Why Generations Clash at Work—And How Great Leaders Fix It | Part One

Why do generations often clash at work—and what can leaders do to bridge the divide? 

In this insightful first installment, Chris Comeaux sits down with nationally recognized generational expert Karen McCullough to explore the perspectives, experiences, and workplace expectations that shape Baby Boomers, Generation X, Millennials, and Generation Z. 

Drawing from more than two decades of research and real-world consulting, Karen unpacks why many workplace conflicts are not personal attacks, but differences in generational perspective.

Together, they examine how communication styles, views on commitment, work-life balance, feedback, technology, and leadership have evolved across generations. Karen shares practical insights for healthcare, hospice, nonprofit, and business leaders who are navigating multigenerational teams and seeking to create cultures where every generation can thrive. 

This conversation challenges assumptions, encourages empathy, and provides a framework for leading through one of today’s most significant workplace dynamics.  

Key Takeaways

• Generational workplace conflicts are often rooted in differing perspectives, not personal shortcomings or character flaws.
• Communication styles vary significantly across generations, creating misunderstandings around feedback, meetings, and collaboration.
• Generation X leaders are often balancing accountability with a growing need to coach and develop younger employees.
• Millennials and Gen Z have reshaped workplace expectations around purpose, flexibility, emotional intelligence, and work-life balance.
• Great leaders build stronger teams by understanding generational differences, adapting their leadership style, and fostering meaningful conversations.  

Guest:
Karen McCullough, Keynote Speaker - Generations and Workplace Trends 26 Years Speaking on and Observing the Generations in the Workplace 

Host:
Chris Comeaux, President / CEO of TELEIOS / Author of The Anatomy of Leadership

If you’re leading a team across multiple generations, this episode is a must-listen. Subscribe to TCNtalks /Anatomy of Leadership, share this episode with your leadership team, and join us for Part Two as we continue exploring practical strategies for building stronger, more connected, and more effective workplaces. Your next leadership breakthrough may begin with understanding a different perspective.

The Anatomy of Leadership podcast explores the art and science of leadership through candid, insightful conversations with thought leaders, innovators, and change-makers from a variety of industries. Hosted by Chris Comeaux, each episode dives into the mindsets, habits, and strategies that empower leaders to thrive in complex, fast-changing environments. With topics ranging from organizational culture and emotional intelligence to navigating disruption and inspiring teams, the show blends real-world stories with practical takeaways. The goal is simple yet ambitious: to equip leaders at every level with the tools, perspectives, and inspiration they need to lead with vision, empathy, and impact.

https://www.teleioscn.org/anatomy-of-leadership

Transcript

Melody King 0:00

Everything rises and falls on leadership. The ability to lead well is fueled by living your cause and purpose. This podcast will equip you with the tools to do just that. Live and lead with cause and purpose. And now, author of the book The Anatomy of Leadership and our host, Chris Comeaux.

Chris Comeaux 0:22

Hello and welcome. I'm excited today. I have a special guest. Today we have Karen McCullough. She's a keynote speaker among generations and workplace trends. She has 26 years of speaking on and observing generations in the workplace. Welcome, Karen. Hi. I'm excited today to be here. I'm excited to introduce you to our incredible audience here. So let me introduce you. Karen McCullough is a nationally recognized keynote speaker and generational expert. She helps organizations break down generational barriers, lead through change, and build energized, inclusive cultures. Her signature keynote is it's not personal, it's generational. It delivers fresh insights with humor and real world stories that make audiences laugh and think and shift their perspective. With a background in retailing and branding, Karen has presented to top organizations and leadership teams all across North America, including Proctor Gamble, McDonald's, and MD Anderson. So Karen, it's so good to have you. It's so cool how we connected and um brought you to our own team. And so I'm looking forward to sharing you with our wonderful audience that we have here on TCNtalks / Anatomy of Leadership. So I prepared you for my first question. What's your superpower?

Curiosity As A Leadership Superpower

Karen McCullough 1:35

Oh, I thought about this for like a second. Um, my superpower is I am always trying to figure out the next trend. I I'm very curious. Um, I've always I've always loved learning. And since I've been doing this a long time, I don't know if you guys can tell, but I've been around a while. I think that my superpower is my continuous desire to keep learning.

Chris Comeaux 2:02

I could, well, I could affirm that. Just a little bit. I've gotten to know you. Um, and just maybe also like an observer. Like they say, the smartest people see patterns that other people don't see. It's and then and then make sense of it.

Karen McCullough 2:14

It's interesting. I have always been an observer. I am the baby of a huge Italian family, and I have watched and I have gathered information from an early age. So when you asked that question, immediately I began to think about why I am always I'm into pop culture, you know, why do I love the trends? And it really fits with studying the generations. It's like a natural.

Chris Comeaux 2:39

That's incredible. Well, well, again, you and I connected, I think, through a good mutual friend. And then I reached out to you, and then I shared you with our whole Teleios team. And so you came to our Leadership Development Institute and you really presented on your specialty, multiple generations in the workplace. And I said, okay, we got to do a podcast together because I want to share you with the broader hospice and palliative care world. So you say frequently in some of your keynotes, you said it in our LDI, it's not personal, it's perspective. That's really, I say powerful framing. What are some of the most common workplace conflicts today that maybe leaders are incorrectly diagnosing as character issues when maybe it's more generational perspective differences?

Communication Styles That Cause Conflict

Karen McCullough 3:22

Yeah, I think the biggest one is communication. Um that what that's the one that I get the request the most to really talk about. And um, I think that there's different styles of communication. I think that we've brought emotions into the workplace when millennials came into work. And so we're misinterpreting communication. We have different communication styles. Some of the generations are much more direct. Um, others want to explain things and they they they love longer, longer emails, which are not being read by young people. So when we start to look at how we communicate and we really look at the history behind why we communicate the way we do, um, I can see where that really causes a problem. And right alongside of communications, then is how we communicate our messaging. There's challenges right now with meetings. Many younger people do not want as many meetings. Well, really, I don't, I think a lot of people, a lot of the generations are not crazy about meetings, but we can talk about that a little bit later. Um, so you start to really begin to look at how work works. And we have a younger generation coming in who sees inefficiencies and they want to see those changes made immediately because the, they're, they're open to it, their fresh eye, so to speak. So, you know, there's just a whole basket full of challenges that are going on right now.

Chris Comeaux 4:44

Well, and we're going to keep unpacking that with each other. So in in hospice, maybe healthcare as a whole for sure, we have about four generations working side by side, caring for patients, supporting the processes that just enable delivery of care during some of the most emotionally challenging times of life. What are the unique challenges and opportunities that having these multiple generations in the workplace, what are what are those challenges that they create?

Healthcare Tensions Around Time And Emotion

Karen McCullough 5:13

I um I don't know if there's any nurses listening right now, but I get it.

Chris Comeaux 5:17

Well, there'll be there are a lot, I promise you.

Karen McCullough 5:19

I actually have been on several podcasts where we talk about this. I've done several. I work with a lot, a lot of healthcare. And there's challenges in we can just start with how we look at work. Uh, we can look at how the day, how the day progresses. We can look at staying late, leaving at five, leaving when your shift is over. I mean, there's just so many ways that we're beginning to look at how these generational perspectives are affecting, especially in healthcare, um, where we've got so many seasoned people, professionals working who have paid their dues, who have put in, I'm talking about time right now. They've put the hours in, they've stayed longer. And then we have a generation that looks at, I've got my work done, I've been very, very efficient. Um, time is my currency, and they look at time very, very differently. That's just number one. Number two is this emotional connection. Hospice is so emotional. I as I told you, my mom, my mom went through hospice, and I was just so grateful for all of the care and the love that she got. So we have generations that express emotions, they express their emotions, how they're feeling. We have other generations that have learned to keep that inside. And so when we start to look at something like healthcare, where not only do we have the emotions of the job, but we have the emotions of the client, of the patient, um, it's how we deal with them, how we talk them through. So I feel like my advice is to I watch the pit. Is anybody on HBO? I mean, that's where I begin to see, okay, how how people deal with authority, how we're teaching, how we're giving feedback, how we're taking that feedback. Do we put our emotions into it? I mean, I take notes watching the pit because it's got all of the generations, and it's it's people who are who are committed to the work, but they're bringing a different way of looking at the work into this. So it's a such an interesting time. I wish I had all of the answers, but I don't. But I I believe that we have to get an understanding of how people are coming, what they're bringing with them into work and their perspectives and bend and be more adaptable.

Chris Comeaux 7:33

Wow. Well, Karen, if you like now, I wish in retrospect we would have used some maybe highlights or some little vignettes from the pit during our LDI with each other, that would have been super cool, actually.

Karen McCullough 7:44

It it is. It's and I and I don't mean to say that I watch TV, but I do I do tell people have you seen the pit? Watch how they deal with this. Because there's there's so much about work then in this show that was so different than ER. I mean, if you compare the two of what it was like back in the 80s, it was about romance and love and relationships. And right now, sure, that that's an ipty-bitty part of it. But what we're seeing is authority, how we're giving feedback, how they're receiving it, the competition with the generations, you know, and um who's adapting? You know, I like to use the word baby boomers, Gen X, millennials, open your eyes to these young people that are adapting, because that's where the gold is, where they they're bringing their perspectives in and they're bending too, and they're adapting. So I just feel like it's a two-way street. Well, we're how excited I got.

Chris Comeaux 8:40

Well, we jumped in right into the meat, but let's maybe just step back for a second. And what I love about you is you don't overly generalize, but paint the picture or regarding the, you know, we've jumped in, started talking about generations in the workplace. But let's back up just a little bit. Just paint the picture regarding the four generations in the workplace that's kind of presenting right now.

Four Generations And How They Differ

Karen McCullough 9:00

Yeah, I, you know, I do this and I get all my laugh because everybody wants to hear about them. And if I get it right, they're like, they're oh, I loved it. Or I just did a group where I left off the Gen X were the latchkey kids, because sometimes that's over-said. And do you know that when I was walking out, they said, but you forgot we're the latchkey kids. So every generation loves this little nostalgic piece in in the talk. So we talked to baby boomers. Baby boomers used to be my entire audience. You know, now when I'm speaking, maybe there are four in the audience right now, but they're still very, especially in healthcare, they're still very, very much a part of it. Baby boomers, 1946 to 1964, the age is kind of there. They're the baby boomers are are the older ones are in their 70s, the younger ones are in their late 60s now. And so what we're beginning to see is uh a lot of retirement, a lot of people leaving, a lot of that institutional knowledge is leaving and with them, especially in healthcare. They're taking with them the keys to the castle, so to speak. So we need to really begin to understand them. Um, but but they have put the hours in it. When I talk to nurses, they've put their time in. When I talk to my own physician, it talks about how we were there, we we we stayed, you know, 20 hours, we slept down and how younger people are getting kind of a a pass on that commitment of hours. So it's a generation that put the time in. I believe that they're adapting the most. I believe that if I have baby boomers in my audience, I commend them because I feel like they've they have really grown with the time with the technology. So let's move on to Generation X. Most in my in my programs, 40% of the audience are Gen X right now. They're in the leadership roles. 1965, that's the oldest Gen X, or to I think 1979, you know, give or take. Interesting, love this generation. Uh, this is the generation that we call it the figure it out generation. As a speaker, I started speaking when Gen X came on the scene. Nobody asked me to speak on the difference between Gen X and baby boomers. There, there was no manual. Uh we threw you in there, we expected you to figure it out, and you did. And you did.

Chris Comeaux 11:17

I'm laughing because I am X. So I totally live this.

Karen McCullough 11:20

Yeah, it's so interesting that uh we kind of we didn't even make fun of you. Baby boomers just plowed right over you. Think about where baby boomers were in their career when you came in. I'm I'm in Houston, Engineer Capital, oil and gas, they're they weren't gonna make room for Gen X. So Gen X had to adapt. I believe that they're the most respectful generation because they didn't, they didn't complain. They kept, I think, a lot of it internally. But we have a generation that's no nonsense. They had to figure it out, they had to adjust, they had to adapt, and they did. And so they take those skills with them into the leadership roles, and they're very much about getting it right, productivity. So it's it's not a generation that they're not at all the slacker that they were called when when uh they when they first came on the work scene. So we have a generation that is is very much about accountability and about getting things done. I could go on, but I go into millennials. When I'm doing this, when I'm speaking to groups, I say now the changes are happening. And so we start to look at the the oncoming of millennials, and we begin to see the phone has come in right now. We were getting that that iPhone is coming in or the the smartphone, and we're starting to see a generation that wants change. The older millennials came to the workplace during the Great Uh Recession. There wasn't a lot of work. So a lot of them did volunteer work, and all of a sudden we start to see this whole idea of the word purpose. That was the very beginning of the change. We see words like equity, inclusion, diversity coming on the scenes. We start to see the whole person coming. And I'll just blame it on the phone. I'll blame it on when you had an opportunity to take a picture of your food. Remember, millennials? When you took pictures of what and you showed us, and then you started taking selfies, you were saying, here I am, here's what I like. I'm going to share my ideas. And I think that the phone, this whole idea began to change the way we look at who we are. So this whole principle and idea of bringing our whole selves to work is beginning. Gen X is kind of giggling at all of this. They're thinking, oh, another picture of their food, because they're pretty much no nonsense and very pragmatic. I apologize to millennials. We made fun of you. We couldn't wait. I'm as a baby boomer, as an open-minded baby boomer, remember that. As a baby boomer, I expected the changes to occur. I was waiting for you to grow up. You didn't. You, in fact, changed me. And so we're starting to see this trend. So these millennials, I think in the beginning, 80 million of them, bigger than the baby boomer generation, brought the change in. And it's it's here. Gen Z, Gen Z, you're not that young anymore. You're almost 30. So uh, you know, but basically what we have now are we start to look at parenting a lot more. And we realize that Gen X are the parents of Gen Z. So with this pragmatic, no nonsense parenting comes a lot of competition. Because now we're pushing the kids. We know what they need to do to get into the right schools. So all of a sudden, parents are becoming much more aggressive and they're they're coaching. And kids are starting to get a point of view, a perspective on work. Where are they getting it from? They're getting it from their parents. Think about it. Parents are now the coaches. And so all of this idea of work-life balance and burnout is coming from a generation that has seen it and is showing their kids, telling their kids take the quicker route, you know, look for, look for opportunities. And so we're seeing a generation that's looking at work much differently. Um they've been, you think about I could put COVID in here, the reasons why. You think about how many younger people, no matter, I have a grandson who's eight, who was three when COVID came, who was in pre-K three on his iPad. Of course he lives on his his his devices. He he pre-K3, he was three when we started showing him that school could happen on this device. So we have questioning now. What are our meetings like? Why do we need these meetings? Why do we need face-to-face? Why can't why can't you make a quick video of how you want this done? And I can look at it at two in the morning when I'm wide awake. So we have a generation that's starting to look at time very differently. And remember, I'm going to keep talking about that emotional piece that came into it. They're bringing their whole selves, they're very emotional. And so now we've got a complex person, which we probably always had, but now we're actually dealing with it and talking about it.

Chris Comeaux 15:52

Wow. This is great. And are the millennials also sometimes refer to Gen Y?

Karen McCullough 15:57

Yeah, oh yeah. Yeah, they're called Gen. I I love when I hear people talk and they're like, oh, and then they throw in the Gen Y's. It started with, you know, Gen X, Gen Y. Um, I don't really know where the term millennials started, but millennials to me, uh, yeah, they're Gen Y. I would think the Gen Y's, if we really want to have fun, if I'm doing a keynote and I'm having fun, I'm gonna I'm gonna call those the Xennials. Because the Gen Y, they were the old millennials, you know, they were the ones that uh uh they like the boy bands. I always I always like to look at that kind of when we look at the music, you know, that was that generation. Yeah. One foot in Gen X, one foot in millennials, their heart is in millennials, their their mind, their work ethic is in Gen X.

Chris Comeaux 16:41

Wow, and you just made millennials. And I plan on so I'm X, I plan on working well into my 80s or 90s. You do Lord will Lord willing, health willing. I won't work at the same rate I work today, but I'm also starting to realize I may actually experience five or six G in the workplace, actually. That just totally just hit me. Um that's incredible. And to think about the the fun challenges that's gonna bring in AI is gonna be kind of mind-blowing.

Karen McCullough 17:10

Do you have any gen alphas in your in? Do you know any? Uh do you have any Gen Alphas?

Chris Comeaux 17:14

Um, actually, we do work with a couple actually fractionally that are on contract basis and they're fascinating. They're their how their um interaction with technology is just I'm envious. And uh I've gotten a couple of compliments. I push myself to always be on the leading edge of technology. It's probably because I grew up with a baby boomer CEO that was the exact opposite, and I felt I felt like it detracted from his leadership. So I almost made like this kind of commitment to myself, I'm not gonna be that guy one day. And so it is cool that our team says, you know, we're never worried about you because I am always I'm an interesting gauge, more from the standpoint of like I'm on the leading, not the very bleeding edge, but the leading edge. But I do that intentionally because I I feel like I set the tone for the rest of the organization. So anyway.

Karen McCullough 18:04

It's so interesting. First of all, I am the youngest of all the cousins. I'm the last baby to be born. If you're the youngest and you're listening to this, the studies show that you're probably more like than the younger generation than you are. You're you're gonna go down to that because you may be the observer, you know, you may be the one that had to keep the family laughing. Whatever it is, whenever I work with the babies uh in groups, they're usually like the younger. So my grandsons um are the six, seven, you know, they're they're the goofy. I hate, I don't mean this, but they're they're in elementary school and they're funny and their language is funny, and they do all the little body things, and they talk about you know, skibbity in the toilet, and they're they just they make me laugh all the time. But then on the other side of it, they're making their they're they're programming, they're they're making games, they're creating their own. I mean, they're doing things they want to get me on the video program. I can't remember what it's called.

Chris Comeaux 19:03

TikTok, probably. TikTok.

Karen McCullough 19:05

No, no, no, I'm on TikTok. That's where I get all my recipes. But no, this one is one where they can make funny videos and they can have me coming out of things and because they've gotcha. Yeah, whatever I'm saying.

Chris Comeaux 19:15

Snapchat, maybe. I don't know if that used to be a thing where you can make the funny videos. It's probably a whole new one now.

Karen McCullough 19:20

Yeah, it is. I can't remember that. But anyway, it doesn't matter. But what I guess I'm saying is I'm learning from eight-year-olds now. They're wanting to come in and help me do my work. It's going to be amazing. And what you said, Chris, is true. Look at your age. If you're Gen X, if you're a millennial, you are going to see two more generations at least. That's why I've been working. I am old. I shouldn't be working on, but I am because I've kept up. And also because it's such a fascinating topic. So we begin to look at really work and humanity through different lenses now than we did, you know, 10 years, 15 years ago.

Chris Comeaux 19:57

Wow. Well, you set the table beautifully. So you describe our Gen X as just figure it out. And younger generations may say, coach me, please. So how, so given this kind of interesting dynamic, how should leaders balance accountability when they're mentoring without becoming maybe micromanagers or to another extreme absentee leaders? Like, how do they do that?

Coaching Without Micromanaging

Karen McCullough 20:23

Yeah, I think that this whole idea of coaching is big right now. And so, first I want to apologize to leaders because we're asking for so much. Many times when I'm when when I'm speaking, people will come afterwards and say, you know, I have my own team I have to manage, but I also have my own work that I have to get done. And now you're asking me to be a coach. Now you're asking me to um to do more than just guide them. And I'm saying, yeah, I am, because that is really where it's going. And so companies are having to do leadership training right now on coaching. When I say coaching, Gen X immediately says, I don't want to do the work for them. Younger people are saying, I don't want you to do it for me. I want you to show me, show me how you want it done. Show me once, hopefully show me twice, and I can then go on and do it. They just need to see, they need a guidance of it. One of my really good friends works um with with some of the uh universities in California, and she says that in the business uh department, and she'll say, the thing that I'm learning about young students right now is they don't know how work works. They really haven't had a real job. A lot of them, you're gonna be their first job. So somewhere along the line, we have to coach them on what a good day at work looks like. So if five, if you're not done, we don't just go, I'm done. Sometimes we have to stay late. Sometimes we have a good day looks like this, and we have to begin to coach them and things that we didn't. Realize we have to coach them in. So it's not just about how do we get that form filled out or how do we do this? Sometimes it's on the processes of working with others. If you call in sick four days in a row, three times a month, somebody's got to pick up that slack. So we begin to coach, not just in the processes, but in how work works, how we build teams, how we work better together. And I think that that is really what we're not looking at. We're looking at how do we get the job done. But I want them to be to coach a broader picture of how do we work together? You know, how do we create this uh synchronicity where we're where we're helping each other. Sometimes we give more and take more. So it's coaching life.

Chris Comeaux 22:46

Wow, that's incredible. Thank you. That was solid gold. And something you're reminding me of, you know, this is an oldie but a goodie. But um, Ken Blanchard, I forget the other guy that worked, but they had this model called situational leadership. And it's basically it's a it's a whole coaching approach, but there is a space for telling, there is a space for coaching, there's a space for participating, and then there's a space for full delegation. And it it teaches you as a leader where to meet that other person depending upon where they are. And so um, we do teach that part of our leadership training, but I've never made the connection, as you just did, of how it even applies to the multiple generations in the workplace. That was solid gold. Let me ask another interesting question.

Commitment, Outcomes, And Hard Truths

Chris Comeaux 23:27

This is one around some interesting tension. Um, one of the biggest tensions today is around what does commitment look like? You know, especially being a generation X who's a bit of a, I love what I do, so I work too much. So older generations may equate that commitment with the hours work. Well, younger generations define by outcomes and also balance. How should leaders think about that shift? How do we reconcile that? You just alluded to some of it, but unpack that a bit more because it probably is one of the biggest rubs when I hear people talk about the frustrations amongst the different generations.

Karen McCullough 24:01

It's hard for me. Just saying that I coach speakers and I, you know, I've been doing this 27 years, 26 years. So I forget sometimes. I forget the struggles. I forget what I actually have to do to get there. And I start looking at my career, which is not even a word that young people use anymore, but I look at what I have done to get here. And a lot of it is a commitment. A lot of it is putting in the time when maybe there's nothing comes of it. So I have a hard time pulling myself away from this question because I'm all about the commitment. I'm all about the hard work. You know, I listen to Jim Rohn, you know, about work hard. I mean, those were my my, so it's hard for me. I am a boomer. I try to be, I try to be open, but when we get to commitment and time, it's I don't, I have a hard time with it. So when I'm working with companies that are accounting, which I do a lot with um, I I won't say the company, but a lot of the Gen Xers and the older millennials talk about when we have to get these these projects done at a certain date, and people are walking out the door because it's five o'clock, and I am still here sometimes till 10 at night because I know the work has to get done, it frustrates me. I get it. So you're asking a question that doesn't have a simple solution. I believe, and I said it before, we have to look for people that are adapting. Because when we can find Gen Zs that get it a little bit and bend as they want me to do, we can put more energy into them. So the question is going to be I'm gonna ask it, who's right? Because I'm questioning myself, Chris. I used to think you had to show up to build a team, you had to be at work, and now I'm beginning to understand, and maybe we'll get into that a little bit about what we need to do in our virtual meetings to connect. But I'm beginning to think maybe I'm wrong. Maybe they can figure it out without the commitment. I don't know. But in the world today, especially in healthcare, where commitment and hours are really not. I mean, I'm you're you may stay late. Things happen. We're talking about human lives here. We're talking about so many variables. Um I don't know. So I guess the conversation needs to be why are you here? What do you see? I think we have to have more conversations with people, more more discussions, and begin to eventually. I I hope I sway younger people to be more committed. And I'm gonna just say this because I'm such a boomer and maybe love the work. Because see, I love my work. So sometimes I don't really even think I'm working. Um, I volunteer, I do a lot. Okay, I haven't something that just came to me. I work um on Thursdays with Alzheimer's patients. I work with the caregivers. We we we we take the we take the the patient and then we give the caregivers a day off. But the caregivers, we have so much fun, they stay. A month ago, we had a speaker come from Rice University who was an undergrad who was in pre-med and talked about the program that Rice University, now we're talking about college kids, we're talking about Gen Z and how Rice University created a program of what we're doing with our thing called the gathering, where Alzheimer's patients and their and their caregivers are coming in. And it's a huge program now at Rice. And he talked about photography and taking pictures of them, and I felt his commitment. And I got goosebumps and I hugged him and I went up to him afterwards. So I'm not going to say young people aren't committed. I'm going to say we have to get to know people and we have to, I think sometimes these generalizations, um, I think that they're they're wrong. So my my whole idea is he and Rice and these young, these young students that created this showed me that there is there is commitment. There, it's just maybe putting their energy into where it wants to be.

Jeff Haffner 28:17

Don't miss part two of this episode coming this Friday.