What I Did for Prada

If you’re going to do whatever it takes to make it to the top, the least you deserve is an expensive pair of Italian high-heel open-toe shoes.

I will admit it: There have been times when I have undermined women in the workplace.

Early in my career, I learned the rush of being the only woman in a meeting. When I started in the CD-ROM business, working with rock groups, I wore jeans and a T-shirt to trick the men into thinking I was one of them. Then I realized that I was benefiting from being the only woman: My voice stood out. My point of view stood out. My legs stood out if I wore skirts, so I did.

As the CD-ROM industry blossomed into something totally inappropriate for the music industry, I sat in meeting after meeting with tables full of men. And I made enough money to buy some Prada shoes for New Year’s Eve.

When the Internet came, I doubled the male-to-me ratio — and I doubled my salary.

And then I did what all Internet professionals do when they double their salaries in six months: change jobs to do it again.

At my new company I built my team from scratch. And I found myself hiring a lot of women, but then, one day I stopped. I stopped hiring women because I thought I’d look less powerful to other people in the company if I ran a department full of women. Instead, I ran an affirmative-action program for tall, good-looking men. The interviews went on forever because phone screening for good looks had bad results, and I ended up scheduling interviews for everyone who applied. You might think this would make for an ineffective team, but not on the Internet: In six months, I doubled my salary.

Now, 10 pairs of Prada shoes later, I am at the semi-top of a semi-large Internet company, and I am being groomed to take over. As a COO who has ripped through the corporate ranks at Internet speed, my business-etiquette skills are about five bonus plans behind my operations and planning skills. For example, I go out for lunch and order coffee and dessert instead of a main course so I don’t fall asleep during the non-business part of the conversation.

My boss comes from a time when etiquette was everything and secretaries did all the work. I know this because he has two lunch dates every day with people whose names I see in Newsweek, and his secretary opens his Excel files because he doesn’t know how. My boss accompanied me to a convention where he made deals and I practiced approaching people I didn’t know, but mostly I just ate a lot of pastries. My boss took a break from his amazingly fluid networking to tell me that there are companies trying to talk to him about sequences and he told everyone that he’d send me over.

“Sequel,” I said. “Not sequences.”

“Whatever,” he said. “I don’t know that Internet stuff.”

He also stopped by the pastry table to tell me that we would be sitting at separate lunch tables.

I told him, “I’m already full.”

He told me, “You need to learn how to leverage a power lunch.”

My boss gave me some tips: “Ask people about themselves. People like to talk about themselves. Figure out why they’ll be interested in your company. Be a good listener.”

I had visions of a used-car dealership.

I told myself this was a good opportunity. My boss was trying to help me. I told myself I would never be able to run my own company until I could be the dealmaker that he was. I asked him how he decides where to sit when he walks into a room.

He said he looks for a chair next to a good-looking woman. He said it’s not that he wants to seduce her or anything; he just knows that women think he’s cute, so they’ll be most likely to talk to him. And besides, my boss said, men look better next to good-looking women.

My jaw dropped. I gathered thoughts for a speech on respect in the workplace. I weighed the idea of focusing on his insecurities to heighten my points. Then I remembered the all-male fiefdoms I’ve built during my Internet life. My jaw closed. Then it opened again when I said, “If there were a seat next to me, would you take it?”

Posted by on October 16, 2000
Deborah Swan