HBR: What experiences have had the greatest impact on your career trajectory?
John McCain took a big chance on me when he named me as his national communications director at a pretty pivotal moment in his primary campaign. We were dropping like a rock in the polls, running out of money, and at that point a number of my friends had left the campaign. When McCain offered me the job, I doubled down. I also grew quite a bit working for Mike Bloomberg in his final campaign for New York mayor, alongside Hillary Clinton’s former communications director, Howard Wolfson—in no other world would Howard and I have come together on a campaign but for Mike Bloomberg. There I learned real lessons about understanding other people’s perspectives. I’ve had the chance to work for, and with, some real greats, from McCain to Bloomberg to Eric Schmidt at Google. Early in my career, an adviser to Rudy Giuliani gave me some great advice: “Act like a sponge and soak it all up.” That always stuck with me.
What obstacles have you had to overcome on your way up?
Well, I moved 10 times in 10 years. I’ve become a very skilled packer. You know, politics can be a bit lonely at times. My friends were living out their twenties in New York and LA and San Francisco, and I was packing up for the next race in the swing states. I had a lot of fun, and certainly it was the right decision for my career, but personally, it wasn’t always the easy decision.
You’ve advanced very quickly. Why do you think that is?
I think life generally rewards risk takers, and I’ve always been willing to take risks and move for the right opportunities. Fearlessness is important, too. There’s only so much training you can do before you go for a live interview on TV or give advice to a politician. I think the best way to learn is to just go for it. I’ve always been confident—confidence is different from arrogance—and I’ve always felt like I could do anything that I put my mind to. Work ethic matters a lot, too. I learned that from my parents early, early on. They modeled that behavior for me, and it certainly stuck with me.
How has your youth helped or hurt you along the way?
I don’t really think of it as a “young” or “old” thing. People are simply more or less experienced. As a manager of people who are my peers, I’ve always tried to remember that. And at this point in my career, I’m fortunate to have had a lot diverse experiences. Certainly there were times, especially in politics, when I was aware that I was the youngest person in the room by a long shot. I remember once during the ’08 Campaign, when I was tapped to give a “state of the race” update to then–Vice President Cheney and a number of the major donors and party big wigs who were in this long, wood-paneled room. And I was not only the youngest person in the room, but the youngest person by about 25 years. So of course, in those moments, you can be intimidated. But I’ve learned to conquer fear by working harder and being relentlessly prepared. When I’ve done my homework and researched my arguments, I’ve stayed confident. And when I’ve had setbacks, I’ve learned from them and moved on. You just have to keep going.
Have your experiences differed markedly from those of your male colleagues?
I don’t think so. At every step in my career, I have had really fantastic role models. In my first job in politics, I worked for a wonderful, strong woman who taught me so much about how to conduct myself in a professional environment. And the same thing goes for when I worked for Bloomberg, and now for Google. A great female executive at Google is my mentor and my boss. I think it’s really important for women to have other great women to turn to when the sea gets rough.
Were there any key “crossroads” moments in your career, when you could have seen yourself taking a different path?
Well, sure. I could have stayed in politics, which was interesting and exciting to me. After the McCain campaign, I briefly thought about running for office myself. Thank goodness I had the foresight to recognize that was probably not a great idea for me at the time. Public service is really important, but you need real life experience in order to contribute in a meaningful way. The Google experience—the Google opportunity—was a real curveball. Working in tech was not something I had previously considered. It’s been a great ride, and a profound learning experience.
John McCain took a big chance on me when he named me as his national communications director at a pretty pivotal moment in his primary campaign. We were dropping like a rock in the polls, running out of money, and at that point a number of my friends had left the campaign. When McCain offered me the job, I doubled down. I also grew quite a bit working for Mike Bloomberg in his final campaign for New York mayor, alongside Hillary Clinton’s former communications director, Howard Wolfson—in no other world would Howard and I have come together on a campaign but for Mike Bloomberg. There I learned real lessons about understanding other people’s perspectives. I’ve had the chance to work for, and with, some real greats, from McCain to Bloomberg to Eric Schmidt at Google. Early in my career, an adviser to Rudy Giuliani gave me some great advice: “Act like a sponge and soak it all up.” That always stuck with me.
What obstacles have you had to overcome on your way up?
Well, I moved 10 times in 10 years. I’ve become a very skilled packer. You know, politics can be a bit lonely at times. My friends were living out their twenties in New York and LA and San Francisco, and I was packing up for the next race in the swing states. I had a lot of fun, and certainly it was the right decision for my career, but personally, it wasn’t always the easy decision.
You’ve advanced very quickly. Why do you think that is?
I think life generally rewards risk takers, and I’ve always been willing to take risks and move for the right opportunities. Fearlessness is important, too. There’s only so much training you can do before you go for a live interview on TV or give advice to a politician. I think the best way to learn is to just go for it. I’ve always been confident—confidence is different from arrogance—and I’ve always felt like I could do anything that I put my mind to. Work ethic matters a lot, too. I learned that from my parents early, early on. They modeled that behavior for me, and it certainly stuck with me.
How has your youth helped or hurt you along the way?
I don’t really think of it as a “young” or “old” thing. People are simply more or less experienced. As a manager of people who are my peers, I’ve always tried to remember that. And at this point in my career, I’m fortunate to have had a lot diverse experiences. Certainly there were times, especially in politics, when I was aware that I was the youngest person in the room by a long shot. I remember once during the ’08 Campaign, when I was tapped to give a “state of the race” update to then–Vice President Cheney and a number of the major donors and party big wigs who were in this long, wood-paneled room. And I was not only the youngest person in the room, but the youngest person by about 25 years. So of course, in those moments, you can be intimidated. But I’ve learned to conquer fear by working harder and being relentlessly prepared. When I’ve done my homework and researched my arguments, I’ve stayed confident. And when I’ve had setbacks, I’ve learned from them and moved on. You just have to keep going.
Have your experiences differed markedly from those of your male colleagues?
I don’t think so. At every step in my career, I have had really fantastic role models. In my first job in politics, I worked for a wonderful, strong woman who taught me so much about how to conduct myself in a professional environment. And the same thing goes for when I worked for Bloomberg, and now for Google. A great female executive at Google is my mentor and my boss. I think it’s really important for women to have other great women to turn to when the sea gets rough.
Were there any key “crossroads” moments in your career, when you could have seen yourself taking a different path?
Well, sure. I could have stayed in politics, which was interesting and exciting to me. After the McCain campaign, I briefly thought about running for office myself. Thank goodness I had the foresight to recognize that was probably not a great idea for me at the time. Public service is really important, but you need real life experience in order to contribute in a meaningful way. The Google experience—the Google opportunity—was a real curveball. Working in tech was not something I had previously considered. It’s been a great ride, and a profound learning experience.
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