Anna Wintour

The Enterpising Leader

Anna Wintour (born 1949) is the Editor in Chief of Vogue, (a role she was appointed to in 1988), and is the Artistic Director at parent company Condé Nast. She is an international fashion icon, and is considered to be the most revered figure in the industry.

Anna Wintour can be identified by her signature pageboy hairstyle and dark sunglasses. Yet, behind those dark rims and innocent appearance, is the critical eye of an icy, powerful woman who has revitalized major publications, and redefined woman’s fashion. The film, The Devil Wears Prada is said to be an accurate depiction of this forward thinking, demanding leader. She is considered to be the Goddess of the fashion industry, and is highly ranked as one of the most powerful women in the world.

enterprising leaders are the natural negotiators and deal makers.

Enterprising Leaders are magnetic, and so everyone in their orbit wants to be associated with them. Combined with their natural charisma, charm, tactical agility, and their hard-nosed utilitarianism, these leaders have a superior advantage when it comes to making deals. Such was the case with Anna Wintour who was able to negotiate her way to the top of the fashion industry. As Editor in Chief of Vogue, she has created opportunities for herself and for those she deems as being extraordinary. It is said that, “When Anna makes a deal, everyone wants in.” She has helped make the careers of such designers as Marc Jacobs and Alexander McQueen. She has been known as a power broker between designers and retailers putting designers like Thom Browne into 90 Brooks Brothers stores.

Enterprising Leaders are shameless in promoting themselves, their people, and their enterprises.

Enterprising Leaders are unapologetic about telling others who they are, and what they want. They have no shame in being self-promotional. They utterly believe in themselves, and this manifests in the confidence they exude. Anna Wintour questions, “Why fit in, when you were born to stand out?” And has also said, “People respond well to those that are sure of what they want.” R. J. Culter, maker of the film, “The September Issue,” once said, “You can make a film in Hollywood without Steven Spielberg’s blessing, and you can publish software in Silicon Valley without Bill Gates’s blessing, but it’s pretty clear to me you can’t succeed in the fashion industry without Anna Wintour’s blessing.” When Anna promotes something, it turns to gold.

Enterprising Leaders draw followers because of their eagerness to take risks and find ways to win.

People follow courageous leaders—it inspires, and emboldens all those around. Enterprising Leaders are audacious, tough warriors who fearlessly slay any dragon in their path. Anna has said, “It’s very important to take risks. I think that research is very important, but in the end you have to work from your instinct and feeling and take these risks and be fearless.” Nicknamed, “Nuclear Wintour” she has said, “I’m the Conde Nast hit man… I love coming in and changing magazines.” Anna fearlessly made the shift to end the supermodel era, by featuring celebrities over models for the covers of Vogue. She was also the first to juxtapose low-end fashion with more extravagant pieces in her magazine. Anna was a trailblazer, and the risks she took resulted in huge wins.

Enterprising Leaders have a tenacity which allows them to get back after a hard fall.

Enterprising Leaders are called in to turn things around. When there is a threat to their business, they can instinctively make the countermove to turn the threat back on any foe. In the face of death, they can bring about a resurrection. These leaders are fiercely competitive, so they refuse to lose. Anna Wintour has said, “I’m very driven by what I do. I am certainly very competitive. I like people who represent the best at what they do, and if that turns you into a perfectionist, then maybe I am.” Anna Wintour was called in to become the Editor in Chief of Vogue at a time when the magazine had been losing ground to a smaller upstart, Elle. Under Anna’s leadership, she has always found a way to blow away the competition to restore preeminence.

Enterprising Leaders have a sense of style that is marked by excellence.

Enterprising Leaders are the true originals. They have too much pride to be an imitation. They aim to be the best, and for them, this means that they will be none other than themselves. They never let themselves be seen as less than. They urge everyone to be completely self-defined. Anna Wintour says, “Create your own individual style. I’m not interested in the girl who walks into my office in a head to toe label look that’s straight off the runway. I’m interested in a girl who puts herself together in an original independent way.” She embodies this belief in her own style with her iconic pageboy haircut (since age of 15), and is known for her large stylish sunglasses, which keep her intentions a mystery.