Navigating Generational Friction at Work With Chris DeSantis

Hello, my friend, and welcome to another exciting episode of Negotiate Anything. Thanks for joining us today. With over 10 million downloads and listeners from more than 180 different countries, it's dedicated listeners just like you who have made Negotiate Anything the number one negotiation podcast in the world. I'm your host, Kwame Christian. I'm a business lawyer, mediator, author, and the proud CEO of the American Negotiation Institute. Now, before we get into today's insightful conversation, I have a golden opportunity for those of you who recognize the power of negotiation in your professional lives. Have you ever found yourself wishing that you could navigate those high stakes conversations with more confidence? Or perhaps you're looking to empower your team with the art of persuasion and conflict resolution? At the American Negotiation Institute, we've crafted specialized keynotes and workshops tailored for those very needs. We've transformed the negotiation skills of professionals worldwide, and we're eager to do the same for you. We believe the best things in life are on the other side of difficult conversations. And our goal is to help you improve your lives and the lives of those around you, one difficult conversation at a time. Don't let another challenging conversation leave you second guessing. Click the link in the description to discover how we can help you find confidence in conflict, negotiate better deals, and have stronger relationships. Because in the world of business, every conversation counts. And now, without further ado, let's jump into the interview.

Chris, thanks for joining us today.

Well, thanks for having me. I really appreciate being here.

It's my pleasure, man. So how would you get us started? By telling us a little bit about yourself or what you do.

Yes. Yes. Again, my name is Chris DeSantis, and what I do is I'm an organizational behavior consultant. And what that really means is I work inside typically professional services firms because those are the people that find me on anything related to how they work together. So performance issues. I address things like building relationships, mentoring, teaming, and dealing with generational differences, which we'll be talking about, or even pitching and presenting. So I look for issues that affect them, and I try to find solutions that are amenable to them.

This is really cool, Fascinating, fascinating work. You have a podcast?

Yes, I do. I have a podcast with my good friend Mary Abhije, and she wrote the book Managing up, and it's a podcast called Cubicle Confidential. If you have a question of me as a consequence of my little time on this today, feel free to write in and we'll answer those questions. We take those once a week.

That's awesome. So everybody will. I'll Put links to Chris's website, his LinkedIn, and of course, Cubicle Confidential as well in the description of this episode. And I'm pumped about this, Chris, because you, you brought up a number of things that have come up a lot with the clients that we work with. And I've seen a lot on the, on LinkedIn whispers about this too. And it's the intergenerational workplace. How do we manage that? How do we negotiate between generations? What are the different styles of each generation? Those type of things. But also the new hybr workplace, and how the generational divides impact how we move forward with largely hybrid workplaces. So let's just start off with what you've experienced because you've been, you know, on the front lines of this. So when, when your clients come and talk to you about the intergenerational nature of work right now, what are some of the challenges that you've seen?

Well, if I can back this up a little bit, because one of the challenges of talking about intergenerational differences is the. You have to make the distinction between what is the perception of difference and what is the reality of difference. And so I think we often confuse the two because the press sort of, I will say, amplifies that of the worst traits of each generation. And so we think that is must be true of them. And so, and what happens is, and this is sort of the salience effect. What happens is we see some of that, and then we presume it must be true of all of them. And so part of when I talk to people isn't just to make the assumption that I'm right about a generational difference. It is to elevate the notion that we have to determine what is true and what is manufactured in our differences. Even though I still believe there are differences between us, I do not think they are of the magnitude as presented often in the press. So I just want to make, because I like to defend the young, because I think the young get a lot of grief.

We appreciate that.

Exactly. Exactly.

This, this, I mean, listeners, just, just a little aside, when you're asking people questions, sometimes it's not just the answers that they give, but it's also how they take the answer. And then sometimes when they reject their question and give you a better question and then answer that question like that shows a level of expertise that, that you need to recognize, because, Chris, this is great.

This is great. Thank you.

Because what you recognize, you've helped us to recognize is that a lot of times we're starting the Conversation in the wrong place.

Yes.

Right. And so let's go deeper into this because this is really interesting because we're seeing almost how this machine is made, this bias making machine, and the different biases that are at play. Because as you're describing this, we have the bias that where we're seeing this pattern recognition, the media wants to amplify the worst of these types of situations. So we see it, see it, see it, we're seeing that pattern recognition, this is kind of attributed or similar to like the availability heuristic. Now it's easier for me, for me to identify and see that problem. So then it makes it more salient and easier for me to see in the real world. And then everything else kind of feeds into confirmation bias where we say this is the conclusion. And now I'm going to cherry pick the information to just continue to bolster that conclusion instead of seeing things objectively. So we need to really go, go very deep here and talk about more about what is manufactured and what is real. And so where should we even start with that?

Well, let me start with the generational lens. Your point is very interesting. Well, first of all, everything you said is very interesting and I can talk to that. But this notion of the assumptions that we have of others and a further notion that we are objective in our views, we are not objective. We are subjective relative to how the experiences we had growing up shape our views. Now, to your point about confirmation bias, we think we're right. What do we do? We surround ourselves with other people who already agree with us. And this is called conversational coordination. Look, if you already agree with me, I don't have to explain the young because you already think the young are problematic. So now I can get right into why they're problematic. What we should be doing is crossing over the difference and saying, look, there's a rational human being in front of me who is doing something that I wouldn't do in that circumstance. So maybe I should ask them why they're doing it that way relative than accusing them of doing it the wrong way or making a judgment relative to that. So the point of this is that every view is subjective and bias comes from generalizing. We are humans, of course we have to generalize. We have to get through the day. And so I use the work of Noam Chomsky. I hope I'm not rattling on. Noam Chomsky has a sort of, I like this process for, from generalization. He goes with deletions. Deletions are things we do when we the more we're alike, the more. The less I notice about you. So I delete all that. It's the exception that I remember, and I remember exceptions. I delete the familiar, remember the exceptions. And then when I remember it, it's a distortion of the memory because the things that are exceptional are not necessarily the normative things about us, but the exception to what is normal. Eventually, though, I accumulate enough of those exceptions, as it were, distortions, and they become the generalization that I have. And then what happens over time? And this is where bias comes in. Think of it like sediment settling into the mind, and then it goes below the consciousness of mind. And then when it reaches that level, it reaches the level of implicit bias. I don't even know. I don't even know I'm doing this. So this is a layered thing, and we do it to. We do it in so many ways, but I think we do it particularly across age because it's a discernible difference in what we notice. I know that went on and on.

Wow.

It was great. I mean, we have barely started, and you see all these notes I've taken. This is incredible, Chris. This is great.

I think.

Where do we even start? Let's go back to conversational coordination, because that is a really fascinating topic. So let me do a brief synopsis, and then I want to go a bit deeper into what you said about Noam Chomsky, because I think that you've really articulated well just how these things grow. It could be something small, and then it becomes something big that is a part of us that we don't even realize, but a major part of us that is steering the ship and having an impact that we don't even fully understand without reflection. So conversational coordination. So we talk to people who agree with us, and then we start off with those shared assumptions, and we just kind of reinforce what it is that we both agree is real without challenging it. Can you go a little bit deeper and tell us more about the ramifications of conversational coordination?

Well, the ramifications of conversational coordination are such that it anchors our assumptions. And when you anchor assumptions, you're less likely then down to question, because you are now you have to go against the normative group who agrees with you. So nobody likes to be the odd man out in their own tribe, as it were. So when you are surrounded by. Let's take the example of this is a professional services firm, all of these are partners, and all of these partners agree that there is some problem with the young and Then you all of a sudden start to state, well, maybe it's us now, you stand out among them by virtue of that. But now the point would be, though, you could argue the difference here. Yes, maybe you're right. But we don't tend to step out when we are already accepted. And I think that's part of the challenge with this is we balkanize our views and when. So we stay within the bubble of our views. Because again, when you step out of your view, you step into, I think, the potential of conflict, as you well know, more than I do. And people are very conflict adverse. So it's better to just go along with what you already think and just find people who already think. It's. It's a shame.

Yeah, it is. And it's a, it's a great example of the comfort zone too, on a number of different levels. Because we don't want to. We're naturally going to avoid discomfort in most situations and social discomfort and the fear of isolation, like that's one of the most significant pains that we can experience.

Right? Absolutely.

Makes a lot of sense.

And so what advice would you have.

For those people who are listening to the podcast? And then they could say, as a group within my organization, I can see this conversational coordination happening. I can see the momentum of groupthink moving in one direction. I want to still feel close to my colleagues, but at the same time I want to challenge them. So how can people challenge the status quo and that conversational coordination that's happening without standing out too much?

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Well, this is an interesting point because I think there's great complexity to this. I just finished a couple books. I really enjoyed Social and the Enigma of Reason and the Blank Slate. And really these books all really lead down the path that we need each other. We are not who we are. We are who we are as a consequence of who we engage with. So it's not just Us alone as an entity, we are genetically predisposed to be social. And so when we think about this as the confirmation bias, let's use that as a perfect example. Everyone walks in the room thinking they are right. I have no problem with that thought. But what we do is when we work with other people, they start to surface how we could be wrong or how other views might be equally interesting in which we take in. That's how we learn and that's how we evolve. So I think arguing is healthy. That's the point. We should sort of understand that we have different perspectives. We should honor the perspectives, and then we should dig deeper into saying, why do you have that? And then we make our case. Each of us should be making our case. This goes back to the notion of diversity. And there's a lovely book on this, the Diversity Bonus. And the idea here is the broader your perspective is relative to having people around you who are diverse. Not just an identity diversion, but diversity. But also in all the things about us that make us diverse in terms of how we think. The less blind spots that we are possessed as a collective and the better the ideas that come forth as a consequence of that. You see, we are. It's just the admission that we need each other and we should be gracious about the need.

Yeah. Wow.

This is.

This is incredible. This is really incredible. And it makes so much sense. Right, because it's going to be tough for us to stand up and stand out and have these conversations. But like you said, it's a good thing. We need that type of friction. I think of it in terms of constructive conflict. It can be either constructive or destructive. And one of the things we always talk about is like, conflict is an opportunity. If you have the skills and you have the confidence, you can turn these situations of conflict into opportunities to learn, grow, and connect. But you have to have the mindset and the skills to put it into action.

Yes. And I think you're the authority here because negotiation is its own unique realm of expertise. And so when you're dealing in that realm of what you're doing, if you get the more positional you get, I think the more dug in you get into particular positions relative to the other. And my point about generational differences is that each of us brings something interesting to the table. But I think what we have to do is understand what they are bringing to the table that is distinctive from myself before we enter into some kind of an exchange. Because we are in a situation of asymmetric power. The people my age group Boomers are probably in charge. And so with that, they are assuming that you are a younger version of themselves, when in fact they're not recognizing that you are a unique entity unto yourself, you see? So they imagine they're doing this for you, and where the other party feels they're doing this to them. And so in that sense, we're not recognizing the difference. It's like, you know, what's interesting in the paradox of this is if they are parents, they recognize the uniqueness of their child, but if they are working with them, they assume this is just a younger version of who I am. You follow? And so we have a disconnect. I'll tell you, poor young people come into the workplace thinking, I'll be engaged in the way that the adults have always engaged me. And then they come into this hierarchical environment where they are not engaged, but rather told what to do.

This is fascinating. This is fascinating, Chris, for. For a number of reasons, because like you said, it speaks back to the mindset. Conflict is an opportunity. All right? We both have different things, different tools, different mindsets, different perspectives that we're bringing to the table. And this diversity of thought is beneficial to the organization as a whole. So instead of looking at this as a liability, we can look at this as an opportunity to learn from each other and share together. But it comes down to the mindset. And this is so fascinating, because, listeners, I don't want you to miss this because what you said, and correct me if I'm wrong on this, Chris, you said that if there is somebody in the boomer age range who sees somebody who is, let's say, a millennial, let's say they're 30, right? And they can look at the person as a child. If it is their son, they could see the person has value. But then let's say there's. That same person is within the workplace, there's no relation. They're just an employee. Now, we see the generational divide as a problem. So it comes down to your perspective, right? So how. What kind of mindset shift could the leaders within a company have to start to look at the generational differences as an asset rather than a liability?

Yes. Well, the mindset isn't that difficult. Because if you look at it this way, think of it as a parenting model, that in the world I lived in, a world of what's called permissive authoritarianism, that meant my parents were in charge and I had to do what they wanted me to do, there was no real dialogue. Now, if we jump to the millennial crowd. They are living in a world as what's called concerted cultivation. That means there's a concerted effort on the part of the parents to cultivate the uniqueness of our offspring, of our children. This is more of a dialogue model. You see, mine was a world of tell, and they are living in a world of dialogues. My point would be very simply, if you just employ the dialogue model that you use in the home, in the office, you will have a better outcome because it's more comfortable for them to engage that way anyway. We confuse their assertion with us with insubordination or challenge, and that is not necessarily what they're doing. They're looking for explanation. Yet when we entered the workforce, we were part of the the permissive authoritarianism, from the parental model to the work model. So we never dialogued with our bosses. We just did what they were told us to do. So that's a congruent experience where the young are having a very incongruent experience.

Wow, this is fascinating because essentially, if you were raised in a household, again, generalizing here, of course, if you're raised in a household where you and people in your age range had concerted cultivation, you had that dialogue model. That's the relationship you had with your parents, oftentimes, maybe the relationship you had with your professors, if you were in school, something a little bit more back and forth. Then you get into the workplace, and then it feels a bit more like command control, where we are just saying, okay, hey, I want to have a conversation, and then it's shut down.

Exactly.

And so they feel belittled and unappreciated and controlled. They feel as though they're lacking autonomy and agency. But then at the same time, the leaders are thinking, are feeling a little bit negatively about the interaction. Like, why would you even want to go back and forth with me? This is disrespectful. It's insubordination the way we used to do it. You just got in line. And so that it's that incongruence that's causing a lot of the conflict.

It's exactly right. I will make one caveat here about the young, because I do not want everyone to think that this entire generation is this way. There's a socioeconomic constraint to this. If you are in the middle classes and above, you experience concerted cultivation, or you didn't. If you are children, possibly of immigrants, who have a different, I will say, trajectory in terms of how they were raised. The second, if you were from the poorer end of the spectrum, you did not experience this. You experienced more of a deferential model. And so in that sense, which is very interesting, because how this plays out in the workplace is the young in the middle class and above are seen as more confident than the young in a lower socioeconomic class because they appear more deferential and they confuse deference with somehow lack of confidence, which is not the case at all. And so that gets in the way. So I just want to bring that up because I don't want everyone to think this is a sweeping group in terms of all young people, but rather confined to the middle classes and above.

We're peeling back the onion here, Chris. This is great. And so let's take a step back and talk a bit more in general. So, listeners, what I want you to realize is how important it is to get deeper knowledge on the differences between the generations in general, but also the differences within generations as well. Because the deeper your understanding, the more readily you will be able to identify these interesting cultural nuances. Because you're absolutely right, the socioeconomic status of the individual in question, whether they are born in America or a first generation American like I am and a lot of my friends are, or an immigrant, that's going to have an impact. So you still might be within a specific age range, but those other cultural considerations are going to have an impact. And so, and I want you to get your thoughts on this is because what we're doing is we're be. By learning more, we're putting ourselves in a position where we can come up with better hypotheses, better rebuttable assumptions about where people are, what they think, how they believe. But then we're flexible and nimble enough to recognize. I'm coming into this with humility. I might not know this is a hypothesis. I might be wrong and I might need to adjust.

That is so good. That's exactly right. In fact, one of the things I tell people every time I speak is when I'm done, I say the same thing. I say, look, the only truth here, the only truth is what is true about you and your experiences. That's our only known. Everything else here is conjecture. It's a theory, it's the possibility. But you cannot surface that until you have a dialogue with the other. And so in a dialogue, always start out with yourself because that gives us implicit reciprocity. That means that it's implied that they may share something, but never insist. People should sort of share as they feel comfortable sharing who they are. And that's what I always suggest in this. I will say one other thing, just as an aside, because this fits who, what you do is that I believe our young in terms of these groups that I'm discussing in terms of the middle class and above. They are probably our best negotiators. They will get because they've been negotiating with you as parents since they were four. Since they were four. So. Yes, yes.

Oh, that's so fascinating. Okay, let's talk about another element of the workplace, the modern workplace that really will have an impact on the different generations in a different way is the hybrid workplace that's essentially coming out as the norm. What are some of the patterns that you're seeing?

Well, here's one of the things. The young feel vindicated because one of the traits of what I have found or what I have come to believe about the young, when I say the young, the young is a very large statement. But one of the traits about them is they are time and place agnostic. What that simply means is their rhythm is not necessarily 8 to 5, or their rhythm might be, you know, midnight to 8 in the morning because they live in a 24 hour window and they're thinking, well, it'll get done when it gets done if it needs to be done, done. So they're not as confined to the construct. And so with the pandemic, the pandemic has vindicated in the sense that, look, people worked remotely and companies did not collapse. And so in that sense, we have launched ourselves five years into the future. And now there's an anchoring or an expectation by the young of greater flexibility. And yet the habits of people my age to a great degree want to return us to the older model because the older model was successful as how we saw success happen. We are not wrong and they are not wrong. But the point is, we have to find out what is the new middle ground relative to this in terms of how will we create a feeling of belonging in a space that has more flexibility about it? We're still experimenting. This is called mimic theory, where humans look for other models of other people doing it. But there's really no model here yet. Yet, in fact, the only models out there suffer from what's called the correspondence problem. We look at remote only companies. Well, they were designed that way. They've always. They were designed that way. So, so to say, oh, we can be like them. Well, no, you can't. That, that's not. No, you can't. You, you are who you are. And how do we get past, you know, this Sort of this. This sea change among us. So that is experimentation is my advice to anyone.

This is great. Yeah, it makes a lot of sense. And it's very interesting, too, because even when we think about individuals, we could replace individuals with generations and this type of thing, because we want to be right, and we always cherry pick the information that shows that we're right. So the younger generation is saying, hey, look, everybody went virtual. We didn't. The company's still here, so clearly it works. And then the older generation is saying, we have these institutional habits, and it got us to this point. We had a blip in the radar. However you want to describe it, a global pandemic is a hell of a blip.

Right? No, exactly.

But people are wanting to get back to the way that things were, because that wasn't fundamentally broken either. And so depending on what information that you want to use, you can come up with a coherent argument for it. And again, that's why we have to remember, like, we cannot just rely on data to win the day. At the end of the day, everybody has to come to the table and have these difficult conversations and to figure out what is right for us. Because like you said, Chris, every company has its own set of circumstances, its own culture, its own makeup and everything like that. Right. So we can be inspired by other people. We might be triggered by a little bit of memetic desire. Right, Right. But at the end of the day, we have to experiment and figure out what works for us. And that's going to require taking the risk of trying something new, but at the same time, communicating throughout the process so we can figure out what the path forward should be.

Exactly right. And by the way, to your point, I could argue either sides of this and probably win the argument because I'm informed, but I would lose the battle, because if one side wins over the other, you lose what we have the capability to do, and that is reinvent ourselves. That has mutual advantage to all concerned, you see? So to your point, we should just keep trying different things, and each time something fails. That's a data point of interest, what didn't work here. So don't do that. Just try something else. Right, exactly. But see, we blame the person for failing as opposed to the circumstance of the failure. And then we say it's an issue of their judgment. And look, judgment is based. Judgment is often judged on the outcome and not the process of judging, which is another mistake. So what happens is these failed experiments get squashed further because people who do want to take a risk are further pushed away if they don't, if they take a risk and it doesn't pan out. You follow?

Absolutely. Yeah. I mean, I think that's an example of the fundamental attribution error in action.

Right.

So if I make a judgment call and I'm wrong, it's because I. The circumstances led me to believe something that led me in the wrong direction. If you make a judgment call and you're wrong, you're a bad person.

Exactly.

You're a boomer or a millennial. You don't understand anything. Right. Whatever the negative personal attribution is, we'll go for that instead of giving them the benefit of the doubt and describing the legitimate circumstances that led them to that decision.

Exactly. I'll give you a perfect example of a generational divide. So here's what the young get accused of. You've heard this. They're not very loyal. They're not very loyal. I love that phrase. I don't agree with that at all, of course, but the perception of loyalty is defined by, well, first of all by this people in charge. And their of loyalty is what will you do to sacrifice on my behalf? What sacrifices you make on my behalf? You see. And so but they, they who have made it to the tops of organizations come from what I call the covenant. And the covenant was if you work hard, you're pretty much guaranteed a job for life. That used to be the model. The model was put up with the grief. And so for instance, I had a bad boss. I'm going to outweigh you. I'll get another bad boss. I'll outweigh them. I'll get another one. And finally I get to be the bad boss. The point would be, is I keep moving upwards through this process. Right now in the world today is this young person who might be attracted to the brand of the organization says, I'm having a really bad experience with this boss that is the organization. And so I will leave now. If they treated me really well and I get engaged and they leveraging my skills and all the things that really bring the best out in me, I will stay with them. That's loyalty. So loyalty has moved from the macro of the organization to the micro of the experience. And yet we blame them for not being as loyal as we were. We broke the promise. We broke the promise of the covenant. So this is just a transaction. And as long as the transaction is viable, I will continue on with it. Wow.

Oh my gosh. This is great, Chris. And this is one of those, those episodes where I'M like, yeah, we're probably. I'm going to need to bring you back on because there's so many more things that I want to explore here, and you've given us a lot to consider. Let me ask you this final question.

Sure.

Let's say if there's an organization who's listening to this and they're saying, okay, Chris, I'm realizing there's some unresolved issues that we need to address, how would you say that they should start having these conversations?

Well, it's a good question because this is a change issue. And my theory on this would be get together a diverse group of the people that other people listen to to. And not a large group, just a few of the most influential people at the firm. Not the people with the highest positions, but rather across the layers, who other people believe, and then pose the question about what do you want to change or make the organization better? They then take in all that information because they are people other people will talk to. They then I will say, filter that information, and then they bring the message back to senior management, because this is your trust link. These people you can trust and they are trusted, and they are taking this in and they're screening out what I will call the peripheral noise and getting into the meat of what we actually can do here. And then you have some viable suggestions. So now everyone feels they can trust the process.

I love that. Chris, this is great. I appreciate this. And before you go, let the listeners know about you, your company, your podcast, and how they can get in touch.

Yes, again, my podcast is called. Our podcast is called Cubicle Confidential with Mary Abhijay. My website is cpdesantis.com and the book that I've written is called why I find you'd Navigating Generational Friction at Work. And you can get that on Amazon or Barnes and Noble or Books A Million. So thank you for allowing me to share that, by the way.

Yes, no, my pleasure, Chris. This was great. Thanks again for joining us.

You're welcome. Thank you. Thank you all for listening.

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