#BeBetter Podcast with Michael Kurland

How to Bridge the Generational Gap Through Active Listening with Katie McCleary

Let go of preconceptions and judgment to foster authentic relationships.

An entrepreneur, storyteller, author, and founder of 916 Ink, Katie McCleary is focused on bridging the generational communication gap in the workplace and in our personal lives. In today’s show, Katie shares the importance of showing up well and how being vulnerable can transform our relationships.

Katie McCleary portrait

“Every day, we deal with five distinct generations of people, and each generation has a different background, view, and language. As a result, such factors are impacting communication and relationships.”

—Katie McCleary

916 Ink

62. How to Bridge the Generational Gap Through Active Listening with Katie McCleary

Key Takeaways

  • Everyday professionals, whether or not they have the title of CEO, can become leaders that empower future generations.
  • Improving all of your relationships will improve your work life and the overall quality of your life.
  • To become a leader in your relationships, you have to truly care about humanity and get rid of identity labels.

Social Links


Katie McCleary is an entrepreneur and storyteller who trains leaders, creatives, and humanitarians to launch big ideas that stick by leveraging their social and cultural capital. She is the founder of 916 Ink, a nonprofit that has transformed over 4,000 vulnerable youth into confident authors. She is the host of “The Drive” podcast on NPR’s CapRadio with the American Leadership Forum-MV in Sacramento. She is the author of Bridge the Gap: Breakthrough Communication Tools to Transform Work Relationships from Challenging to Collaborative (McGraw Hill, Feb 17, 2022)

“If you really want collaboration, if you really want to have connections, if you want to do great things in the world, how you show up matters.”

—Katie McCleary

916 Ink

Podcast Transcription

Hello. I’m Michael Kurland, CEO and co-founder of Branded Group, an award winning facility, maintenance and construction management company that services multi-site commercial properties such as retail restaurants, health care facilities and educational institutions. Welcome to the Better Podcast. Each week, I interviewed thought leaders from a variety of industries who will share their stories and the lessons they learn as they strive to be better for their clients, partners, employees and their community. Are you ready to be better?

Michael Kurland: Hello and welcome to another episode of the Be Better podcast. I’m your host! Michael Kurland. Joining me today is Katie McCleary, co-founder and author of the book Bridge The Gap and host of the podcast The Drive on NPR and a relationship expert. Katie, welcome to the show. Please tell the audience a little bit more about who you are and what you do.

Katie McCleary: Yeah, thanks for having me. So I’m really passionate about curiosity and storytelling and leadership and how our back story, our biology, the way that we sort of operate in the world impacts other people. I firmly believe that if you are the leader, you are a channel. And I also believe that everyday professionals, whether or not they have the title of CEO or management, you guys can become leaders in all of your relationships and it will improve your work life, but it will overall improve the quality of your life.

Michael Kurland: I love it. I love what you said. If you’re a leader, you’re a channel. Can you go into that a little bit more? And what? What exactly do you mean?

Katie McCleary: Absolutely. One thing that we talk about a lot in our book is that you are a kaleidoscope. So do you remember that old sort of toy Michael where you have all these jewels right at one end? When you twist it, they fall and they make different patterns? Well, your mind, your body, your spirit, your lived experiences, your culture, your geography, your age. All of that is your kaleidoscope and how you show up in the world, even in those first few critical moments of interaction with others. It really matters. And your being, your kaleidoscope is at play at all times, as is other people’s kaleidoscope and being at all times. So if you really want collaboration, if you really want to have connections, if you want to do great things in the world, how you show up matters. How you twist your kaleidoscope and understand the kaleidoscope of others is the secret sauce.

Michael Kurland: I love it. So it’s kind of like, you know, you’re always on when you’re meeting new people and your first impression is, is what is lasting? You know, everyone says you never get a second chance for a first impression, I guess, right? And so you got to be on, you’ve got to be focused and that’s what you’re putting out there and that’s what people are perceiving. So you’re talking to the person, you’ve got to be present, right? And sometimes it’s hard to be present when you’re out there. But if you’re not present, then you’re not giving your best foot forward and you’re not you’re not putting your best ability to meet someone. And that’s how they’re going to remember you. You’re not going to have a good impression. So let’s talk a little bit about your book Bridge the Gap. What inspired you to write this book? What’s what this book is really about for the audience is information.

Katie McCleary: Yeah, well, I think we can all agree that we’ve come off a pretty rough two to three years and we’ve been under a pandemic, political polarization, lots of disconnection and fractionalization. And we have all changed during this time period and now we’re all returning to work. And as changed people and changed environments, changed cultures, how are we all going to get along better? So my coauthor and I wrote this book based on a bunch of our client work, but also on the fact that we had to bridge our own differences. So if Jennifer were here, which I’m so sorry, she couldn’t be here today, but I’m a Buddhist. She’s a Christian. We both grew up working class, but now she is wealthy and upper class, and I’m sort of growing out of the middle class. She is a conservative Republican. I am a Liberal Democrat, and we use our tools all the time to communicate and connect across the divide because the world wants to split you. The world wants to tear you apart. And as human beings, we’re biologically wired towards negativity, fear and by bias than we are for curiosity, communication and openness so that we really can move forward together. And that’s really what inspired our book.

Michael Kurland: Well, that’s great. And you couldn’t have picked two, you know, farther sides of the spectrum. So how did you guys meet and how did that work? How did that happen?

Katie McCleary: Yeah. So we actually met in a women’s leadership circle and I was finishing up writing a book for sort of serial entrepreneur millennials who have all these wonderful ideas about changing the world. At the same time, Jennifer was writing a book about a particular conversation method that she knew to be true to really unlock people, leaders, entrepreneurs. So when we got together, we sort of felt a connection despite our really vast differences. And you have to remember that this is under 2018, 2019, and we wrote the bulk of our book in 2020 during the election. And so we would like to flip between Fox News and CNN. We would have side conversations with friends and family, and there was just so much division and so much activity around trying to tear us apart that we just became more committed than ever to say, You know what? There’s more that unites us than divides us, and we’re going to make the choice to not engage in drama triangles, not engage in all the noise and choose to have good conversations that unite us over division.

Michael Kurland: That’s so refreshing to hear. It’s I mean, you brought up so many things that I could deep dive into, you know, politics divides and just the media in this country in general. And I do agree with you that I don’t know if it’s the world that wants to tear us apart. It’s just the media that wants to tear us apart and get us all fighting because they like when we’re talking that bad publicity is still good publicity, so. But that’s a wormhole that we don’t need to go down. So you wrote this book and you’re hoping to inspire bridging the gap with every different kind of sect of person in this country. So what are you finding now that the book is out there and people are reading what’s what? What is happening now that people are reading your work?

Katie McCleary: Well, I have to say, Michael, I think one of the things that’s kept me up the most at night is the reviews, right? I really, really, really love feedback, and I’ve been working on my craft for a long time. So this has been a nail biting moment for me. And the reviews are in and they’re great. They’re all like five stars. We were named by Ink Magazine as one of three business books to read in 2022. And I think that what’s coming out of all of it is truly the power of curiosity. And how do we show up curious, how do we show up present? How do we show up with connective magnetic energy that disarms the other person? Because there’s this really great quote by Seth Godin that says, basically, you have no chance of real communication if you don’t travel to the side of someone else’s sense of right. And I think that’s a real lost art that we’ve come to in this country. I mean, so many of us are unwilling to hear, to listen, to understand someone’s perspective and point of view. And so we’ve given a framework that is replicable. It’s architecture. You can do it over and over again. It doesn’t trigger you. It doesn’t trigger them, right? And it moves you to a place of trust and respect where you can really actually listen to one another and move forward. And that’s just been incredible to see. And it’s all about curiosity. Right? This thing that we sort of just take for granted all the time. So I’m super passionate about that.

Michael Kurland: So you hit on a few things I want to ask you about because you said, like getting people to stop and listen and you put it in different phrasing, but basically get them to imagine walking a mile in your shoes and vice versa, right? Because we don’t come from those places anymore. And I want to ask you, you also said that, you know, you wrote a book about millennial entrepreneurs. So do you think that this is a generational thing? Do you think that trying to bridge the gap is becoming a generational thing and the media is focused towards the baby boomers who are watching the Fox News and the MSNBC’s and the CNN’s? And now your book is trying to bridge that gap for the millennials, who I think we still have a chance with, right? Because they’re not buying into all the hype of the heart of my French horseshit media that it’s fed to us. Right? You know, my mother will sit there and watch the news on Fox News for hours and hours and hours, and I finally had to ask her, You can’t live with me for a few months? And I said, You can’t watch Fox News in my house. It’s just it’s just garbage in, garbage out. So anyway, I digress. But do you feel like that’s kind of what’s happening here?

Katie McCleary: Yeah, so there’s a lot of invisible forces at play, and one surprising piece of research that most people don’t know is that five generations of people go to work every day now, Michael. Five generations, they all have different upbringings. They have different ideas about language. They have different ideas about listening, about what it means to show up authentically, right? And so those things are getting in the way of communication, and the media is absolutely, absolutely a huge part of this equation. People are aligning and fighting so hard in their identity boxes, right? Well, I’m this and I’m not. And here’s where I live, and this is who I am now. Come on. You are a human being like the rest of us. Yeah, we’re biologically wired in certain ways. And so we bring a lot of neuroscience into the book and we try to break it down. And it’s like the most simple level with like memorable metaphors and analogies so that you can understand that you’re a social creature and actually you’re quite predictable, which makes other humans quite predictable. And so when you know how to sort of maneuver in that, you have a great chance at communication and you don’t even have to, like, step into their shoes. I think that it’s really about saying, “What is your lived perspective, Michael?” “What is your backstory?” We all have a back story of where we come from, and most of us think that our back story is our identity, rather than evaluating our back story, understanding it, learning from it, and where do we want to go and how do we build a vision? That’s the thing we’re not teaching in schools. So I don’t know. I’ve sort of digressed a little bit here, but I think that if you really want to become a leader in your relationships, if you truly care about humanity, we’re going to get rid of identity labels. We’re going to treat each other with dignity and respect. And we’re going to understand that all of us are just a kaleidoscope. And how do I see the patterns that you’re seeing and how am I jostling you to see new patterns and possibilities? That’s the art of it all. That, to me, actually is leadership.

Michael Kurland: Yeah. I mean, yes, I liked where we were going, but I like that we’re coming back here to the leadership conversation piece of it. And I think that’s what you touched on. Five, five generations are going to work every day, right? And they were brought up by five other generations. And so there’s all the ideologies of those generations pushed down upon them and how they think. And what you said is, you know, you, you bring your backstory, you bring your baggage, right? That’s pretty much what it is. Everyone’s got baggage, some way, shape or form, and everyone thinks their baggage is the worst baggage. I know I think my baggage is the worst baggage. I’ve had the roughest life ever. So, you know, but I think the biggest problem we have is that people don’t listen, and they wait for that, they just wait for their turn to interject and talk, right, so that they can push their thoughts on you and tell you how right they are. I think that you said all that and that’s just me summing up what I heard. And I think that you’re doing some great work here. Then if you’re bridging that gap and getting these people to start realizing that leaders need to for lack of a better word, just, you know, shut up and listen a little bit, right?

Katie McCleary: Yeah, there’s a great adage that the word listen when rearranged spells silent and that is silent internally. That is silent externally. So we talk about in the book that everybody’s wearing a pair of invisible headphones. Some of us are tuned to have suspicious defensive thinking. Well, where did you learn that? Where did you get that idea from? Right? Tell me more about that, because I’m not entirely convinced some of us are on the other spectrum, which is what we call passive. Please listen. Anybody just yes you to death, Michael, when you have a conversation. Yep. Mm hmm. OK. They’re totally checked out. They’re not even listening or engaging. And then you have biased listening. Well, I’m an expert. In my opinion, this is my lived experience, and then they’re not listening at all. Then we’re sloppy listeners, right? All those internal and external distractions. So we should, we tell people to show up clean and curious? To be clean means that I am in a calm state where I’m not triggered by a million to-do lists by awkward, fraught energy. So show up clean. Disrupt yourself, coach yourself to have a clear, spacious mind. That’s why meditation is so important and why it’s kind of like really popped up in the leadership world the past couple of years, right? Show up with a clean, spacious mind and then show up with curious, responsible ears. Expect, expect that you’re going to learn something new. There’s stuff that you don’t know that you don’t know. And to follow the energy of their thinking and their language. So that looks like this. I know I’m talking to let that stop the point right next. So we say do not ask questions of measurement, and we’ve been taught that those are the best questions to ask in our country. Who, what, when, where, why and how. Stop, don’t ask why anymore, because honestly, Michael, do you ever like being asked why? No, Michael, why is there no coffee in the cupboard? Yeah, right. Why do you think that way? No, just it shoves people into biological reactions. This is like brain science 101. So lead with questions that are. Tell me about your weekend. Tell me about what’s happening in your sales pipeline. Tell me about what you’re celebrating these days. Tell me what’s going right in your business. Tell me how I can help you and show up better when you use that. Tell me about phrases. It’s whatever is top of mind for them and then your job is to listen for the energy words that they’re giving, and an energy word could be a value based word. Family freedom. Right? You can also hear it in their tone of voice. An energy word for you, Michael, is media. I can tell you got a lot of thoughts about the media, right? Michael, tell me more about the media that you do pay attention to. Right, right. Oh, well, their conversation. And you don’t need to show up. You don’t in the first part of a conversation, have a one way conversation. You don’t need to be seen as clever to be seen as smart. Right? You are more connective and magnetic as a leader, as an entrepreneur, as a team player. When you show up in service. To the other person.

Michael Kurland: I mean, yes, yes, yes and yes. And what I’m really hearing is that and I’m guilty of this as a leader. Most leaders get to where they’re at because they have an ego. And I think when you get to a certain point, you believe you have to sound clever. Still, to justify your role as a leader, you need to ask that question to feed your ego in the way that it’s an expert. You know, I’m the extra. I’m the CEO, I’m the expert. So I’m going to ask this question from my ego to make me feel like, you know what I’m doing. But in reality, you’re shutting out the people that you’re trying to lead. And I’m sure we’re all guilty of that at some time in our lives, right? But it’s human. It definitely is human. But I think, you know, to your point, if you can listen and ask those probing questions and draw out of the people what you said, the key words right? Media is a key word for me, right? So I don’t think it was called the keyword, but it’s an energy word. Yes, media that I would never have even thought about that. But yes, it is. Although I’ll tell you, I don’t watch any media because it’s all garbage and it’s my brain. I don’t need to fill my brain with that stuff. But to the point, I just think, I think if leaders can lead with empathy and put their egos aside and start listening, which is everything I’m hearing from you, we’re going to be on a much better, you know, trajectory for the future.

Katie McCleary: It will be on a more collaborative trajectory for the future. And, you know, our egos are always at play. They keep us safe. They keep us moving forward. They keep us desiring. They keep us wanting. I think the balance is sort of in the vein of what Lencioni says. How do I remain humble, hungry and smart? And smart people smart? That’s what he meant by smart. How do I remain humble and gracious so that I can be present? How can I remain hungry so that I do keep going after dreams and what’s possible, and I need people all along the way to help make that happen? When you get real clear about that, things really shift and no longer become about you. It becomes about the “we”.

Michael Kurland: I love what you’re saying. Humble, hungry and smart, especially smart people. I think that’s what’s made me very successful in my career as being smart and having empathy. I will say hunger, I’ve started the hunger again because I don’t know what my next steps are going to be after that, after my current, you know, Branded Group experience. I’ve thought about that a lot, and I thought about it this weekend. I’m going way off topic here, but I want to open a winery, not a winery. I want to open like a little wine shop with a little bar and grill inside. But that’s neither here. Well, hopefully we’ll see. One day we’ll see.

Katie McCleary: Well, you’re really talking about something that’s so important is intention, right? The whole point. Some of the well, not the whole point, but the biggest point of our book, too, is to operate with intention. How am I showing up? How am I being experienced? Those are two great questions to always ask: How am I showing up? How am I being experienced by others? What do I want? What do they want? What’s the greatest outcome here? And so many people, as you probably know, Michael, are not operating with intention. You have to build it in your mind. You have to be cognizant of it. And if I could teach anything to young people in high school now, it would literally be about the power of intention. And how do you build a vision and then move through all your struggles? To heal and to get there.

Michael Kurland: Do you feel like this generation that is coming into more prominence lacks intention? Is that a problem that you’re seeing?

Katie McCleary: I think I think that’s hard to say because I work with so many amazing young millennials and even Gen Z that they have intention. They know what they want. Where they’re shooting themselves in the foot is how they articulate what they want and how they’re getting at their intention. I think it’s easy to be divided. Like I’ve said a million times to say, Well, I’m not like you. You don’t understand me. You’ve never held my heavy baggage. Right? They’re lacking curiosity to connect. And when I truly operate in presence and curiosity to connect, I hear your story. And when I hear your story, I cannot refuse your humanity. I’m in a relationship with you now, and your social capital is literally the most important capital you will ever have in your life. So how do you leverage your social capital, how do you build off your relationships to create and execute upon your intention and your vision? Is everything? And I think this younger generation feels a little bit alone, and they need to know that they’re not alone, and I need more bridge builders of Generation X. I’m an X-er, I’m going to guess that you’re an X-er too.

Michael Kurland: I think that’s the one before millennials. That’s whatever. That’s yep.

Katie McCleary: Yep, yep, me too. And then there’s boomers, and we all have our own kind of personalities as a generational group. And I think it’s going to be really the X-ers who have always been bridge builders. Always. We’re always getting it done. We’re crazy. Do it yourself first if you know any hardcore entrepreneurial X-ers like yourself, we’re all like that. We need to help bring up the millennials. We need boomers to open up a little bit more too.

Michael Kurland: Yeah, it’s funny that we’re recording today, and I don’t think it’s by accident. I just wrote an article about this very same thing about leadership and communication across generations. And you know, that’s what has made me so successful. To your point, is my ability to communicate with boomers and the ability to communicate down with millennials and Gen Zers and kind of, you know, not to be cheesy, but bridge that gap, right? Because,  the Boomers they are great with. You know what? They were taught by their parents, which is to show up on time, work 80 hours a week and, you know, grind it out and have that face to face conversation, communicate and for the generations below. It’s, you know, I want freedom. I want to flow, but I don’t know how to have interpersonal communications as well as, you know, Gen Z and Baby Boomers, and there’s something that can be learned cross generationally from everybody. But we’re way off topic right now. I think so. But it’s still a good conversation. So let me ask you this: where do you think leadership is going in the next five, 10 years? With everything we’ve just talked about because it’s really interesting to me to think about that. And I’d like to get your take on that.

Katie McCleary: Yeah, so I think that leadership is being impacted definitely by the work of Dr. Brené Brown. I think that we’re going to be having a lot more conversations about what it means to be vulnerable and show up as our whole selves. And I think that those who pooh pooh, Dr. Brené Brown probably aren’t understanding what she means by vulnerability and showing up whole. It does include building boundaries. It involves clear communication and expectations. So I think that’s one way that leadership is going to go. I think we’re going to see a lot more, a lot more leaders empowering others instead of top down delegation. That’s one. I think the other thing that we’re seeing shift is just the attention paid to culture. You get culture right, and this has been going on for years since the eighties. But if you get culture right, people will bend over backwards to perform. And so we’re going to see a lot of workplaces shift, especially in things like the Great Resignation and the Great Reshuffle, because to attract the younger employees, the really super skilled and talented employees, they’re not going to be treated like shit. They’re going to they’re not in it for the paycheck and the vacations. They’re in it for the culture and alignment. Can I belong here, right? Those are the perks for them. And then I think the third thing is that we’re actually going to see shifts at a board level, which nobody really ever talks about. But I’ve seen it happen all over California and sometimes the way that California is of the way that the nation goes, whether or not people agree with that or not is that we’re going to see a lot more about shared governance. So boards typically have a real top down sort of structure. I think that we’re going to start seeing a lot of employee stock and share programs where we begin bringing in employees instead of giving them shares and options into a company and having more of a shared governance model rather than selling off to straight on IPOs.

Michael Kurland: Interesting. And I like everything you said. I mean, Dr. Brene Brown changed my life. I watched that vulnerability Ted Talk. I mean, I’ve watched it. I don’t know how many times now, but the first time I watched it, I was in a different place in my being and I was just starting Branded Group. I was coming out of a divorce and I was trying to connect and I was scared to connect because I had been hurt, you know? And so I knew I had to be vulnerable to get to where I wanted to be. And it was everything I needed to hear at that time. And I’ve actually shared that with other women, a part of an entrepreneurial group that, just like you said, they’re all Gen Zers just like me, and they’re all like go getter doers. But they don’t always lead with vulnerability. And I’ve shared it with a lot of those guys and it’s impacted them. I don’t think the same way as me, but it definitely has impacted them. So, you know, to your point, I actually just downloaded her new book. I haven’t gotten a chance to start listening to it yet, but I look forward to that.

Katie McCleary: I think one of, I think, one of the best things that she says that I really have to hold for me, and I think this totally applies to leadership in any aspiring leader and relationships is that people are people are people, are people are people. And when we put people on pedestals and when we demonize people, they’re no longer people. And that’s where we become guarded. We began to get it where we lessen our curiosity when really like people are people, we’re all on a playing field. And so how can I be connected? How can I be magnetic? How can I create a team?

Michael Kurland: I love it. I also take a lot away from when she says, Remove your armor. Because if you’re going into every conversation with armor and how can you listen? How can you listen? How can you hear? Right? So yeah, that’s all good information there. So we didn’t get a lot of opportunities to talk about your podcast, The Drive. Let’s talk about that a little bit right now. Tell me about it.

Katie McCleary: Yeah, so I get the great honor of interviewing leaders from basically Sacramento, Northern California, also down to the Bakersfield region. And what I’m really it’s a mix of sort of community leaders and corporate leaders, and what I talk to them about is their personal story. So all my questions are: Tell me about your mom. Tell me about where you grew up, because what I’m listening for in this podcast are the leadership lessons that they’re channeling because of their lived experiences. And I think that we often forget that our back story is showing up every single time we open our mouths. And I am a firm believer that once you master your back story and you understand it and you own it, man, we become limitless. And these leaders exemplify that they do. They exemplify curiosity, grace, grit, tenacity. But that all comes from their personal journey and moment. And let’s face it, like leaders always want to be on, they always want to perform. My job as a podcaster is to disarm them is to say I need that real vulnerable, raw and honest story because stories are how we make meaning of the world. We’re doing it nonstop, 24 seven. And so if you really want to influence and lead people and get them to stop and think, huh? Tell a story, don’t just give them data and facts and lip service and buzzwords.

Michael Kurland: Yeah, I think everything you just said is spot on. I actually, unbeknownst to myself, I’ve perfected my back story. That’s what I talk about all the time. And I think the biggest thing that perfecting my back story gave me was I disarmed my fear and I became vulnerable and I became free, and I had the freedom to put my baggage down and know that my baggage doesn’t weigh that much anymore. So I love what you’re doing with your podcast.

Katie McCleary: Thank you.

Michael Kurland: So, Katie, it has been amazing having you on the show. This has been a great conversation. If the audience wants to get a hold of you, how can they do so?

Katie McCleary: Pretty easy. I’m online at how to bridge the gap dot com.

Michael Kurland: Awesome. Easy. How to bridge the gap dot com. All right, Katie, thank you for coming on the show. Appreciate it. And the audience until next time.

Thank you for tuning in. I hope that today’s episode inspired you to become a purpose driven leader in your career or your community. There’s no doubt that when we lead with purpose, we can change lives. If you enjoyed today’s show, I’d be grateful if you would take a moment to rate us on your preferred listening platform to learn more about Branded Group’s Be Better experience and how we provide industry leading on-demand facility maintenance, construction management and special project implementation. Visit us at www.branded-group.com. Be sure to follow us on social media and you can also reach out to me directly on LinkedIn. Until next time, be better.

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