Confessions: Anna Wintour's Ex-Assistants

"She's always talking to you. It would just be constant emails, she was just firing away all the time."

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Anna Wintour’s former assistants often say that the job is like the movie The Devil Wears Prada. Yes, there are differences — Anna doesn’t throw her coat and handbag at them each morning when she gets there — but she does have a habit of checking out what they’re wearing and telegraphing, through an unspoken reaction, what she thinks of it.

When I was writing ANNA: The Biography, I knew talking to former assistants (she typically had two or three at any given time over the course of her Vogue editorship) would be crucial given that many people only know about Anna as the inspiration for Meryl Streep’s Miranda Priestley character. Though this group was perhaps more skittish than other sources to discuss Anna with a journalist, a number of them were happy to talk. I was utterly fascinated by their stories and insights into how she operates as an executive. Here is a compilation of some of what three of them said. (Note that some of this reporting was done by the utterly brilliant Raquel Laneri, who helped me with research for the book and about whom I cannot say enough good things.) Identities have been hidden for reasons that are likely obvious. Of course, you can learn more about Anna and her assistants in ANNA: The Biography.

How early did you start each day?

Assistant A: The very beginning of the day is essentially setting up her office. So the reason you come in at 7:30 is because she comes in before 8:00. She might come in anywhere from 7:45 to 8:00. So the 7:30 to 7:45 gives the second assistant the opportunity to gather all the things she'll need for the day – printing out or setting up her schedule, listening to the voicemails and leaving out any messages that might be urgent for her to respond to in the morning, making sure all the periodicals and newspapers that she'd want to read are set out. And then, depending on when she is definitely coming in, potentially getting her coffee and breakfast.

Assistant C: You'd get into the office around 7:30, and then you have to respond to any emails that Anna sent over the night before. Then get your own work done. Each assistant was responsible for their own set of things. Whenever she wasn't in the office was when you were able to get those things done. Then she'd come into the office. It was very much like in The Devil Wears Prada when they're all like, "She's coming!" I was always scrambling to get ready. You're literally putting things away, making sure everything looks great. Then once she's in the office, it was kind of like, whatever she asked, you do it.

What were some of her more challenging requests?

Assistant B: Oh my God. [Requests came in] day and night. I had dreams – I would wake up in the middle of the night and think, Do I have to check my email? She's always talking to you. It would just be constant emails, she was just firing away all the time. It would literally range from everything — like, “I need to see this person,” “get me on the phone with that person.” When she was in the office, she would email, “Coffee, please.” Literally just that. We would always have one for her in the morning before she got into the office, and then maybe like three to four on average [after that].