Video highlights from our talk with Silicon Valley influencers

Recently we invited some of the top Silicon Valley summer interns to the new Asana HQ for dinner and a Q&A with Ben Horowitz (of Andreessen-Horowitz, Opsware, Netscape), Matt Cohler (of Benchmark, Facebook), along with my co-founder Dustin Moskovitz (Asana, Facebook). These guys are three of the mentors who have been most helpful to me in my own growth and decision-making, so it was a real honor to help share their collective wisdom with the next generation of technologists.

Our discussion covered a lot of ground, from the practical to the philosophic, including themes like leadership, entrepreneurship, decision-making, motivation, and success. These themes make for particularly exciting discussion since technologists today have astonishing leverage to tackle the biggest problems and take on bold missions.

We’re happy to share some video highlights from the event (you can check out the entire video here). We hope these will inspire and help guide anyone who strives to do great things with their talent, whether that’s joining an important effort already in motion or starting something that truly needs starting.

What should leaders work on?

Generally, “obsoleting” themselves. That is, every time you identify something that you’re doing that you could instead be mentoring someone else to do, mentor rather than falling into the trap of doing it yourself. With one huge exception: when you’re the absolute best person in the world to do it. Don’t fall into the Product CEO Paradox.

How do you balance long-term vision with short-term needs?

It’s a balance. At Asana, we have punctuated times of reflection, doing a full week of planning three times a year to look ahead to the next four months. This ensures we always have time to reflect on how we’re doing against our long-term vision and correct course, while also allowing us to put one foot in front of the other for most of the year.

How do leaders improve their skills?

Certainly by doing. But also through mindfulness, both as self-reflection and feedback from others. Asana, for example, provides opportunities for personal growth by facilitating peer reviews and peer-mentor relationships, and generally promoting an open and honest culture.

How do you create great culture?

Start early, be explicit, repeat your values all the time (not just mentioning them in onboarding), and walk the walk. At Asana, we wrote our values in the first week of starting the company. We list them on our website, explain how they apply in meetings, and routinely take the time to explain them. The result has been powerful: teams can resolve issues and diverging points of view quickly by having a compass. It took a lot of work, but now we collectively understand and embody our values.

Should you start a company?

There’s been an increasing fetishization of entrepreneurship over the last several years in Silicon Valley. While starting a company is often the best vehicle for bringing a new idea into the world, entrepreneurship for its own sake may be fracturing our collective efforts. This is discussed quite a bit in Wired’s article covering the event, which led to Dustin’s nuanced take on Good and Bad Reasons to Become an Entrepreneur.

We’d love for the discussion of these themes to be an ongoing and evolving conversation, so let us know what you think in the comments!