When it comes to taking risks, Anna Wintour is a firm believer in provoking a conversation, having a strong point of view, trusting your own instincts, and learning from your mistakes. Here are five tips from Anna Wintour on making decisions and taking risks.
Expect the unexpected.
Anna Wintour’s first American Vogue cover was very different from those that preceded it: The photo crop was wider; the model was not looking directly at the camera; the clothing had a casual sensibility, mixing a Christian Lacroix couture top with Guess jeans. In other words, it made a statement and spoke to what Anna wanted to convey, which was that fashion can be accessible, spontaneous, and fun. Ironically, that particular photo was never intended to be a cover. But as soon as Anna saw the image, she realized its potential and pivoted accordingly. When you are in a new position, it’s important to find opportunities to communicate to others what your vision is and what type of leader you are going to be.
Follow your instincts.
For Anna’s first September issue cover, in 1989, she featured Naomi Campbell in a sequined pantsuit because Anna felt Campbell “represented everything that was happening in fashion at that time.” Some at Condé Nast questioned her decision, but Anna ignored them and followed her instincts.
Be generative and reactive.
In addition to creating new ideas and concepts that will set the cultural barometer, it is equally important to take stock of what is happening around you and react to it. Take, for instance, Anna’s choice in the early aughts to start featuring celebrities rather than models on Vogue’s covers. At that time, actresses were starting to engage with fashion more and more, which is why Anna and her team felt they made sense as cover subjects. It then became cyclical. As celebrities saw their peers getting attention in a positive way from the fashion press, they themselves became more engaged with fashion and designers. It might be hard to imagine today, but back then it was considered somewhat radical to put Hollywood stars on the cover. Anna and the magazine received a lot of criticism and pushback, but she knew it was the right decision based on the wider influence celebrities were starting to have in popular culture.
Find good collaborators.
Good collaborators can come in any form. For Anna, it is important to feature a cover subject who is eager and engaged with the process. She uses Sienna Miller and Lupita Nyong’o as examples of perfect subjects: Miller was game to traipse all over Rome in the fall collections despite a heat wave, and Nyong’o arrived to her fitting with mood boards and suggestions for featuring African designers. A fashion editor or photographer can also surprise you with their vision, as was the case when Irving Penn shot Nicole Kidman, or Tonne Goodman turned Rihanna into a modern-day mermaid.
Don’t get stuck in your own ways.
Challenge yourself to consider whether there is a smarter way to be doing something. When Vogue began posting its cover stories online in 2010, there was concern that the website might “scoop” the print edition (and thus rob the magazine of newsstand sales). By experimenting with different timing, though, Anna and her team learned that there was great benefit in posting the cover online early because it created hype around the forthcoming issue and appealed to a wider audience.
Anna Wintour is the Editor in Chief of Vogue magazine. She presides over the Met Gala and is a fixture in the front row of New York Fashion Week. She is also the artistic director for the Condé Nast media empire, the most powerful woman in the fashion industry, and a role model for business leaders worldwide. Anna’s consistent ability to make important decisions that will shape the media and fashion industries speak to her unique success, one that’s built on vision, creativity, and commitment.
source: https://www.masterclass.com/