“Did I tell you about the part where I got my photo taken with Denard Robinson?”
Dick Costolo, ’85, CEO of Twitter and former stand-up comedian, already had told the audience of his photo opp with the former U-M quarterback right before he delivered the 2013 U-M Spring Commencement address.
This was just one of many U-M stories he shared on April 23, at an event hosted by the U of M Club of Greater San Francisco. More than 180 people, including alumni from the U of M Club of Silicon Valley, were eager to hear from the man who stands at the helm of one of pop culture and information technology’s most influential companies. Alumni Association president Steve Grafton interviewed Costolo, who described the value of unconventional paths and leadership.
Growing up in a family firmly entrenched in the automotive industry, Costolo took the opportunity afforded by attending U-M to take an assortment of seemingly random courses. This approach solidified his mindset for the future: constantly moving out of his comfort zone and trying new things.
Although Costolo’s degree is in computer science, he took up acting and stand-up comedy in his senior year. After graduation, he left not for Silicon Valley, but for Chicago and the renowned Second City improvisational comedy troupe. Not only did he form lasting relationships with then-burgeoning performers like Steve Carell and Rachel Dratch, but he learned valuable skills that helped prepare him for the tech industry, adaptability and the ability to listen chief among them.
“No one would have said about the graduating seniors in 1985 in the computer science department, when you looked at the list and one of them was going to Chicago to try to get into Second City, ‘That’s the one…that’s going to go be the CEO of a big technology company 25 years from now.”
But that experience formed his outlook as he became one of the most recognizable business leaders in the country. One of Costolo’s most famous quotes concerns leadership: “As a leader, you need to care deeply, deeply about your people while not worrying or really even caring about what they think about you. Managing by trying to be liked is the path to ruin.”
This interview allowed him to contextualize that saying. “The first part of that quote is important. Because I used to just say, ‘Managing by trying to be liked is the path to ruin.’ …The way to deal with that is to always be forthright with everybody and make sure you’re always trying to get to the truth, irrespective of how much it might pain people to hear it right now. “But, I realized that the problem with just saying that was people interpreted that as ‘OK, Dick is saying I should be a jerk…’ No one wants to work for a jerk. I’m saying you have to care about your team, your people deeply, but not worry about ‘What do they think of me?’ Because you have to make decisions that are right for the company, and a lot of times people won’t like you…but, ultimately, they’ll trust you. And that’s what’s most important.”
In the past year, the San Francisco Alumni Club has hosted over 25 events related to community service, young alumni, social, and career/personal development events. “In the Bay Area we are trying to focus more of our efforts in the career space since there is a high level of interest from our alums,” said Halley Crast, president of the U of M Club of Greater San Francisco. “We were thrilled to host Dick Costollo to learn more about Twitter and his leadership style. We hope to continue engaging more and more alums in the Bay Area.”