
Leadership coach Judy Hoberman and Jim Bouchard discuss five divides leaders face: cultural, political, generational, gender, and age. Only 10.4% of Fortune 500 CEOs are women, held back by a "broken rung" early in their careers. Hoberman emphasizes listening without agenda, asking open-ended questions, and placing people in roles where they can thrive.
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Cultural divides, political divides, generational divides, gender divides. This has been identified as one of the top 5 issues facing leaders in 2025. We're going to tackle it with a very dear friend of mine today, Judy Hoberman. You know, sometimes we lose touch with people that are special to us, and you know, I'm the worst one. It could have been 2 weeks ago, I saw you 20 years ago. I don't know. I think I've just seen you yesterday. But anyway, the important thing is that you reconnect, and when that happens, it can be really special. It's a blessing. I think, you know, most people say, hey, you pick up with your best friends, you pick up right where you left off. No, you don't. You pick up where you are now and you keep moving forward. And that's what we're going to do today with today's very special guest, the author of Selling in a Skirt, international speaker, and a very dear friend, Judy Hopperman. Okay, like I said, Judy Hoberman, here she is live and in person. Finally, right, Judy?
Finally. I thought you're gonna start singing to me or something. Here's the thing, it's like we never skipped a beat. That's the thing.
I don't sing. I could pick a little guitar for you, but if I sang, you'd probably leave the room.
You'd probably leave. Yeah, but truthfully, that's how you know that you're good friends because You might not have talked in a minute or years or whatever, and as soon as you start talking, everything's back in the universe. And so just, that's how I felt when we talked the last time.
No, and it's cool. It's cool to see all the changes that have happened in your life too, and all the remarkable things. You always do remarkable things, but even bigger and better. You never stop, you know? That's really cool. Why don't you catch us up real quick? What's going on today?
So today, let's see, where am I today? I think that over the last couple of months or so, almost a year now, I've decided that I'm old enough and I've been in business enough to decide what I really wanna do and what I don't wanna do. And I think that it takes a lot of guts to do that because I do a lot of things. If you read my bio, I get exhausted thinking about the things that I actually do. But I decided that the two things that I really, really, really love more than anything are executive coaching and masterminds. And so everything I do goes towards that because those are the things that I get to spend time with the people that I love the most, that I, that I really feel I can support and serve and do great things with. So, I mean, that's a huge change for me because I've done like lots of things and sometimes I'm doing things going, why am I doing this? I don't even like it.
Yeah. You know, well, you know, one of the coolest things is that, you know, not just knowing you, but I've met several of your clients and You know, they sing your praises. I mean, this is— it's really cool to be able to make an endorsement, not just from me, but because I've met people at conferences and whatnot that have worked with you, and, and, uh, and they enjoy your work. So I'm going to put out the endorsement, and Judy's website is right there, sellinginaskirt.com, and get in touch with her because you're going to be hurting if you don't.
Okay, there you go.
So today, today I thought it'd be fun to talk about one of the areas that you're You know, you're really a leader in all over the world. One of the challenges— in fact, we're going to have Judy on one of our live streams coming up too, because one of the issues we're going to tackle— we decided the first 5 live streams are going to be the biggest issues that leaders are saying they're facing today, the biggest challenges. And one of them is this idea of the divides. Now we kind of combined them because we've got generational divides, we've got gender divides, we've got cultural divides, we've got political divides. You and I talked about that a lot when the microphone wasn't working last time. Yeah, I mean, all these things are— all these are issues that leaders have to face and manage every day, right? I don't know that I have a right or wrong way to respond to these things. I know we spend a lot of time in workshops trying to help people figure out how they're going to do it in their own organizations because each has a different culture, each has a different approach to it. But I know you have some real solid pieces of advice that I think will fit no matter what the organization is, no matter who the leader is. So what are your thoughts on that? And absolutely, you don't have to stick to just the gender one, right?
Well, I mean, you know, because of what I do, it is about gender, but you can also throw generational in there. But one of the biggest things for me is that you have to understand the current landscape where we are today, not where we were 5 minutes ago or 5 years ago, because it's all different today. But despite that, when I was thinking about like this whole gender divide, there are so many things that we talk about, and yet we we're still talking about them. That's the problem. We're still talking about it. Like, one of the things is leadership representation. And we have made some significant progress. We have. But we continue to fall behind when it comes into leadership roles. As of 2024, I believe it's as the end of 2024, women held only 10.4% of CEO positions in Fortune 500 companies. Only 10%. And that's not a lot of people either. You know, it really isn't. And sometimes it's because we don't know who we're looking for. We overlook people. Women don't necessarily raise their hands. But there's also that broken rung where women are promoted at a lower rate than men early in their careers. So that was going to impact the pipeline in leadership. So you think about all of that. Well, it's the same thing for generations as well, because there are a lot of women that are in the C-suite who have been there for a while, and they're not leaving. And so there's not as many opportunities for some of the newer, younger generations to come up with, to come up. So that, that's also, and that's true in a lot of things, you know, it's not just, you know, the C-suite, it's, it's true in a lot of things. A lot of the boomers are not ready to go anywhere. They're still, they're happy, they're thriving, they're relevant. They're, you know, their experience, you can't pay for that experience. So, you know, it's, you can combine those two.
No, you're right, it's a double-edged sword, isn't it? Because we certainly want people to contribute and be productive longer, but it has created this kind of logjam, right? And then all of a sudden, we've noticed too, some of the clients we work with, all of a sudden they'll reach a point where these folks are aging out, wanting to retire and whatnot, and then there's that gap. So it's really important that we provide some kind of opportunities for people to develop as leaders all the way through, even if the management position isn't open, right? Now, you talked— it's interesting, you know what's really fascinating? Maybe they all read Selling in a Skirt, I don't know, or came to one of your sessions because one of the encouraging stats was that the rate of women entering the C-suite is increasing exponentially. And not just here, it's really interesting. I was just at an event in Las Vegas where there was a group from Africa. And they said there it's really exploding, like women are taking over leadership positions all over the place. So I'm not going to discount the fact that they probably read your book, but are there any reasons you're seeing for that? Or, you know, what are some of the things that they might have gleaned from what you share that are making this happen?
Well, you have to remember that a lot of women, especially like I met a lot of women from Rwanda, and they are all entrepreneurs. I mean, they are amazing entrepreneurs, and they have taken business by storm. They decided they want to do this, they want to do better for their families, for themselves. And so they decide on something that they really, really care about, and they do it. And a lot of them are, you know, they're— some of the women that we met are in travel and hospitality, some are in coffee, you know, all these different things that they're able to do. And so they have decided to really you know, put a stake in the ground and do it. The same thing in Africa. There's a lot of companies now that are really run by women. Women have a lot of different qualities, and, um, there's a lot of them. It's not just the soft skills, although we talk about soft skills and then most people say, well, that's just for women. It's not just for women, but there's a lot of skills and qualities that they have that it's a different perspective. So when you bring a woman into that position, a management position, you know, leadership position, it's a different outlook. They're bringing different pieces to the puzzle, to the table. So I think that's also— they're looking for change. You know, everything is the same old thing. We've done this the way it's always been, like this, blah, blah, blah, blah, blah. But you have to be able to be willing to accept change. And I think that's part of the problem, that a lot of people don't want change.
Yeah, that's too bad, because, you know, I think Pliny the Elder said it pretty well a couple thousand years ago, the only constant in life is change, right? If we're not embracing change, and I'll argue, I make this argument all the time, I think one of the key roles of leaders are that we're in the transformation business.
Absolutely.
We're all about change, we're changing ourselves, we're helping other people change, we're helping organizations change. If you don't change, you're dying, especially today. But I'm glad, you know, you mentioned a couple of, well, you stimulated some thoughts there. And one of them is, you said, it's not just about women and their unique qualities, because I suppose psychologically we could say, I think we can still say this, right? There are qualities that we consider feminine qualities and there are qualities we consider masculine. Masculine. Professional speaker. Masculine qualities, right? Yeah. And any individual human being usually has combination of these things, right? And without touching that third rail too much, we're seeing that now with people who are transitioning, right? So we've got all kinds of different— we've got all manner of people thrown into the workplace. And let's not forget that generational one, because it's for the first time ever we've got 4— did you tell me there's 5 generations now working at some point?
5.
Isn't that amazing? So within the last year We added the fourth one, which was groundbreaking, and then we've got five. Holy cow. So all these things. Now, to me, what's interesting, I think the differences can make us very interesting. I think the differences can make— I don't think differences do make us stronger. I think the differences can make us stronger if we learn how to appreciate it, right? And we access the various talents and qualities that we have. So that's my mindset. Am I Fred Flintstone or is that more?
No, no, I truly believe that you can learn something from everyone. You may not learn, you know, an entire skill. You may not learn, you know, how to do something that is very expensive to learn from somebody. But when you work together, you can learn so much. You know, when, when, um, the youngins used to come into the, the, uh, corporate side, guess what they were, you know, assigned to? An older person teaching them how to do computers. Okay, that was one of the first ways that you would say, oh, we can take these two people and, you know, buddy them up, and the young one can teach the older one about computers, and the older one can teach the younger one about, you know, the skills of being successful because they both had different skill sets. And so that's still true. However, a lot of times, and we have seen this a lot with women, and I hate to even say that, but a lot of times women do not want to train the younger generation or, you know, any— because they've worked so hard as the trailblazers to get over here. And now you're expecting them to bring somebody up with them. Now, that's very old school, and I don't see it as much anymore. I mean, I was part of that. You know, people didn't want to help me because I was young. But truthfully speaking, we're seeing more that the women that are at the top are pulling the kids up. And I say kids, the young ones up. But, but the truth of the matter is, Jim, we have to be able to offer our, our, um, experiences as a mentor. If we don't start mentoring the young ones, we're not going to have leaders of tomorrow.
Amen.
Because it, it doesn't work like that. We have to be able to— you, you can find a lot of young ones who want to be mentored, but you don't find as many mentors. And I think that is starting to change a little bit because women are starting to say, "Hey, you know, pick me. I'm happy to do this." And the women that I work with, that's part of their responsibility. I'm saying air quote responsibility as a leader, because how else can you create these emerging leaders into what you, you know, these amazing leaders of tomorrow? How do you do that if you don't share what you learned? Right.
So no, you're knocking it out of the box. I mean, you know, you've heard me say this. I mean, to me, if I have to summarize it, leadership is sharing. A leader shares. The rest of the conversation is about what you share and how, right? And mentoring, you know, it's once in a while I get challenged, you know, because you know the 3 keywords that I always use: inspire, empower, guide, right? Yeah. And sometimes those are nice words. I said, no, they're not freaking nice words. That's not what it is. They're, first of all, they're the most essential disciplines That any leader needs to adopt if we're going to be effective, right? And when you're talking about, you know, the mentoring, that's what we're talking about really when we're talking about the guide part of it, right? To be willing to share your experience, your wisdom, your knowledge face to face. Now, I understand sometimes why it's interesting to hear you say that lately or recently some women leaders have been hesitant to share. I've seen that right along with leaders across the board and I get it sometimes. Sometimes they don't want to train the person who they know is going to knock them out of their job, right?
But isn't that the job of a leader? A leader's job is to promote out of their position. That's their job.
Yes, because one of the saddest things I ever hear in workshops, and I'm sure you've heard this too, once in a while, a couple of times a year, somebody will come up to me and say, "Hey, I was being groomed for this other position, but I couldn't take it." Why? Because I didn't have anybody to replace me. I said, well, whose fault is that?
Right. Right.
Yeah. You should always be training your replacement. And if you— I don't know, maybe— I think we'll be in agreement with this, but I think if you're in a— and there are companies that do this. If you're in a company or an organization where, yeah, they're really just abusing you, they've told you that they want cheaper and younger, and that's why you're training the next person. Well, if you're in that company, get the hell out of there. That's not an environment to be in. And they're going to treat the next person the same way.
Well, a lot of times that's in a company, an organization where they all want to be the same, you know, they don't like outsiders. And I, I actually, in my years and years and years and years ago when I was a manufacturer's rep, I did all the major companies, I, you know, all the catalogs and the major people, and one of them only hired themselves, basically. And if you were, if you were privileged enough to get a position, your job was to train somebody that was from their circle. And so you could be there today, but tomorrow, if you train somebody really well, you'd be out the door. And I found that to be very counterproductive because they were throwing away all these great people who weren't who didn't look like them.
I agree with you.
And, you know, and I remember how many times I would go in and I would have my sales calls and it was always with a different person, always with a different person.
Yeah.
And, and, and, you know, and part of that goes to a different piece of this puzzle because I truly believe that you have to be qualified for the position. I don't ever, ever, ever recommend anyone for any position that I know they're going to fail. Because they're not qualified. And a lot of people say to me, because you work with women all the time, you probably just want women in the C-suite and doesn't matter if they're qualified or not. And I'm like, you don't even know me. And if you knew me—
Yeah, they don't know you if that's how they—
I would never do that. So I think that's another problem that we're seeing with the gender divide. Like sometimes they'll throw somebody in there. Well, here's a woman. Okay, check the box. We just checked it. And she has no qualification. She has no history. She has no experience. And you know she's not gonna make it, and then I'll come in and say, well, let me work with her. Let's give her some tools. And sometimes they say yes, sometimes they say no, but then the next thing you know, they say, oh, we tried it, done. How does that work? That doesn't work. So you have to put qualified people in the spots in the first place.
No, that's a struggle I've had for years where sometimes it's due to regulations or policy or whatever, and I'm not questioning intentions a lot of the time, right? There's great intentions behind some of these things. But when you get to a certain point— in fact, I was just telling somebody, it was yesterday in a meeting, we were talking about kind of this same topic. And I shared with them a story I heard from a guy from West Point. West Point is one of the toughest schools in the world, not even in the country. It has one of the highest attrition rates. But what this guy was saying, he said, "We're not just trying to be tough." He said, "We don't want to fail people," is the way he phrased it. Framed it, right? He said, "We do everything we can to get people to succeed in our program." He said, "Now, some are not going to make the standards." He said, "But our goal, our mission, and we have an awful lot of support to try to help people rise up to those standards." And I thought, "Yeah, you know, that's perfect, right?" There are people who aren't going to make the cut in any particular endeavor.
But that's true. Not everybody is 100% qualified to do anything.
Yeah, I'm not. Despite what I say, no, I never— you've never heard me say that.
Yeah, yeah.
Quite the opposite, right? So that's another problem. We'll go into that another day. But yeah, no, I think it's prudent to help people rise to the standards. But now I'm going to flip this to the other side because I think one of the responsibilities of people, even if they're not in management or leadership positions at this point. You know, there's— I run into— well, gladly I see it changing. I'm very happy to see it changing. But for a long time, I kept running into younger people or heard managers and leaders complain about this from younger people, saying, I'll do X when you give me Y, right? I'll perform at that level when you pay me this. I'll do that job, or it's just not my job. In fact, Dr. Phil just did an episode, I think was last year, And he had these younger people on and they were very happy to do that. There's one young lady who was teaching, she does a YouTube channel and teaches other young people how to say no when their bosses ask them to do something that's not strictly in their job description. And I'll tell you what, that's something that's so counter to the way I think.
Yeah, yeah, yeah. It's so interesting because the way we were brought up, I believe, was, Don't ask somebody to do something that you wouldn't do. And don't think that your title, you know, that you're entitled to not do things. When I was an agency manager in financial services, I did everything. I did everything because I would never ask somebody to do something I wouldn't do. I took garbage out, okay? I cleaned off tables. I set things up. I got everything ready for a training. I would never ask somebody to do something if I wasn't willing to do it. Now, if I asked somebody to do it And they said no, I would stop the conversation. I would stop right there and I'd say, "Why would you not help?" And they never really had an answer. "I don't know, I just don't feel like doing it." Okay, well, okay, I'll just keep moving along. And I would remember that because when they needed something, I would say, "You know, I just don't know if I feel like doing it." And then they would say, "Oh, that's what I said to you, right?" Yeah, okay. And so it stopped, it does stop. But if they're not willing to do something or keep saying no to you, there's something wrong with this whole dynamic. You have to sit down and get to the bottom of it because that's ridiculous. That just doesn't make sense to me. How can anybody be successful if you're not going to be part of?
And I don't want people to misunderstand either. If someone's completely satisfied in what they're doing and that's it, that's where they want to be, I mean, I'm not judging. You measure what's enough for you in any area of your life. But having said that, you know, You and I are working mostly with people who want to do more, right? To want to serve more and to want— and along with that goes advancement, right? Hopefully. And so in our Rising Leaders Workshops, one of the strategies we share is ask before you're asked, right?
Right.
Do what you need to do, but act before you're asked and ask before you're asked. And I think that's a— I think that's a value we have to really emphasize again and bring back. And I will say this, and risk sounding like an old guy, but this really has never changed. People will notice you when you do that. Like you said, I love the examples you gave. And you know our friends Dennis and Danny Snow, right, who preach the Disney gospel. And one of the most impressive stories they share, and it's a true story, that Walt Disney himself, even when he, you know, after the Empire was built, he'd walk around the park. If he saw trash, he'd pick it up.
Yeah.
He didn't tell somebody to go pick up that garbage. He would just pick it up.
Just do it.
Yeah.
You know, it's very interesting. I want to go back again to when I was an agency manager, when I was recruiting, and I would find somebody that I wanted to bring onto my team. I would always ask them, tell me, number one, why this company? And number 2, where do you see yourself in this company? And I didn't give them 5 years, 10 years. I just said, where do you see yourself? And there was only 3 answers that they would have. Number 1, they would say, I just want to be a producer. I want to worry about just me and no one else. And I would say, great, I'll show you the journey. Number 2, they wanted to go into leadership. And because they really love people, they want to sell, but they also want to go into leadership. I'd say, great, I'll show you the journey. Number 3, they would say, I want your job. And first I would laugh because I thought, oh my God, they have no idea what they're talking about here. And then I'd say, absolutely, I'll show you the journey. The reason I say this is because I knew my people. And I always say you have to know your people. I knew what made them, you know, what drove them. I knew why they were here. I knew what their thought process was. So if there was a stumbling block where they weren't feeling like doing anything or they felt, you know, too entitled or whatever the wording is now, I would sit down with them and I would say, okay, Jim, do you remember when I asked you where you wanted to be and you said you wanted to go into leadership and yet you don't want to field train somebody? Okay, tell me what that looks like. What is happening here? And maybe you decided, I really don't want to be in leadership. I want to worry about myself. Or maybe— And that's fine. And that's what I'm saying. Know your people. That's what we can do about the gender generational divide. Know your people. Know what you're working with because you will know who is gonna be there to support and who is not. And that's your choice, you know, how you wanna develop the culture or not develop the culture. But I always, I knew my people backwards and forwards. I knew what I can expect and they knew what they could expect from me. So that worked.
Yeah, and you know what, remind me that that's what we're talking about now, knowing your people, because there's two things, two real strong thoughts you triggered there. And one of them was this idea that I don't want to be a leader. Now, first of all, and I know we're absolutely singing in harmony on this point, leadership has nothing to do with rank or title or position of authority.
Absolutely.
You're a leader whether you know it or not because you inspire people, because you empower people, you give them what they need and you guide them. Everybody does this. Now, how you do it and whether or not you have a title is different. How conscious of it are you? And how intentional is it? Like you said, is it something you're doing with the hope of advancing and getting into management positions? Or is it just something you do naturally and you feel good about it? And some of the best leaders are those people right on the front lines. They don't want a rank or a title. So I think that's important to understand. So all of us need to embrace these disciplines and cultivate them, and an organization is best served when they do that. Now, the other thing you talked about, knowing your people. Man, to me, that's it. And to me, that's at the heart of solving. I don't wanna say solve. I just stole some Thomas Sowell. I know you like Thomas Sowell too. And he said, "There are no solutions, there are only trade-offs." And I thought, "Boy, that went all the way in." I said, "Yeah, and how dull would life be if we solved all these problems anyway?" But we're in a constant state of perfection, right? We're trying to resolve, we're trying to manage these things and move them forward. So how do you solve, resolve, resolve instead of solve? How do you resolve the, The generation divides, the cultural divide, any of these divides at any given moment, generationals particularly because the language changes, right? Okay. Well, cultural too though. So you may meet somebody from a different culture. The language has changed. The context has changed. So it's to get to know the person, right? It's to make an effort to reach out and understand. Stephen Covey said it great. Seek first to understand. The more we can understand one another. But now here's the caveat, because some people, And some leaders will push back and they'll say, well, that, you mentioned the word entitlement. I can't just bend over backwards for everybody. No, that's not what we're saying, right?
Understand.
Totally not. And then that's the beginning of the conversation. Now you can start to say, what can I accommodate for this person? Does that fit with the organization mission? Does this person fit into the organization vision, right? And those are the decisions, but you can't make any of those decisions.
Sometimes they don't. Sometimes they don't fit into the organization and sometimes they're in the wrong position. I was in a company where they asked me to do coaching for the whole accounting department and they were the saddest looking bunch I have ever seen. Like they look like, you know, wah wah, like Eeyore. Like they just were so unhappy. And so, and I said, well, why don't we bring lunch in for everybody? They didn't even want to be with everybody. They didn't want to be there. And so I talked to each person individually and I just asked them certain questions. And it turns out that the woman who was like, she was such an extrovert, was given the job of doing like work in the back all by herself. The woman that was the introvert and hated people was given, she was customer-facing. Okay, so they were all in different positions, in the wrong positions. So I talked to the CEO and I said, you know, I think one of the things that is going on here is that we're putting people in places where they don't belong. And if it were me, here's some of the suggestions. And I gave him some suggestions and he just looked at me like, well, you know, I don't know if I really want to do that. And I said, what if we did an experiment? Let's try it for 30 days and see what happens. Oh my God. They moved people around. When I came back in, because I came back 30 days later, They were all having lunch together.
Ah, nice, huh?
Okay, so when— if you don't know your people and you're just putting people in places, and sometimes you come in for a position and the position's not right, maybe there's another position. Like the same thing when you go in for sales and you know you're coming in for this particular sale, but as you're talking you realize that's not as important as this, and you flip, and then people are really excited and happy and, you know, and they're sharing you with all their friends and family because you actually really listened. That's what it's about. It's about knowing your people and you listen. You ask questions and you listen. And when, you know, you were saying that sometimes, you know, they're just not in the right position or they're not in the right place or wherever, whatever it is, you also have to think about asking the right questions. And so when somebody says something to me, my favorite question of all times is, so tell me what that looks like. And then I don't say another word because you're asking, you're not saying, So you don't like this, you do like, it's not a yes or no, it's like, so tell me what that looks like. And they go into, after they think about what I just asked, they go into pretty much detail of what they're talking. And if you are a good listener, you are gonna hear something that they probably haven't said out loud in many times. And so tell me what that looks like. And I have a client, she does that all the time now, all the time. And when we were talking—
So it's about listening without an agenda too, right? Because if you—
Absolutely.
Right, if you're listening in order to elicit to get ammunition to respond in a way that you think is going to move it in the direction you want. That's not as productive. That's why I think sometimes I like the idea that you said that asking fairly open-ended questions. The broader the question is— we can all craft questions that are going to lead us to an expected response. That's not that hard. A lot of assessment companies make a lot of money doing that. Yeah, the idea is if you ask a broad question, if you ask an open-ended question and then listen, listen intently, because, you know, to me, if you don't care, don't bother, right?
Right, right. Yeah, I used to ask my clients, are you okay if I take notes? Like, yeah, I mean, who's gonna say no? Like, really? And so as there's— as I ask the question and they're talking to me, I'm like, uh-huh, I got this, because I am writing it down in their words.
Yeah.
Not just paraphrasing, in their words. And so when I come back and they say something, they're like, oh my God, you really listened. That's the best compliment you can get is you really listened, because you allowed somebody to speak and you held space for them, and then you listened. I mean, these are just like things that you do— well, things that I do naturally, because I— well, I've been dubbed the question queen, so I do ask lots of questions, and people roll their eyes, but I don't care Because it just lets them know that I'm interested in them. Not interesting to them, interested in them.
It guides them too. You know, it's funny, as you were going along, I felt the need to, I was gonna break the rules. I'm gonna apologize because my eyes are darting out around. I'm learning this new system for our podcast. And so I'm trying to get all the technical side done. But I am listening intently. And when you said that too, what came to mind is, It's not just listening for you. When you ask great questions, you ask meaningful questions, and I'm responding to that, I'm getting a lot out of it. I mean, that's really what a therapist does, right? A therapist doesn't give you all the answers. A good mentor doesn't give you all the answers. They ask the right questions. And then in the process— that's why I love to guest on podcasts, especially if the the host is asking really challenging questions because it forces me to think, it forces me to learn, it forces me to grow and reorganize or focus my thoughts or embrace something brand new that might not ever happen if someone didn't ask me that question.
Right, and you're also asking, you're giving somebody permission to share something that could be just hanging in their head all this time. I know I ask a lot of CEOs one question, you know, because they always tell me that this is what I want to do and this is what I'm like, Okay, but what do you still want to accomplish? They've told me everything they've done. And then I'll say, well, what do you still want to accomplish? And there's absolute silence for maybe, you know, 20, 30 seconds. And then most of them have said to me, no one has ever asked me that question before. And I hear things that I am sure are like these giant dreams of what they want to do next. And it's just, oh my goodness, it is so incredible. But it's always, No one's ever asked me that question.
That's an old martial arts sensei technique, actually. It's really cool that you're sharing that from a different origin because that's what it's all about. I used to have masters that were always asking questions. I remember one time I took this lesson. I paid this guy a lot of money for a private lesson and all he was doing was asking me questions. He said, "Well, what do you do with this move?" I said, "Jesus, I just paid you a couple hundred bucks. You're supposed to tell me." And he laughed. He said, "No, no, no, that's not how this works." And I realized that the best instructors, the best teachers, the best coaches and mentors were the ones— they weren't the ones with all the answers. And it's the same thing. The best leaders are not people that have all the answers. We have another name for that person. Starts with an A, ends with an E. You fill in the blank. We don't like people that come at you with all the answers. The best leaders are the ones that constantly know how to formulate the right questions and be able to turn those questions inward, right? I think it's very valuable. We have to ask ourselves some open questions every year. For me, it's who am I and what do I do? And I ask leaders to— those sound like two ridiculously stupid questions.
But they're not.
They're not.
No, and sometimes we don't even know who we are. That's why I said in the beginning, when you said, what are you up to? I have decided that at this particular stage in my life, I want to do what I love to do, not what everybody expects me to do, because I've done that. I've done that most of my life. I've done everything that people expect me to do and then some. But I really want to do things that I love, that actually they, they, they help expand you, right? It looks good to me, but it also— I know that it supports, it supports especially women. It supports them and gives them a place to be heard and gives them a, you know, a chance to say the things that they really want and helps them grow as well. So, you know, I don't want to do all this stuff anymore. It just doesn't work for me.
No, you know, that's so cool to say that too, because this challenge came up twice in my life. Once when I was actually working in self-defense, right? And once when I was working in— starting to work in, if we want to call it self-improvement, right? And people were telling me, well, that's kind of selfish. Yeah, well, it is. And it takes up a lot of time. But here, I said, what I came to was this. I said, improving yourself, and in this context, like I said, expanding what you really want to do, following your heart, what you really want to do, that's one of the best ways. That's the key to improving yourself, right? The least selfish thing you can do for others is improve yourself continually. You've heard me tell the story about my black belt, right, how it tears out and the white belt comes underneath to remind us all the time, you know, the more we are along this journey, the more worn out our belt gets because we've tied it and untied it and worn it out being dragged across the floor and all that stuff. When that white belt's exposed underneath it, it's to remind us about beginner's mind. Always be curious, always want to grow, learn, develop. That's the trick right there. And like I said, it's the least selfish thing you can do for others because you're making yourself a more valuable resource, aren't you? And like I said, now you're right, you're going into— well, you've always been in that area, but to go really to focus in that area to help.
Yeah, but you're also— you're being selfish if you don't do that for them. Yeah, you know, yeah, it's— you're not being selfish, you know, to do it for yourself, but if you don't do it, you're being selfish because then they don't have access to you and, you know, and the things that could possibly come out of it.
I hear you. Now, before we wrap up, I want to hit this. I'd love to hear your thoughts on this. To me, a lot of this depends on a quality that we call courage, especially to reach across these divides. It takes courage. You don't know how that other person's going to react. If we're talking about the age one, the last couple of years, sadly, the political divide got so toxic, right?
Yeah.
And people were afraid to even talk to people who were from the other side, whatever the fuck that means, right? But it's interesting. I see it with the generational divide. Well, I'm afraid to go. I just had someone say they were afraid to go do this talk because it was for younger people. I don't know what language. I said, no, no, no, you go there. What can you do? Share, share yourself, right? Now it does take courage. And in fact, it's funny because somebody recently before an event, she said, you don't look nervous. I said, well, I'm not really nervous. I'm more excited than nervous. I said, but what I've learned to do, I said, I have some trepidation. I don't know how you're going to react. I don't know how you people are going to react to what I'm going to say. But I've learned that I have no control over that. The best I can do is share what I came to share. And I said, I substitute courage for confidence. And what I mean by that is courage is not the absence of fear. The absence of fear is stupidity. Just developing that quality where we can go out and do something we're afraid to do, to go into an area that we're afraid to go into, to approach someone who makes us nervous. I think that's key. So the only answer I have when people say, "Well, what do you do?" I say, "Well, get the courage." "Well, how do I get the courage?" By doing it. There's no other way. Who's ever come up with a better way? Courage doesn't exist without that fear. Courage is only defined by the fear, by the risk, by the danger. So yeah, it's a decision. We have to go out and do it. And I think leaders, we have to support people in that effort. So I don't know. I rambled a little bit, but what are your thoughts there?
No, I think courage is one of the greatest qualities. It's in my book, Walking on the Glass Floor, because I believe it's one of the top 7 qualities that a leader should have is courage. Do something that you're afraid of. You know, it's that— because here's what I know personally. There's a lot of things that I'm afraid of. And I, you know, and then I think about it. I really think about it. Now, why am I afraid of it? Am I afraid because this and this and this is going to happen? Am I afraid of the unknown? Which is legitimate. Yeah. Right. And so you just, you muster up the courage and you say, what's the worst? What's the best? The worst that's going to happen is I'm not going to go through with it and it's just going to be horrible. The best that's going to happen is going to be the best thing ever. And so, you know, as a leader, you want to be able to invest in, you know, developing your people, right? It takes courage to say, I'm going to create this program, I'm going to create this opportunity, I'm going to create this new role for people in my company because I really believe in them. If I invest in them, they know that I believe in them. That changes the whole dynamics, and it also changes retention. You know, you have to really learn how to invest in your people. That takes a lot of courage. It takes— because now you're spending money that you could be using somewhere else. That's courage. All of it is courage. So I always say, you know, if you don't invest in your people, somebody else will. They will. So Right?
There's that great meme that was going around last year on LinkedIn. It may have gone longer, but I saw it last year. The question starts, "What if I invest a lot in training my people and they leave?" And the response is, "Well, what if you don't and they stay?" That's right.
That's right. That's right.
No, the courage, that's it. And it's part of your job. I mean, to be blunt, if you accept leadership responsibility, like I said, these terms get a little weird, but if we're going to accept management positions to frame a technical sense and embrace that, and you want to be a leader in a management position, then that's part of the job. You have to find the courage and there's ways to do it. I'll help you. Judy will help you. Yeah.
If you think about if you're a leader in 2025, you do have a choice. You can acknowledge the gender divide, the generational divide, whatever it is, Or you can work to close it. So, you know, you invest in, you create opportunities, you invest in your people, you lead by example, you know? And you know, when I talk about women, you know, when women rise, that's what they always say, when women rise, so does everybody else around them. So this is not a gender issue. This isn't a women's issue. This is not a leadership issue. It's a business issue.. And if we all work together, guess what? It's going to work.
I'm glad you framed it that way too. It's kind of interesting because one part of the problems, and then we'll have to try to wrap things up, but one of the problems I think people are having right now, too many people are too easily offended. And that might not be the PC thing to say.
Okay.
But for instance, you've been talking about things from the perspective of a woman and you've been saying, a woman is— now I know people who would be offended men who would be offended by that. Well, I should include men too. Well, wait a minute. Judy is a woman. She's talking about it from a woman's perspective. That shouldn't be offensive at all. And it's up to me to say, hey, what Judy's saying, does that make sense? Can I make that work in my life? What difference does it make, right? We have to differentiate between substantial divides and insubstantial divides, meaningless divides. The fact that you're talking about it from that perspective to me, I don't even hear that anymore. You know, to me, everything you're sharing is universal.
So it is. And I was just gonna say, you know, I don't ever, you know, exclude men either. I don't. When I advertise something and it says, you know, for women, I get men that show up also, because men want to know how to do this. How do you work with? How do you work for? But the thing that I always say is, if you are, you know, an advocate, if you are a sponsor, or if you are somebody that really is a champion for women, you're more than welcome to be here because that's what I want. If you're gonna be obnoxiously rude to women, I wouldn't want you even if I only worked with men.
Yeah, right, yeah.
You know, that's just not who I am. So I wanna make sure that you understand. People will say to me, just because you like women, you hate men? I'm like, no, I'm married to a man. I could care less about that. It's not what I'm saying at all. What I'm saying is, I encourage, I encourage people to step up and say, I want to be part of this. I do. I want to be part of this. Fine. Let's go. Let's go.
There you go. And that's what respect is all about, taking care of one another. And that crosses all the barriers. That's what we need to focus on. That's so cool. Judy, it's so cool having you here today. Let's talk about how people can get in touch with you.
So you can find me on LinkedIn under Judy Hoberman. I'm on LinkedIn a lot. You can email me at judy@sellinginaskirt.com. Jim just, he gave you my website, sellinginaskirt.com. You know, I'm all over social media, so you can find me.
I think we still have that there. There it is. I'm learning this system. All right. No, hopefully, and all joking aside, we, I was telling Judy before the program, actually Judy was one of the catalysts for this. We did a podcast a couple of weeks ago and the sound didn't work. And I'm not going to jump on the company because it's a good company, but at any rate, we couldn't get the issue resolved. And so I went to another platform, which is really powerful, and it's allowing us to do these a lot quicker, to be honest with you. But I've got a learning curve here, so pardon me if my eyes were dotting around and things like that. And the cool thing about a podcast though too is I was I was definitely paying attention to Judy, as you should be, throughout the program, but now I can listen to it again. How about that?
That's right.
Isn't that cool? So Judy, thank you so much for being with us today. And we're definitely going to have you the next live stream we're doing. If you're watching before this is the Hybrid Hustle, we're going to be talking about reconciling that remote work and in-office needs, right? So we'll be talking about how What can we do to face that challenge together? And then Judy, I'd love to have you come back because like I said, we're going to do one on these divides and how to work through those. So if you'd like to be part of that.
I would be honored.
Sounds like fun. All right. Stay tuned to the next episode of Keep It Human. Watch for Leadership Reactor. That's our newest program where you can come on one of those too, Judy. So we're going to sit there and poop all over some video.
Okay, that'd be fun. Yeah, totally.
There you go. All right, thank you so much.
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