Cindi Leive is Glamour magazine’s editor in chief, a role she has held since 2001. Under Leive, Glamour runs its Women of the Year awards, one of Condé Nast’s marquee events that celebrates female leaders in a variety of fields, including entertainment, the arts, education, politics, media, philanthropy, science and business. On Monday, Glamour will honor Lupita Nyong’o, Chelsea Clinton, Laverne Cox, Robin Roberts, Natalia Vodianova, Sarah Burton, Samantha Power, Mindy Kaling and Dr. Sylvia Earle. WWD caught up with Leive to talk about the awards, her views on the changing landscape of women’s magazines and why “Homeland” is an ironically uplifting show for working moms.

WWD: Glamour fetes its 24th annual WOTY awards. Please talk about why and how you selected this year’s honorees.

This story first appeared in the November 7, 2014 issue of WWD. Subscribe Today.

Cindi Leive: Lupita Nyong’o is our cover girl. To me, you could not have done anybody else this year. It was so her year. In the eyes of the world, she kind of came out of nowhere. In her very first major acting role, she completely nailed this performance and then also, as luck has it, she’s this exceptional woman of gravitas. She can speak really eloquently about issues of beauty and identity. She kind of has it all. She’s a fashion plate and a real Glamour girl, and a real woman of substance. We were kind of like, slam dunk, it’s got to be her.

WWD: What about Chelsea Clinton? Why did you pick her and why now?

C.L.: The interesting thing about Chelsea is that she, by all accounts, totally came into her own now that she’s working at the Clinton Foundation. She’s a self-described data geek who is working incredibly hard. She’s getting kudos from some of the top public health experts in the world for the work she’s doing, like actually saving kids’ lives in Africa. That’s pretty impressive because not everybody with a big last name like hers actually works that hard. She really does. She puts in the time. She’s the real deal. I love that.

WWD: How does one become a WOTY award winner?

C.L.: We look for this year’s big stories. You want to honor people this year that you couldn’t have last year or the year before.

I also like to honor women who are using their platforms to make the world a better place for women or expand everybody’s ideas about what women can and should do. We look for women who are a little badass, too.

It is also important to honor people you’ve never heard of before. Sylvia Earl is certainly not an unknown if you’re a fan of oceanography — but here is this woman who is the world’s pre-eminent expert on our oceans. She is still on or in the water three months out of the year at age 79 and they call her “her deepness,” my favorite phrase ever. She’s going to be incredible on stage.

WWD: What makes a good magazine?

C.L.: I think what makes a good magazine reading experience is that feeling of discovery of being introduced to somebody and kind of falling in love with somebody you never even would have known had you not picked up the magazine in that particular moment in time.

WWD: Who is the Glamour reader? Who is she, how old is she?

C.L.: You can’t totally generalize about an audience of 12 million, and that’s in print alone, and then we’ve got digital and all that stuff. But she’s in her 20s, 30s early 40s, who absolutely works. It’s a big part of her identity. We know that about half of our readers are married, half are single, many have children but they don’t really want to read about their kids when they pick up Glamour. This is their moment for them. It’s their escape. They actually get annoyed if we talk too much about parenting.

WWD: The women’s magazine space is crowded, and you speak to a broad audience. How do you pick covers and stories to appeal to your reader base, but still stand out as unique?

C.L.: Obviously there are going to be differences about how a 20-year-old looks at the world versus a 40-year-old, but there are also increasingly things that they share. The generation of young women right now who are in their teens and early 20s, they actually grew up being really close with their moms in a way that women who are currently in their 40s were not necessarily. Many women in their 20s talk to their moms on the phone every day. For that reason, and a lot of reasons, they are interested in reading about women who are not their exact age who have advice to give them, and wisdom to offer. They want to learn. That idea of, “I don’t want to have anything to do with someone who is 15 years older than me,” is really dated.

If you’re 20 or you’re 45, you still think Beyoncé has got it together. I don’t think there’s a divide there.

WWD: Who would you never put on your cover?

C.L.: We don’t really do train wrecks. When a woman buys Glamour, yes, she’s getting great fashion ideas and beauty inspiration, but she’s also reading about her own life, her friends’ lives, her work life, her career issues. The woman on the cover has to be someone she respects. She has to feel like — ‘yeah, that girl’s got it going on.’

WWD: Would you ever put a guy on the cover?

C.L.: Very rarely. I believe there was a Fred Astaire cover back in the Forties. And we did do a Matthew McConaughey seven or eight years ago. I won’t say never — because well, I won’t — but it certainly isn’t something we do often.

WWD: The importance of women’s magazines hit a high in the Sixties and Seventies. How do you view their role today?

C.L.: Young women in general, up to their 40s, are much more willing to call themselves feminist than 10 or 20 years ago. I think we’re seeing that this year. There’s a reason why Emma Watson’s speech at the U.N. went viral. She struck a chord. The negative connotations that might have stuck to a word like ‘feminism’ five or 10 years ago, young women aren’t really aware of those. This is about the basic idea that men and women should have equal rights. Well, duh, end of story. It seems very much like common sense to them.

WWD: Let’s switch gears to the business of media. How do you view native advertising?

C.L.: Native advertising is like any other kind of advertising: some of it’s good, some of it’s not. When we run it, the guideline is first of all, does the reader know what she’s looking at? Is she looking at something that’s sponsored? Is it clear? If it is, is it interesting?

Native advertising will work when the content is interesting. Ultimately, the goal should be in creating great native advertising, create an environment that exists in the best print magazines where women are buying them to read the edit and to also look at the ads that they love.

WWD: Do you have a separate group under the publishing team that works on native ads, or does edit work on them?

C.L.: The deals are sold by our ad team and then worked on in partnership with our own team.

WWD: has a strong presence on the Web. What’s your digital philosophy?

C.L.: I think we took it seriously relatively early on and we also made a lot of mistakes before we started getting things right. I believe in involving our digital team in every aspect of everything that we do at Glamour, so that they are not working in some different wing. When I walk outside of my office, the digital team is right there. They are part of everything that we do from the beginning. I don’t think they ever feel less than or second fiddle to the print team, and I hope that emboldens them to come up with big ideas and to propose things that can get them noticed.

WWD: Is the magazine’s redesign finished?

C.L.: Any editor will tell you, it’s never done. When you’re done, you get bored. The reader can feel that. The major creative changes that we made at the magazine last year, that Paul Ritter made in the design and the photography, and that Jill Davidson made in shaping her fashion department and upping the ante on the styling and the fashion fingerprint of the magazine, that work is pretty much what you see in the magazine now.

WWD: Does Anna Wintour still work on the magazine?

C.L.: Yes, thank God. Yeah, I mean, she’s an incredible resource to have. Her brain is a beautiful and stupendous thing. She knows fashion, she knows photography. She’s infinitely helpful.

WWD: Is she working on stories in the magazine or just fashion shoots and covers?

C.L.: You would have to ask her, but I think she would say she’s there for anything we want to take advantage of her expertise. She’s just a great resource overall.

WWD: Have you noticed a change in culture at Condé Nast since the executive team has been reorganized over the summer?

C.L.: I think it’s probably a little soon to know what the full ripple effect of those changes are, but I think the bottom line is that Condé Nast feels to me like it’s in a forward-leaning phase right now. There’s enthusiasm for digital, as you know there’s big enthusiasm for video. I think there’s an understanding that Condé Nast is a real true media company that produces spectacular print magazines, but also truly amazing stuff across all platforms. That’s not lip service. I think everybody up and down the company believes that and feels it. One of the things that Condé Nast properties do really well is storytelling. I don’t see that changing at all. There’s real enthusiasm for that and real respect for that.

WWD: What’s your end game after Glamour?

C.L.: Oh God, I don’t know. Does anyone ever have a good answer to that question? When I know, I’ll know. When I know, you’ll know.

WWD: Don’t you want to be a TV star?

C.L.: A TV star? No thank you. I get too impatient in the makeup chair. I think the amazing thing about being a magazine editor today is that the business has changed in lightning speed over the last three years. You can’t have your eyes open and be bored. There’s too much change — it’s too exciting. It still feels like a lot of fun to me.

WWD: Aren’t you a little bit nervous? There seems to be layoffs every week in the media industry.

C.L.: I think if you weren’t a little bit nervous, you’d be lying to yourself. Our industry has gone through huge changes, and our industry is going to continue to go through many, many more. That is the nature of media right now. If you’d told any of us that people check their phones 150 times a day, you’d think: ‘what sci-fi movie am I in?’ If you’re smart and awake you should be a little nervous, but you should also be coming up with great, creative ideas and throw yourself into it.

WWD: OK, you don’t want to be on TV, but what do you watch for fun?

C.L.: I’m addicted to all the predictable addictive TV shows. I’ve cycled through “True Detective,” “The Americans,” “Orange Is the New Black,” and I’m kind of cooling a little bit on, well never mind.

WWD: “Homeland?”

C.L.: Yes. “Homeland.” I do still watch “Homeland.” If Carrie Mathison could just have all the screen time…

WWD: She really hates her baby, though, I must say.

C.L.: I’m just waiting for that baby to grow up and have a spin-off. That baby needs a spin-off: “Abandoned Spy Child,” and I will be addicted to that show, too.

As a working mother, I think it is helpful to have Carrie Mathison around because you know what? No matter how bad a mom you are, you’re always doing just a little bit better than she is.

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