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Unformatted text preview: July 17, 2010 Never Duck the Tough Questions By ADAM BRYANT This interview with Dawn Lepore, chairwoman and chief executive of Drugstore.com, was conducted and condensed by Adam Bryant . Ms. Lepore is also a director of eBay and The New York Times Company . Q. Do you remember the first time you were somebodys boss? A. I was hired at Schwab in 1983 to be the manager of the information center. The person who wanted the job was way more technical than me, and that was the reason he didnt get the job. He was in love with the technology I wasnt. He was not happy about having me come in over him. And he said, O.K., youre so smart lets see you do it. Those were the days when the computers were shipped in, and they were not all put together. So youd get these little chips, and you have to put them in the motherboard. And so he said, Well, theres a shipment here for you. So I go to the dock and there are all these boxes with computers in them. I put together 30 computers. After the guy saw me do that, at least I had a little bit of his respect, and we went on to have an O.K. relationship. Q. What was the lesson for you? A. Every time you take on a new role, building credibility is incredibly important. I dont think you do it by being smarter than everybody else or knowing more necessarily than everybody else. I think you do it by rolling up your sleeves, by showing commitment, by proving that youre willing to learn, by asking for help. All those things earn you credibility, especially if the people who work for you feel like youre not going to sit back and take credit for what they do, and if they get a sense that youre going to support them, help them grow. Q. Other key moments like that? A. My biggest promotion was moving into the head technology role at Schwab. Its an important job at Schwab; it reports to the C.E.O. I was 39, and it was very unusual to be a woman running technology. I remember the person who promoted me said that he had several board members call him and say: Why did you do that? That was a really dumb decision, putting a woman in charge of technology. Q. Just because you were a woman? A. There were no women C.I.O.s back then. And I dont have an M.B.A.; I didnt have a computer science degree. I have a music major. Its a very unusual profile to be in that position. The reason I got the job was that I took on really tough assignments, things nobody wanted, things that people thought were kind of impossible or thankless tasks. So I tough assignments, things nobody wanted, things that people thought were kind of impossible or thankless tasks....
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- Fall '08