Ready, Set, Go!

Throughout her extraordinary, unpredictable career, Y-Vonne Hutchinson has identified opportunities that address acute problems affecting the labor force in the US and abroad

Y-Vonne Hutchinson, the founder and CEO of the diversity, equity, and inclusion consulting firm ReadySet, is an excellent example of someone who has bucked convention to follow her instincts, heart, and smarts—and forged a wide-ranging, impactful career that has firmly placed her where she belongs.

Hutchinson, who grew up in Texas, originally wanted to be an actor. She attended Carnegie Mellon University as an undergraduate acting major. But while in school, she happened to see a documentary on the Rwandan genocide. “And for me, a sheltered kid from Texas, it was just staggering that genocide still happened,” she says. Hutchinson began reexamining her career choice and made a dramatic pivot. “I began looking at TV and realized they did not have a lot of representation of people who looked like me. And so I asked myself, ‘Am I just going to be the sassy little Black best friend forever?’”

So she leaned into her newfound interest in the justice system and international law. Hutchinson started taking conflict resolution and foreign policy classes, and after graduation matriculated at Harvard Law School. She focused on the intersection of international law and human rights, which led her to Nicaragua, where she worked at a nonprofit. She also studied structural violence against sugarcane workers as well as the health ramifications of this brutal work. This led to her next epiphany—that vastly inequitable power dynamics, sometimes resulting in physical hardship, even violence, particularly against people of color, were playing out in some form at companies across the United States. Then came a new pivot: launching ReadySet, to teach organizations how to level the playing field and shape safer, more inclusive workplaces for all.

Diversity Woman: You have a diverse and unusual background for someone doing DEI work. How did you get from law to launching ReadySet?

Y-Vonne Hutchinson: My background is in international human rights law and labor rights advocacy. And my last role prior to starting ReadySet was with a nonprofit in Nicaragua that was working with sugarcane workers who were dying of occupational illness. We were seeing a lot of trends that were killing this community, that were reflective of the broader future of work.

As I was thinking about that broader future and labor protections, I was doing academic research. And eventually I said, “Hey, I just want to go ahead and get my PhD and study the future of work more closely.” I applied, got in, and then last minute I said, “I’m not going to do that. I’m going to start a company instead.” So my parents obviously freaked out!

DW: How did you make the leap from this work to ReadySet?

YH: This was in 2015, and so much workplace analysis was happening right then. I didn’t want to be in school studying for another five years to get a PhD when I could be working on the stuff on the ground right away. And ground zero for a lot of these changes was Silicon Valley and the tech industry. So I decided to start ReadySet. And it quickly became apparent to me that the labor issue, the future-of-work issue that was most salient, and going to be most important, was the issue of diversity, equity, and inclusion.

I couldn’t stop thinking, “These companies are driving the workplaces of tomorrow, and there’s no one in there that looks like me. And they have no idea of what people like me need.” So I started ReadySet with that in mind.

DW: DEI training has exploded in the last 18 months. How do you differentiate yourself from the multitude of groups that are also doing this work today?

YH: Early on, we developed three core principles.

First, we’re very data-centric. When I started ReadySet, I started working primarily with tech companies who said they were data-centric and said they were rigorous. And they actually seemed to be in almost every aspect of their business—except DEI.

People were not taking evidence-based approaches to the work. You saw people who were doing DEI as a second job. You had people who were very inexperienced being asked to own diversity, equity, and inclusion for an entire company. You wouldn’t ask an intern, if you’re a company of hundreds of people, to own your marketing strategy, but you saw that in DEI. And then also you had people who were doing a lot of feel-good moves but were applying approaches that weren’t rooted in evidence.

The second differentiator is that we’ve been intersectional from the jump. I remember the very early days in ReadySet, people would come to me and they would say, “Y-Vonne, we want to do DEI.” And I’d be really excited. But then they would say, “We just want to start with women.” And my face would get crushed.

And third, we’ve always seen DEI as touching everything. In the early days of DEI, you saw a lot of emphasis on recruiting, but less attention on culture, retention, and advancement.

At ReadySet we said, “Okay, it’s about all of that. But it’s also about your core business strategy as well, the thing that you’re building.” So if you’re Twitter, and you’re building a platform where people are marginalized and bullied, there’s something going on that’s a DEI question. Or if you’re building a product that tags Black people’s faces as gorillas, there’s something going on there, right?

DW: Tell us about your childhood and how it influenced your life and career today.

YH: My dad was a foster child in San Antonio; my mom grew up as a sharecropper in Louisiana. And they both clawed their way into the middle class. They were both really good at making something out of nothing and taking advantage of opportunities. From a very early age, my mom taught me to walk through those open doors. She showed up and advocated on my behalf. When teachers tried to put me in less advanced classes or hold me back, she was like, “No.” She was there front and center. Lastly, I grew up with no sense of a ceiling. I was taught, “You do what you want to do as long as you excel.”

DW: What advice would you give young women aspiring to advance into greater leadership responsibilities?

YH: Building your network is important both inside of the office and outside. Who are the women who can give you advice? Who are the women who can alert you to opportunities? Who are the women who you can bounce ideas off of?

Inside your organization, seek out not just a mentor—sometimes I feel like women of color are actually over-mentored—but a sponsor. Someone who’s going to promote you when you’re not in the room, who is going to offer you great projects, who’s going to increase your visibility.

But here’s the God’s honest truth, and I hate to say it: You also want to be realistic about whether there’s a ceiling where you are. And if there is, do not waste your time. That is the biggest advice I could give a woman of color at work, regardless of where she is. And that’s why your external network is so important. I don’t advise people to job hop, but I do advise that if your options are limited in a particular company, that’s likely not going to change by you beating your head against the wall.

DW: You have a book coming out soon, How to Talk to Your Boss About Race: Speaking Up Without Getting Shut Down. What motivated you to write it?

YH: I didn’t want to write a typical business book. I wanted to write a book where I could pour myself into it a little bit and unpack some of the things that have happened to me. I wrote it to be personal, and also to be actionable so that folks could really walk away feeling like they knew what to do, and also walk away feeling seen. In some ways, the topic of the book is a little bit of a bait and switch. Yes, the book is all about how to talk to your boss about race, but it’s also about how to talk to anyone who’s in a position of power about race. And how to think about pushing for systemic change in any given environment where you may feel like you’re the lone voice.

I also write about how to frame the conversation. What are some strong cases for DEI? It’s not just the business case—everybody loves the business case, but it’s so, so much more than that. But how do we think about reputational costs, legal risk, our social obligations? And then how do you actually have this conversation? What are some tips when you’re sitting face-to-face, or Zoom-to-Zoom, with your boss and you’re opening your mouth? DW


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