On this week’s episode of Conversational Selling, we’re joined by special guest, Judy Hoberman, President of Walking on the Glass Floor and Selling in a Skirt. She is an international trainer, coach, author, and mentor, and her 30 years of business experience has given her both the knowledge and a great sense of humor about how men and women sell, work, and live differently. She is also one of the female pioneers in the insurance world and is the host of the weekly podcast, Selling in a Skirt.

“Sales today is a little bit more difficult than it was, but it isn’t outrageously difficult. I always say that now is the time to share opportunities and collaborate. It’s the time to find people that you can do things with and make yourself even stronger. In that, you can also be a champion, whether you’re male or male or female, you can be a champion for another woman in business that you can open a door up to, or you can collaborate with, or you can show an opportunity to,” says Judy.

We chat about her goal to empower women and give them the tools they need to be successful, as well as:

  • Her shift towards virtual coaching
  • Prejudgement
  • The differences between how men and women work and sell
  • Why humor in sales is so important
  • The women’s roundtable
  • And more

Listen now…

Mentioned in this episode:



Nancy Calabrese: Hi, it’s Nancy Calabrese and this is Conversational Selling. It’s the podcast where sales leaders and business experts share what’s going on in sales and marketing today, and it all starts with the human conversation. Joining me today is Judy Hoberman, President of Walking on the Glass Floor and Selling in a Skirt. She’s an international trainer, coach, author and mentor.

Her 30 years in business has given her both the knowledge and a great sense of humor about how men and women sell, work and live differently. She’s one of the female pioneers in the insurance world and is the host of the weekly podcast Selling in a Skirt. You know, Judy, I could go on and on about what you do and your successes. I absolutely love humor in sales and I think it’s so important, you know? And I’m really excited to learn more about what you have to say about the differences in genders. So welcome to the show.

Judy Hoberman: Thank you so much, Nancy. I’m excited to be here and couldn’t wait for today.

Nancy: Oh, boy, you know, I think this was a long time in the making, wasn’t it?

Judy: Between weather and sickness and everything else, yeah, but we’re here and we’re gonna do this.

Nancy: Alright, so, you know, in contemplating what to ask you, I kept saying, Well, where do I begin? Where do I begin? Your background is really diverse. Why don’t we start about what you do today and how you juggle it all?

Judy: So what I do today is really what I’ve done forever, just a little bit more intentional. So I do executive coaching, I do sales and leadership training. I’m a speaker, I am an author. I do my own podcast and I was on radio for many years. And I just want to make sure that what I do every single day is empower women and giving them the tools they need to be successful, as well as encourage men to become champions of women.

Nancy: Yeah. And, you know, we spoke earlier that you’re considered to be one of the female pioneers in the insurance industry. We have a common bond in the insurance industry. I think it’s fantastic. How did you earn that title?

Judy: When you’re the only, you get that title, but you have to earn it, you know, so people start to respect you. I believe that once you show that you know what you’re talking about and that you have results, and anything that has to do with sales is always about results. It could be dollars, it could be numbers, it could be whatever. So when you start to prove yourself, people start to take notice and they start to listen. So today, when I go out, and I talk to companies or I work with individuals in the financial arena, they know I’ve been there, they know I’ve done that. And so it’s a very different relationship because I can say something and they know that I know what I’m talking about because I’ve done it. So it’s different and it’s fun.

Nancy: That’s great. So you still play in the insurance world.

Judy: Yeah, it’s almost like going home. You know, I go in lots of different industries and I love all the industries I work with. But when I go back to financial, it’s like, ahh, I’m here again.

Nancy: You’re there. You’re there. So I know you have a great story to share with the audience, you know about your future in business. Let us know about it.

Regular Self-Reinvention

Judy: So I reinvent myself quite often. And it’s only because I need to make sure that I’m shifting. Wy word for 2020 was shifting and who knew how relevant that was going to be? A lot of the things Yeah, I know, a lot of the things that I’ve done before, I have to figure out how to make them relevant going forward for the future. And, you know, I was, I mean, I work with a triangle. My triangle is speaking, coaching and training. While we all know that in March, all live speaking was eliminated and live training was eliminated, so two-thirds of my triangle was gone.

So going forward to the future, almost everything I do is virtual. And if it’s not virtual, yet it is becoming virtual. And I do believe that you can have the same relationship and have the same success virtually if you do it right. So those are the things that I am working on to make sure that I do the things that will not only continue my business but also continue making a difference in everybody’s lives because that’s truly what I want to do. I want to continue that.

Nancy: Yep. Yeah, have you found the transition to be challenging?

Judy: I think in the very beginning, it was very challenging only because, you know, you look at yourself and you look at your business, and it’s different, and, you know, everything’s gone. You have to basically start all over again. So it was challenging then. But when you put your mind to it, it’s all about mindset. When you put your mind to it, you think, okay, so we can move this around, we can move that around. And as long as you stay in contact with your clients and they know that you’re still there and you’re worried about how they are, it’ll work out.

Nancy: Yeah. You know, I know that you’ve spoken on TEDx Talk. Is there a particular story that you can recall that might also be of interest to everyone?

Judy: So my TED Talk was about being, prejudgment, and I have been prejudged my entire life. One of the stories that I tell is about the one thing that women are always freaking out about and it’s always about not being enough. And one of the stories is when my father told me that all I was pretty and I’d never amount to anything else because I wasn’t good enough and I wasn’t smart enough and then wasn’t bad enough. When you tell the story, yeah, well, and it was a very emotional story to tell out loud for the very first time on a TEDx stage. So it was, yeah, it was pretty powerful.

Nancy: I bet you that resonated with a lot of people, a lot of women.

Judy: It did.

Nancy: And it could also be men, too.

Judy: Yeah, I was, yeah, a lot of the men said, you know, I have to make sure that I don’t ever do this to my children and myself and, you know, so yeah, it was very powerful.

Nancy: Wow, wow. And so taking that empathy that you have must really add a lot of value in your work relationships, your coaching and your training.

Judy: Yeah. And I, you know, what’s happening today is, it’s everything’s becoming much more empathetic, more nurturing, more, you have to be more concerned about your people now because everybody is separate. And so people don’t feel connected. And if you don’t connect people and connect with people, you’re going to lose people. So I would say know your people and know what they need.

Nancy: Yeah. You know, and, you know, maybe that’s the silver lining in all of this right now. That people are making a concerted effort to connect in different ways, right? We can’t be physically around each other so we use other skills to convey that. You. I’ve gotta bring this up, I have to hear about the differences in gender and why I find it so humorous.

Gender Differences in Sales

Judy: Okay, so you know as well as I do that men and women are different. That’s where it starts. Men and women are different. And it’s a very profound statement. But the truth of the matter is, if you watch what happens in a sales process, it is very different. And some people like, they prefer to work with men more than women because men make decisions quicker. Women have to marinate it. They have to make, you know, have a relationship with us in that. I am that person. So I try to understand who my contact is, who my new connection is, who my new prospective client is.

And I ask a lot of questions. And so I have been dubbed the question queen. So I’ll get in there and, you know, I did a lot of field training. And all, of course, everybody I was with were men, and what I would do field training, they would always say to me, why do you ask so many questions? I said, because I’m interested. And when you’re interested, it’s a very different feeling than being interesting. And so as a man, I would, you know, most men, and I say this with a caveat, not all men, not all women. But generally speaking, a man would go in and they would say, you know, what do you want?

How much do you want to spend? Boom boom boom, get in, get out and get the check. Women go in and they want to know, how is this going to affect your family or the other people in your life? How is this going to work for you? How can I make your life easier? So it’s a very different conversation. And, you know, you can have fun with it. And I always like to team up men and women so they can see the differences and use them as assets instead of liabilities.

Nancy: Interesting. And so there are two schools of thought, right? What you described initially is maybe going in and doing features and benefits versus the opposite, the polar opposite is what is it that they need? What are they struggling with? Can we fix it? Would you agree with that?

Judy: Absolutely. Absolutely. And both are important. Both are important. And so if you go in with this second way, and you start to be interested and find out what they need and what they want, you’re also going to give them the features and the benefits. I mean, like a perfect example is when I was selling insurance, I would never say to someone, do you want life insurance? How much did you want to spend?

Who’s the beneficiary going to be? I would never ask those questions. However, what I would ask is, tell me why it’s so important for you to have a policy in place today. Well, in that conversation, I’m going to hear how much they want to spend, when do they want to start, who’s the beneficiary all of that. But I don’t have to ask that because I asked the other question which was a much bigger question that when the answer it, you get everything else you need.

Nancy: Absolutely. And you’re earning trust because you’re focused on them, not on yourself. Okay. This kind of leads me to Selling in a Skirt. And I have to confess, I immediately passed judgment on this. It’s about women in sales. So tell everybody why I was wrong.


Judy: Well, okay. When I originally started telling people about Selling in a Skirt, the first response I would get is men would say, Oh, it’s only for women. Oh, I don’t know, don’t wear a skirt or anything like that. And I always said, If I would have $1 for every time that was said to me, I would never have to work again.

But the truth of the matter is when I was writing the book and when I was, you know, creating my company, I wanted to do something that I knew about. Well, I knew about sales. I also knew about women. And so skirt is definitely not the article of clothing. It’s an acronym. However, you have to be very careful how you brand yourself because I have to wear a skirt all the time. People come to see when, you know, where I’m showing up to see if I’m really wearing a skirt. And the acronym is

Nancy: Do you always wear a skirt?

Judy: Always. Always Always. I was actually called out in a FedEx office. The young man behind the counter that I always see and I always bring stuff in and he’s always very kind to me. It was the middle of the winter and my husband and I were bringing in cartons of books that I had to send out. And the place was packed. It was right before the holidays. And he yells out yo, Selling in a Skirt, where’s your skirt?

I was in sweatpants, and a baseball hat and a big sweater. It was freezing. And I looked at him and everybody looked at, they all looked at me and I said to him, I’m not selling today. I’m shipping. And he goes oh no, no, you tell us you’re selling every single day. Well, he read my book, which was the funny part. And everybody in the place was laughing. But after that, I never appeared without a skirt.

Nancy: Oh, that’s so interesting. That’s great. And you look pretty good in a skirt, too. Yeah. So what does the acronym stand for?

Judy: So the S is standing out. The K is keys to success. The I is inspiration. The R is results. And the T is time management. So everybody struggles with at least one. I struggled with all five. It happened to spell out SKIRT.

Nancy: I love it. There you go. Okay. So why is humor so important in sales and just in life in general?

Judy: Well, if you take everything seriously, it’s pretty dull. When you can either laugh at yourself or make you know, appropriate jokes it, you know, it works and people get, they calm down a little bit, you know? Sometimes when you’re meeting with somebody, they’re just as uncomfortable as you are. You don’t really want to be selling, they don’t really want to be buying.

And so, you know, if there’s some way that you can, you know, bring it down a little bit so it doesn’t feel so forced, and so I always find something funny. And I do, a lot of times, I laugh about things that I do. And I’ll tell people when I mean, obviously, you know, it has to be appropriate, and it has to come up in conversation that’s relevant. But I’ll always use myself as an example. And people just start to laugh. And I am my own best audience. So if people don’t laugh at a joke or whatever, it doesn’t matter because I laugh anyway.

Nancy: Good to love yourself, right? I think that’s great. Okay, we had talked earlier about your Woman’s Roundtable. Can you share that with the audience?

The Roundtable

Judy: Yeah, so the Roundtable is a place where you can have, you know, a small group of women, it’s 10 to 12 women, and you are able to have your own personal board of directors. So we, you know, we problem-solve together, we are, we have each other’s backs, we talk about best practices. And it is a group of women that stay together for at least six months. And it’s very, very powerful.

And you can see how the trust and the respect starts to evolve after just one time together. You know, the first time like anything else, you’re kind of guarded, but all of a sudden, everybody’s telling their story. And so it’s a wonderful program that I put together. I do it inside companies, I also do it for individuals outside companies. So that is one of the programs that I offer.

Nancy: Okay, and I’m curious When you say women in any position in business, do you focus on sales?

Judy: We, okay, so it’s really what they need. So the first thing that I always ask is tell me what your biggest challenges are in business. Nine times out of 10 it’s sales, okay? It could be any part of sales, it could be prospecting and networking, it could be whatever it is. So I take whatever they tell me and as a facilitator, that’s part of the agenda. So we talk about that. We, you know, we also have, you know, what’s your story.

Tell us your story. Or what are you committed to doing and, you know, let’s put together a group project. We do things together as a group and it is the growth itself, the transformation, sometimes it makes me cry when I think about it because there is such a huge shift. We watch it. You can see it. And because we do it virtually and everybody’s on the screen, you get to see everybody together and you watch how the body language in the first week is very different from the body language in the second week because everybody, okay, they all want to talk, they all want to share, they all, you know, so it’s amazing and I just adore it.

Nancy: Why only six months? So I would think that if the group is pretty tight, they want to continue.

Judy: Yeah, but it’s a minimum of six months.

Nancy: Oh, a minimum of six months.

Judy: Yeah. A minimum of six. And they can go on forever.

Nancy: That’s wonderful. Yeah, so we’re gonna have to learn how to find that. But what is the one takeaway you’d like to leave the audience with?

Be a Champion

Judy: So one of the things that I want to say is that it’s, you know, it, sales, especially sales today, it’s a little bit more difficult than it was, but it isn’t outrageously difficult. I always say that this is the time to share opportunities and work together. Collaboration. This is the time that you find people that you can do things with and make yourself even stronger.

And also, you know, in that, be a champion, whether you’re male or female, be a champion for another woman in business that you can open the door up to or you can collaborate with, or you can show an opportunity to. Because I’ve always said that, you know, my mission has always been helping one woman a day. And my tagline is women want to be treated equally not identically. So when you put that all together, it just means let’s work together. Let’s be respectful. Let’s have fun, and let’s make things happen.

Nancy: Yeah. Wow. So how can my audience find you?

Judy: Well, I am all over social media, LinkedIn, Facebook, Twitter, Instagram under either Judy Hoberman or Selling in a Skirt. Anywhere, that’s where you’ll find me. And my email is judy@sellinginaskirt.com and my website is Selling in a Skirt. So you can find me anywhere. I answer my own emails. And, you know, that’s how I, where I am.

Nancy: Great. And everybody go to her website. You’ll see a nice video, she introduces her office space, welcomes you to the site. Really enjoyed speaking with you today, Judy, and I hope you come back in the future to talk more.

Judy: I would love that. Thank you so much for having me and for the opportunity to share some information.