The Leader Mentality
The Leader Mentality
What If Generations Are Your Advantage
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Four generations are working side by side right now, and a lot of leaders are still trying to manage that reality with stereotypes and frustration. We sit down with Nick DeStefano to talk about leading across generations in a way that actually improves communication, accountability, and team performance, whether you’re managing in an office, on a jobsite, or running your own business.
We start by calling out the real problem: lack of acceptance. “Boomers can’t do tech” and “millennials don’t work hard” are lazy shortcuts that keep you from seeing the person in front of you. We walk through common generation ranges (Gen Z, millennials, Gen X, baby boomers), why those labels can be helpful without becoming a box, and how cusp groups remind us that people are always more nuanced than a chart.
From there we get practical about leadership in a multigenerational workplace: pull strengths from each group, put people in roles that match what they do well, and encourage cross-generation learning. We talk Gen Z’s drive for efficiency and flexibility, the value of face-to-face communication, and why purpose-driven work is not a weakness. We also connect generations to defining events (JFK, Challenger, 9-11, COVID) to build empathy for how different formative experiences shape trust, risk, and work expectations.
Subscribe to the Leader Mentality Show, share this with a manager who needs it, and leave a review if it helps. What’s the toughest generational gap you’re trying to lead through right now?
Why Generations Matter At Work
SPEAKER_00Welcome to the Leader Mentality Show with Rob Clemens, and we have Nick DiStefano back with us. Welcome back to the show, my friend. Good to have you. Um, today we're gonna dive right in because it's such a big topic. It's about a 20-minute show we're gonna do today, but but I want to hit the biggest topics of it. It's a massive one, no matter what you're doing, okay? No matter what you're doing, because generations play a role in everything. Yes. You might be at work right now looking at your baby boomer working over here, your millennial could be over there, your Gen Xers over here, and guess what? Your Gen Zers are mixing in. They're in there. Um, probably not a lot of the silent generation people left doing jobs. Maybe. No, there's possible. Call us if you're if you're still working and you're a silent generation. They're gonna send us a letter.
SPEAKER_01They're gonna send us a letter or what we'll get in. Sorry, I will not take shots at generation this entire show. That's one of my favorite things to do is joke about generations because this is such a fun topic, but it is also one of the topics that can be so polarizing. I love it when people are like, these millennials or these my baby boomer parents. Listen, can we set all that as well? Throw a bunch of stereotypes out. No, that's not what it's about. It's about how do we lead across the generations, right?
SPEAKER_00You know, no, I I appreciate that. And and and look, it's fun to have a little fun with it, but you're right, this is a super sensitive topic, really. There's a there's age discrimination out there, and there's and there's all kinds of things. So you have to be careful as you're walking through this, but I love this topic. Um, the actual topic of the show is leading across generations. And what we're really talking about is if you're going to effectively do your job, we know connectivity and communication are always the biggest part of that. Look, it it's never been about can I make the greatest principles ever? It's can I can I get people bought in on a principle? But when you're dealing with that across multiple
Stereotypes Versus Real Leadership
SPEAKER_00generations with multiple ways of doing things, communicating, it's very tough, man. Right? It is so tough. Uh what are you seeing out there right now? You you're you've talked to so many businesses, so many people over the last you know few years. What are you seeing that the are the biggest challenges people have as they're dealing with generational stuff?
SPEAKER_01So honestly, the biggest challenge I think is just a lack of acceptance. And I say that because far too often, and I I jokingly say that obviously this is a polarizing subject, but far too often we like to label, stereotype, and not accept that even within generations, the idea of a generation is these are all the people that were born within this time frame, and the reason they might act a specific way is because of the things that happened during their formative years. If you're a millennial, you were born between, depending on which organization you look at and how they define it, anywhere from 1983 all the way up to about 2000. Well, that means when you were in high school or early college years, 9-11 happened. That doesn't define you a hundred percent, but it might define some of the ways that you might generally think. Generations are about how people generally think, and what we often do is we say, this millennial, oh or they're a millennial, or oh, they don't know what they're doing because they're a boomer and they have no idea what they're doing with technology. You don't know that. That is our assumption because of the generalized time when they grew up. And I
Simple Guide To Generation Ages
SPEAKER_01know lots of baby boomers that are way better at computers than I am, and it's not because of when they were born.
SPEAKER_00Well, I'm I'm gonna go ahead and set the stage for that right now. Let's talk about just in case you're listening to the show for the first time, and I really do want to give people some value with this. Just here's the age ranges, and of course, there's different resources and things you can look at. But Gen Zier, if you're born between 1997 and 2012, you are what we would call a Gen Zier. So if you're listening, you're in the age range. And that's that's that's a lot of employees now.
SPEAKER_01That's that when you think about that, that's there is a workforce. It's a bunk workforce is I've got Gen Zers working for me right now.
SPEAKER_00I know I totally agree with you. Millennials, you are from 1981 to 1996. Now, look, here's the thing I've found about that. I mean, you'll you'll find, depending on what chart you're looking at, some people will say uh millennials started in 1979, some people will have it growing a little longer. But it really doesn't matter, you get the general uh gist of it. Gen X, we'll look at 1965 to 1980. So these are the people who you know they kind of experienced a lot of the tech boom from back in the early 80s, thinking about Apple computers and all that stuff that was going. And then we have our boomers, uh, and we'll stop at the boomers for now, but generally they have them as 1946 to 1964, somewhere in that range. So if you have found yourself in one of those categories, there are truenesses in all of them. Absolutely. Here's the fascinating thing is we're talking about not judging people. Um, there's some of these people that are on these, like they're kind of on the fine line. Yeah. You know, you're like 1980 and you're somewhere between Gen X and millennial.
SPEAKER_01Like an well, I've heard people say they're an elder millennial. Right. Or like they're they're uh um what uh xenial, like it's like you're Gen X and millennial, and you're a little bit of both.
SPEAKER_00Well, the truth is um fascinatingly, uh, millennials actually are almost spread into two significantly different groups. Yeah, it's such a giant group and it's such a giant divide. If you get the younger millennials, they tend to be more like the Gen Zers. You got the older millennials that tend to be a little bit more like the Xers almost, you know. When so there's some fascinating things that uh are in there. And so as we sit here and we're just throwing labels on people, you're a millennial, you're a gin. Now, here's my question for you. Um, in an organization where you have that, uh, you know, how how do we actually maximize the strengths? Now, hear me out. When I'm saying the strengths, I'm like, look, if you this is my estimation of things that we don't want to stereotype, but the the baby boomers, a lot of them were around the World War II timeframe, and they've learned all about a hard day's work and consistency
Turning Differences Into Team Strengths
SPEAKER_00over years, and they're kind of like a lot of loyalty in them right now, and and and I and I think it's a loyalty that to the younger groups is not really on the overall doesn't feel to be there, and I think that's hard, but you know, then you got your your Gen Xers, and I think the Gen Xers to me were kind of like the ones who it's kind of like fight the power, man. We can do this ourselves.
SPEAKER_01Yeah, it's very you know, it's almost like independence. I like to think of the Gen X as the latch key generation, and that you grew up and you came because your molecular boomer parents were so hardworking and so organization loyal and driven to like put in that hard day to work that like you came home and strike the guests. You got under the the key the you know the mat and you got the key and let yourself in after and you made yourself dinner and you made yourself a snack and you took care of yourself, and that was your upbringing. So when you look at the next level at the millennials, and you think they have no hard work or ethic because they can't figure anything out for themselves. And see, that's what drives me crazy.
SPEAKER_00See, the millennials that I know, very driven group. And and quite frankly, like here's the thing I'm gonna say, and and we we have a fairly short show today, but we can break this into two or three parts. Absolutely. The thing I've experienced, Nick, is that while we have all these these labels and these expectations, I find beautiful things that come out of each generation. Here's my fun one. Now, the Gen Zers, now they have all these things like 6'7 and all this stuff, and stuff that like every other generation's like, what the heck are they doing? We have things too in another generation. No doubt about it, you know? Yeah, yeah, yeah. Right. Sorry. Did you just say all right, anyway, so uh folks, I'm sorry. I apologize for Nick. Uh no, no, no, it's my favorite topic to talk about. But but no, but look, look, here's the thing. You know what I found about the Gen Zers? They are all about efficiency more than any of these other groups that I've seen. Oh my god, so they are like, look, why would I spend eight hours doing something I could do in four hours? Yep. And shouldn't I be rewarded if I can do it in four hours instead of eight hours? It's flexibility. And here's the thing. I'm talking to a builders group about, I don't know, it was at the state convention last year. And I said, look, here's the thing I think. I'm a builder. What do I want? I want efficiency, I want my jobs going quickly, I want them staying in budget. I'm like, you know what? Maybe some of the gyms here should be. Yeah, come on now, guys. Find out a better way to do it. 100%. So I think there's things that I almost have the different thing. I would like to see each group take traits of the other groups and become like this perfect, well-rounded little and that's what leading across generations is.
SPEAKER_01We talked about it in past shows, but like getting the right people in the right places. It's how do I put the person there because this is something they're good at, but also how do I get the group to recognize that in each other? And that when I need to have this tough conversation, I might want to bring someone in from a boomer generation who is more comfortable having a face-to-face conversation. That's something that I can and I can learn from it. And that's what I wish every generation would do is think about what I can learn from this person. And that's what good leaders do, period, is we ask ourselves, what can I learn from this experience? What can I learn from this person, from this generation? And when you're talking about them all kind of coming together, it's the beauty in it is I'm accepting the fact that you're different from me in your generation versus mine. And how do we not get frustrated with that? But see the good in it and accept the strengths that they bring to the table instead of going, oh, here's another, you know, frenzy person who doesn't want to work, they're not motivated. No, they're very purpose-driven and they are very, you know, mission conscious. They're very much interested, and that's the reason they want to be efficient, is because if I'm more efficient and I have flexibility, I can take care of the things that matter to me. And it might not be your organization, but it they want to work the best they can for your organization so they have more time to do the cause that they care about. That's not a bad thing.
SPEAKER_00Well, you know, I I tell you from a management standpoint, and I I know sometimes I throw in, hey, I'm a manager of people, so I like to talk about it in a real world. My favorite thing to do is actually bring people in and get their perspectives. I I very much enjoy that. And why you have me on the show? Yes, exactly. I want to hear your perspective because otherwise I'll just sit here talking about my beliefs for uh 30 minutes straight, and nobody likes that. But I will tell you, seriously, I can look at my organization right now. I actually have all four generations represented, just barely on the boomer, but I have all four that we just mentioned. And here's the thing that I found about it. I like to talk to each and kind of say, hey, look, here's a perspective I'd like to get from you. Um if it if it tends to be on the younger side, I'm like, I'm actually more interested in what's tomorrow look like. Look, if we want to sit here and talk about whatever we think about things, all of our buyers, 10 years from now, not all of them, but a large portion of them are gonna be Gen Zers and young millennials. That's gonna be our biggest part of the buying pool, 30 to 40 years old. Absolutely. And if you want to sit here and burn those bridges right now because of all your, you know, in my day type of talk, whatever age
Shared Values Across Age Groups
SPEAKER_00you are, that's not gonna be good for you. Now, at the same point we live in the present, I still need to be appeasing baby boomers and GXersers and older millennials. And so here's the thing: I need a perspective on each, right? I can't abandon any of the groups, so let's embrace that.
SPEAKER_01Yeah, you know, and you know what? What's really cool as you say that is that we, and I'd be curious to get your thoughts on it, but I think we often put people into these labels and we say there's these groups, and we look at all the differences between them, but I think there is far more similarity and connection between the groups than people realize. Okay, okay. You know, I think about like some of our, and part of the reason I think that happens, and I'd be curious if you agree with this or not, is that because you're raised by I I'm a millennial, so I wasn't raised by Gen X, I was raised by baby boomers. You know, a Gen X, you're probably raised by the silent generation, and so I think so much of like what we learn is passed down from the people above us. And so then I now as a millennial look at what some of Gen X is doing and think, okay, I don't I like some of that because like that's the opposite of what my parents did. And so there are more similarities, I think, in terms of what we do and believe and think because of our generations generally. But I I agree, you know, and that's good and bad.
SPEAKER_00Yeah. Like I like honestly, this might be the first show where we're just really rapping about life because at the end of the day, besides the fact I think we can agree we need to make common bonds between if you want to be successful in life, you need to find a way to make the common bonds, and you can't turn it into us against them. But but here's the deal. I look at it sometimes and I think, you know, we tend to look at our parents and and and our parents look at us, and we have almost a mutual contract in a in a good family unit, which is the parents want better for their kids than they had, and the kids will tend to want better for themselves than their parents had in a lot of cases. And so, for example, if I've watched you my whole life, this is what they said about millennials. Everybody said, Oh, millennials, they want to take off all this time from work and go travel the world. Yeah, da da da. And they say, well, why do they do that? Because they watch their Gen X parents or baby moomers work 60 hours a week and then, you know, and and then it's all gone. And they go, Well, I don't want that for myself, and the parents don't want that for the kids. Well, each generation's passing down a little bit of a bias, right? Or not maybe not a bias, but a presumption.
SPEAKER_01Absolutely. Well, and it's we're you're passing down what is almost an an expectation or what you've seen in terms of your own. It's really it's a it's kind of like a social construct in the sense that like this is what's what I've seen, so this is what how I should live my life. Like I, you know, I never grew up in a time when you just walked onto an airplane. You know, I grew up in a post-9-11 world, you know. The I think the first time I went on an airplane was after 9-11. And so that's something that for me changes how I view things like safety. You know, I I think about the idea that sometimes folks, you know, my parents, they, you know, they work their hardest, and then there's the the you know the recession in in 2008, right? The housing crisis and like that that sort of stuff sees people lose their job. Those things don't leave individuals, it stays with them. Those are the the kind of the trauma that like that are part of each individual, but you cannot, if you're if you're listening to this, you cannot just assume that this person acts this way because they had these parents or because they grew up in this generation, because it's again, it's so large, but also again, it's a generalization around a group of people. And this minute you stereotype label, put someone in a box and say, This is who they are, you miss out on all the stuff that we've talked about in every other show, all of the opportunity to empower, to be a like, you know, and this is one of those topics that can be polarizing, and they go, you know what, I'm not working with this person because they're just a lazy millennial. You've missed everything else we've talked about on any other show. I think, well, right, yeah.
SPEAKER_00No, I know.
SPEAKER_01Go back and listen to them.
SPEAKER_00Well, I mean, we we have common things we do beat the horse
Big Events That Shaped Each Generation
SPEAKER_00on, but I'm gonna change the vibe up a little. Like, so you guys know these things, and and we're talking about how to work with people, and we know, we know, communicate. So here's something that's gonna be fun. I'm gonna test you out, okay? There's not a perfect answer here, but they say that generations tend to, and I've done quite a bit of reading on this, they say generations tend to associate with a major, major event depending on which generation they are. Let me set the stage and we're gonna kind of probably have just enough time to get through this. Uh all right, so number one, you're a baby boomer, all right? Uh the each generation will tend to say, I lived through something major, something that everybody in that generation can go, yeah, I remember that. And then later generations would be probably too young to really remember that. That thing that you go, I yeah, I remember how that went down. It was a very moving moment to me. Um, and I've got answers for this, but I'm gonna see if you can get them. Uh some answers. There might be multiple answers. Okay, so here we go. Baby boomers. There is an event that happened for baby boomers that I think that largely across the board they would go, oh yeah, that was a biggie for me. But they grew up. So give me the give me the use for baby boomers again. The baby boomers, we have on here 1946 to 1964, and of course you got that's a big, big era, but that's why they call it the baby boomers. So it's uh uh for them, it's all the things that probably living through and thinking about related to you want me to talk about. I'll give you I'll give you one just to get I'll to wet your whistle here. So here's one that the baby boomers, JFK assassination. There's a big one. Civil rights movement. Like I could never well, it and and the civil rights movement was a whole thing, but we're talking about a specific moment. You go to a moment in time. And I'm just, you know, like I said, sure. There might be others, but JFK assassination, if you could ask any baby boomer, you're like, where were you when this happened? What was it like? I I would I don't know about that time. I wasn't alive when that happened. So that's a fascinating one. How about uh they did one on the Gen Xers? Challenger, exactly. If you're a Gen Xer, you will tend to have remembered either where you were or it was so fresh, even if you were young when it happened, it was so fresh that you're like, oh yeah, there was that Challenger explosion, man. It happened on a very big way on the national stage. Now, what do you think about millennials? Now, millennials are an interesting one, but you it's an easy one.
SPEAKER_01It's it's 9-11.
SPEAKER_009-11. 100%. 9-11. And and here's the fascinating part. Like, I'm I'm giving these people some stuff to listen to, our viewers, because you might go to you might go, well man, I'll never forget 9-11. But guess what? Who doesn't? Gen Zers.
SPEAKER_01They don't like they're no, absolutely. It's and it's wild to think about. Like, I have a sister who was born in 2000. She's in the Gen, she's the beginning, she doesn't remember, she was one, two, like she's barely, you barely. They're like, that's crazy. Wow, that's crazy.
SPEAKER_00I wonder what that was like. But it doesn't, and so for Gen Zers, we the the this was a little bit more interesting, but they but it is a little bit of an overlapping one. We're still trying to figure out what it is, but there's one predominantly one thing.
SPEAKER_01I don't know if you would consider it, but I would say probably COVID is a big thing. And you you hit it, man. Very good job.
SPEAKER_00Yeah, they say if there's one thing for the Gen Zers, because they'll all remember when they were at home during school, the world is everybody's dying.
SPEAKER_01My junior and senior year of high school, and I had to be virtual. Yeah, exactly. Absolutely, yeah.
SPEAKER_00And so we talk about major events, but but here's the takeaway. And why did I even do this right now? I did it because what I'm trying to say is if there are such wildly different things, JFK to the Challenger to the 9-11 to COVID, just think about how impacted each of these generations were by these major, major events and put some respect to it, man. Absolutely. Look, if you had somebody who's been through something like that or or would experience something, you have to say, look, your your experience is unique in your formative years, you saw those things. So how can we not just accept it, but how can we maybe learn from it and grow up on it? Exactly.
SPEAKER_01I think what's what's neat about that though is that we oftentimes, and I think I see our older generations do it, is that they live through it. So boomers lived through all of those things. Yeah. And X lived through three of them, right? Millennials of two of them. And so we're like, well, I live through it too, and you don't know what it was like because I was I had two kids when this happened, or you know, and and and I don't that's what we should not be doing. I want people to hear me say that, and that it is if you I want people to try and I think of the beauty in leading across generations, is try and be empathetic to that generation that they were 12 to 22 years old, whatever it was when that thing happened, in a moment where they're never going to forget it. Just as much as you might never forget it in a different generation when that happened to you, but you were a grown person, an adult, and we're not fully developed, like developing who you are and figuring out you know your personality.
SPEAKER_00And that's I mean, one thing about one thing about it is you're you're very you're like one thing about you I like is you're always consistent with empathy for your fellow man, and I dig it. The thing I'm going with is I'm looking and saying, look, there is a thing that we should respect people who are older because they have lived through more that wisdom, that experience, 100% knowledge. Don't like shortcut it just because I know a little bit more about technology or I know a little bit more. And for those older groups who are like, oh, these kids don't know anything. It's like, well, just remember that their formative years were were developing at a time where yours weren't. So maybe they do have a little jump on you in a few things, and that's okay too. And the best thing
Empathy Respect And Next Steps
SPEAKER_00is they have a lot more to grow from. We got to invest our youth, we gotta invest our young people and let them thrive, man. Like, push it on. All right, that's my PSA for today. Let's call this part one. We got to do some more generational talk. Um, uh, for this time, I'd say we're setting the stage for leading across generations. So I appreciate the conversation, Nick. Let's think about next part, part two. Uh, for you at home, like let's continue to grow up on this and uh we'll think it up next week.
SPEAKER_01I'd love to continue the conversation. Maybe if people have thoughts on challenges they might see around specific generations, let us know. Like, you know, just reach out on social media and tell us I struggle with this thing because there's a lot of things about generations that you know we could talk about specifics of certain generations and then just how to lead across them. So I'm excited for a part two and continuing it. I'd love to hear what people have to say.
SPEAKER_00Yeah, absolutely. Well, we'll leave that as uh uh end of the show here. Uh, make sure to uh send in your questions. You can send them over to mentalityleader at gmail.com. You can also go to the leadermentality.com online. Uh look us up, ask your questions. We'd love to get those incorporated. And uh yeah, uh let's let's pick it up next time. Nick, thank you for being on the show again with us. And we will see y'all next time on the Leader Mentality Show in Myrtle Beach, South Carolina.
