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Twitter CEO Dick Costolo: What I've Learned

The captain of the world's most ubiquitous social media platform talks leadership, disruption, and why he follows Mia Farrow.
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There are certain things you’d expect of the CEO of the fastest growing, most disruptive, 140-character communications platform in the world. For starters, you’d expect him to spend a lot of time thinking about the future, much of which his company is driving. You’d expect him to be scrambling to keep up with explosive growth. You’d expect him to be pithy: anyone viewing the world through 140-characters updates ought to be pretty good at concise expression. And you’d expect him to be surprised by nothing.

Well, three out of four isn’t bad.

Dick Costolo’s path to CEO of Twitter has actually been full of surprising twists, and the company he runs has been a continual source of amazement--to him as well as everyone else. Costolo came to Twitter in 2009 as COO and took over as CEO, supposedly temporarily, when co-founder Evan Williams went on paternity leave. (Moral: Don't go on paternity leave.) He was interviewed this week by Jason Mendelson of the Foundry Group at the annual meeting of the National Venture Capital Association, the venture capitalists’ trade group. The following is an edited version of his remarks.

On his not exactly straight career path

 Costolo was a classic engineering geek at the University of Michigan. To fill out his degree requirements in his senior year, he began taking acting classes--and wound up stage-struck. On graduation, he spurned tech job offers to head for Chicago and the famous improv comedy troupe, Second City, where he worked alongside, among others, a young Steve Carrell.

Acting is a hard profession. After Second City, I was getting auditions for things, but I didn’t get any parts. I guess in retrospect that was all part of my career strategy.

What launched me toward Feedburner? Well, the Internet happened. When I saw Mosaic, I thought, “I gotta do this.”

I founded and sold a few companies. Feedburner was my fourth. [It sold to Google in 2007 for a rumored $100 million-ed.] Carrell and I were recently reviewing where everyone in Second City with us had ended up. Steve turned to me and said, “Too bad things didn’t work out for you.”

But I do think the theater background has helped. One of the things that I think I do well as a CEO is that I’m present. When I’m with my employees, I’m there in the moment. That’s something you learn in improv, where what’s here right now is all that matters.

 On starting up outside Silicon Valley

 Taking the helm of Twitter meant moving to Silicon Valley, which Costolo views as a mixed blessing.

 It's absolutely possible to do start ups outside of the Valley. I loved Chicago for the same reason Warren Buffett likes Omaha. When you’re outside the Beltway, as it were, you are spared a lot of distractions. You’re not always being told “This or that is a great deal. Everybody who knows anything is getting into it.” I remember one can’t-miss deal in particular. The company raised a lot of money and went out of business six months later. There’s a benefit to not having to deal with that stuff.

 Another thing: The competition for developer talent is really tough in the Valley, It’s remarkable how much attention you have to devote to making sure you have the most appealing work environment. It’s distracting always to have to worry that if my company doesn’t have the best burritos all my developers are going to leave.

 In the midwest there’s not so much competition. You should think about the work environment somewhat, but you can focus less frequently on the quality of the  burritos.

 On management and leading

Twitter had 50 employees when Costolo joined. It now has 2,000. Not surprisingly, Costolo spends a lot of his time recruiting, hiring and trying to maintain a coherent company culture.

 I try to spend a lot of time with people outside my direct reports. The view from the top is totally distorted. If you only spend time with your directs, you have no perspective on what's really going on.

 For example: One time an employee came to me and asked whether employees should be having one-on-ones with managers or not. His manager where he used to work in the company had one-on-ones every week; the manager in his current assignment didn’t believe in them.

 That’s when I realized we had no consistent management style at Twitter. People just carried over what they had learned the last place they worked. They’d just think, “This is how we did it at Google, or at eBay.”

 So I created a management course, and I teach it myself because I want my managers to realize how important it is to me that they manage correctly.

 One thing I try to impress on all managers is that they make sure everyone on their team understands what they understand. When that happens, office politics kind of drift away. You don’t have people saying, “What are those guys doing over there in that group? They goof off and don’t work the same hours we do." You don’t have people saying that kind of divisive thing.

I also try to set an example by telling the staff when I screw up. That is super-important because it empowers everyone to say to me or to their manager, “I screwed up. What should I do?” I want everyone on my team doing that and not covering up mistakes and not getting help they need.

 A lot of young managers think they have to be omniscient. They think, “I’m the manager, I’m supposed to know that.” I tell them, “It’s not your job to be omniscient. It’s not your job to make all the decisions. It's your job to make sure the right decisions get made.”

 Remember, as a manager, you’re totally transparent. If you’re making decisions about things you know nothing about, your team will see that and they will realize you’re going to make their life miserable. You need your team’s trust and you build that trust by being honest.

 On Twitter’s role in change--and culture

 One of the things that amazes me about Twitter is the way it utterly eradicates artificial barriers to communication. Things like status, geopolitics and so on keep people from talking to one another. Those go away in Twitter.

You see exchanges that would never happen anywhere else. You’ll see a woman in Canada direct a question to Paul Kagami, prime minister of Rwanda and get an answer. I remember seeing a rapper bragging that making the first million is the hardest. Within seconds T. Boone Pickens tweeted back that the first billion is a lot harder.

But my favorite Tweet started with Sara Sliverman. She was saying that if being around your family annoys you--this must have been during the holidays--just pretend you're in a Woody Allen movie. Mia Farrow  tweeted back. "I tried that, and it didn't work." I followed Mia Farrow immediately.

Last updated: May 17, 2013

ERIC SCHURENBERG | Staff Writer | Editor-in-chief, Inc.

Eric Schurenberg is the president and editor-in-chief of Inc. Before joining Inc, Eric was the editor of CBS MoneyWatch.com and BNET.com and managing editor of Money Magazine. As a writer, he is a winner of a Loeb and a National Magazine Award.




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