Lessons in Leadership in More Than 140 Characters: A Fireside Chat With Dick Costolo

I recently had the privilege of hosting Dick Costolo (@dickc), CEO of Twitter, at Andreessen Horowitz for a fireside chat. The event was the second in a series hosted by my firm aimed at strengthening the network of military veterans in Silicon Valley and expanding this network’s connection to the greater tech ecosystem. (As much as I’d love to claim that we precipitated the filing of Twitter’s S-1, this event and the S-1 occurring on the same day was purely coincidental.)

What is not a coincidence is how Dick’s leadership style and personality have transformed Twitter into one of the most successful technology companies of our time.  We had the opportunity to spend an hour together and here’s what I learned about leadership, culture and veterans at Twitter:

How has Twitter’s culture changed over your tenure as CEO?

Dick joked that when he came on board someone could have “thrown a hand grenade into the company at 5:30pm and only hit the cleaning people.” He started holding people accountable and rewarding projects where hard work was visible. He’d go into the office at 10pm, got to know the people who were around and then prioritized their projects. People quickly got the message.

Dick describes himself as a hands-on manager and expects the same from his team. He instituted a leadership class for all new managers, which covers topics like how to give transparent feedback (hint: don’t sugarcoat it) and how to deliver difficult news to your team, like your project getting axed (hint: don’t throw leadership under the bus). Of course, he also practices what he preaches, holding weekly 1:1 meetings with direct reports and remaining accessible to employees, regardless of rank.

Open communication is a nice objective, but how does Twitter do this given its size and scope?  

Dick admits open communication is difficult to maintain because of two opposing pressures: the first is the desire to limit communication to reduce the risk of leaks; the second is simply that everyone can’t know everything. Dick leans toward over-communicating and trusts management to synthesize relevant information, rather than publishing a transcript of every meeting. As the company continues to grow, synthesizing is increasingly important.

On leadership and veterans

Dick’s passion for good leadership is an anomaly in the tech industry. And I don’t think it’s a coincidence that Military Veterans are under-represented in a sector notorious for shunning authority.

Dick certainly made a strong statement traveling from Twitter’s HQ in San Francisco to our office in Menlo Park, in the middle of rush hour, to participate in our event for local veterans on the same day that Twitter filed its S-1. He clearly understands and appreciates the value that military talent can bring to the table (case in point: Russ Laraway, a rising star at Twitter, oversees their SMB unit and is a former Marine).

As for hiring vets, I couldn’t agree more with Dick when he said there are lots of roles in the technology industry for which the job requirements are a load of hogwash. For example, I can’t understand why engineering skills are part of the criteria for project management roles. Good communication skills and adherence to strict deadlines are not strengths for many engineers. But I can think of more than a few vets who would really shine with this responsibility.

On behalf of everyone at Andreessen Horowitz, I want to thank Dick and our veteran community for making this event the absolute highlight of my week!

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