How 6 Powerful Women in Media and Marketing Redefined the Rules of Leadership

Women are having a moment.

Ignited by Sheryl Sandberg's manifesto, Lean In, the issue of gender equality became part of the national discourse.

And it has remained there thanks in large part to inspiring creative like Under Armour's "I Will What I Want" campaign by Droga5 as well as evangelists like Mika Brzezinski, co-host of MSNBC's Morning Joe and author of the best-seller Knowing Your Value and this year's follow-up, Grow Your Value.

Droga5, MSNBC and Adweek all saw the issue of female empowerment as one to be addressed, especially given that recruiting and retaining talent are top of mind today. So we pooled our resources and, with some ninja scheduling efforts, brought together a formidable group of leaders from the worlds of banking, advertising, media, e-commerce, fashion and professional sports. Here, these extraordinary women share valuable lessons on leadership and insights on how they get the very best out of their teams, and themselves.

Mika Brzezinski, co-host, Morning Joe: I just want to ask by a show of hands, and we'll go from there: How many of you see yourselves as risk takers? (All raise hands.) Wow, I did not expect it to be unanimous! What's your biggest example of risk taking, Liza?

Liza Landsman, chief customer officer, Jet.com: I just joined Jet.com, a brand-new startup, about four months ago. It's a huge, audacious thing coming out of many, many years in corporate America.

Brzezinski: From eTrade? A comfortable job?

Landsman: As a chief marketing officer, I could have stayed for a long time. I'm in my mid-40s, and I just thought, if not now, when? And it's interesting. A close colleague of mine said to me, "God, did you ever really consider that you have to be prepared to fail big and publicly if you do this?" And it never occurred to me. I've never made a decision based on fear in my life, and it seemed like a bad time to start.

Sarah Thompson, global CEO, Droga5: To Liza's point, about seven years ago, I was very settled in a network ad agency. I had a lot of goodwill there, probably could have done anything I wanted, and I went to this tiny little startup agency called Droga5. I was also six months pregnant. I went in there and just felt like it was a point in my career—I was into my late 30s—that I would have regretted not doing something because of fear that felt instinctively right.

Kristin Lemkau, CMO, JPMorgan Chase: I take personal risks; I try not to take a lot of risks on my job without being thoughtful. One of the things you have to learn on the job is how to fail. When you're at college, you get good grades and work hard, and it's all equitable. But when you're working, you need to actually learn to accept failure as important and necessary and part of your growth and learn that it's OK instead of tearing your hair out.

Brzezinski: So, Dawn, do you like to take risks?

Dawn Hudson, CMO, NFL: I grew up playing competitive tennis. If you get on the court and play it safe and keep the ball in play, you're going to lose. You've got to take some risks to see your opening, and you have to take it. And it actually has given me a lot of skills for the business world. You don't want to take foolish risks, but success comes from taking appropriate risks. Wall Street rewards growth. Now I work for owners; they want growth, and that tends to not be static—that tends to be things where there's innovation and big change. The ability to take risks is the ability to make big differences in businesses.

Rebecca Minkoff, fashion designer/co-founder, Rebecca Minkoff: I would say that I didn't realize how risky some of the moves I made were. Moving here, no place to live, two suitcases, with an internship and then starting my company three years later on the heels of 9/11. Starting my company at 21 was a huge risk. Then we actually saw our biggest growth when the world was changing. Weblogs, as they were called, were just starting. Chat rooms were just starting, and I discovered these women were talking about me and the bags, and I thought I should probably talk to them. And every editor, every buyer said if you talk to your customer, it will destroy your career. You're supposed to be removed. You're supposed to be in your ivory tower, and we're the people that should be talking to them. And my brother and I, who's my business partner, said, "No, let's talk directly to our customers. Let's get on Twitter and let's get on Facebook" when it went broad, and that changed the base of our company.

Lemkau: You know, one of the best pieces of career advice I got was: If you want to get your job, you need to make your own job bigger because women wait and pull back. If you're confident in your job, they already see you there. Men do that. Women, I think, don't naturally do it as much.

Brzezinski: Dawn, I do wonder about the differences between working for Pepsi and the NFL. That must have been a big transition.

Hudson: I knew the NFL well when I was at Pepsi; I signed a sponsorship deal with the NFL. I thought I knew the NFL, but that's from the outside looking in. It's a very different organization when you're on the inside looking out. The commissioner called me and said, "Will you help me find the right woman for my senior team? Will you help me find my person? Is there any chance you'd be interested?" And I very quickly said, "I would, of course, be delighted to try to help you find the right person." He said, "Well, let's talk again in a few days," and hung up. And all of a sudden, I'm saying, find the right person? I want this job. And I called the next morning and I said, "I want to do this job." Then, [the domestic-abuse scandal around former Baltimore Ravens running back] Ray Rice happened. So many people said, "Will you take the job now?" I said, "Absolutely. I'd be making more of an impact now. Actually, it's a better situation, and I think the league will be open to more change, and that's a good thing for somebody new coming in trying to think of new ways to do things." The biggest difference is not the fact that I'm back in a male-dominated sport or that I'm in sports; the biggest difference is that we are a collection of people working on behalf of owners, and we're a league. And there's a different dimension to that than a publicly traded company.

Brzezinski: Any challenges getting your point across?

Hudson: Honestly, no. I came in with a perspective of a point in time in my career where I'm not climbing the ladder anymore. I'm coming in to do a job to make a difference, and you can listen to me and I can help you, or not. It's not that big a deal for me. It is probably the most collaborative group. For the former players I work with, it's really not about the business or about the sport; it's about why they got into the sport. And I've learned so much from them. It's just such a pleasure.

Defining Your Value

Brzezinski: We're all in leadership with brands to build. If you could put a number on your value, would you know what that number is?

Minkoff: I'm going to still try to figure it out. I know I'm valuable, obviously, but I think I'm still learning, I'm still growing. I'm still in the wide-eyed excitement of my career.

Brzezinski: So Dawn, for your last negotiation, did you know your number?

Hudson: I asked for it. I got it. I did it over the phone, too.

Lemkau: There's a number and then there's a value that you bring to the organization. I think I know the number. I would struggle with that a bit more than my intangible value to the organization, which is broader than that.

Thompson: What I can say over the past five years is I am much more clear than I was in the 15 years prior. So I guess my answer is, it took me a long time to get to, in total honesty, really knowing what my value is and expecting it.

Landsman: I would love to say yes. I think I know it. I think I still sometimes struggle to ask for it. Actually, I know I know it and I know I sometimes struggle to ask for it.

The Balance of a Personal Brand

Brzezinski: I feel like it's talking about weight or something. It's hard. So, let's talk about our brand. My brand is: I'm Mika Brzezinski, co-host of Morning Joe and founder and creator of Know Your Value, and I teach women to understand what their value is and communicate it effectively. If that's my brand in 20 seconds or less, what's yours?

Thompson: Let's see. I am Sarah Thompson, global CEO of Droga5, and my brand is providing the leadership to take great ideas and creativity and create influence in the world.

Landsman: I'm Liza Landsman, and I am pulling a sequoia out of the ground in birthing Jet.com.

Brzezinski: I like it. That's a good one.

Lemkau: I'm Kristin Lemkau. I'm Natalie and Sam's mom and I'm trying to lead an organization to follow a purpose instead of a product.

Hudson: Oh, that's a tough brand to follow. I guess my business brand would be, I'm somebody that understands, observes consumers and figures out how to use creativity and innovation to create opportunities with consumers. It's a real lens into people and what motivates them. From a personal standpoint, I'd really rather be known for being a mentor and a leader—of men and women, somebody who galvanizes teams to achieve what they didn't think they could be doing.

Minkoff: I'm Rebecca Minkoff. My greatest creations, like Kristin, are my two children. Second, I have a business and it is fashion-based, but what we are really striving to do is make a product that is accessible, that makes us feel confident and that won't break the bank. It's also about empowering more women to be self-made.

Walking the Leadership Tightrope Without Falling Into Stereotypes

Brzezinski: So, we all know what our brand is. How important is it to draw on that as you play out the role of being a leader in your company? What are some of the challenges leading as a woman, and what are the surprising open doors that you've seen along the way?

Lemkau: I talk to my team a lot about the difference between being a team and a tribe. As a tribe, you have each other's back and you're much more invested in work, and I find I get their output from them. They feel their work is more meaningful; they understand the value of it. I don't know if that's a gender-based thing. I'll tell you, men are rallying around it, too. It just makes work feel more purposeful.

Thompson: I feel incredibly comfortable and confident now that I have a different style than many men that I work with who are leaders. And I like that style, and I know the results that come with that style of bringing tribes or teams together and getting everyone focused on a common vision and not always being the person who has to win the meeting.

Minkoff: I think it's challenging sometimes because I don't like to ever be a bitch, right? I want to lead by being nice, but then sometimes the team might not take you as seriously. And in my industry, being that it's more female-driven, you see the women that are considered the ones to look up to as more mean and catty. It sets this ongoing example of how you should act. It's an internal struggle for women at least in the fashion industry.

Brzezinski: Absolutely. I think you've tapped into something that is a huge issue for women as they develop their leadership skills. Knowing the difference between friendly, warm relationships and wanting to be friends with everybody and being tough and being a leader. I struggled a great deal before I got fired from CBS. I look back on my career there, and I realize I was friendly with like 100 people. And that's unsustainable. It's also not necessarily a way of life that generates respect. It's respect that needs to come first; so all those qualities and ability to know where people are coming from are great, [but] they're also stumbling blocks for us. Does that make sense?

Landsman: Yes. In a weird way, it's the same with my children. I love them and I also like them, but there's no question that I'm the parent and they are the children and we're not friends.

Lemkau: People just want to know that you care about them, and part of caring about them is being honest with them or telling it to them straight when they're struggling and even if they're not making it in a role. If they know you care about them, you can be nice and tough.

Brzezinski: But the balance that Rebecca's talking about is, sometimes we come off as a stereotype, and I do think that still is a little bit of an issue. Dawn, it doesn't seem like you've worried about this.

Hudson: I would say my perspective has changed around teams because I think the definition of teams has gone from being linear—who works for you—to being matrix cross-management—leading people across different functions, and that really becomes an appreciation of diverse opinion as opposed to just gender-based. So I found myself focusing more on how do you teach people to be the good members and willing to offer different points of view in a team environment because it's that diversity of experience and opinion that leads to better, quicker decisions. So it's evolved for me a little bit more than just a male/female thing to more about, how do you encourage teams to respect different points of view and get them on the table?

Retaining Good Talent Starts With Good Managers

Brzezinski: I want leadership tips on retaining talent. How are you the greatest boss ever to work for?

Landsman: I have one of the closest mentor/mentee relationships I've ever had with a woman who, when she first worked for me, I gave a terrible performance review. And I worked at an organization where people did not do that. And she said, "I'm shocked. And why are you being a bitch about this?" I said, "I'm not. It's because I think you're incredibly talented with so much potential." Sometimes you've got to be cruel to be kind.

Thompson: I know I have really high expectations and the agency works really hard across the board, but positioning people for success means empowering and believing in them. And I know certain people have moved up the ranks in our organization and have been pushed out of their comfort zones just like I was at different points in my career—and I think that is the world of leadership. It's belief but not blind belief.

Brzezinski: And to your point, Liza, about that person that you gave the critique to, I truly believe that some of the best people I have worked with, I am incredibly blunt with from the get-go. The relationship had a place to go.

Landsman: I think for high performers sometimes that's the thing that holds them back, which is that they are consistently told how wonderful they are …

Lemkau: No, but to get that person who's been overpromoted and overpraised and who believes their own bullshit in a bad way. If you really care about them, that will make the toughness feel kind. They know you have their interest at heart and that you believe in them.

Hudson: The one thing that continues to come out of almost every personnel study I've seen is that people leave because of the immediate boss. (All signal their agreement.) The importance of the immediate boss to what they believe in their career, where it's going to go, are they going to get training? Are they going to get development? Are they going to get sponsorship? It is so much the organization of great culture. They could be doing great things. They could be growing. Today, it's about authenticity, and that doesn't mean mushy kindness and it doesn't mean meanness all the time. What it means is that I understand you, you understand me, and we are able to have an authentic relationship. I've spent a fair amount of my career mentoring women of color who are a key [group] for the business going forward. They're graduating from college at high rates, they're going to be a bigger part of the workforce, and they have a tough time getting an authentic relationship because they often have both a racial and a gender difference. And so they don't feel able to speak freely, and the boss doesn't speak freely to them either. If you don't have an authentic relationship, then you can't build from that to give direct feedback to a sponsor. So really, working on authenticity is what we want to do.

Lemkau: And you can show your scars—you're not trying to be perfect. You let them know you have weaknesses, too, and it's OK.

Minkoff: I think listening is key. No matter where they are in the organization, they can come to me and say, "I'm having a problem." Don't say, "Go speak to HR." Also important is knowing that nothing you ask of them you're not willing to do yourself.

Leadership Advice From Those Who've Made It

Brzezinski: We'll close by just going around the table—leadership advice. Mine would be: Respect first, friendships follow. Liza?

Landsman: Certainly that, but I would also say: Know where you are going because you can't bring people with you if you don't know that.

Thompson: I'd say: [Have the] confidence to roll the dice. Sometimes a decision needs to be made and be comfortable weathering it if it's a failure and have the energy to move on fast.

Lemkau: Learn from everybody, but be yourself. Be confident in who you are and your style.

Brzezinski: That's hard. That takes years sometimes. Dawn?

Hudson: Share a vision.

Minkoff: Be your own entrepreneur whether or not you work for someone else. I'm most proud when someone says, "I quit. I'm starting my own company." That's what I'm most proud of.

Brzezinski: Very cool. Ladies, thank you so much.

Mika Brzezinski

Photo: Kevin Scanlon; Makeup: Wilbert Ramos; Dress: Karolina Zmarlak

As co-host of MSNBC's Morning Joe, Brzezinski's success didn't happen overnight. It took time for Brzezinksi to realize her value and to share those lessons to help empower women in the workplace. Aside from her best-selling book, Knowing Your Value, and this year's follow-up, Grow Your Value, she has partnered with NBCUniversal on a series of live, Know Your Value events across the country. Each conference gives women networking and coaching opportunities to help create a plan for success. The next event will be held in Boston on Oct. 23.

Dawn Hudson