetup.  We were discussing the trap women leaders often feel caught in, between being perceived as ‘likeable’ and being viewed as ‘competent.’  Somehow that’s become an either/or (though only for women, it seems) and it goes like this: If you’re likeable, you can’t be competent.  If you’re competent, you can’t be likeable.  (Hmmmmm.) We concluded that this was, to use a technical term, B.S., especially since each of us in that meetup felt we were both.

And yet… women leaders often feel they must twist themselves into contortions to project themselves as both. Where a man makes a direct request, he is simply seen as assertive, a quality valued in competent leaders. A woman making the same request?  Bossy.  If she sugarcoats it with niceties first, she’ll win points for likeability, though the request may or may not be honored.  A male leader voicing a strong viewpoint: competent to do so (he’s a leader after all). A female leader doing the same?  Bossy.  And the viewpoint possibly suspect.  She could couch it in language suggesting there are other ways of thinking about this topic. More likeable? Yes.  Seen as competent?  Well, it helps that she acknowledges other viewpoints….

Ladies, let’s not step away from this.  Let’s reclaim the B word.  After all, what does Bossy really mean?  Well, I’d say it means “like a boss.”  And when you are a leader of a school, a division, a department, a group of people… well, you’re a boss.  So: be ‘bossy,’ in a way that suits your leadership style and helps you get things done. Sometimes you can do that and be ‘likeable.’ Sometimes you’ll ruffle a few feathers.  That’s the reality of leadership: male or female.

I like another definition of ‘bossy,’ this one derived from more modern uses of the word ‘boss’ to mean excellent.  “That was a real boss move!” So to be bossy is to be outstanding. Yah! Men, you could get behind that one too.

One of the members of our Sidecar Rally cohort confessed that she’d been given a nickname by one of her students at her current school.  He’d termed her ‘Bossy Boots.’ It was a compliment, acknowledging her leadership role (Elementary Principal) and the cool boots she was wearing that day.

Those boots are made for walking around the campus as a leader who knows her worth, and that her competence needn’t be questioned if she’s also likeable and has good fashion sense.

Yours in re-framing yesterday’s insults, and searching the web for boss footwear,