What was your first job?
Rebecca: My first job was working for a dentist. I did insurance claims, kept track of deposits and such, and they would call me in when procedures were particularly messy. I had no desire to be a dentist, as at that time I had already started programming. I’d fallen in love with computer science and so I knew I was going to be a geek.
What did you want to be when you grew up?
Ange: I’m still not someone who knows what they want to be when they grow up, which I know seems a little ridiculous: I’m aware of that level of comedy. I tend to gravitate towards things that I don’t know how to do. It can be hard to predict those things at times, so I keep an eye out for the potential side adventures along the way.
Was there a moment you remember when you realized you wanted to be in tech?
Joanna: For as long as I can remember, I’ve always wanted to be an engineer. My father was an engineer and I was always encouraged to pursue math and science. I remember this story that my mom loves to tell: I was a young girl, and I was in the kitchen doing dishes with my father. My mom walked in and said, “Don’t teach her how to do dishes, teach her how to be an engineer.”
What do you love about tech?
Rebecca: I love the fact that it’s always changing. I’m a language geek, so I like to think about languages, what constitutes “good” in a language, and issues of language design. But I also like the fact that it’s puzzle-solving. To me, working in technology is creative: it’s figuring out how to approach a problem and how to solve it. There’s something so nice and clean and objective about it. You know that it’s working because the tests pass; in so many other things, that notion of success is so much more subjective.
What drew you to ThoughtWorks originally?
Jessie: I found ThoughtWorks to be super interesting. Most organizations are very hierarchical and people are afraid of speaking up if their thoughts are different from their manager’s, but ThoughtWorkers are so different, so I was really curious.
You were a ThoughtWorks University (TWU) trainer, how did the experience impact you?
Joanna: In 2006, I was a trainer at ThoughtWorks University in the very early days of the program. At the time, the course was held in Bangalore. It was my first time visiting India, which was in and of itself a life-changing experience. TWU was an incredible experience for me; it was the first time that I really dove into teaching and learned that I loved it. You just walk away feeling so connected and so immersed in the company. And you leave with these friendships across the globe.
Is there a moment in your career where you feel like you failed? How did that help you grow?
Jesse: In my 15 years at ThoughtWorks I’ve experienced many challenges. The most memorable one is when I was working on a big client program. We had a fairly large team and there were so many things to balance: the client relationship, delivery, and motivating the people on your team. I was struggling…I cried at home and even sometimes at work in front of the people I trusted. But I think the good thing about ThoughtWorks is people do give you support when you need it. So with that support, I managed to overcome the challenges and we achieved the outcomes we set out to accomplish. I always tell this kind of story–I hope they can help other leaders grow and build their confidence.
When did you realize you were a leader?
Ange: I think it was in talking with my mom, who is a retired teacher and principal. I realized that leading is something I’ve always done; it’s arranging people and things in such a way that the collective can be more successful. So I had a lightbulb moment with her, which was, “Oh, that’s actually a thing.” It’s that ability to arrange and herd so that a group of people is motivated by the same outcomes and has got a way of moving together towards that outcome.
Did you always aspire to be a leader?
Joanna: The founder of ThoughtWorks once called me a “reluctant leader.” I was full of a lot of opinions and I was not afraid to share them. So it was really his encouragement to say, “Hey, you can take those strong opinions and you can actually do something about it,” that pushed me into accepting leadership roles.
What’s important for aspiring leaders to know about leadership?
Jesse: Resilience is important and you need to be patient. You may feel you’re the only person who can complete some of those complicated tasks. You still need to build capability in others for the long term. It’s that strategic way of thinking about what will help the company and team be successful in the long run.
What do you appreciate the most about working at ThoughtWorks?
Rebecca: Well, one of the most important things is I feel valued for who I am and what I can do. I don’t feel like I ever have to worry about being a woman in tech. One of the other things that I really love is the intelligence of ThoughtWorkers and the passion they have for technology — they care about improving the state and practice of technology. I also appreciate the extent to which we take our values seriously and try to live them and own up to it when we feel like we’ve made a mistake. We’re certainly not perfect and we don’t always get everything right, but we try and we own up to it when we don’t do as well.