New York Times Interviews Rosensweig ’83 – Hobart and William Smith Colleges \
The HWS Update

New York Times Interviews Rosensweig ’83

An interview with Daniel L. Rosensweig ’83, who joined Chegg as president and CEO earlier this year, ran in The New York Times, July 9, 2010. In the interview, Rosensweig discusses leadership, his first days at Chegg, and many aspects of his leadership style.

Prior to joining Chegg, Rosensweig was president and CEO of Activision Blizzard’s Guitar Hero franchise. His accomplished professional life has been focused in media communications and Internet industries, including roles as Chief Operating Officer of Yahoo!, President of CNET, and CEO of ZDNET. While working in those roles, he created internships for HWS which provided the opportunity for a number of students to work directly with him and offered them job opportunities following graduation. He dedicated the Rosensweig Learning Commons at HWS in 2008.

During his time as a Hobart student, Rosensweig was a political science major as well as a member of the Kappa Sigma fraternity. He studied abroad in London. The full interview follows.

The New York Times
Remember to Thank Your Star Players
Adam Bryant • July 9, 2010

This interview with Dan Rosensweig, president and chief executive of Chegg, was conducted and condensed by Adam Bryant. Chegg rents textbooks online and by mail.  
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.
Q. You just started at Chegg this year. What was your first-day speech to the staff?
A. 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.
Q. So how did you define success with the group?
A. One of the things you just have to appreciate is that nobody has all of the answers to anything, particularly in a growth company that’s breaking new ground. I think having a lot of humility is important in a C.E.O. role. You have to have confidence, but also humility. You have to know that you can pull off what you say you are going to do, but you really need to solicit opinions from inside the company and, frankly, from outside the company.
Inside the company, we spent the first month with the management team and we asked every one of them to come in with the 10 most important priorities that they thought that the company should have and order them in terms of importance.
It took about a month to debate these points, to articulate these points, to have people have their say. What I did was coach them to communicate them clearly, as opposed to saying we should do this, this or this.
These sessions go three or four hours once a week, and people come back and then you assign an order toward the end. Then you define success and reportable metrics, put them together and the team votes and agrees. And it’s not just having 10, it’s having them in the right order.
What you get is a much more focused company with a clear definition of success, and a real enthusiasm from people knowing what to do. One of the biggest problems employees have is when management fails to communicate to them what’s a good decision and what’s a bad decision. Where should they spend their time?
So we say, if you are not doing something that contributes to one of these 10 priorities, stop doing it. If your manager tells you to keep doing it, see me. And it’s amazing how people rally behind it. And it’s fun.
Q. How do you run meetings?
A. Probably the biggest lesson I’ve learned over the past couple of years is to be present, because it’s so easy to get distracted in the worlds of BlackBerrys, iPhones, Twitter, Facebook and 500 e-mails a day.
So with our management team, when we’re in a meeting, it starts on time, it ends on time, no technology. It’s just, let’s stay focused, and we have a much more healthy conversation. People really listen and contribute and we move on. It works well in your personal life as well – wherever you are, be all in.
Also, one of our rituals that we start every executive staff meeting with is sharing one personal and one professional thing occupying our minds. The goals are for the team to get closer, build trust and to help understand anything that might be distracting us.
I think the way to get employees all in is to listen to them. Every six weeks, I meet with small groups by their function. The rules are, it’s their meeting. They can ask anything, they can communicate anything as long as it’s about how to improve Chegg’s business or our relationship with our customers.
Q. What are some other leadership lessons for you?
A. One inflection point was from selling advertising. You learn that the money doesn’t come to you – you have to go get it. If you sit back and wait, you are going to be waiting a long time. So you have to go to where people are and you have to listen. You have to make sure you are able to learn to communicate differently with different people. You have to study and prepare. Hopefully it will look effortless, but a whole lot of effort goes into preparation.
Q. How would you say your leadership style has evolved?
A. It’s more being present and overcommunicating. I try to be more descriptive, as opposed to prescriptive. And I want to create a culture where the best performers don’t have to work hard to let you know they are performing well.
We spend a lot of time in all of the companies that I run or work in making sure we know who the star performers are, rather than forcing them to send an e-mail or come see you or brag about themselves, which they are really uncomfortable doing.
I call them and say: “How are you? I understand that you are a star performer. You’re doing great and here are the two or three things that you are doing. You are knocking the cover off the ball. I just want to say thank you and let you know you have an open dialogue if there is other stuff that you think we need to be doing.”
So I do a lot more of that because I know I would appreciate it. I’ve learned that they appreciate it because they then can focus on doing the job and not worry about whether people are noticing.

Q. Let’s talk about hiring. What do you look for? What questions do you ask?
A. By the time they get to me, they’ve been vetted in enough ways that I know functionally they should be able to do the job. So I spend a lot of my time doing two things. I ask them very few questions, mostly around, how do they approach a situation? How do they personally define success for themselves? What do they want for this company? What attracts them here? What do they need to be successful? How do they want to be managed? And then a lot of the conversation stems from there.
And then I really turn it over to them and say: What questions do you have? What do you think you need to know to decide whether this is the right environment for you? Whether we can utilize the talents you bring to bear? Whether we are the right place at this moment in your career? And that dialogue generally leads to a really great outcome.
Q. What are the most important qualities you’re looking for?
A. One is attitude. Some people spend a lot of time focusing on how difficult things are. You don’t get jobs like these unless the situations are difficult. So I like to hear people talk about how they love to approach a challenge, and that’s the thing that gets them excited.
I’m also looking for people who appreciate the fact that the definition of success is the company and not an individual. I’m looking for people who can communicate. I mean, quite frankly, most of the things that break down when you are running a business are transparency and communication. If you have people who are reluctant to share information with their peers, particularly in a very small company, it’s not a healthy dynamic.
And I look for people who generally, as I said earlier, think big, want to achieve big, aren’t afraid. They have that level of humility to know it’s entirely possible we may not succeed, but, man, it’s worth trying.

Q. And if you could ask somebody only one or two questions in a job interview, what would you ask?
A. What matters to you in your professional career in the next five years? And the second would be, what do you think you need to be successful in that goal?

Q. What about feedback? What’s your approach to difficult conversations?
A. I have found in my career that once you know that someone isn’t doing the things that they need to do or they are not going to be successful, then every day you wait it’s really your fault rather than theirs. And the first thing I ask is, did I ask somebody to do something that they weren’t capable of doing?

There’s nothing worse than somebody you like and respect doing something you know they can’t be successful in and knowing that you were the one that did that to them. I try very hard to understand, before I approach the person, why they may not be successful in that particular role. Because, normally, the people I work with have been extremely successful in their careers, so the expectation is that they are going to be successful.
But the longer you wait, the worse it gets. Very few problems correct themselves. And the philosophy of sticking your head in the sand and hoping it goes away has never been that effective for me. So you sit down and have an honest conversation. I think people respect honesty without attitude.
Q. And what about getting feedback?
A. I ask employees, “If you had my job, other than giving yourself more vacation and a raise, what’s the first thing that you would do that you don’t think we’re doing yet?” I try to make it comfortable when you do the review process by asking people: What do you need more of from me? What do you need less of from me? What is it that I’m doing that you would like me to stop doing completely? And what is it that I’m not doing enough of that you’d like some more of? From there, it becomes a much more comfortable conversation.


Q. Tell me about some important leadership lessons.
A. 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. 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.