Never Duck Tough Questions, Says Drugstore.com's Chief 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 somebody's 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 didn't get the job. He was in love with the technology - I wasn't. He was not happy about having me come in over him. And he said, O.K., you're so smart - let's see you do it. Those were the days when the computers were shipped in, and they were not all put together. So you'd get these little chips, and you have to put them in the motherboard. And so he said, "Well, there's 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 don't 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 you're willing to learn, by asking for help. All those things earn you credibility, especially if the people who work for you feel like you're not going to sit back and take credit for what they do, and if they get a sense that you're 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. It's 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 don't have an M.B.A.; I didn't have a computer science degree. I have a music major. It's 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 proved that I could take on things I didn't know, and learn. I was willing to take risks, and I've always been a good synthesizer. And I was good at building relationships across the company. Q. So how did the transition go? A. The first year or 18 months were rough. I found out later that people were calling me the Ice Queen. And I was devastated. But it's because I felt like I had to be perfect - I couldn't show any vulnerability. I had a boss at the time who called me and said: "You know, I really believe in you. I gave you this job, I want you in this job, I really believe in you. You have to get better, though. You have to hire a coach, you have to improve, here are the things you have to do. But just having him tell me, I really believe in you, I want you in this job, it made me relax. It was like, O.K., I'm not going to get fired. He's going to give me a chance to learn on the job and so now I'm going to be a little bit more open and be willing to ask for help. Q. What other feedback did you get? A. So, I'm incredibly intuitive. As the technology was evolving and the business was evolving, it was very intuitive to me what we needed to do. But I was not very good about putting that into words. And so people wanted to know, where are we going? And I was absolutely convinced that it was going to be fine and we were going to figure it out. I'm very comfortable with ambiguity. But when you're leading a large organization, people are not as comfortable with ambiguity and they want you to be clearer about what's happening, where you're taking them. So I had to get better at communicating what I was thinking.