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What I Learned From Anna Wintour

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For eight months, from January to August of 2007, I filmed with Anna Wintour and her team at Vogue as they created the September 2007 issue of the magazine. Known throughout the fashion industry (with and without irony) as The Bible, this particular issue was 840 pages long and weighed in at just under five pounds. Now safely identified as a relic from another era (oh how long ago that was), this particular edition of Vogue turned out to be the single largest issue of a magazine that has ever been published.

During those eight months, my crew and I shot over three hundred hours of footage, the result of which is the feature documentary The September Issue, which premiered at the 2009 Sundance Film Festival and has grossed more than $8-million in theaters around the world. This coming Tuesday, February 23, the DVD of the film, along with a separate DVD's-worth of deleted scenes and other goodies, will be released. The occasion has given me the opportunity to reflect back on the experience of shooting the film.

While making The September Issue, I observed Anna Wintour day-in and day-out as she single-handedly commanded the $300-billion global fashion industry. In a business where last week's fashion shows are already old news, she has been at the top of her field (and the top of her game) for two decades and counting. Shortly after we began filming, I observed to a friend who asked what it was like to watch Anna work, "Well, you can make a film in Hollywood without Steven Spielberg's blessing, and you can publish software in Silicon Valley without Bill Gates' blessing, but it's pretty clear to me that you can't succeed in the fashion industry without Anna Wintour's blessing."

I was being dramatic, of course, and all rules have their exceptions, but the point was clear -- if you're going to get ahead in fashion, you'd best have Anna on your side. As viewers of The September Issue have seen, even Burt Tansky, the enormously powerful CEO of Neiman Marcus, turned to Anna for help in speeding up delivery of fashion product to his stores. Her absolute power over a single industry reminded me of Mike Ovitz when he did, in fact, rule Hollywood and all deals seemed to somehow pass through his desk. Or of Frank Rich when he was the Head Drama Critic for the New York Times and his review alone determined a new production's fate -- advance sales, other critical responses and celebrity names on the marquee be damned.

During those eight months in 2007, I was given complete access to the process of creating Vogue. At the end of each day, Anna's assistant would email me her schedule for the following day and my crew and I would plan which of her meetings to film. For me, just reading her daily schedule was startling -- the parade of editors, stylists, designers, writers, models, art directors, photographers, retailers, filmmakers, actresses, socialites, moguls, politicians and even the occasional tennis player was head-spinning. As Vogue's then-publisher Tom Florio says in the film while discussing her legendary inaccessibility, "She's busy." But regardless of how busy Anna was, what struck me most through the shoot was that she always kept her team moving forward and that every month, like clockwork, another issue of Vogue hit the newsstands.

What is her secret? How does Anna Wintour do it? Of course my answer is, take a look at the film and you'll see it all. In the meantime, though, here are Four Lessons about Management that I learned from Anna Wintour while making The September Issue:

Lesson 1: Keep Meetings Short

I work in the film business, where schmoozing is an art form, lunch hour lasts from 12:30 until 3, and every meeting takes an hour whether there's an hour's worth of business or not. Not so at Vogue, where meetings are long if they go more than seven minutes and everyone knows to show up on time, prepared and ready to dive in. In Anna's world, meetings often start a few minutes before they're scheduled. If you arrive five minutes late, chances are you'll have missed it entirely. Imagine the hours of time that are saved every day by not wasting so much of it in meetings. It's not by accident that during the final scene of The September Issue, Anna Wintour is in her office alone, waiting for a meeting to begin, and we hear her voice call out, "Is anyone coming to this run-through except for me?"

Lesson 2: Trust Your Instincts

One of my favorite moments in the film is a short scene early on, in which Anna is reviewing some boards with Fashion Market/Accessories Director Virginia Smith. Anna rifles thorough the boards, saying "yes" and "no" as she goes. It's quintessential Anna Wintour: knowing what she wants, making clear decisions and moving on. I once asked her about her creative process and she answered with some frustration. "I can't explain it," she said, "I just do it." To me it was all very telling -- here is someone who knows that her gut instincts have gotten her to where she is, so she listens to them, trusts them and isn't afraid to put them on the line.

Lesson 3: Surround Yourself with Great Talent

The September Issue is really a film about Anna Wintour's relationship with long time Vogue Creative Director Grace Coddington. The two of them have been working together for two decades and the extraordinary symbiosis between them has left an indelible mark on the fashion industry. But if Anna's collaboration with Grace is remarkable (and it is), equally impressive is the astounding level of talent represented by all of the other senior members of her team at Vogue. Seriously, filming The September Issue was like walking into the clubhouse of the 1927 Yankees -- every one of these people (Andre Leon Talley, Tonne Goodman, Sally Singer, Virginia Smith, Phyllis Posnick, Hamish Bowles, Elissa Santisi, Alexandra Kotur and on and on) is a future Hall of Famer. The lesson is clear -- Anna Wintour knows that you're only as good as the people who work for you, that bad leaders are threatened by strong team members, and that success comes from surrounding yourself with the most talented people you can find.

Lesson 4: Don't Look Back

If I had to choose a statement that summarizes Anna's management style, it might come from her own comment at the end of The September Issue, when she says, "Fashion's not about looking back. It's always about looking forward." Or it might come from Karl Lagerfeld whose favorite expression, Anna once told me, is "On to the next."

In recalling these two statements, I'm reminded of an early morning at the Vogue offices several months into the shoot. The night before Anna had hosted the annual Costume Institute Gala -- the massive charity event and celebration for the Costume Institute of the Metropolitan Museum of Art. The event had featured a who's who guest list of luminaries from the fields of fashion, art, film, music, business, politics and society, all dressed by the world's leading designers in clothing inspired by the seminal fashion figure Paul Poiret. Hosted by Anna, Cate Blanchett and Nicolas Ghesquière of Balenciaga, the guests had partied vigorously in the Met's Charles Engelhard Court, serenaded by recent Vogue cover girl Jennifer Hudson who had only weeks earlier won an Oscar for her performance in Dreamgirls. The Gala carried on until well after midnight and the guests then gathered at after-parties around Manhattan until dawn. After six months in the planning, with more than $5-million raised for the Met, there was no way to characterize the evening other than as a complete triumph.

The next morning, my crew and I were in the offices of Vogue shooting a long-planned meeting on the publishing side of the magazine that began at the ungodly hour of 8:30am. Once the meeting started, I took a walk down the empty Vogue hallways, where I noticed that Anna had just arrived. I complimented her on the success of the Gala, and thanked her for having included me in the festivities. "Were you happy with how it turned out?" I asked. She smiled and I knew that she was proud of what she had accomplished. But her words had another message. "I'm just happy that it's over," she said. "Now we can all get back to work." And that, to me, is Anna Wintour's management philosophy in a nutshell: Always move forward. Don't dwell on the past. Life is short and there's lots to get done.

Or, as Karl Lagerfeld would say, "On to the next."

Clip: Anna Wintour Discusses Political And Fashion Coverage In The Magazine With Her Editors

R.J. Cutler is the award-winning director and producer of The September Issue, currently available as a 2-disc DVD featuring Cutler's commentary and 90-minutes of deleted scenes. Customers who purchase at Barnes & Noble will receive and additional DVD with Cutler's 30-minute documentary short, The Met Ball.