So… I read Anna Wintour’s biography.
She is exactly how you may think she is.
‘The Devil Wears Prada’ gets ample accuracy points. Finding out that she is hard to please, straightforward, constantly going, and high maintenance (with an honestly very discriminatory history) was not shocking to me. As someone who keeps up with fashion industry news and has a weird interest for villainized women, I already got the gist of all of this.
What did surprise me a little bit was what I learned about her as an effective leader, and the similarities I found between us– and the leader I see myself being. There are aspects of her leadership style that we can take notes from and some we should definitely see as a cautionary tale for what not to do. Let’s dive in!
First, I’d like to acknowledge the obvious detail that people like to bring up in the debate on whether or not we should hate or cut Anna some slack: she is a woman. We’re reminded by some– and Anna herself– that the disdain people have for assertiveness is for that exact reason. That she had to be cutthroat in order to be respected as men are. This is true for many professional women. But there is a fine line. When we adopt the leadership style of men, we are adopting a leadership style that is historically and systematically discriminatory, exclusionary, and abusive. It’s not sustainable.
I would say that Anna Wintour has always had to walk this fine line. Her leadership style is evidently extremely productive and has made Vogue Magazine the powerhouse that it is. Only since Anna assumed the role of Editor in Chief has the magazine actually had the social power and respect that we know it to have. However Anna has trotted on the bad side of this fine line in her career history far too many times, and proudly.
When Anna teaches us what not to do:
She famously does not respect the work/life boundary of her employees.
“Her requests for her assistants were constant–day and night, weekday and weekend… This meeting was last-minute, and she asked her assistants to attend, which was unusual. No one knew the purpose of the gathering, but they did know that when Anna called for one, if you didn’t arrive early you were late.”
Throughout the book, there are many examples of Anna being so demanding of her employees, at any time of day (or night) or week that they’re always exhausted, miserable, and anxious. There is a brief telling of how one time, she called an all-hands meeting at 7:30– after they had just called it a night and went home around 4:00 AM– and the exhausted staff were called back in for a meeting.
She only had a change of mind as far as inclusivity because the social climate called for it, not because it ever came naturally to her
When asked how she would feel about a fashion editor that was 250 pounds but ingenious, she said, “I would have a problem with that.”
Another Anna Wintour quote: “I just felt [Oprah] would look more beautiful 20 pounds lighter.” In the wake of internet social discourse, call-outs, Black Lives Matter, and our general calling for progress. Anna has struggled to get it right, despite her many recent attempts. People question if her shifts in beliefs are authentic. Sure, we’ve all had to learn to be better people in recent years, but Anna Wintour’s “missteps” were acknowledged and negatively received even in the past. It’s been that bad.
What we can learn from Anna:
Anna embraces change, what’s new, and has been progressively rebellious
Anna loves change. Although her ideals for beauty standards have stagnated the most, so much of her business success is due to her futuristic nature. She keeps an eye on trends and has been able to keep Vogue at the forefront of innovation. She embraced the internet early, and when someone on a flight commended Vogue for being classy and never having someone like Madonna on the cover, Anna put Madonna on the cover (it was a huge success).
Vogue’s cultural relevance is due to Anna’s leadership. There is a reason why it’s the staple magazine and media outlet for the fashion industry and that is because Anna has embraced our changing culture and aligning with what’s new.
She understands the importance of having a good team and community
“You are nothing, nothing, without a good team. So I have always tried to surround myself with people that I enjoy — people whose opinions I respect, whose minds I respect, whose taste I respect, that isn’t always in line with mine.”
Wherever Anna went career-wise, she brought her trusted team with her. Whether you feel positively or negatively about the fact that whenever she assumed a new leadership position at a new company she got rid of most of the current staff and replaced them with people she trusted and could execute the job better, Anna knew the power of loyalty and having a good team. She regularly preaches about how we are nothing without a good team. There is a story in the book about how someone who approached Anna and asked for a job opportunity actually got one from her later on, and Anna made sure they were taken care of.