10 Leadership Lessons from a Queen.

Dame Anna Wintour, a #girlboss and influencer from way back.

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When I was a lawyer on training wheels, I may or may not have snuck off after work to fashion illustration and pattern making classes. (FYI, I tanked at both). I may have moonlighted on the weekends as a retail sales associate for an Australian fashion label for 12 years, right up until I became a General Counsel of the subsidiaries of the world’s largest cosmetics company.

In 2005, I may or may not have also spent hundreds of dollars to have a copy of “Front Row” air freighted via Amazon to my law firm office. Whence it arrived I didn’t think twice about swapping an afternoon of billable units to devour it. My then office buddy had me covered.

A subscription to US Vogue in my teens. Tick. Watching The Devil Wears Prada on repeat. Tick. Several job applications sent to Condé Naste. Tick. Analysing The September Issue over and over. Tick. Staying up late to catch the Met Gala coverage. Another tick.

If it’s not coming through, I have always been in awe of Anna Wintour, who has since 2017 earned the title of Dame.

She’s the ultimate influencer and #girlboss, way before the advent of the social media versions. Since 1988 she’s held the top seat as Editor in Chief of Vogue USA, and Artistic Director of Condé Naste. She is one of the most powerful women in media globally. She is an icon. She might as well be royalty.

When the Queen of The Fashion World made her first trip to Oz for the tennis in January, I wanted nothing more than to be in the same room as her. Lucky for me, an unexpected (but oh so welcome) work invite had me sit three tables away from her at the Australian Open Inspiration Series. And the following day, after paying a haute couture entrance fee, I attended the Vogue Australia event at the National Gallery of Victoria.

On both occasions, Anna made a nuclear impression.

Here are 10 things I learned about leadership and influence from THE Anna:

  1. Focus on what’s next. When introducing Wintour, Baz Luhrmann described Anna as always being about the future.
  2. Age is just a number. At 69, one can still be stylish, relevant, on top of their game, make a difference and still feel blessed about coming into work each day.
  3. Attack things with confidence. Have a vision. Have a strong point of view. It pays off, either quickly or eventually. Ensure those whom you hire work with a sense of purpose too.
  4. Make Decisions. As a captain of instinct, the final call rests with you. Take it, even if it’s wrong.
  5. Give back. Anna has raised over US$200million dollars for the Metropolitan Museum of Art in New York and its Costume Institute.
  6. Mentor others.
  7. Know that the company you keep rubs off on you. Anna is close friends with Roger Federer, Serena Williams, Lady Michelle Obama, Baz Luhrmann, plus many other distinguished and accomplished individuals.
  8. Honour loyalty. It is not dead. It’s priceless.
  9. Be a leader just by speaking up. And Wintour certainly does not waste nor mince her words.
  10. Don’t be in fashion if you don’t like disruption. (Side note – I yearn for the day that legal leaders are saying this about the legal profession).

And yes, sunglasses were worn while writing this blog post. Because, Anna.


Originally published as a blog post on

Image by Pro Church Media via Unsplash.

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