Never Duck Tough Questions, Says Drugstore.com’s Chief

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…

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