Tips On How To ‘Work It’, From Some Of The Boldest Women In Business

Carrie Kerpen, CEO of Likable Media
Photo courtesy of Carrie Kerpen

[The following is the full raw transcript for a LEADx Podcast interview, which has been lightly edited for clarity.]

Kevin Kruse: What is the best advice from the most successful women in business? Hello everyone, and welcome to the LEADx show. Kevin Kruse here, helping you once again to get 1% better today, just a little bit better. Have you checked out yet? No? We serve up a new free course of the day on management, leadership, productivity, communication. So when you get into work, fire up your browser, and go see what's free today.

Today on the show, you're going to hear from the CEO of a social marketing agency who interviewed some of the most successful women in business to get their success secrets. We talk about the challenge of communication as a leader, how she got a hold of Sheryl Sandberg starting off with a cold email, and our challenge of the day inspired by one of her tips is to use your mental mute button. We are all so uncomfortable with silence that we tend to jump in after just a couple of seconds of silence, so today instead, when you're asking someone to give you feedback, when you're asking your boss for a raise, when you're asking a peer to do you a tough favor, a big favor, ask and then hit your mental mute. Don't talk; just let the seconds tick away. Don't fill the silence. Wait until the other person responds.

Our quote of the day: “Life shrinks or expands in proportion to one's courage.” Anais Nin.

Our guest today is a keynote speaker, columnist for Forbes Inc., and CEO and co-founder of Likable Media, an award-winning content studio that achieved Crane's sixth “Best Place to Work in New York City.” She's the author of the new book Work It: Secrets of Success from the Boldest Women in Business. Our guest is Carrie Kerpen. Carrie, welcome to the show.

Carrie Kerpen: Thank you so much. I'm excited to be here.

Kruse: Now, I sort of have a tradition with all of our guests: they get the same first question because I love failure stories. I think failures are just stepping stones to future greatness, who knows what or where.

Kerpen: Yeah, yeah.

Kruse: Tell me about one of your best failures and what did you learn from it?

Kerpen: I love failures, actually. I hate them in the moment, but I always love them looking back. One that comes to mind for me would be when I took over a client here at Likable from somebody else that was in distress. We just didn't do a good job. I think we probably accepted the client around a service that we didn't do well, and I think we overshot. I came in with total hero complex, total hero complex, and I walked in the door. They were a global organization and they were headquartered actually out of the Middle East. I walked in their New York office, and they said, “Oh, you have to fix this, Carrie. Only you can fix this.” I said, “Okay, I tell you what: I will actually go to your Middle East office. I will immerse myself in your stuff. I will do it, and if you don't like it, I'm going to give you half your money back. Just pay for my travel or whatever. I'll give you half the money back,” because they had already paid. They were like, “This is great. This is awesome. Let's do it.”

I go out there. I have total hero syndrome. I spend days upon days. I do all of this work to try and make something perfect, and at the end of the day, it still wasn't what they wanted. I ended up giving them half their money back. Now I don't know if that's because they just were trying to really back their money and get a thing and like, “Oh no, Carrie, this isn't great” or if it really just wasn't great. It wasn't the core of what we did at the time. It was a great lesson for me in, A) focus is key and don't do things outside of your wheelhouse if you don't know how to do them or have a good partner who can execute them, and B) You know what? You don't have to be the hero. It doesn't have to be so much about you. I think it was my own ego that was so focused and like, “Oh, I'll save this.” I literally flew to the Middle East because I was so obsessed with my own ability to save the day. That for me was a big wake-up call. Can't always be the hero.

Kruse: Yeah, it reminds me of that psychological thing about sunk costs where-

Kerpen: Oh, yeah.

Kruse: Once we've lost some money at that blackjack table or whatever, it's hard to walk away. It's like, “Oh no, we'll win it back. We'll win it back.”

Kerpen: 100%. 100%.

Kruse: Great story.

Kerpen: I've had lots of other failures, but that one I remember because giving half that money back was not fun.

Kruse: Yeah, I can imagine. So, I mentioned in the pre-show of course, your new book again is Work It: Secrets for Success from the Boldest Women in Business, and you do have advice from a lot of really high-profile women.

Kerpen: A lot.

Kruse: How'd the book come about?

Kerpen: Well the book is actually really interesting because I run a social media agency that I co-founded with my husband in 2007. In 2013, I took over as CEO and it was really a very scary experience for me if I'm being honest. I'm an operator and somebody who can really hold stuff together, but having that actually vision was really terrifying for me, especially because in 2013 as a social media agency, it's a much more crowded landscape. At the time, what I decided to do was use the fact that in social media, most of the founders and most of the leaders were very loud, very extroverted, and male, and they were all talking about themselves all over social media. I felt like, “Oh crap, how am I going to grow this business? I don't want to do that, and I'm definitely not a male, and I don't want to be talking about myself all the time.”

I decided that to grow the agency, what I would do would be instead of telling my own stories, I would tell stories of other women in the industry. What I would really do is focus on people who worked at the brand level and expand my own networking capabilities. I invited great guests on the show and asked about their business challenges, and then boom, we'd be friends and then eventually we'd do business. It'd be great. I started a podcast called ‘All the Social Ladies’, and what I found was that I wasn't just interested in my own selfish reasons like, “Oh, I can grow my business,” but I also was fascinated with their career tips. I was like, “Wow, this could really work well for young women and people midway in their careers. When I was approached by Penguin Random House to do a book, I thought that this was an excellent opportunity to give these stories more voice. That's really where it came from, and I expanded beyond just social media, which is primarily what the podcast is about, to be about life lessons.

We need more than just one philosophy, I think. Things like Lean In and Girl Boss are great, but they're like, “Here, do this.” I believe ultimately that you have to hear lots of different things from lots of different people to get your own inspiration. That's what the book tried to do.

Kruse: In this short podcast, we can't go through all of it-

Kerpen: No.

Kruse: But you said lots of jam-packed advice. Give us a couple of the secrets that stand out for you or you find most interesting yourself.

Kerpen: I mean, there's so many I find interesting, but I think there's a few around networking that I think are really key. One story that I love came from Sandy Carter who has been at many Fortune 500 companies, was leading social change at IBM and a lot of different places. What she talked about was very early in her career, she would sit at her desk during lunch, keep her head down, and get her work done. Because she was racing, right? One day, a supervisor came to her and said, “Do me a favor: go down to the cafeteria and see who's down there,” and it was all men. The reason it's all men is that men understand the power of networking with one another and the importance of networking with one another. I think that women are like, “Oh my God, we have to be so competent. We have to get our job done, we’ve got to get it done, we’ve got to go.” I think they don't take the time to network as much.

I think those tips around using networking as a part of your job, making it a part of your job versus “Oh, something I need to do later” is key. I think that all links back to a lot of the stories in the book, which are around women focusing on being the best at their job. Competence versus having confidence in the ability to talk about what they do. The confidence is as important as competence, so there's tons of stories about that that can really, I think very practical, can help women. There's a ton that I love. There's a lot around “how to listen to your gut” and things like that, but I think the practical stuff around how to have confidence is what's key. Also good stuff about making money, too. That's good.

Kruse: Well tell me how to make some money.

Kerpen: Oh, okay. This I love, this story. This is not for us entrepreneurs, okay? This is really, although it can be used in any negotiation. Cara Friedman from ClassPass, I love Cara. She used to work for me, and she tells this story that is so dead on. Best advice. Ready? When you're going for a new job, if you're on a phone interview, ask, “What is the salary for this position?”, and then hit mute. Force yourself to put the awkward part of a negotiation on somebody else. That doesn't just work for salary; that works for anything, and not just mute on the phone. Learn how to use your mental mute, because if you learn how to use your mental mute, you can negotiate for a lot more. “How much is this project going to cost?” Mental mute. “Where do you see me going in five years at this organization?” Mental mute. For acquisitions, you name it. Just learning how to mute yourself, you have to own that feeling and like the feeling of awkward, and then you can become really, really good at getting more money. I love that tip.

Kruse: For all the podcast listeners who can't see the video, you've got like evil glee with this tip. I love it.

Kerpen: You have to own the awkward. To me, which is such a light bulb, once you just say, “You know what? Screw it; it's awkward and I'm going to love it.” You just love that and you put that onto somebody else, and then you're sitting there and you own the feeling of silence. It's so great.

Kruse: I wrote down “mental mute.” I like that. I love alliteration; I'm always looking for ways to anchor ideas. I got similar advice for a different context from Kim Scott. Now she created the Managing at Apple program and all that, and I was talking to her about how do we get feedback from people. She said that, “Nobody wants to give their boss feedback. You're scared to actually say what you really think.” She said the key is to ask for the feedback. They usually say some little thing, and then you say, “And what else?” Then you just stop talking.

Kerpen: Mental mute. “And what else?”

Kruse: Mental mute. She says, “Six seconds. Nobody can sit there for six seconds without saying something, but most people, if you're the boss or in this case, you will jump back in to fill the silence. Don't.” It's like the mental mute, and then people will start to tell you what they really think. I love that tip.

Kerpen: Yes. You have to get comfortable in silence. I think that that's key on a lot of things, by the way. If you're comfortable in silence with yourself, it can help you better channel your gut and learn what you really want. I believe when you're able to listen to your gut, you're able to make decisions better and faster, and a lot of that is just sitting with yourself in silence. You have to mental mute yourself, too.

Kruse: Right, mental mute yourself.

Kerpen: Mental mute.

Kruse: So, you say women should ditch the five-year plan to build a killer career for themselves. What do you mean by that?

Kerpen: Okay, so if I said to you, “What are you going to be doing five years from now?”, you might have an idea but the reality is that most of the careers that will be available in five years don't exist today. If we had said to you in 2003, “What are you going to do in 2008?”, I never would've been able to say, “Oh, I'll be running a social media agency,” because social media was not a thing.

I believe that in this current economy and this current state of the world, we are seeing things evolve so quickly with technology, we need to be really thoughtful about where we want to be in the here and now, and what our next step may be. The other thing is that a five-year plan, sometimes when you're setting a plan that's aggressively straightforward, up in the air, you're forgetting about making your career more like a jungle gym. Instead of going straight up, you can try new things and do new things at the same level. It doesn't hold you back.

That's what we've seen more recently, especially with the millennials as they're taking a lot of different choices and steps in their careers. It's not a ladder, it's not necessarily a ladder; it's really more of a jungle gym.

Kruse: Yeah, that's great advice. I have a 19 year old daughter, a 17 year old daughter, and we were just having this conversation.

Kerpen: Yeah.

Kruse: I'm purposefully being an alarmist when I talk about, even today's email news blast was about “Look out for the artificially intelligent robots that are going to come and take our jobs.” It's not that every job's going to go away, but I keep telling my kids, “Don't worry so much about your first job out of college. You're going to have choices in five or ten years that just don't exist today. You can't pick something that just doesn't exist today.”

Kerpen: Exactly, and that's why you have to try lots of things. I have a 14 year old, so I'm not quite where you are yet. 14 year old daughter and a 10 year old daughter, and a 2 year old son which is a whole other story for another day. My 14 year old-

Kruse: I didn't know about the two year old.

Kerpen: Oh my goodness. Love him. Got the two girls and then the little baby boy. It's just very crazy getting this all done, but yes. My 14 year old, I tell her to just try lots and lots of things. I think that's what's really key.

Kruse: I love that.

Kerpen: You’ve got to try it and see what you like.

Kruse: So, again, lots of high-profile people in your book. Very successful women. Who's maybe one of the highest profile? Is it like Sheryl Sandberg I know?

Kerpen: Yeah, I think Sheryl Sandberg, Barbara Corcoran, Reshma Saujani who founded Girls Who Code and did that incredible Ted talk on teaching women, teaching our girls not so much to be perfect but to be brave. I think that, again, ties back to the competence and confidence thing.

A lot of high-profile women but a lot of women who are just like you, just like any woman out there. That's what I loved about it. High-profile women are fabulous and they are there for a reason. They get a lot of attention, but there are so many stories out there that need to be told that are more than just the women whose stories we've already heard. That was what was so exciting to me.

To interview Sheryl Sandberg on the same day as I interviewed Anita Rosner, who had a comeback from her career. Had a career on Wall Street, ended up staying at home to raise her kids, talked about that experience, and then came back into the game as an actress. Really just interesting people who you've never heard of. That I really loved, seeing that context and that juxtaposition between women who are kind of notable and women whose stories have never been heard before.

Kruse: I'm wondering if you could share briefly how you got to interview Sheryl Sandberg because I think people who haven't read your book are just going to assume, “Well, you're a successful entrepreneur, author. You guys probably just work out at the same gym. She's your friend and that's how it came about,” but I think there's some lessons to learn, some career lessons even to learn just from how you got that interview. How'd it come about?

Kerpen: Well it's really funny that you asked me that because I don't know if you read this part, but I actually write a whole story about how I got the interview with Sheryl Sandberg. I'll tell you in a nutshell: many years ago I was a startup social media agency. I had followed Sheryl from her time at Google, and she had recently come on board. This was before Lean In, when she was at Facebook. I emailed her and I said, “Oh, I'm in the Bay Area for a meeting. I love you,” all the things I loved about her-

Kruse: Cold email. She didn't-

Kerpen: Cold, cold. “I know you through this connection, you know so-and-so,” I go through the whole thing. I say, “Would you like to meet up?” She says, “Oh, I can't do this day but are you in the Bay Area often?” Well, I am never in the Bay Area ever. Ever.

Kruse: You're in New York.

Kerpen: Right, so of course I responded, “Yes, I'm there all the time. When is a good day for you?” She gives me a day and I'm like, “Oh my God, I'm going to meet with Sheryl Sandberg.” I went there, and she of course as the chief operating officer of Facebook had ten million things come up, but she didn't know that I was there just for her. She was like, “Oh, I'm so sorry. Can you do tomorrow? Can you do whenever?” I ended up having a parent-teacher for one of my kids, and I had to get back so I said, “So sorry, can't meet up.” I had kept in touch, every once in awhile. She sent me the Lean In book. I nurtured the relationship but without being annoying and a stalker. Eventually years later, I send her an email and I say, “I have to confess something to you.” I told her the story and I said, “By the way, I was never in the Bay Area. I just wanted to see would you be open to giving me,” maybe at the time I think it was a blurb for the book.

She was like, “Oh, I'll do an interview.” It was so amazing. So generous of her. She owed me absolutely nothing-

Kruse: I love this.

Kerpen: To me, the lesson on this is really being fearless in the ability to reach out, and especially with social media today, the access is really there. If you use LinkedIn or Twitter or anything of these things properly, and you can do it in your own way. Not everyone is comfortable cold emailing, so maybe you can get introduced through a friend of a friend of a friend, or you can do something. Again, it's not always about meeting the biggest star. I believe that there's a whole level of successful women that are not in this high ecosphere that are accessible to you that you can connect with and be inspired to do so.

Kruse: Kerpen, you're a better parent than I am because I would've so blown off that parent-teacher conference. I'd be like, “Sheryl Sandberg, I will be here every day until we get this meeting in.”

Kerpen: You know what? Let me tell you something: I felt really bad not saying that, but two things. First of all, I think the mom guilt game is strong.

Kruse: Sure.

Kerpen: I think it was out of mom guilt, and I knew where my limits were. I also believe that for women and men, you have to set the limits to create the kind of life you want. For me, if it meant that I wasn't going to grow faster because I was going to parent-teacher, I was okay with that.

Kruse: Right.

Kerpen: I always was, and I think that that helped keep me grounded and actually it helped me grow the way I wanted to.

Kruse: That's great. A question not directly related to the book but as a successful entrepreneur, business leader, give us some advice for being a great manager, a great leader. How do you lead your people?

Kerpen: A great leader has to inspire. Definitely I think for me, I think it's very, very important to realize the weight of your words as a leader. They should be inspirational and you have to know that anything you say matters a lot more than you think it matters. If you give a comment off the cuff, it could really matter a lot. I think a great manager and leader has the ability to deliver feedback in a way that is true and likable, so learn how to give feedback. Dave talks about this in Art of People. My husband Dave Kerpen wrote The Art of People. It talks about the feedback sandwich, like something positive, constructive feedback, something positive again. I think really learning how to give that type of feedback and have fearless feedback is key as a leader. Then always know that the person in front of you is thinking about, “What's in it for me? What about me?” If something happens like, “Okay, how does this affect me?”

Always with thinking that in mind as a leader, you can choose your words carefully and direct to somebody to help realize, “Okay, this is what we're doing. Here's how it's going to impact you, and most important, here's how it's going to impact the org.” All the leader's thinking about is, “Here's how it's going to impact the org,” but ultimately recognizing that you need to think about how it's going to impact them is what's going to be key. To me, the biggest thing is feedback and the good ability to listen as a leader.

Kruse: That's great. You mentioned when CEOs and leaders say something and it gets kind of magnified through the organization-

Kerpen: Ugh, yes.

Kruse: I had an event and the speaker was Dick Costolo, who was CEO of Twitter at the time. He made the same point. He said one day he made some comment about the potted plant in the corner of the thing, like it was ugly or it was dying or something. He said, “Oh, that's ugly” or something like that. The next day, there were no plants at Twitter.

Kerpen: None.

Kruse: They just removed all plants through-

Kerpen: Plants all gone. Yep.

Kruse: CEO says “no plants throughout headquarters,” so …It was crazy.

Kerpen: All the plants, immediately.

Kruse: Carrie, how can our listeners find out more about you and your new book?

Kerpen: Okay, so lots of ways to find me and my new book. You can go to Has every retailer under the sun or Amazon “Work It: Secrets for Success from the Boldest Women in Business.” On social media, I am Carrie Kerpen just about everywhere. Then if you want to see what I do in my day job, which is really fun which is creating content for large brands and social media, you can go to too.

Kruse: We'll put all of those links in the show notes. Carrie, thanks for coming on to the LEADx show.

Kerpen: Thanks so much, Kevin. I really appreciated it.


Kevin Kruse
NY Times bestselling author, Inc 500 entrepreneur, and keynote speaker on Wholehearted Leadership and Extreme Productivity. Download 'How Millionaires Plan Their Day: A 1-Page Tool' at