Grokking the Connections: an Interview with O’Reilly VP Sara Winge

Grokking the Connections: an Interview with O’Reilly VP Sara Winge


Sara Winge is VP for O’Reilly Radar, the division of O’Reilly Media dedicated to anticipating emerging trends in technology. She’s also one of the pioneers of the unconference and her vision for participant-driven events like Foo Camp and Ignite strongly influenced the character of tech events over the past decade.

Winge exudes a sense of warm professionalism that draws out the best in people. She’s got a keen sense for what’s interesting, what’s going to be interesting in the future, and how to execute on it. We were delighted when she agreed to an interview about her habits.

You seem like the quintessential connector: you’re active in a variety of communities and frequently bring people together in interesting ways…and often in ways that require enormous amounts of energy and stamina. What habits do you cultivate day-to-day to support doing that?

In my first college Cultural Anthropology class, we studied the wildly diverse kinship systems that humans have concocted. I thought they were fascinating, and I grokked the principles that governed the various systems pretty easily. I suspect I just have a connector’s brain—I get a kick out of bringing people, information, and resources together so that stuff happens. Paying that kind of attention comes naturally to me, but I work to consistently do something about the opportunities for connection that I see—making intros, sending information to colleagues, maintaining a contact database that includes information about people’s interests and accomplishments. As for bringing people together, I’m just barely an extrovert. I’ve learned to turn on “gregarious mode” when I’m in social situations, and then to plan for quiet, solitary down time, to recharge.

As a manager you’re known for enabling your employees to do their best work, often under challenging circumstances. What habits do you think a person should cultivate if they’re interested in in being a good manager?

Listen, especially classic “active listening,” during which you focusly intently on what the other person is saying (and not on what you’re going to say next), then paraphrase it back to them. It’s a very good way to make sure you understand, and to help the speaker feel understood (which helps them relax and focus on what’s next).

Explain the “why” behind the “what”—with enthusiasm!—when you set direction or assign tasks. People are more likely to do a good job (and be able to solve problems that they encounter) if they understand the reason for it. And excitement is contagious, so get you some, even if you have to fake it ’til you make it.

Manage your stress. If you don’t, you’re likely to over-react, lash out, or withdraw at those tough times when you most need to be a leader. None of those reactions helps your employees do a good job. Figure out a practice that helps you physically relieve stress, and also something that strengthens your ability to know what you’re feeling and how you’re expressing it. For me, my daily yoga practice is enormously helpful on both fronts.

Hmmm, my responses are more about “how to be” than “what to do,” so I suppose that says something about how I try to be a good manager.

Are there any habits you’re trying to develop now? What motivated you to work on them?

Practicing piano. I played as a kid, and recently got an old beater upright. I’m motivated by my desire to make that sound, which I love, and by the fun of learning. It feels great when old knowledge and reflexes kick in, and when I make new connections about how the piano works, musically. My piano habit isn’t about productivity. It’s about carving out time to play, as in “do something for the fun of it,” as well as “perform on an instrument.”

Who or what inspires you? Whose habits would you like to know more about and why?

Zoe Keating is an inspiration. She creates absolutely beautiful music, and works really, really hard to create a life that allows her to keep doing that. She handles the business of music with skill and integrity—she uses social media skillfully without being the least bit smarmy, and is thoughtful and remarkably transparent about how she is paid for her work. And she keeps playing, no matter what.

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