Why I Love the Troublemaker

Over the past few years, I’ve poured my heart into diversity and inclusion initiatives at Square Root. We’ve added generous parental leave, supported a local STEM education non-profit that benefits young girls called Girlstart, created sensitivity training, and fostered internal communities. With our efforts came a diverse team. We span generations, education levels, genders, sexual orientations, political views, socioeconomic backgrounds, ethnicities, and so on.

But we realized in all our efforts to build a diverse team, we neglected to welcome diverse thoughts. And, after all, isn’t the benefit of diversity the uprising of new perspectives?  So, I’m on a campaign to craft a safe space for the folks I’ve (lovingly!) dubbed – The Troublemakers.

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Who is the Troublemaker?

Troublemakers find us at all stages of our lives; we might even be former, current, or future troublemakers ourselves. Folks that ruffle feathers or go against the grain can be unsettling, intimidating, or even annoying, but we need them.

My career began at a private school teaching kindergarten. Five-year-olds are curious, energetic, and just starting to figure out social dynamics. In each class, there’s a troublemaker. Mine was Kyle. He knocked over block towers, refused to engage in naptime, and considered coloring instructions optional. But he also sparked some of the best conversations with my kids. We talked about how it made us feel to have our block tower destroyed, and learned to color outside the lines.

Every organization has their own Kyle, their own troublemaker. Someone that keeps the team on its toes, keeps them challenged, and keeps it interesting. Without Kyle, I’d have followed the provided lesson plans to a tee, no questions asked. It’s so tempting to go with the flow, and not rock the boat, and it’s rarely fun to find your “block tower” under siege. But when norms are questioned and perspectives are challenged, magic happens. Do any of us really want to be coloring inside the lines anyway?

Why Do We Need the Troublemaker?

There’s this idea that if you hire for diversity, you’ll be dripping in diverse perspectives. That’s not necessarily the case. All too often we hire folks with diverse perspectives and sit back waiting to reap the rewards. Instead, you have to nurture diverse perspectives. That task, commonly known as inclusion, is a biggie. It requires an environment so safe that a different idea can be said not just thought. It requires encouragement from anyone in a perceived position of hierarchy (ahem, managers). And it requires a company cultural shift.

For me, the cultural shift came in the form of empathy for both our users and our team. We’re a software company, and our users are diverse, so we need folks to pipe up with their point of view if something isn’t jiving for them. We even made empathy for our users and buyers our annual goal to make this a priority at every level.

Empathy in product development struggles to emerge when we don’t have empathy for individuals on our team. We have to be willing to listen to each other. We have to be curious. Most importantly we have to be okay with being wrong and with others being wrong.

Over the past year, our team dug deep into finding avenues for active listening. For example, our Recruiting Manager, Rachel, created Meeting Magic. It’s a multi-channel program designed to nurture an internal meeting culture, with one of the core pieces guiding folks to include every personality under the sun in a brainstorm session.

It’s more than just including every personality; it’s having empathy for the troublemaker and making sure they know their ideas are valued. We need diverse perspectives, we need our assumptions questioned, and we need to listen to and debate even the wackiest of ideas. It’s easy to dismiss a divergent thought or disruptive thinker as a “troublemaker.”

While teaching, my instinct was to gloss over what was happening, but my kids were curious. I stopped letting my first instinct get the best of me, and started offering Kyle’s perspective to the class for discussion. Wheels started turning, ideas were generating, and it also gave the other kids a chance to empathize with Kyle and really see his perspective. At Square Root, we follow a similar process knowing that one divergent perspective could spur our next big innovation.

Make Trouble-Making A Part of Your Culture

To nurture the wacky in our team, we’re taking the stigma out of troublemaking. It started with a letter from me to the team, introducing the concept of the Troublemaker.

Now, we’re acknowledging (lightheartedly) when someone is being a Troublemaker and seeing it as part of our roles to start some trouble. Keeping your perspective to yourself, or squashing someone else’s without hearing them out first, is no longer welcome. We want folks to share real, honest, raw, wacky perspectives. They might be wrong, they might ruffle feathers, but they’ll make us think. I genuinely believe we’ll only grow from taking the time to debate our different perspectives, and hopefully, something wonderful comes from it.

Inspiring troublemaking hasn’t been the uphill battle I anticipated. Perhaps, it’s because we’ve all been secret Troublemakers all along. I’ve been the person holding back great ideas in fear of stepping on toes or not being on the right track, but I’ve learned that stirring up the dust results in trust and acceptance more often than not. The people I trust most in life are the ones who tell me when I have food in my teeth. Being a Troublemaker is a bit like pointing out all the teeth with food in ‘em.

At Square Root, we’re often asked if we have internal communities for diverse groups, which we do, but we’re never asked if we have internal communities for diverse thought. You can have the most diverse group on the surface, but if you’re not welcoming what each individual has to offer on a deeper level, you miss the inclusion aspect. For inclusion and diversity initiatives to thrive, companies need to focus on what makes each individual unique and ensure a safe space for that not-so-popular opinion. So here’s to making some trouble!

Courtney BransonCourtney Branson is Director of People + Culture at Square Root, an Austin-based technology startup that creates Store Relationship Management software for some of today’s leading automotive and retail enterprises.Courtney brings her creativity to everything she does and Square Root is no exception. She handles a little bit of everything but is especially good at employee relations and HR. Mom to a little girl, Courtney’s compassion and patience keep our team grounded and thriving. Prior to joining Square Root, she spent years in HR for large companies, focusing on culture and employee morale. She knows just what it takes to pull the best out of people and has a knack for inspiring and connecting the right folks. Courtney has a degree in English with minors in philosophy and history from Texas A&M University. When she’s not busy building our award-winning culture, you’ll find Courtney reading, blogging, hula hooping, or spending time with her husband, daughter, two dogs, and cat.

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