Jessie Woolley-Wilson (C.E.O. of DreamBox Learning) in “The Corner Office”

Adam Bryant conducts interviews of senior-level executives that appear in his “Corner Office” column each week in the SundayBusiness section of The New York Times. Here are a few insights provided during an interview of Jessie Woolley-Wilson, C.E.O. of DreamBox Learning, a provider of online math education software for children. To read the complete interview, check out other articles, and obtain subscription information, please click here.

Photo credit: Earl Wilson/The New York Times

* * *

What were your early years like?

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.

* * *

Adam Bryant, deputy national editor of The New York Times, oversees coverage of education issues, military affairs, law, and works with reporters in many of the Times’ domestic bureaus. He also conducts interviews with CEOs and other leaders for Corner Office, a weekly feature in the SundayBusiness section and on nytimes.com that he started in March 2009. In his book, The Corner Office: Indispensable and Unexpected Lessons from CEOs on How to Lead and Succeed, (Times Books), he analyzes the broader lessons that emerge from his interviews of hundreds of business leaders. To read an excerpt, please click here. To contact him, please click here.

Posted in

Leave a Comment