Anna Wintour Masterclass Review 2024

Published by: Julia

Anna Wintour’s Masterclass is for anyone who wants to be a leader in their field. But, those who work in the creative industries, particularly, fashion will benefit the most from her leadership tips.

An insight into the mind of Anna Wintour

Anna Wintour is a fashion journalist and magazine editor. At the time of my writing this review, she is the Editor-in-Chief of American Vogue and is the Conde Nast Artistic Director and Global Content Advisor.

She is without a doubt a strong leader, who has run numerous successful teams, across the world. Her leadership style is highly effective.

For years, everyone in the fashion world and beyond has marvelled at how she does it. But, up until now, Anna has rarely spoken about her day-to-day approach to managing a creative team.

So, this masterclass is, without doubt, the best way to learn about this remarkable woman. It provides you with an insight into what truly makes her tick, so that you have the chance to replicate her success.

By the way, we recommend purchasing Masterclass for more than just one single course. The value comes when you take several. If you want to read our review of the whole platform, check out this Masterclass review article.

If you want to just find out what some of the best masterclasses are, this is the article for you.

Anna Wintour’s Management Tips

Anna makes a great start to her course. She starts by explaining that you are nothing without a good team. It was very clear that she genuinely appreciates having a diverse group of people around her. In the video, she shares the qualities she looks for in her team members. Importantly, she also talked about the questions she asks before hiring someone.

It was also refreshing to hear her explain that she was going to share her leadership style. She clearly understands and values the fact that not everyone will do things her way.

Here is a summary of the main leadership tips she shares with her students during this excellent masterclass.

  • How to hire and build a great team
  • How to build a system for keeping track of your work
  • Why you need to give feedback quickly and be direct
  • Learning not to micromanage and why it is important
  • Being thoughtful about how you run meetings and why

How to be true to yourself and your vision

One of the biggest challenges leaders face is dealing with criticism. The temptation to be swayed and driven off course by what others say about you and your way of doing things should be resisted. You need to stay true to yourself and your vision.

There is no doubt that when you do some people are going to be upset or feel uncomfortable. But, you need to resist the temptation to bend and try to make people feel happier.

You can’t be everything to everybody.

Anna Wintour –

However, Anna is not saying that you should totally ignore what everyone else has to say. You need to learn to listen to others, understand their perspective and not be afraid to question what you are doing. You just need to be sure to do it in a healthy way.

Anna demonstrates how she balances listening to others, while still championing her vision by letting you sit in on a meeting at Vogue. It was a great way to better understand what Anna is teaching. As well as providing an interesting insight into the way the magazine works.

A masterclass in editorial decision-maker

Deciding what to publish, which story you are going to tell is impossible to get right all of the time. In this video, Anna walks you through some of the decisions she has made. Both good and bad.

She starts by blowing up the myth that you can create an audience. Or, manipulate things. Anna has learned that the only thing that really engages people is passion. If you are not interested and passionate about what you have to say, nobody will be interested.

At this point, Anna lets you sit in on the editorial meeting for the March 2024 edition. She shows you how they decided what to include, what to leave out and how ideas evolved during the meeting. It is a fascinating watch and very informative.

I am not a regular reader of Vogue. But, since taking this masterclass, I have bought a couple of editions and read some back copies and have come to understand that Vogue is about far more than just fashion. It reflects our culture, in its many forms. So, anyone involved in sharing media with others can definately benefit from this masterclass.

Know when to break the rules…when to literally lead the way.

Don’t be afraid to make and own your mistakes

But, as you will see Anna has made some mistakes. She shares some and explains how to deal with the errors you are bound to make.

Executing your vision

This was by far the most entertaining and, I think, inspirational video in the course.

In it, Anna speaks about how, over the course of 21 years, she and Andrew Bolton the Head Curator of the Metropolitan Museum of Art’s Costume Institute in New York City transformed the MET annual gala. This section provides you with another chance to gain an in-depth insight into how this amazing event evolved over the years.

Always think about the bigger picture and how your work can have the widest possible impact on the world at large.

Anna Wintour – Teaches Creativity and Leadership

To be able to build your vision and realise it to the full, you need patience. Over time, you learn to build the working relationships you need to be able to bring together all of the elements you need.

It was also interesting to hear how Anna uses deplomacy in her role as a leader. She explains how to know when to push and when to hold back.

You also gain an insight into how Andrew and Anna choose a theme and build it out. As you will see it is vital when it comes to marketing your event.

Using the power of the image

If you want to have an impact, you need to take a visual approach. This is the case almost regardless of what you do. Humans respond most to what they see. Over half of the human brain is given over to picking up and processing the visual world. So, if you really want to influence someone, you must learn to use images and other visual cues effectively.

In this section, Anna demonstrates the power of pictures. She does so by sharing how some of Vogue’s photo shots have captured the spirit of an era.

There are several examples, but the one that resonated with me the most was the China shoot Vogue did. It showed a China to people that they had never seen before. At the same time, it recorded a moment of time in the history of China. A country which, at the time, was still quite closed off from the outside world.

If you find this section of the course of particular interest, I would recommend that you take either Annie Leibovitz’s or Jimmy Chin’s photography masterclass. Or better still treat yourself to an all-access pass. It only costs $180, which is the price you would pay if you were to take just 2 masterclass courses. Remember, that pass provides you with the chance to take over 60 different masterclasses.

How to put your brand at the centre of all of your creative decisions

This was another fascinating section of Anna Wintour’s masterclass. She explains that a good leader will always be looking forward and working to keep their brand relevant and attractive.

That is not easy to do. It is important to keep your ear to the ground and your eyes open. A good leader will watch what is happening in their industry, and culture, as well as trends in the market that they serve.

Using a range of iconic Vogue covers, Anna ably demonstrates how she has done this over the years. For example, at an early stage, she spotted the trend towards models not wanting the supermodel lifestyle. Anna noticed that a lot of her younger models really just wanted to do the modelling work and go home to lead ordinary lives.

But, the magazine still needed exposure across other types of media. They needed to use people in Vogue who had broad appeal. It turns out that the solution was to start shooting stories using celebrities. Something every fashion magazine now does. Vogue was definitely at the forefront of this new style of fashion and photojournalism.

Stop re-hashing and really start creating

At this stage, Anna emphasises the fact that you really need to be creating trends. It is all too easy to get lazy and simply rehash what everyone else is doing. You need to lead the way, to be able to see when something important is about to happen, then find creative ways to tap into that shift in the culture.

To be sure of what is right, tap into your instincts and don’t be swayed without good reason.

If you are doing it right, the reaction you get from your audience will never come as a surprise. You will have anticipated and responded to the mood perfectly.

Learn about design from Anna Wintour

I did not expect this section of Anna’s masterclass to be in any way relevant to me. After all, I am not a designer and am not even that interested in fashion. But, despite this, once again Anna came up with advice that applies almost regardless of who you are or what industry you work in.

For example, her advice to young designers is not to play it safe. To try something extreme, take things as far as you can. This is a great way to explore who you are. To discover what is not right for you and what is. When you are still studying you can afford to go to extremes, to explore and discover. So, be sure to take full advantage of that stage of your career.

If you are a budding fashion designer, or even, just interested in design, this section of the course is a mine of information. Anna explains how to use your creativity and be true to who you are. I particularly like the ideas she shares for young designers who need exposure for their work.

There is no longer any need to fund a full fashion show. You just need to be creative and think outside the box.

Refreshingly, she points out that being a successful fashion designer does not necessarily mean that you have to work for a big design house. Or, set up your own label. There are lots of ways to work in the industry that you love.

Anna rounds off this section of the course by talking about the creation of the CFDA Vogue Fashion Fund. If you are a young American designer hoping to secure funding, watch this video carefully. Watching the selection process will provide you with an insight into how to put together the best possible application.

Learning from other creative leaders

It is great to see Anna sharing examples of other creative leaders that you can learn from. As you would expect, they are all from the fashion industry.

She explains how each of them managed to set themselves apart from the crowd. Anna talks about the following creative leaders:

  • Christopher Burberry
  • Michael Kors
  • Miuccia Prada

Leading with impact

Once again, Anna reminds us of the need to do everything in a thoughtful and meaningful way. To be purposeful, so that you and your brand can have a real impact.

To demonstrate what she means, Anna talks again about the Met Gala. She also shares with the audience why Vogue Forces of Fashion was created. This unique conference that has become an extension of the Vogue brand while inspiring others in the industry. Moving things forward in new and innovative ways.

If you want to have an impact, you need to reach out to people in different ways. You need to tap into and be prepeared to use all kinds of platforms.

It is naive to think that you only have one type of customer, who wants to be spoken to in only one way or through one medium.

Anna Wintour – Leadership

Anna Wintour’s creativity and leadership workbook

If you have already read a few of my masterclass reviews, in particular, my overview review, you will already know that I really like the workbooks. Anna’s is no exception. It is excellent and I particularly liked the layout. It is a much more visual than other workbooks, which makes it really easy to use and the points made more memorable.

My final thoughts

Fashion fans, leaders of all kinds, photographers, people interested in social history and writers will all enjoy this course. It has something to offer practically everyone regardless of what career path they are on or what their interests are.

As someone who is not interested in fashion, at all, I was not expecting to enjoy this masterclass or get much out of it. But, as it turns out I was wrong. It was actually very interesting and I did learned about being a successful leader.

The otherthing that surprised me was just how personable Anna is. She has a bit of a reputation for being a tough lady. A force to be reckoned with. So much so that, for a time, her nickname was Nuclear Wintour.

There was no sign of this in her masterclass. She was easy to listen to and refreshingly, regularly gave credit to those who she had worked alongside, over the years.

Right, that’s it for me. Review over, I’m off to do a mood board … take the course if you want to see why I am planning to do that.

5/5 - (1 vote)

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