Dan Rosensweig in “The Corner Office”

Dan Rosensweig

Adam Bryant conducts interviews of senior-level executives that appear in his “Corner Office” column each week in the SundayBusiness section of The New York Times. Here are a few insights provided during an interview of Dan Rosensweig, president and chief executive of Chegg.  To read the complete interview, please click here.

Bryant: Tell me about some important leadership lessons.

Rosensweig: One of the blessings I’ve had, really for my entire career, is working with founders of companies, whether it was Bill Ziff at Ziff Davis or with Jerry Yang and David Filo at Yahoo [click here http://topics.nytimes.com/top/news/business/companies/yahoo_inc/index.html?inline=nyt-org]. What I love about that culture is the energy, enthusiasm and the unbridled passion for what’s possible, as opposed to spending a whole lot of time trying to figure out the obstacles.

In Silicon Valley, if you spend a lot of time thinking about the obstacles, you’ll talk yourself out of everything, because the more you look at it, the less logical something sounds, since no one has done it yet. Founders simply ask what needs to be done and what’s the best way to do it. And that’s fun. It’s had a significant impact on the way I think, the way I lead, the way I manage, and the opportunities I seek out.

I like being surrounded by people who have very little fear and very little respect for the past — not in a negative way, but in a positive way. They appreciate everything that’s been done, but they constantly look for how to do it better. When you lead with what’s possible, and how you create value for people, it’s energizing. Being around that kind of energy and inspiration has allowed me to think bigger than I probably ever would have thought.

Bryant: You just started at Chegg this year. What was your first-day speech to the staff?

Rosensweig: I articulated why I came. What’s the opportunity we see? How do we want to define success? What’s the bigger dream? Many people work really hard every day, but they’re incrementalists. When you are in a growth company, you have to really open people’s eyes to the bigger possibilities, so they think differently. Once they understand how to define success and what their role is in success, they make better decisions and you can push decision-making down.

Stylistically, I try very hard to be descriptive about how we want to define success and not necessarily prescriptive on telling them exactly how we want to do it — because, frankly, many of them are a lot smarter than me at what they do.

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To read several of Bryant’s more recent interviews of other executives, please click here.

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