This interview with Jeff Lawson, chief executive of Twilio, a cloud communications company in San Francisco, was conducted and condensed by Adam Bryant.
Q. When you were a kid, were you in leadership roles or doing entrepreneurial things?
A. I started my first company when I was 12, doing video production. I’d videotape weddings, bar mitzvahs, birthday parties, sweet 16s. By the time I graduated from high school, I was doing full weddings and making a few thousand dollars a weekend.
What about early leadership lessons?
My grandfather was a big influence. He started a paint company in the 1930s, and sold it in the 1970s. He built this company for 40 years, and you’d think he would have retired, but he did not. He became a manufacturer’s rep for all the paint accessories. He would go all around Detroit and sell to hardware stores. He did that job until literally the day he died. He was 98.
He was still working at 98?
Other people would drive him around. The owner of every hardware store in Detroit came to the funeral. That was amazing.
Credit Earl Wilson/The New York Times
What about your college years?
I studied film and computer science. This was when registering your domain name required you to fax documents to people. My friends and I just wanted to play with this technology, and we started a project to do that. We noticed there were companies that hired students to take notes and then sold copies of them to other students.
This was a cottage industry, and it seemed ideal for the Internet. In 1996, we started a company, Notes for Free. We hired college students to transcribe their notes into a Web-based system. We’d give them away and sell advertising on the site. We then raised money, and I dropped out of college during my senior year to work on this full time. We were close to 50 employees in Ann Arbor, and at that point we moved the whole company out west in late 1999. About six months later, we were selling the company to a competitor that had filed to go public. It was an equity deal, and then the dot-com crash wiped us both out.
You were a C.E.O. early in your life. Any early lessons from running the start-up?
We were all roughly the same age and we were just sprinting together. One thing I noticed was that when there was discord and we couldn’t agree on things, we tended not to address those issues head-on. When there was disagreement, we’d all kind of put it aside and say, “Let’s get back to work and go.” That didn’t serve us well.
So in our current company, when people see conflict, they address it, talk about it, bring it out in the open. Conflict shouldn’t be taboo. In fact, resolving conflict is one of the key things companies do, since you have lots of people with lots of ideas about how the company should proceed.
And do you also try to create that kind of culture for giving people feedback?
We don’t wait until the annual performance review to give feedback. You never want to have a surprise. This is especially important with millennial workers, who really want feedback. They want to always be learning, always be growing, and they’re looking for that constant feedback. It’s not that they’re looking for constant praise, but rather they want to keep score. They want to know how they’re doing.
Part of it is the short cycle of Internet feedback, and people who grew up with the Internet just expect quick feedback on things. That’s just part of the changing ethos, especially with younger workers. If you get into the habit of regular feedback, it’s not confrontational; it’s just the ebb and flow of conversation and a constant tweaking of how you work with somebody.
Tell me about the culture at Twilio.
A lot of our values are about empowering employees. “Draw the owl” is a favorite. It’s based on the Internet meme of how to draw an owl. It says: “Step 1, draw some circles. Step 2, draw the rest of the owl.” That’s what it takes to be an entrepreneur — you have to put aside all the reasons you think you can’t do something or figure it out. Our job is to come in every day and take a vague problem that we don’t know how to solve and figure out the solution.
How do you hire?
I look for a certain spark. It’s almost like having a chip on their shoulder — there’s something they want to get done in life, and they’ve got something to prove. If I can help them do that, they will be massively contributing to the company. That’s where you get the passion and drive and energy to do great things.
One of my favorite questions is, “What do you want to learn next?” Another way to ask that is, “What are the properties of the next role you want?” Some people say, “I want to join a start-up,” or they give some attributes of a company. Then I’ll say, “What I’m really trying to understand is, what is it that you are going to find interesting?” I’m trying to find if they have a clear sense of what makes them tick.
Your advice for new college grads?
Every industry will become a software industry because of the pace at which software people innovate. Think about your thermostat or even the payment terminal at the corner bodega. Now you can have software updates every week to add new features and functionality and remove bugs. Think about Tesla. It’s a rolling piece of software. So my advice for college students is, “Really think about that mentality and think about all the ways in which the agility of software is able to meet a market need faster than the legacy industry.”
You don’t have to be a developer, by the way. You can be in any discipline. But if you look at a problem for your customer or within your company, and your first thought is, “How can software solve this problem?” then you’ve got that software mind-set. You’re a software person. I believe that the future is going to be owned by people who think that way.
Twice a week, Adam Bryant talks with top executives about the challenges of leading and managing.