Leadership, But Make it Fashion

Hannah Fleishman
3 min readAug 17, 2018

Fashion isn’t my forte. In high school, my friends clapped when I showed up to class in a striped shirt. For me, that was a bold sartorial decision.

But one thing I do know is that styles go in and out of fashion. What was trendy in the ’80s, wasn’t in the 90s’, but might be again in the ’00s. The thing that doesn’t change though, is personal style. You may be influenced by trends but underneath your bell bottoms or Von Dutch hat, you’re still you.

Leadership isn’t all that different. We each have our own authentic leadership style. And that doesn’t change. But like fashion, I think we dress the part for the stage we’re at in our careers.

According to Social Styles, a work personality assessment, I’m a Driver. That’s my personal style. Drivers are described as action-oriented (check), results-driven (check), and are the first to start a conversation in an awkward room (check).

That style has been in fashion for me in my 20s. In other words, I truly think it’s helped me get to this stage in my career. Having a bias toward action means I got to fail fast, learn faster, and gain some visibility in and outside of HubSpot.

But I want to be a Director one day. A VP. Maybe even have a C in my title. And who knows where or when that will be. But I don’t think I’m going to get there by only having one leadership setting. Sometimes you need to hang up your duds and try something else on for size.

Because lately, when I work with a leader who isn’t a Driver, I find myself thinking: How can I be more like them? I admire their empathy, strategic thinking, and humility. Actually, I’m kind of jealous of it. Those qualities don’t come naturally to me.

But neither did boyfriend jeans at first. Loose-fitting, light-wash, ripped jeans in 2018? No way, nuh-uh; I draw the line at stripes. But they looked so cool on other girls, and I wanted to look cool, too. So I tried on about 12 pair that were a hard “no” until I found the perfect ones. I thought they’d clash with my own personal style, but actually, they just evolved it.

Chances are, I’ll look at a photo of myself in ten years and laugh, thinking “Why would I ever wear those?” Like we all do. Once a decade. But we cut ourselves some slack because it’s just a sign of the times.

I’ll always be a Driver. That’s who I am. But I’m going to try to stop being jealous or discouraged by leadership qualities I don’t have, and instead find ways that they can help me evolve as a manager.

Because authenticity never goes out of style. (And hopefully boyfriend jeans won’t either.)

Thank you Tyra Banks for bringing the “..but make it fashion” motto into this world.

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Hannah Fleishman

Director of Employer brand & Internal Comms at HubSpot. I like puns.