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5 surprising things I learned about leadership in Anna Wintour’s MasterClass, from owning controversial decisions to building a dependable team

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In her MasterClass, Anna Wintour shares her best leadership and creativity tips, from owning difficult choices to building a dependable team.


  • As the manager of a team, I rely on leadership books and classes to keep improving.
  • I found Anna Wintour’s MasterClass on creativity and leadership especially insightful.
  • It taught me how to lead with a strong point of view and select the best team members.

MasterClass, an online subscription service featuring video lessons from celebrities and experts, is one of the best investments I’ve made in my personal development. I love it so much that I’ve gifted it to others twice this year. 

606efe824d3e410018b6ff12Masterclass All-Access Pass$180.00 FROM MASTERCLASS

My career has taken a bit of a whirlwind over the last year: I started a new job in 2020 and quickly found myself in a leadership position, helping guide a team of 30 journalists and editors. As a result, I’ve become a voracious consumer of books on leadership and management, and one of the main reasons I took the plunge on a $180 annual MasterClass subscription was the chance to learn from leadership luminaries about their secrets to success.

5fe3758da644880018193263MasterClass: Anna Wintour Teaches Creativity and LeadershipLegendary Vogue editor-in-chief Anna Wintour shares her tips for leading with vision and boldness.$180.00 FROM MASTERCLASS

Few of those leaders have been as intriguing to me as Anna Wintour, the editor-in-chief of Vogue. As a fellow woman working in media, I’ve always been fascinated by Anna’s career path. There’s so much lore about her leadership style – several popular books and movies are rumored to be based on it. But I’ve always felt she was a bit misunderstood, that people don’t and wouldn’t say the same things about men in the field as they do about her. 

Anna Wintour walking down a crowded street in a black and white checkered coat

Edward Berthelot/Contributor/Getty Images

Regardless of what you feel about her leadership style, you have to argue that she gets results: She’s been the reigning editor at Vogue for over 30 years, is responsible for the success of the Met Gala (one of the most well-known annual charity events in the world), and has helped launch the careers of hundreds of designers, photographers, models, and writers. 

In her MasterClass, Anna gives specifics about her leadership philosophy, and while a lot of the content is geared toward fashion and media hopefuls, so many components can be applied to any leader of any business. I loved the class so much that I watched it twice — and took notes along the way. 

Here are five things I learned about leadership from Anna Wintour’s MasterClass:

1. Lead with a strong point of view.

Anna Wintour in her MasterClass


This was the overarching piece of advice I took from Anna Wintour’s MasterClass: Leaders should lead, not follow. It seems almost comically simple, but hearing it made me realize how often I rely on consensus or direction rather than my unique point of view. 

While Wintour recognizes diplomacy as a tool, she emphasizes it’s critical as a leader to communicate your point of view with clarity and decisiveness, rather than bowing to pressure to follow other people’s way of thinking. To her, the mark of a true leader is to push boundaries and provide a more exciting vision than others can initially see. 

Now, when faced with a tough leadership decision, I try to remind myself that my team is looking for me to make the best decision, not the most popular or safe choice. 

2. Always stay open and interested in the world around you.

Anna Wintour in her MasterClass


One surprising tidbit I picked up from Anna’s MasterClass was how much time she spends engaging with the world around her to inform her point of view. “Spend as much time as you can on creative exposure,” Wintour emphasizes. For her, that means using her free time for taking walks, reading books, seeing plays, and “watching the world.” 

I was especially tickled by Anna’s anecdote about how so many prospective employees worry about what to wear when interviewing with her and neglect to think about what she really cares about: Their passions, genuine interests, and the last great book they read. (In fact, she says she doesn’t pay very much attention to what they’re wearing at all.)

For me, this advice is an excellent reminder that the way we spend our free time has a significant impact on our decisions, our teams’ well-being, and even the world at large. It can be a potent tool for pulling myself out of mindless social media scrolling and redirecting my energy to activities I know will fill me up, like reading, exercise, and writing.

3. Build a diverse team of highly dependable people.

Anna Wintour in her MasterClass


When speaking to her hiring philosophy, Wintour stresses finding self-reliant and diverse people in their way of thinking and observing the world. Once she finds those people, she likes to give them assignments they’re passionate about and entrust them with a large amount of autonomy. 

While Wintour recognizes that her communication style isn’t for everyone, she feels it’s important to make feedback quick, fast, and direct so that there is no ambiguity in the direction. She stresses getting back to people quickly to keep the work moving.

Though Anna’s communication philosophy isn’t my preferred way of engaging with my direct reports, her advice about hiring people to fill your blind spots is always on my mind as I look for new people to join our team. Recognizing how powerful diversity can be in creating a robust and effective team is critical: People with different backgrounds and experiences can only make our work better and more far-reaching. 

4. Don’t be afraid to make the “wrong” choice from time to time.

Anna Wintour MasterClass


As someone who uses data to make the majority of my decisions, I was surprised to learn that Wintour believes data is a bit, well, overrated. “Data can’t tell you everything,” she says. “You can’t develop an audience through data; it comes through the creative talent.” Her opinion: If you speak with passion and authority, people will listen — and an audience will find you. 

In an algorithm-obsessed world, it’s hard to imagine making any choice that isn’t backed by an endless amount of data at our fingertips, but I think Wintour has a point. There’s something to be said for being “ahead” of the data, anticipating people’s needs before they know them, or writing about a topic before it’s trending. It goes back to her first tip about leading and not following.

Wintour emphasizes making the “wrong choice” every so often when it means a chance to move the conversation forward. However, that doesn’t mean being reckless: “Controversial decisions have to have meaning, and you can’t make them all the time,” she warns. She also stresses that bold initiatives take time, and it’s important to be patient when determining the success or failure of any outside-the-box decision. 

5. Know your brand, but don’t be afraid of evolving it.

Anna Wintour at a Vogue meeting in her MasterClass


Wintour stresses the importance of understanding your brand and keeping it front and center in all your decisions. However, she also recognizes that it has to evolve to stay relevant constantly. “Our brand has to be at the core of everything we do: What is it, what does it stand for, and how do you move it forward?” she says. 

People want change, so we always have to look for new ways of connecting with our audience. “It is naive to think you only have one customer, who wants to be spoken to in one way or through one medium,” she says. Wintour and her team are frequently looking for ways to talk to their audience in a way that feels more personal. 

As for figuring out your brand, she cautions that it’s more important to define what your brand is than what it is not. “It’s very easy to say, ‘This is not us, this is not who we are.’ It is much harder to say, ‘This is what we believe, this is what we stand for,'” she says. 

I think about this often when giving feedback: Am I providing a clear vision of our brand, or am I defining our brand by what it is not? 

The bottom line

Anna Wintour MasterClass


As a middle manager in media with plenty of room to grow, I found Anna Wintour’s MasterClass invaluable. Her advice drew a clear line between who is a leader and who is simply a manager, and I use wisdom gleaned from her MasterClass when I show up for work every day and try to be the best leader possible for my team. 

I highly recommend Anna’s MasterClass for any leader or potential leader, but this course is particularly relevant for women and those working in media or fashion. While an annual MasterClass subscription ($180) gets you access to hundreds of celebrity-led video courses, the insights I’ve gleaned from Anna Wintour’s MasterClass alone have more than made up for what I’ve paid for my subscription in value.

5fe3758da644880018193263MasterClass: Anna Wintour Teaches Creativity and Leadership$180.00 FROM MASTERCLASS

606efe824d3e410018b6ff12Masterclass All-Access Pass$180.00 FROM MASTERCLASS

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