Chris DeSantis | Why I Find You Irritating: Navigating Generational Friction at Work

Elise Holtzman: Hi, everyone. It's Elise Holtzman here, a former practicing lawyer and the host of The Lawyer's Edge Podcast, where I sit down with successful attorneys, legal marketing specialists, business leaders, and authors to talk about how lawyers and law firms can grow and sustain healthy, profitable businesses.

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I am super excited to welcome today's guest, my friend, Chris DeSantis. Chris is a speaker, author, consultant, and most recently, podcaster, specializing in management and organizational development issues and interventions.

He has more than 38 years of experience in training and development and specializes in assisting individuals and groups in identifying and overcoming obstacles to effectiveness. Chris has an undergraduate degree in business from the University of Notre Dame, a graduate degree in organizational development from Loyola University in Chicago, an MBA from the University of Denver, and previous work experience in manufacturing, professional services, and not-for-profit environments.

I'm very excited to report that Chris is the author of the newly published book, Why I Find You Irritating: Navigating Generational Friction at Work. You can also listen to his advice podcast, Cubicle Confidential, along with his co-host, Mary Abbajay, who is also a friend of mine and has been a previous guest on this very podcast.

When he's not traveling to give his wildly popular workshops, Chris can be found at home in a quiet corner of Lincoln Park in Chicago reading an astounding number of books.

So Chris, Chris, welcome to The Lawyer's Edge.

Chris DeSantis: Thank you, Elise. I really appreciate your having me today. It's good to see you again. And I enjoyed our time the other week for dinner.

Elise Holtzman: Yeah, we got to have dinner in Chicago. That was really fun with a couple of friends of ours.

So I'm so excited to have you here, partly because, as you know, I think you're fabulous. And I also love this topic. I think it is just endlessly fascinating.

And I want to start out by saying that quite literally everything I know about generational differences, other than a few observations that I might have come up with myself, I learned from you. So I'm excited to learn more today along with my listeners.

So let's start out with, I guess, the first question about your book: Why did you write a book about generational differences in the first place? What's compelling about it for you?

Chris DeSantis: Well, to back it up about 15 or 16 years ago, I do a lot of work with professional services firms who use young people, meaning that they're important employees and they come in the firms usually in large numbers. What they started to notice was—and this is when they started to bring me in on the topic—was these young people weren't acting as they "should," meaning that they weren't as the people that were supervising them, when they were that age, had acted they acted that way.

So they didn’t. So in that sense, that became peculiar in their eyes and they wanted to say, "What's going on here?"

I then started to do some homework on the topic. And so as I started to read it, and there was some information out there, and as it's expanded in terms of the information out there, over the years, I’ve just accumulated more and more information. I probably have about 60 or so of these books under my belt.

And then I’ve also expanded understanding about how children are raised and how the mind works and all of these other things that play into the perception of generational differences. And I thought at some point, “Hey, I know enough about the topic to be dangerous. Is there an opportunity for me to write about it?” which I did.

And so this is really the compilation of my homework and trying to find a space that hasn’t been covered yet, I would say, by what’s out there in the literature.

Elise Holtzman: How is this book then different from others on the topic? Because you mentioned that you’ve read—and I know you read constantly. So for anyone who’s listening, when Chris said he read 60 books, he’s not kidding. He really did.

So what makes this book different than the other ones that are out there?

Chris DeSantis: Well, first of all, I cover four generations in the workplace. You see, I’m not looking to talk about the lives of all of these people outside of work, but rather how we interact.

And the other thing about that is I spend a lot of time talking about how we develop perceptions of others. See, I’m generalizing, and I think that’s one of the arguments against generational differences is, "Well, everyone’s generalizing." Of course.

And I make the case that, well, why do we generalize as humans? And so I explain how we get to this point of generalization and how that helps us navigate through the day. Because if you did not generalize in certain categories, it would be very difficult to treat every human being as a novel event. It would make for a very long day.

So I talk about that. And then I talk about the point of view that we each develop. And the point of view is, I’m a boomer, I have a point of view about how I see the world, and then I judge you, who are not me, through the lens of who I am.

And then I look at all of those lenses, and then I started to look at how do these lenses come in conflict? And so the second half of the book really talks about how do we help the workplace function a little better, that embraces the differences as opposed to trying to correct somebody for being different. And so I hopefully have found that space in which I'm presenting novel information in a way that is compelling to people in the workplace.

Elise Holtzman: The concept of generalizing is really interesting to me because, for some reason, this popped into my head while you were talking, if I know that I could get hit by a Toyota, and when I'm crossing the street, I'm only looking out for Toyotas. And I don't realize that the other cars could hit me too, because it's just Toyotas and it's not all cars.

So, as you say, we use them to cut down on all of the work that we have to do to interact with other people. And look, I mean, in so many other ways, people put each other in boxes because we need generalization, but then to your point, it can get in the way.

Chris DeSantis: Yes. See, the idea of generalization is really, the way I present it, it has an element of what Pascal Boyer would call folk sociology. It's "we think we are right about humans." There is not a human you've met who doesn't say, "Oh, I can read people. I can read people."

So, in that sense, what they're doing is they're really projecting the generalizations that they have of the categories they're interacting with. And often what we do is we just look for confirmation of what we already think. In fact, it's called the Tesla effect. Once you buy a Tesla, all of a sudden you notice all the Teslas. So just to your point, once you're hit by a Toyota, all of a sudden you're leery of all the Toyotas.

So, in that sense, what we do is we already have a predisposition. And I will talk about that momentarily when we get into this. So what we look for is then that confirmation. Then the other piece of this is it also shortcuts the conversation we have to have with another person about others. It's the coordination concept.

That means if we both think this way about millennials, I don't have to explain millennials to you. I just get right to the point of how troubling they are. You follow?

Elise Holtzman: Right, yeah.

Chris DeSantis: It's a coordination effort. So this generalization is pervasive throughout society just because it makes society easier to navigate.

Elise Holtzman: Let's go back to basics and talk about the different generations. So you mentioned four different generations in the workplace today. What are those four generations?

Chris DeSantis: Well, in the workplace, they are... I talk about in the book boomers, Gen X, millennials, and then Gen Z. Knowing full well, there are traditionalists still out there, they precede the boomers. And then the next generation is called Gen Alpha. They're called Gen Alpha simply because it's a placeholder name. They're starting the alphabet again.

Elise Holtzman: Oh, I was going to ask you about that because I don't know where these names come from. "I feel like there's a Wizard of Oz behind a curtain somewhere, like the generation wizard who gets to name these generations." Like, who comes up with this stuff?

Chris DeSantis: Well, baby boomers have always had that moniker simply because we are a product of the baby boom, after the war and so many of us were born.

Gen X is a product of the book Gen X. And so that was sort of the angst that they experienced that everybody related to in that generation, and therefore that became the moniker.

Millennials were actually Gen Y, because X, Y, they didn't like that. As it was the turn of the millennium, it was millennials that became the hook.

And as we got to Gen Z, Gen Z was also Zoomers. Or, so in that sense, Zoomers was the other name or this Generation Z, but then it became the one that seems to be sticking was Gen Z as a subsequent.

Elise Holtzman: Chris, what are some of the primary characteristics that rise to the top for each of those generations? How would you describe them?

Chris DeSantis: Well, think of it this way. Rather than just the characteristics, think about where the characteristics derive. They derive from, in my mind, a couple of things.

One is the socioeconomics of when you were raised, meaning when you were a child, what was the world like for you? Remember, in my world, my grandparents all saved everything. They were children of the Depression. And when you're children of the Depression, that shapes you.

So you have the socioeconomic characteristic, then you have the cultural events, or the cultural catalysts, I call them. Those are the things that happen when you're growing up that you notice, that leave a mark upon you.

I came of age when we landed on the moon. We were getting to the moon. Yay. I also came of age when Martin Luther King was assassinated. And so when we have certain events that we remember, that starts to shape us as well.

Then the other part of this is, too, is what values seem to be emphasized by society as well. What's going on in the society in terms of what are we starting?

For instance, I think for the young today, one of the things they recognize, climate change, existential threat. Now, as a young person, I think the code red in the school districts for these young children, they're seeing that as well. So these events start to shape how you see the world and then carry forward.

The third one is what is the parenting model? How were we raised? I was raised under what I will call permissive authoritarianism. Our parents were authorities, but permissive relative to the generation that preceded them.

The next generation forward, they were raised under what I will call natural growth. This is from a book called Unequal Childhoods. I lifted the title of that. I like it. Natural growth means they're more on their own, the latchkey kid.

Then we move into the millennial, and they were raised under the most elegant of terms: concerted cultivation. There's a concerted effort to cultivate our child and develop them, almost like a plant, I guess.

And so in the last one is the Gen Z, who is raised under a corollary model, slightly different, called co-piloting, they are co-pilots. Meaning that the parents are not saying, "You should do this and I will determine who you will be," but rather they act as guides and then are Socratic in their questioning.

"So is this what you want to do? What is the consequence of doing that? Well, have you thought about this?" And so they then suggest to the child, "Maybe you want to think about this, this, and this." And then the child still owns the decision, but they are guided as opposed to determined, where the millennial child had more of the parent determination.

Elise Holtzman: One of the things that I remember you saying in one of your seminars that I attended that made me laugh, everyone in the room laughed. Everybody always laughs in the room with you, Chris, because you're so much fun.

But you had a room full of younger Gen X and older millennials. You asked the question, how many of you have kids? So the hands went up. And then you said, "Okay, how many of you tell your kids you love them?" And there was a buzz in the room.

Of course, we all tell our kids that we love them. Then you said, "How often?" and the whole room exploded, "Every day." And you said, "I'm a boomer. My parents' love for me was implied."

And so I’m curious, what made you say that? Why was that such a difference between you and the folks in the room?

Chris DeSantis: Well, one of the points I make about this is that the expression of your love to your children is explicit. The expression of the love I received was implicit.

This explicit messaging in terms of "I love you" and saying this is reassuring. By the way, I think that translates into the workplace. Not that we should be saying to our employees, "I love you," which I would never endorse, but rather, "Hey, how am I doing?" "Well, you are doing well."

So the idea here is to be more explicit versus implicit. I was using that as sort of a metaphor for what we could be doing or should be doing in the workplace, because we have shaped them in a way to be receptive to these messages.

Elise Holtzman: One of the things that stuck with me about that conversation, and I’ve talked to my daughters about it. As you know, I’ve got one who’s very young millennial and one who’s very older Gen Z. They're a few years apart.

I talked to them about it before they started their jobs. I said, you know, it all starts with what Chris said, “So Chris said that you’ve been raised to be part of the conversation. You’ve been raised where you’re getting constant feedback, where we are having these conversations about everything.” So you’re always included in the conversation.

Then you’re going to go into the workplace. The workplace can be very much a top-down sort of a situation. That was eye-opening to me. That had never occurred to me.

So do you think that that is a big reason that there’s so much struggle in the workplace when it comes to generational differences?

Chris DeSantis: Yes, because what I call this in the book is these children are raised in what I will call an engage-discuss model. We engage with them and then we discuss. That’s just the habit of who they are.

Now, when they come into the workplace, that is incongruent with how the workplace has operated. The workplace is more tell-do, right? "I’m going to tell you what to do."

Now, what happens is this young person is not aware of the rule until they break the rule. So all of a sudden, they’re having a dialogue or they think they’re having a dialogue, when they’ve actually been given an order.

This is heard by the powers that be as something insubordinate, in like, "What? You’re challenging me?" And they're in no way challenging—maybe to some degree—but the reality is very simply, "Look, I wanted to talk about it."

And so they’re incongruent with the experience that they had growing up. But in their defense, they get onto the game. Everyone gets onto the game. It’s just disappointing that it has to be that way, because dialogue is a better way to get people to commit to something than orders or compliance. Compliance is the minimum of performance. Commitment is the maximum.

Elise Holtzman: I was recently listening to an episode of your podcast that you and Mary did together, and you were reporting on some questions that people had asked you.

So, you guys have people ask the questions and you'll try to solve some of their challenges on the podcast. I thought, "You know what? I haven't done that before." So I'm going to reach out to a couple of young people I know who shall remain nameless and ask them if they have any questions about generational differences.

So what I heard from a young woman was something like the following: "Why are some Gen X women"—and again, this is one woman's opinion—"why are some Gen X women so actively adversarial to millennials and Gen Z women, even in women-dominated environments?" Do you see that? Because there's a lot of talk even on social media. There are a lot of sort of battles on social media between Gen X and the younger generations.

Do you see that as a Gen X versus millennial thing?

Chris DeSantis: Well, let me unpack this question. First, I'll answer the back end of this. Adjacent generations typically have the most friction between them.

So, boomers and Gen X have some friction between them. It's much like a sibling issue, I think. And then Gen X and millennials have some friction. But when you get to millennials and boomers, they are far enough apart.

A) In the workplace, they don't always interact directly anyway. But also B) they have a more coincidental sensibility. And the same would be for Gen X and now Gen Z, they will probably get along a little better than the adjacents.

Elise Holtzman: So what do you mean, Chris, when you say coincidental sensibilities, what do you mean by that?

Chris DeSantis: Well, boomers and millennials are both products of economic uptick. So there's an optimism part of their expectation of that.

Interestingly enough, boomers consider themselves team players, which they are. But their idea of a team player is, "Somebody's in charge, and the rest of you do what I say." Whereas millennials really is a true team in terms of they're highly collaborative.

Then, when you get to the Gen Xer and the Gen Z, these are more independent. They're children of more economic downturns, and therefore, they're more pragmatic about how they view life. But also, they're a little more independent in their interactions and a little more private.

So, in that sense, those sensibilities are sort of reflected in them. Because part of who they are is what they heard when they were growing up. What they heard when they were growing up from their parents was probably, if they're a Gen X parent, "You've got to be able to watch out for yourself, be a little more careful out there." All of those things about being protective of self.

It's why, in Gen Z, one of the characteristics that seems to come up in the press a lot is that they have a curated self. Curated in the sense that we know aspects of them, and then to other people on the internet, other people know different aspects of them. So, they curate who they are relative to others.

Whereas I think when you met a millennial, especially in the first wave, you knew everything about them. It's one of the reasons why the Gen X don't trust them as much because they overshare.

I make the argument, I'm not convinced that millennials overshare. But because I believe Gen X is more reluctant to share, and therefore when they hear another person sharing, they view that as more information.

Elise Holtzman: As oversharing, yeah, that's perspective. I know you've always been very quick to say, "Hey, stop cracking on millennials, everybody." There's some really great stuff going on.

So, what about that? Actually, I'm interrupting you because I want to hear your answer to this question that my young person—

Chris DeSantis: Let me go back and answer that question. Because what this young lady is saying is these women, by the way, it is not an attribute necessarily that they are Gen X, they're doing this to a millennial.

This is a hierarchical issue. What happens is, in a hierarchical issue like this, with women in particular—because this is the case—the women who are Gen Xers who are in a management position had to get there because they had to report to boomers. Boomers in particular.

And the rule of thumb typically was—and you know this probably better than I do because you work with women—is to get a promotion from a boomer, you had to act in the way that they would accept you to act. And therefore, you had to be more masculine. I don't say masculine in your physicality, but rather in your sensibility. Because those were the traits men at the top, see what I'm saying, the top.

So, these women that moved up were probably displaying some of the traits that aligned them with this group. And at the time, I would argue—or I would think—there were fewer of them fighting for fewer slots. So, they had to be in a competition to get the seat.

So, you have the hierarchical issue. And then you have these young women who are coming up thinking, "Hey, you have it a lot easier than I did. I've got to pretend to get along with the guys and go out drinking with the guys and all that. You don't want to do those things because you don't want to rearrange yourself to be more like them."

So, I think part of this issue is that they are content in larger numbers now and they expect to be promoted as they are, not as someone wants them to be. You see what I'm saying? The traits of who they are are authentic to who they are. And I don't think they're going to change who they are, because they can see, "Hey, I've got more role models now. I can become any one of these things," as opposed to the narrow role model of what I have to be that gets to have succeeded in the generation before me.

Elise Holtzman: They have more choices, and they're more willing to look around for something that aligns more with who they are. Perhaps that's why we see them moving jobs more than the prior generations did.

Chris DeSantis: I think that's part of it as well. And this goes to your point—because you work with very talented women who go through the same process—the good old boys network is sort of slowly decaying or breaking up and so now, we've got business schools graduating far more women than they are graduating men. So, sooner or later, they're going to bubble up, and we're going to see a change in what is normative in terms of things like executive presence.

Elise Holtzman: It's not going to look just like the male model anymore.

Chris DeSantis: No, it's not. It's going to be more—and in fact, it's already out there, right? We talk about Brené Brown and being more vulnerable, being more empathetic, all those models. Those were not the eugenic traits of a leader back in the '50s.

Elise Holtzman: For those people who are still in the workplace complaining about millennials—and I do—or these younger people... "dot, dot, dot" like we're all supposed to know what that means, what would you say to them about millennials? How would you educate them a little bit to understand and appreciate millennials a little bit more?

Chris DeSantis: Well, first of all, what they're saying is perceptual, not actual. And this is one of the points that I make in the book as well, that there may be some actual differences between us, but there are a lot of significant perceptual differences.

This notion of entitlement is almost manufactured in the sense of how we see them, because news and the press are typically negative about the millennial. It's kind of like the "Florida man" headline, right? Every headline about a Florida man is a disaster.

So in that sense, we start to think Florida people are disasters. But the reality is, they're not. So the perception shapes the view.

Therefore, when a millennial says to you, "Oh gosh, I think I'd like to take off early today," or "I'd like a little more flexibility," or "I'd like a promotion sooner rather than later," we think, "Well, you're entitled. Oh, you want it all."

So they read it through the lens of that skewing of that is versus seeing this as just a person who's assertive. I think what we have to learn from them is I'll tell you a couple of things. A: What's wrong with being assertive? What's wrong with being in dialogue with other people in terms of understanding what you do, why you're doing it, and then negotiating how to do it better?

And what's wrong with being collaborative on a team and saying, "I want to take this on, and here's my thoughts on doing that," and participating more actively in meetings as a consequence? Those aren't bad.

I think what the deal is, there are already rules in place in offices that we don't know until we break them. So if you really want them to align with who you are and be less disappointed in them, start telling the rules earlier rather than later.

Elise Holtzman: That's an excellent point. I think that's been the case for all of us in the workplace. You show up, and you're just expected to figure it out. You figure out the rules, you figure out the politics, and nobody's outlining it for you.

Chris DeSantis: No. I'll tell you who's great at that, Gen X. If you're classic in this category—and once again, I’m generalizing—but if you were a latchkey kid who just figured it out, "How do I make dinner?" Well, you'll just have to figure it out. "How does the laundry work?" You just have to figure it out.

So in that sense, they are self-sufficient. You know, I think this is interesting—I know I digress—but the pandemic, Gen X is the only generation designed for the pandemic. Because it wasn't a big change for them. "I'll just figure it out."

Elise Holtzman: I never thought of that before.

Chris DeSantis: Yeah, yeah. Boomers are like, "Oh my God, what are we going to do? We're supposed to be in the workplace." And millennials are like, "Where is everybody?"

Elise Holtzman: Well, and it's funny, because this is like a lightbulb moment for me. I work with a lot of law firms, as you know. And the law firm leaders are now typically older Gen X.

I can't tell you how often people like professional development professionals or marketing professionals, will go to the leadership of the law firm and say, "We want to do seminars on this. We want training programs or coaching programs."

And the management committee folks come back and say, "Why can't they just figure it out? If you want them to bring in more business, tell them to develop a business development plan and then have them execute on it."

And now that's actually really helpful information to have. It really does point out how differently we all look at the world.

Chris DeSantis: Yes. Because one of the challenges with this is they're going to blame these young people for not showing initiative.

You see, because initiative is the product, to a great degree, of the situation you're in. "If I'm not going to eat unless I make this dinner, I'm going to figure out how to make this dinner."

So in that sense, I think the millennial would like to have some structure about: "Okay, how do I achieve here? What are the rules here? What don’t we know? What do we know?"

And what's wrong with teaching them what you need them to do well? But at the same time, to balance that against, "Well, some of this you will have to discover." It's a combination, not one or the other.

Elise Holtzman: Let's talk about some of the suggestions that you have for people in terms of navigating some of what you call generational friction. One of the methods you mention in the book, you refer to as embracing lopsidedness. What do you mean by that?

Chris DeSantis: Well, I came up with this. It actually comes from a book called Different. It was written by, I think, Moon. I think her name is—she’s a professor. I can't remember if it’s Harvard or Stanford. But it's an interesting book.

In Different, there was a category of marketing, or companies, that are lopsided. A lopsided company is one that has a certain strength and that's what they play. I'm not good at other things, and I don't worry about those other things.

And I think, yeah, that ties to this—what is it? Marcus Buckingham’s StrengthsFinder, about the strengths that we have. And so with that, I started to think, “Okay.” And the young are told—Millennials in particular and Gen Z who follow—"You are special." Yes, I have come to the conclusion, yes, you are special, but we are all special. But we are special in our own ways.

So in that sense, I have absolutely the worst computer skills—irrelevant to my life—because I don't make my money or my future or my interests lie in that category. My interests lie in learning new things and then sharing that with others. So I am lopsided by my nature. I think we are all that way.

And my point is the work has to re-examine how we do the work we do, because I think work is ever more complex, and we are dependent upon others to do the work that needs to be done. So why not accept that we are strong in certain categories and only need to be good enough in others?

You see, my problem in the workplace is that we have performance appraisals that mark you across all things. Then what you end up doing is you end up spending time trying to be better at things you will never be better at, that have very little value for you in life, and that don't propel you forward. What propels you forward are your strengths.

So lopsidedness is the embrace of those strengths and then supplementing that with other people who are willing to work with you. That’s what the Millennial is. They're very collaborative, and they're willing to say, “I'm good at this, but I need you for that.”

Elise Holtzman: Presumably, it's a lot harder for the older generations to accept that.

Chris DeSantis: Oh, yeah. You know why? Because we use the notion of A players. “Oh, that's an A player.” And an A player assumes that you must be good at all things. Well, I'm not sure you need to be, because there's an interesting book called The Diversity Bonus.

And if you put a team full of A players together and a team full of people that have complementary strengths, you are more likely to get a result of high performance from the complementary strength team than from the A player team. So in that sense, because the A players play for themselves, complementary strengths play for each other, because we need each other.

Elise Holtzman: I suspect that if you put people in a room and you had this conversation with them, that from a logical perspective, it's kind of hard to argue with.

Yet when they put people into the workplace and they're going through their daily activities and trying to achieve things in the workplace, they don't see it that way. Because as you say, there's all of this cognitive bias and all kinds of other things going on like, “Well, they're all this way, and those people are all that way,” and “The way they're doing it doesn't work.” But I think it's kind of hard to argue with that logic, isn't it?

Chris DeSantis: Oh, I'll give you a perfect example in the field of which you are a part, because you do business development and you teach people how to do this well.

One of the categories, remember this one for partners? There were three kinds of partners: finders, minders, and grinders. And a finder is the person who gets that work. A minder is the person who takes care of the organization, and a grinder is the person who puts the work out there.

Now that's interesting, because those are three paths to success. Yet the path to getting to that success is through this commoditization: “You should all be alike.” When in fact, that's not what's going to happen to you in the future. You're going to be one of these. I say start that earlier than later.

Elise Holtzman: What are some of the other things, Chris, that you suggest to people for navigating some of these generational challenges?

Chris DeSantis: Well, part of it is just be willing to reserve judgment and give people the benefit of the doubt. These are people that may not do it the way you do it, but it can still be done.

You see, I think one of the challenges of being successful—and you know this, you're working around successful people all the time—is that they think there's only one path to success: the path I took. I am suggesting that, by the way, this is historical, we have judged negatively every generation who follows us. That’s just common. That’s just what we do.

So if that is the case, then we're failing up if that's the way we're failing. Because I think we have to say, “This is what I want to accomplish,” and I think avail yourselves to listen to how they might go about doing it. Guide them through the process and say, “Well, that might work.”

Again, you know what I've always said—or I believe—Gen X and Boomer parents are great parents. They engage with their children. And yet when they come into the office, they quit looking at these young people as the possibility of being young children, or their own children, but rather young versions of themselves.

So what they end up doing is they manage them through how they learned to manage, which is a generation off of the experience they're actually having today.

So I would say, apply some of your parental skills in terms of get into a dialogue, challenge them on this in a reasonable way. Come up with some solutions, get some alternatives. Doing all those things will probably have a better outcome than trying to be a "tell-do" in the managerial sense that you were taught.

Elise Holtzman: That's an excellent point. And also, look, I mean, to the extent that people complain about millennials or any generation, like, the ones who are complaining are typically the ones who raised them and raised them in a different way than they were raised.

When we all look at our parents and say, "Well, you know, they did some great things, but they also did some things that I will never in my lifetime repeat..." What always makes me laugh is that I got a lot closer to my parents' parenting style than I ever anticipated I would. You know, they actually did a pretty good job. Don't tell them I said that.

But we're the ones who raised them. So I think you're right, that going back and understanding that these are the same people we raised, or pretty close in age to the people we raised, and talking to them that way.

Chris DeSantis: I would also make this case. I like this as a thought experiment. Where would you like your daughter or son to work? What would define the environment of how you'd like them to work?

And if I said to you, "Well, okay, it's going to be an environment where you only do what you're told to do and never what you're not told to do. You don't ever talk to other people. You don't engage with them. You just follow orders blindly..."

Elise Holtzman: It seems such an obvious point, but that's not what we do. Now that's a really good point. I love that. I think opening up this conversation and dialogue is very important because, again, you and I—and some of our colleagues in the professional and personal development realm—we talk about this stuff all the time.

But for most people who are doing something completely different professionally, they're almost never taking these things into consideration. They're never talking about them because they're busy serving their clients or doing whatever it is that they do.

So I think opening this up for conversation and doing the kind of work you do is very important.

Chris DeSantis: Well, to your point, you work with lawyers. And the most precious commodity among lawyers is time, because of that billable hour.

So they will want to maximize their time, and dialogue is not a maximization of time, it takes time to do that. So what happens is, we aren't overt about it, but we end up giving more work to the people we have to spend the least time with when we get the deliverable from them.

You see, if I get a really good deliverable from you and I spend no time, I'm going to give you more work. Now, if I have to teach you how to do this and it takes more time and you eventually get it, that’s nice, but so what happens is, the more time you take from me in terms of the deliverable relative to what I expect from you, the less likely I'll use you again.

So we end up finding younger versions of ourselves that we promote, as opposed to embracing that somebody is actually different from us.

Elise Holtzman: Yeah, that explains a lot, Chris. That makes a ton of sense.

What about people like me who are not squarely in one generation or another? So, you know, I'm going to give away my age here, but I was born on the cusp of boomers and Gen X. I'm in the first year of Gen X.

And the truth is, I don't totally relate to the common wisdom, if you want to call it that, about Gen Xers, how they're usually described. I don't feel that way about the boomers either because, of course, they're older than me, and they seem a little stuck in the mud and overly traditional. But I have elements of both.

Most people are not smack in the middle of their generation in that year. So what do you find with people like me, who are kind of in between?

Chris DeSantis: Well, first off, I would never have said you were in that year. I would have guessed 1975 or 1978.

Elise Holtzman: Yeah, you're good, Chris. You're good.

Chris DeSantis: But having said that, when I talk about this in the book, I call this generational waves.

You see, the categories are artificial. They're constructs, constructs that run roughly 20 years, although they seem to be shrinking, which I’m not convinced is sufficient, a sufficient reason because they think there’s a change to the net. But the point is, there are these rough 20-year windows.

And this is a construct in terms of the silo that’s been created, but it’s a fake silo. It’s not really a silo. Think of it more like water. It’s a wave.

The first wave of a generation starts to identify the difference. You see, when we come of age, we sort of rebel against that which is our parents' view of things and we create our own identity, thus the hippie. You see what I'm saying? So in the first wave of the boomer generation was the birth of the hippie.

The second wave, there was no hippie, there was maybe the yuppie. So it's the second wave of the generation that lives under the auspices of that which has already been established. But we're really not them. We're really not. We're something that has drifted away from that, but we don't have a clear identity yet until the next wave, again, emerges and is distinct again.

So you fall into this valley of the difference. So you might have traits that sort of fit across both. They try to explain this because you'll see this in the literature, you'll see exenials. You will see the Oregon Trail generation. You, another one I just heard recently, the Jones generation. You're Jonesing. So in that sense, you fall outside of that.

I used to call myself a disco boomer because I was born later than the first wave because I didn't get all the aspects of that, but I fell under the auspices again of what I'm considered to be. So that's why this washes into the next.

Elise Holtzman: I like the idea of the wave. That makes a lot more sense because to your point, in the boomer generation, someone who's born in 1946 and someone who's born in 1964 are completely different.

Chris DeSantis: Completely different, completely different.

Elise Holtzman: So it's helpful information, but it's not obviously dispositive. So you can't look at somebody and say, "Well, this is how you think, because this is the generation you're in." We know that, but we tend to do it anyway, as you point out in the very beginning, because we need to bucket people to understand them better.

Chris DeSantis: Yes, yes. By the way, this is where peers come into play. There's an expectation that you align with your peer group, your cohort group. So our group has to be like others in the group. There's a book called Social that I thought was very interesting about this idea.

"I'm not necessarily who I think I am. To some degree, I'm who I think you think I am." So the people that know you feed into the perception of who they think you are that reinforces who you think you should be. So we do that.

So the peer group, sort of the cohort group, because you usually hang around with people your age more than not. So that sort of influences as well, and that creates the monolithic block or the perception of a block. If you fall outside of it, you are seen as an anomaly. "Like, what's wrong with you?"

Elise Holtzman: Well, that's what I was going to say is that, you know, and especially if you're talking to a group—but in my case, for example, if I'm talking to a group of Gen Xers, and they're 10 years younger than I am, and they're talking about all the stuff and I don't relate to it—I say, "Well, that's not how I am at all," you are different, you are seen as different. So yeah, this is really interesting stuff.

Chris DeSantis: Yeah, I think people force you to want to fit in, or, and if you don't, then, you know, there's something off.

Elise Holtzman: Right, there's something weird about you.

Chris DeSantis: Right, which is terrible.

Elise Holtzman: Well, if you grew up in a hippie generation and you were somebody who was very straight-laced and you were following the rules and you were kind of a goody two-shoes, that was weird.

Chris DeSantis: Yeah. Well, and this is to the point of this, is that every generation is diffused and diverse. When you generalize, you're generalizing some of the normative behavior. What is normative? What is acceptable as the norm?

Not because there's variety in every generation, intergenerational differences are something, but there's also intra-generational differences. There is not a millennial I have met who is over 35 who doesn't say, "I'm not like those millennials, the young ones. I'm not like anything like that." You see what I'm saying?

We do that. We say, "I am separate from that." But when you're outside of that generation, I just see them as young people. I don't make the nuanced decisions around, "Well, this one's this way or that one's this way." I just see the group, because that's what I take in.

Elise Holtzman: I think that, you know, as you mentioned, this is what we do. These are social constructs. So it's useful information.

Chris DeSantis: Yes. But to your point, the only thing that's really true is what's true about you. The rest, as you alluded to, is fodder for the conversation, is, "This is what I heard. What's true about you relative to that?" So it sort of ignites the exchange.

Elise Holtzman: I like that. We can use that to start the conversation. It's a great place for a starting point, but it's only the starting point.

Chris DeSantis: Exactly. It's not the judgment you're making. It's the starting point of trying to understand who they are, and then you'll judge them.

Elise Holtzman: It's almost like generational differences should be taught to people when they're younger and when they're older, because it's not like this is going to stop, right? It's not like we're teaching this stuff now, and that 300 years from now, nobody's going to have this problem.

The way you're talking about how we're shaped, every generation has its different—you know, my kids were maybe six and three or five and two when the World Trade Center came down. And so their entire lives, they don't remember a time when you could just walk into the airport and get on a plane, right? So their entire life has been shaped very differently. You talked about that early on. So every generation needs this, but we don't tend to talk about it very much.

Chris DeSantis: Well, I think it's also because it's associated with age. And so we don't always get into age. I don't know if age is a category, although ageism is an ugly thing, but I don't know if we talk about that.

But I view generational things not so much as just the only topic, but rather, to your point about teaching people to reach across difference. You see, I think generational differences are a gateway issue to diversity. It's the easiest difference to talk about. Differences between men and women become a little more robust in that sense. But if you learn—to your point again—if you learn to talk about difference reasonably, you learn to understand.

This is what you do in your profession when you're coaching people. You're saying, "Okay, well, what's going on here?" That's a super way. Questioning helps.

Elise Holtzman: I think that's a good thing for everybody to remember. Chris, as we start to wind down our time together today, I want to ask you the same question that I ask all of my guests at the end of the show. There's a phenomenon called the curse of knowledge, where experts sometimes forget that what is so obvious and natural to them is not at all obvious to others. When it comes to navigating these generational frictions at work, what's a principle or piece of advice that may seem super obvious to you, but is really important for people to hear?

Chris DeSantis: Well, here's the deal. The book was called Why I Find You Irritating. So there is something that somebody is doing across from you, or in some situation, that is irritating you because it's not what you would do.

So my advice is very simply this: that person, they're working there, you're working there, our first assumption should be, that's a rational human being. So why would a rational human being behave the way they just did?

And so what that requires you to do is get outside of yourself in terms of your own self, and step into the shoe of another and say, "What might cause a person to behave that way that is totally rational to their worldview?" So it really boils down to the benefit of the doubt and saying, maybe I'm the one in this situation that's being irrational because I'm viewing the world in a little different way than it should be viewed. So I would say, think rational.

Elise Holtzman: I certainly hope that people take your advice, Chris. I think it would make the workplace a lot more easy to navigate for people of any age and stage. So thank you so much for being here. I always love talking to you. I always learn something new. You know, I might have to have you back someday to talk about this topic.

Chris DeSantis: I would love to be back.

Elise Holtzman: Thank you for tuning in. If you've enjoyed today's show, please subscribe, rate, and review us at Apple Podcasts, Spotify, or your favorite podcast app. In the meantime, be bold, take action, and make things happen. We'll see you next time.