Art of Leading
A Key Test For Leaders: How Do You Influence Others When You Are Not In Charge?
Art of Leading
Khozema Shipchandler, CEO of Twilio, shared his key insights on leadership beyond job titles. This interview is part of our Art of Leading interview series with The ExCo Group‘s Adam Bryant.
Q. What are the three core things in your leadership playbook?
A. Number one for me is people and leaders—hiring well, recruiting well, and then cultivating talent over long periods of time. Everybody’s good at different things, but I’d characterize that as my superpower. I am really good at hiring and identifying talent, and I spend a lot of time coaching and developing folks.
The second is to be realistic about the facts and circumstances of whatever situation you’re encountering. Context matters a lot. You can’t just make grand pronouncements about the future if you don’t really understand your current situation. Throughout my career, I was thrown into situations in which I knew nothing. So you develop skills around how to learn through ambiguity very quickly, how to understand the facts and circumstances that matter most, and how to separate the signals from the noise.
Third, we must be honest and transparent with everybody about where we are and where we’re trying to go. I never shy away from telling folks the truth and being transparent about facts and circumstances. First of all, I think it’s a lot easier when you’re telling everyone the same thing to get everyone on the same page. There’s no tax to pay that way, in the sense that there’s no confusion. That approach also helps you to rally teams.
Q. So, how do you hire? What qualities are you looking for?
A. If you assume they have the expertise we’re looking for, then I’m looking at leadership and intellectual curiosity because they trump everything else. Curiosity shows up when the candidate is asking you more questions than you’re asking them. That’s important because I want them to question things when they join us, including what the company can become five years from now.
In terms of leadership, there are people who figure that they are leaders because of a title. But the real leadership chops I’m looking for are how you show up when you’re not in charge. What happens then? For example, let’s say that you were part of a club in college, and you were surrounded by type-A folks who were jockeying for positions. Whether it’s through your inspiration, your charisma, your ability to organize—whatever the case may be—you were able to lead in that setting.
I like to work with people who get things done without taking credit for their efforts. There are just so many decisions that have to be made day to day, and you want folks who feel empowered and can get on with it. You lead because the times and/or the context warrant it.
Q. With all the coaching and mentoring you’ve done over the years, what themes come up most often when you’re giving people advice?
A. There are two big ones. Some people are not great at executive communication, which is a skill that I think can be trained. It’s about being concise—using just a handful of words to create impact—and finding the right attitude.
The other theme plays out at two ends of a spectrum. Some leaders are very hard-charging, and they sometimes don’t realize the repercussions of their style. I probably would have put myself in that category earlier in my career, and I certainly received a lot of coaching about that. I knew what I wanted. I could be very tough at times and harsh in my feedback—not nasty, but I wouldn’t sugarcoat things.
But not everybody receives that well. You’ve got to realize at some point that everybody has a different work style. Reflecting on my own experience, I’ve tried to feed that back to others. Everybody wants to move faster. But there are a few key times when it helps to move slower and to just take a breath and get some context and understand the other person.
On the flip side, I’ve also seen some great leaders who are overly quiet and just never take credit. Nobody like likes a prima donna or a blowhard. But if no one knows what you’re doing and contributing, that’s not great either, because then it’s kind of hard to advance in your career. It’s a delicate balance.
Q. This is your first CEO role. Was there any gap between the reality of the job and what you expected before you sat in the chair?
A. One is the constant context-switching. You go from meeting to meeting, switching quickly between different issues and audiences. When you’re leading an individual function, there’s more consistency during the day. But the real art is sitting back at the end of the day and reflecting how the dots connect among all these seemingly unrelated things. And then how do I apply those insights to the story arc for tomorrow, for next week, and then for the next year, as we’re trying to build the company?
The second one is that I’m the only person who has nearly perfect information for making decisions. There are times when I have to make a call that maybe my direct team, or all our 5,500 employees, won’t necessarily understand because they don’t have the same information that I do. As much as I try to be transparent, I usually have information that others don’t always possess for making quick calls. It’s not harder, necessarily, but it is very different.
Q. What were important early influences for you?
A. I grew up in Fort Wayne, Indiana. My parents immigrated from India, and they were very focused on education. I was also very focused on tennis. My parents pushed me, but it was never overbearing. It was always done in a very nurturing, loving way.
I caught the leadership bug in high school. By the time I was a senior, I was president of the student council, I was editor of the school newspaper, I was captain of the tennis team, and I was vice president of the PTA. I really found those experiences to be formative, and then I was also in a lot of leadership roles in college.
I also spent 22 years at GE, which was the ultimate learning and leadership factory. They were constantly putting you in new situations and challenges. If you performed, you were given a lot of leadership training.
Q. Given all the disruption and ambiguity of the last four years—and the growing expectations of CEOs—it seems like leadership has gotten a lot harder. How do you navigate all the complexity of the world today?
A. I don’t entirely agree because the things that have always mattered still matter. Yes, the hours are longer in these roles. A “work smarter” strategy doesn’t exist. You just have to put in the hours. But none of the other stuff matters if you’re not running a good business.
I’ve really tried to focus in my first year on just running the company. There’s always going to be noise from different dimensions, but the job is to run the company well. If you don’t do that, then you don’t have permission to have a perspective on all the other things. Other CEOs may have different views about that, but that’s my view.