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Anna Wintour
Chief Content Officer (Condé Nast) and Global Editorial Director, Vogue, Condé Nast

Anna Wintour: Leadership Lessons from the World of Vogue

📅 Feb 26, 2026 WE Council 40 MIN 244429 VIEWS 44 SEGMENTS · 2 SPEAKERS
An exclusive interview with Dame Anna Wintour — CH DBE, Global Editorial Director of Vogue and Chief Content Officer of Condé Nast — recorded live at WE Convention 2025 in Dubai. The conversation is moderated by entrepreneur and WE Convention founder Mila Semeshkina. In this wide-ranging conversation, Anna Wintour shares her perspective on leadership, creativity, global media, women’s empowerment, and the responsibility that comes with influence. In this interview: — How leadership is formed and why presence matters — Starting a career in a male-dominated industry — Leading through crisis: 9...

Questions asked in this interview

12
  1. 0:55Tell us, when did you first realize you had the qualities of a leader, and how did it shape you in your early ages?
  2. 2:40What drew you to this, and what were those first steps like for you?
  3. 5:39Looking back, what has been the most challenging thing in your career, and what was the moment that truly tested you?
  4. 8:59How do you build and sustain teams that embody this balance?
  5. 11:26What tells you that a creative talent has the potential to change fashion itself?
  6. 13:47In your view, who has had the single greatest influence on fashion across all time?
  7. 18:58How do you approach leading such a diverse global network while still maintaining the unified voice and vision of Vogue?
  8. 21:36Do you believe a glass ceiling still exists for women today?
  9. 23:21And did you have one when you were just starting out?
  10. 27:28What inspired the concept, and where do you see it going in the future?
  11. 33:54What values did you try to instill in your children, and what kind of future did you hope for them?
  12. 36:50You've said, and I love that, 'the more you do, the more you can do.' What personal systems or practices make you so effective?
Moderator 0:00 ↗
So please let's meet our long-awaited guest, Global Editorial Director and Chief Content Officer of Condé Nast, Anna Wintour, companion of honor. I would like to thank our moderator, the venture capitalist, president and founder, for moderating this session. Anna, the floor is yours.
Ladies, stand up with a huge applause.
Anna Wintour 0:33 ↗
Thank you, thank you so much.
Moderator 0:43 ↗
So dear Anna, thank you so much for coming to Dubai. It's such an honor to have you here.
Anna Wintour 0:50 ↗
Well, thank you for having me. I'm thrilled to be here. Yeah, I love Dubai.
Moderator 0:55 ↗
So, let's start our conversation. We have only 40 minutes and we have a lot to discuss. You've been called the most powerful woman in fashion and perhaps the most mysterious too. Tell us, when did you first realize you had the qualities of a leader, and how did it shape you in your early ages?
Anna Wintour 1:16 ↗
Well, I don't think that there is ever a one-size-fits-all for leadership. I was very lucky to grow up in a house that was full of creative people. My father was a very well-known editor in Fleet Street in the UK. So I grew up with writers and politicians, artists, and it seemed always—I was always convinced that working in journalism was something that I wanted to do. And I think the most important thing as you develop your career is to learn as you go along and always to listen and be aware of how other people are leading. I think it's more important to be a solution-oriented leader than someone that is around damage control. I also think it's incredibly important to communicate clearly and make your opinions well known. But I also feel that by far the most important thing—and it's a rule that I always have—is when you hire people or you ask people to join your team, I say to myself: if they are going to walk into my office, am I going to be pleased to see them or not? And if you're not going to be pleased to see them, don't give them the job.
Moderator 2:40 ↗
I love this idea. So you chose journalism at a time when the field was largely dominated by men. What drew you to this, and what were those first steps like for you?
Anna Wintour 2:58 ↗
Well, I think you're absolutely right. When I was growing up in London at that time, journalism was completely dominated by men, and women only worked in cooking or interior decorating or, you know, female-oriented positions. But because I saw how exciting it was to really work in a newsroom as my father did—in those days there used to be so many editions of a newspaper, you'd start with a racing edition and you'd end with the late news edition. Things were always changing. I even remember being on holiday as a kid, I think we were in Venice, and my dad got a call and Marilyn Monroe had just died, and we all had to pack our bags and go home. In those days there was no internet or cell phone, so we just had to get on a plane and go back so he could cover the news, because he said otherwise they would mess it up. So I think I learned from him that it was so important always to be personally involved and personally make the decisions and be there. I think an absent leader is not a leader. For me the most difficult time in my career was during COVID when people weren't coming to the office and you had to exist solely on Zoom—as useful as Zoom is, it doesn't develop creativity. So being in the room with the people that you're working for as much as possible is so important. One of the meetings that I enjoy the most was when we all go to Paris during the collections, and the ten owned and operated Vogues—we have twenty-eight but ten are owned and operated—we meet in Paris and we have a very lively discussion about what we're seeing, what we're feeling, what we think is important at that moment. Obviously, this past season was so important because I believe there were thirteen or fourteen different new creative directors in Paris and we couldn't keep them straight. So I don't know how their customers could keep it straight, but it was just so important to have that personal exchange. And when you're working with people, including Manuel who leads Vogue here in Dubai, to understand what it means in different territories—because what might work in Australia or India, what might work in London or New York, might not work here in the Middle East. So it's very important to have those in-person conversations.
Moderator 5:39 ↗
Thank you. Looking back, what has been the most challenging thing in your career, and what was the moment that truly tested you?
Anna Wintour 5:50 ↗
Well, I think as a leader, you always have to recognize when things are very difficult. And obviously living in New York, 9/11 was a very challenging time for everybody, and then coming out of COVID. So in both incidences, those were moments when I thought: how can we be helpful? I mean this is a very small thing, but 9/11 happened on the very first day of New York Fashion Week, and as a result every single young designer in New York lost deposits, they lost revenue, they were floundering—and we were all floundering. We didn't know what to do and how we could be helpful. So I decided that we would support all the young designers in New York. It also gave something for our teams to do at a moment where they were really lost and bewildered and traumatized. And we put on a fashion show in New York for all the young designers, which turned into the CFDA/Vogue Fashion Fund, which now exists around the world. It's been in existence for over twenty years. And out of the fashion fund, incredibly young—then young, now maybe older—designers have emerged, like Jack and Lazaro who are now the creative directors at Loewe, or Johnathan who has a very successful business of his own, and more recently Rachel Scott who just was one of our winners. So it was a way to be helpful, but it was also a way for Vogue to become part of the future of fashion by discovering and nurturing and mentoring these young talents. And then when COVID happened, obviously that again was a very difficult time. And what we decided to do was to take the money that we had raised for the fashion fund and turn it into something which was called 'A Common Thread.' And with the CFDA, which is the governing board of American fashion, we announced that we would be—we raised a great deal of money and we announced that we would be giving out grants. And within a few days we had hundreds of applications for these grants, because designers that you would be very surprised to hear their names on this list were struggling so much for funds, for how they could keep their businesses afloat. So through A Common Thread, I can't remember now how many grants we gave out, and they ranged in value, but there were many, and they helped so many designers at a time when they needed it most. So again, I think as a leader, when things are at the most difficult, it's when you can be your strongest, and it's when you can help the community that you work in and the community that you work with.
Moderator 8:59 ↗
Thank you. You are known for blending creativity with discipline and artistry with business. How do you build and sustain teams that embody this balance?
Anna Wintour 9:15 ↗
I think the most important thing is to recognize that you need to surround yourself by people not only who you like to see when they walk into your office, but who are creative and don't always agree with you. I think to surround yourself with people who say yes to everything you do, A, is really boring, and B, is not productive. So I think creatives that look at the world differently—I am not a creative person. I'm like a producer. I know what I'm good at and what I'm not good at. And I can't draw, I can't make things, I'm terrible with my hands, but I can recognize talent and I can recognize good ideas. So I think to maintain that discipline that you were talking about, it's about relying on the very best and surrounding yourself always with the very best, which I always try to the best of my ability to do. And I'm so lucky to work with these teams around the world, whether it's in France or Spain or wherever it may be, and learn from them. And it's always, I think, so important to listen and to hear what's going on in different territories—to understand what works here in Dubai may not work in New York and vice versa. And also working with the global network the way that we do today, it gives you the ability to put a spotlight on talent from around the world. Before we globalized, we were very local and I think much too narrow in our thinking. And right before COVID we globalized as a company, and it's made, I think, the work that we do so much more interesting, so much more varied. But it's opened up our network to work with people that I've learned so much from every single day.
Moderator 11:15 ↗
Thank you. You've discovered and championed designers like John Galliano, Alexander McQueen, and Tom Ford—
Anna Wintour 11:25 ↗
Sarah Burton.
Moderator 11:26 ↗
Sarah Burton, yeah. This is actually my most favorite designer. So this is Giambattista, and this is her creation by the way. So thank you, Sarah. What tells you that a creative talent has the potential to change fashion itself?
Anna Wintour 11:49 ↗
I think the great designers have a very strong point of view. They are not concerned about what other designers may be doing. They're not looking to the left or to the right. They're very convinced by who they are and what they stand for. I was recently very honored to be asked to speak at La Scala in memory of Giorgio Armani. And when I was thinking back about his incredible body of work—and there was an extraordinary exhibition the same night of his work in one of the museums in Milan—when you looked at his work starting when he began in the seventies and right up until the present day, the thread was so strong. You understood, whether he was designing for men or for women, exactly what he believed in and what he thought and what his ideal was. And he also recognized, I think before so many other designers, the importance of the celebrity. He understood the importance of working with the great film directors of the time. He opened up his world so he wasn't existing just in a silo of fashion. And I think when you think of the great designers like Giorgio who work in fashion today, certainly somebody like Miuccia Prada—they are very influenced by so many different artistic endeavors. In Miuccia's case, she loves art, she loves literature, and you see that in her work—she loves architecture. Or the late, great Karl Lagerfeld, who knew everything about everybody and everything and was extraordinary. So I feel that designers that are very open but are also very true to their own spirit are truly always the greatest.
Moderator 13:47 ↗
Thank you. In your view, who has had the single greatest influence on fashion across all time?
Anna Wintour 13:58 ↗
Well, I think it's very difficult to choose one designer, but since you ask, I think I would have to pick Karl Lagerfeld.
Moderator 14:11 ↗
The Chanel team is applauding you.
Anna Wintour 14:15 ↗
You know, he was someone that I was lucky to know for so many years. And it was interesting—we would have a ritual every time I would come to Paris. We would have dinner at the Ritz and we would talk for hours, but we would never ever talk about fashion. We would talk about art, we would talk about architecture, we would talk about books, friends, my children, his cat—and we would cover the universe in those hours that we spent together. But if you look back at his body of work, he really understood what I was saying earlier, that fashion doesn't exist in a vacuum. And he understood clearly before anyone how the fashion show could reach millions and millions of people. If you think how our fashion shows started and they were for the elite, for the rich, for a very small body of people, and then gradually as our world changed, the fashion show changed too. And Karl understood it had to become, for what he believed in, like a show—whether it was Chanel the supermarket, or Chanel with a rocket taking off, or Chanel on the beach remembering his childhood. It was just like stepping into this incredible visual world that told you so much about what he believed and what the clothes were saying. He was a master at storytelling and he made it all fun as well as great clothes and great design. He understood the power of communication. He was a journalist, he was a designer, he was an illustrator, he made movies—there wasn't anything Karl couldn't do. And he was ambitious, he was competitive. You know, you would be sitting there and he watched every single one of the shows before you probably had time to see them yourself, because he was just so interested in the world, and it's what kept him alive and working up until the very end. He was just the most extraordinary person.

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APA, MLA, BibTeX
APA

Wintour, A. (2026, February 26). Anna Wintour: Leadership Lessons from the World of Vogue [Interview transcript]. WE Council. CEOInterviews.AI. https://ceointerviews.ai/interview/1040554/

MLA

Anna Wintour. "Anna Wintour: Leadership Lessons from the World of Vogue." WE Council, 26 Feb. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/1040554/.

BibTeX
@misc{wintour2026_1040554,
  author       = {Anna Wintour},
  title        = {Anna Wintour: Leadership Lessons from the World of Vogue},
  howpublished = {Interview transcript, WE Council. CEOInterviews.AI},
  year         = {2026},
  month        = {feb},
  url          = {https://ceointerviews.ai/interview/1040554/},
  note         = {Speaker-attributed transcript with timestamps}
}