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This interview with Jessie Woolley-Wilson, C.E.O. of DreamBox Learning, a provider of online math education software for children, was conducted and condensed by Adam Bryant.
Q. What were your early years like?
A. I grew up in Wilmington, Del. The reason we ended up there starts with my father, who came here as an immigrant from Haiti in 1956.
He’s a surgeon, and when he came to this country, black surgeons were not granted admittance privileges at hospitals. So you needed to find another doctor who had admittance privileges, and ask them to admit your patients for you. And for that privilege, you would pay them.
He got to know a doctor of Jewish heritage who said to him: “I understand oppression. I’m going to admit your patients for you, and I’m not going to charge you.” They were in Kansas City at the time, and later the doctor said: “I’m moving to Delaware. If you want to follow me to Delaware, I’ll continue to do this for you.” So that’s how we ended up in Delaware.
My mom is from Texas, so we had kind of a blended home. When our extended families would get together, it was about building bridges across language and cultural differences.
How did that influence your leadership style?
The Haitian side of the family was very vocal, and dinner conversations were important. I remember being a child and looking at my aunts and uncles and asking them why they were always arguing.
What I realized was that they were very engaged in discussions about the economy or about what was going on in different countries. I was witnessing the best part of “benevolent friction” — to be hard on ideas but soft on people — because there was a lot of love and hope about the future.
When my father came to this country — remember, this was pre-civil rights — people would say to him, “Why did you choose the United States?” And he said, with unwavering confidence: “I read about Bobby Kennedy. I listened to Martin Luther King. I knew that America was on the ascendancy. I knew that with a great education, with the support of my family, I could make a life for myself and my family.”
That really resonated with me because it meant that despite the challenges, there were always ways to win. So if you try a tactic and you’re thwarted by external factors, you can try another pathway.
Retreating and trying another pathway doesn’t mean defeat. It just means you’re not going to succeed in that lane right now. So maybe you go back to that lane when you have more education or more experience or more leverage and you try again.
Tell me more about “benevolent friction.”
In a start-up, you don’t know what tomorrow will bring, so you have to be constantly learning and be adaptive with your colleagues. You might think you have a role to play, but you have to listen and be responsive to your colleagues in order for the team to really win.
In the beginning, some people didn’t like it when I used that phrase because they felt that friction is a negative thing, and they didn’t want to have any friction with their colleagues.
I would explain that if you don’t have pressure on the carbon, you never get to the diamond. You can still be very respectful, and assume everybody has a spark, but we have to subject our ideas to the toughest scrutiny because our work is important.
Other leadership lessons for you?
Early in my career, as a woman of color in financial services, the expectations for excellence were either really high — so it’s hard to live up to them — or really low, with people assuming I was here because of affirmative action. It’s not like you’re just you.
So you have to work really hard to demonstrate to people that you have intellectual capabilities and that you’re a valued addition to the team. You have a spark. If you’re given the mask of being extraordinary, then you spend a lot of time trying to convince people that even when someone manifests as extraordinary, they have foibles like everybody else. There’s pressure with that.
So you try to create your own mask, but it’s still a mask and it’s still limiting. Ultimately, you have to define success for yourself.
How do you hire?
I look for that spark. I invite them to tell me their story and how our company fits into that story. You learn a lot when people tell you their story: what they care about, their integrity, their passions and the choices and sacrifices that they make. When you overlay the technical capabilities on top of that, you have a pretty good sense of someone.
I also look for what I call “nimble intelligence” — people who can take in information, harness collective wisdom and make good judgments. They can adapt and pivot, and they’re always in motion.
And how do you get at that quality?
I ask people about situations they’ve faced when they were caught off guard and what they did about it. I ask them about a situation where they felt totally ill equipped to succeed and what they did.
I also ask people about job transitions. What was lacking in the job you had that made you start looking? And when you landed in the new role, did you find what you wanted?
And if you found it, was it something that was waiting for you on a platter or was it something that you had to manufacture for yourself? What did you learn from that?
What career and life advice do you give to new college grads?
I made the mistake early in my career of going into a field I didn’t have passion for. It doesn’t mean I wasn’t good at it, but it didn’t inflame my passion. The advice I give people is to spend time really understanding what you care about, and what you’re willing to do with joy even when it’s really hard.
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