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How to Navigate Generational Friction In the Workplace with Chris De Santis

How to Navigate Generational Friction In the Workplace with Chris De Santis
How to Navigate Generational Friction In the Workplace with Chris De Santis

You’ve probably heard the stereotypes of different generations in the workplace, including millennials just wanting trophies and more seasoned workers being averse to technology. These are the signs of some of the generational friction that exists in (and out) of the workplace. These challenges can be mitigated through a better understanding of the narrative identity each generation has of work (and the world) and why these narratives exist.

My guest Chris De Santis is a speaker, podcaster, and consultant with over 38 years of experience in training and development. He’s also an expert in generational differences in the workplace. And he joined me to discuss the impact of generational theory on his work, which he wrote about in his humorously titled book, Why I Find You Irritating: Navigating Generational Friction at Work.

In this episode of the Branding Room Only podcast, you’ll learn about how the upbringing of each generation, and the traits they take on as a result, affect workplace dynamics. We’ll dig into the importance of understanding and adapting communication styles across different age groups, the shift towards a new career progression model, the role of technology in the workplace, and so much more!



Available on Apple Podcasts

Available on Spotify

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1:03 – Personal branding versus reputation and how you are the actor, agent, and author of your life

4:43 – The ability to authentically align with certain characteristic traits for a short while and a fair point about authenticity

8:00 – Chris’ upbringing, career trajectory, and the benefits he sees in having a background in improv

18:15 – One differentiating factor influencing the four current generations in the workplace and perceptual differences that cause friction between them

26:58 – The mistake being made in the workplace with millennials (and Gen Z) and what the emerging adult is looking for in their career

36:47 – How generations tend to be talked about differently when it comes to technology and the evolving workplace (and its dynamics)

48:37 – The one thing Chris will never do to hurt his brand and the Branding Room Only attribute that makes him unique

Connect With Chris De Santis

Chris De Santis is an independent organizational behavior practitioner, speaker, podcast host of Cubicle Confidential, and now an author of “Why I Find You Irritating: Navigating Generational Friction at Work.” He has over thirty-five years of experience working with clients in professional services firms, technology companies, and financial services, and often, based on their sponsorship, working with their clients, both domestically and internationally. While he has been speaking on behalf of embracing generational diversity for past fifteen years, this is his first book on the topic. He has his undergraduate degree in business from the University of Notre Dame, his master’s degree in business from the University of Denver and a master’s in organization development from Loyola University.  He lives in a quiet corner in the Lincoln Park neighborhood of Chicago.

Chris De Santis | LinkedIn

Cubicle Confidential

Why I Find You Irritating by Chris De Santis

Mentioned In How to Navigate Generational Friction In the Workplace with Chris De Santis

The Art and Science of Personality Development by Dan McAdams 

2024 Intention and Goal Setting Webinar

Improvisation for the Theater by Viola Spolin 

Impro: Improvisation and the Theater by Keith Johnstone 

Generations: The History of America’s Future, 1584 to 2069 by William Strauss and Neil Howe

Leadership Council on Legal Diversity (LCLD)

“The secret to career success may well be off to the side” | The Economist (paywall)

“How to Practice the Art of Managing Up and Navigating Feedback with Mary Abbajay”

Sponsor for this episode

This episode is brought to you by PGE Consulting Group LLC.

PGE Consulting Group LLC is dedicated to providing a practical hybrid of professional development training and diversity solutions. From speaking to consulting to programming and more, all services and resources are carefully tailored for each partner. Paula Edgar’s distinct expertise helps engage attendees and create lasting change for her clients.

To learn more about Paula and her services, go to or contact her at [email protected], and follow Paula Edgar and the PGE Consulting Group LLC on LinkedIn.

Paula Edgar: Welcome to The Branding Room Only Podcast where we share career stories, strategies, and lessons learned on how industry leaders and influencers have built their personal brands. Now, let’s get started with the show.

Hi everybody, it’s Paula Edgar, your host of Branding Room Only, and I am super excited to have my guest today who is going to wow you with his fabulousness, like he wowed me when I first met him, and each time since. Introducing Chris De Santis, who is a speaker, podcaster, and author with over 38 years of experience.

His new book, Why I Find You Irritating: Navigating Generational Friction at Work, is among many topics in which he is conversant. He has a BA from the University of Notre Dame, an MBA from the University of Denver, and an MA in organizational development from Loyola University. He lives in the quiet corner in Lincoln Park neighborhood of Chicago. I’m in Brooklyn and we are going to talk.

All of my listeners, you know that we usually start with a similar set of questions, but we’re going to do a little bit different today, which I think is going to be indicative of our conversation generally because I’m going to define personal branding, and then we’re going to talk about what that means. I think that’ll help me where I want to get into.

Chris, for me, personal branding is like your magic. It is what your skills, your experiences, the way you deliver who you are, and what you’ve done. Like a can of Coca-Cola is what you can expect each time because there’s consistency, because there is strategy and it all gives you the promise of the person.

When we’ve got on, we first started talking a little bit about how that can differentiate from what your reputation is. So I think the difference in reputation and personal branding is that your reputation is what it is because it’s what people are saying about you, what you’ve done. Your brand is that, plus how you want to shape it as you go forward. It’s the strategy of those things. What do you take from that in terms of my definition and how I laid it out?

Chris De Santis: Well, I like your definition. It clarifies for me because when I was coming on the call, I was thinking, “Okay, I don’t know how she sees brand. So I might be talking about one thing and she’s actually referring to another.”

So I didn’t want to come out here, “Oh, no,” but having said what you’ve said, what I’d like about it, I’d like to build on that a little bit, because I was reading a very interesting book by a man named Dan McAdams. He’s a professor at Northwestern, and he aligns with you in the sense that his book is called The Art and Science of Personality. It’s layered. We are layered.

His point is, or his many points, one of them is, that there are dispositional traits that we all possess, meaning that you are extroverted. By the way, if anyone’s seen Paula present, which you should see, which you should see, you will see an example of a very extroverted, I will say agreeable, conscientious individual. These are some of the traits of dispositional traits.

Low on neuroticism, you’re not neurotic at all, at least I don’t see that, and you’re open to experience because you’re willing to try things. All of those things, those are your traits.

Then there’s the next layer of you, as he would call them and as you would allude to, is what are your goals, dreams, and desires? Who do you wish to be? What do you wish to do in all of that?

Where it gets to use in particular, and this is the third level of this, is what is your story? What is the narrative of who you are? He calls these layers the actor, the agent, and the author.

Where we are with this is the authoring of the story that is really the compilation of the trace that we embrace, and also the desires that we have in terms of the goals we wish to set. I think we’re on the same page. It’s the articulation of this because my problem with branding to some degree is it has a showman’s quality to it, but does it have the weight behind it? You see what I’m saying?

Paula Edgar: Yes, yes. I think that, first of all, I’m really glad that you explained that because number one, I have to get that book.

Chris De Santis: That’s good.

Paula Edgar: But also because for me, a personal brand is not truly a brand unless it’s authentic, unless it has the things to back it up. So, superficial brands, I don’t live in those places either. I think they truly tend not to be consistent either. So, it loses some of that weight. I love that fleshing out.

To that end then, how would you describe yourself in the framework that you just laid out from–

Chris De Santis: Yeah, what’s my story?

Paula Edgar: Yeah, what is yours? Yes.

Chris De Santis: Yeah, what’s my story? Well, my story is a little different than yours in the sense that my traits are not your traits because I’ve seen you in action. You got a real presence about you. I can put on presence for a little while. Don’t ask me for more than an hour.

You sort of say, “What would the audience want?” You have to give the audience what they want in terms of they have expectations of what you’re going to say, but they also have an interest in how you convey it. You have to be amenable to what they respond to.

I’ve noticed that some of the things they respond to are energy, are joy. In that sense, I picked up on those, again, they’re aligned with who I am, but they’re not necessarily my 24/7 life, but I can certainly do that.

I think part of my brand or part of the person that I am tries to reflect back to them what I believe in a way that is palatable for them to hear it. That’s part of who we are.

To your point about authentic, this is the other thing, authentic is a very interesting thing. I want people to be authentic in a pro-social manner. I think we get confused here.

Authentic to some people means “I can behave any way I want because that’s the way I behave, because that’s who I am.” I said, “Well, you could be an asshole, but that’s not who I want to be around.” You see what I’m saying? Authenticity is lovely as long as you are being pro-social in terms of how you manifest it.

Paula Edgar: Absolutely. I heard a general counsel say once at a panel, “Authenticity is not keeping it real. It is aligning with the nuance that’s required from the situation,” to your point about being pro-social and also being who you are.

Chris De Santis: There are three layers to what your point is. There’s another book on this, but it’s called Authenticity. But it wasn’t a great book. But I liked what they said. There were three things. One is know yourself. You already said it already. Be yourself. You already said that already, and own yourself.

Own yourself is the idea that “Look, you are not perfect. You are not perfect and so we have to own what we are, who we are as opposed to pretend we’re not something we are.”

Paula Edgar: Yes, and there’s some accountability in that place too.

Chris De Santis: Yeah, right, right, right, right.

Paula Edgar: I love that kind of layering of it too because so often the conversation on authenticity has some lacking authenticity, but it’s very superficial and you don’t get into the nuances of what it actually means. So I’m glad that our conversation is going that way.

Chris De Santis: Yeah, because I think that’s so important because you got to say who are you. By the way, who you are is not universal in how it will work with everyone. I mean, I accept that about myself. I don’t play well in all circles. But I try to understand where I can be most helpful. In that sense, I know that I’m not universally loved, but I know that I can help in certain circumstances, if that makes sense.

Paula Edgar: Yes, I modulate my communication for whom I’m interacting with.

Chris De Santis: Oh, yeah, I love that phrase.

Paula Edgar: That’s a best practice that everybody should employ.

Chris De Santis: I agree, right. Exactly right. Exactly right.

Paula Edgar: Tell me, where did you grow up and how do you think that shaped who you are now?

Chris De Santis: Yeah, yeah, that’s, again, I grew up in a very small town in Western Pennsylvania, so I came from a place called Sharpsville, 6,000 people, now it’s 6,120, and it’s very small in the sense that it was clearly a steel town when I was there, it is no longer a steel town because steel faded, but my father was a dentist there.

It was a nice life. A lot of cousins, I had 26 cousins so I knew people around. I moved away when I went to school at Notre Dame. My life started to change rather rapidly as a consequence of that because I would only go back for vacations after that.

But at the same time, I think what it instilled in me is more of a feeling of egalitarianism, meaning that, “Look, there is no great differences between us.” I’m pure middle class, in the sense that, “Look, I would like everyone to be in the middle class.”

I’m not saying that I should take it from you if you’re rich, but I would say to you that being in the middle class says, “Look, we all have something to say.” I respect that. I respect that quality. I’m appreciative of where I sit with that. At the same time, I’m not grandiose in my expectations of things either.

Paula Edgar: So 26 cousins.

Chris De Santis: Yeah. I have a lot of cousins.

Paula Edgar: I know that is a lot in terms of, I think, how it also maybe helped you to have to navigate amongst a lot of people, and different personalities too.

Chris De Santis: Well, when I was young, that was the case. But it wasn’t so bad though. Children who you are related to seem to have a natural affinity in a way. It was so easy with my cousins, whereas school kids were not as easy because you had cliques and all of those things, but family’s family.

Paula Edgar: Yeah, yeah. Well, I guess maybe my family has more cliques than I need. But anyway.

Chris De Santis: Are you from a big family?

Paula Edgar: I wouldn’t call us big, but I have a lot of extensions on my family.

Chris De Santis: Ah, yeah, yeah, yeah.

Paula Edgar: A lot of cousins that aren’t actually cousins, but they’re cousins because that’s how we bring them in. So yes, there were a lot of personalities in my family. I’ll put it that way.

Chris De Santis: Oh, yeah. I could imagine, I could imagine.

Paula Edgar: From Notre Dame, I see you collected a lot of letters.

Chris De Santis: Yes. Then after Notre Dame, I went to Denver to graduate school and that didn’t take very long and then I couldn’t stay in Denver because at the time, in the early 70s was during the oil embargo and the crisis in Denver with an oil town so I couldn’t stay.

I came back to Chicago. I have friends here at Notre Dame, half our graduating class always comes back here. I stayed with friends. I eventually started life here. In fact, being a very shy person at the time, but being funny, I lived in Old Town, which is only two blocks away so I ended up taking classes at Second City, and I became an improv guru.

Eventually, I ended up teaching improvisation because I liked it. I see the utility of it. I still see the utility of it today.

Paula Edgar: That is fascinating because you may not know this but I do have an annual goal-setting session every year, Intention and Goal Setting. My word of the year this year is joy. One of my goals is to take improv and improv class.

Chris De Santis: Oh, you’d be good.

Paula Edgar: I’m so excited about that, that’s fantastic. I love that.

Chris De Santis: Oh, yeah, let’s see, you’re in New York?

Paula Edgar: There’s a bunch of different places, but I’m thinking about this summer in Chicago of going to a class in Chicago, so I might do both.

Chris De Santis: Well, they’re very fun. I’ve always recommended them for a couple of reasons. One is if you’re young, particularly a young person who’s new to an area, you get to meet a lot of people. There’s a lot of people.

It’s almost like its own community. You end up being in an improv class and then you have a little group and then you’re going to these clubs and you’re watching everyone else. That’s all fun by itself.

The other thing is you learn ensemble work. You learn about giving. You learn about making someone else look good. In that sense, this work of the ensemble, I remember years ago, Robin Williams was a performer years ago when I was a young person, he was a young person as well, and he had a bad reputation because he was not a giver, he was a taker on the stage, brilliant individual, but nobody liked to work with him because he wouldn’t share the space. In improv, you learn to share the space because you need your team.

Paula Edgar: Yeah, yes, and.

Chris De Santis: That’s why the whole yes, and thing comes up. I’m telling you, do it.

Paula Edgar: I’m going to, I’ll report back. I’ll report back how it goes.

Chris De Santis: Exactly.

Paula Edgar: I will tell you that somebody who likes control, like myself, I’m nervous about it, but I also think it’ll help me to grow. I do have a mindset. So, yes, and is something I incorporated after someone taught it to me just about they had learned it in improv, but I was like, “I love that for diversity and inclusion work,” for thinking about professional development, like it’s all not being stuck. It’s “Okay, and what else?”

Chris De Santis: Absolutely. There are games you can play. The mother of improv is Viola Spolin. Viola Spolin had a son, I can’t think of his name, but he’s a famous director who then became one of my teachers. She wrote the book Improv. It’s like the Bible of improvisation.

Paula Edgar: Okay. You got all kinds of recommendations. I love this. The show notes, they’re going to be great.

Chris De Santis: I don’t know. But yeah, it’s good. If you’re a teacher, it’s a great book. Because it teaches you how to play the games with kids. But the games are the same games that adults play. Improvisation for the Theater, it’s called. Improv is another book by a man named Johnstone.

Paula Edgar: Okay, so tell me more about your career journey.

Chris De Santis: Okay, so I eventually worked in corporations as anyone did in the ’70s. I ended up in the area of training and development. I fall into that space because it just worked for me. But I kept getting let go because, again, training and development is the canary in the coal mine.

I hate to scare people who are in this profession, but the reality is if there is a contraction, this will be one of the first to be– because where can we cut? Basically, we cut our future is what we do. But anyway, I had had a number of interesting jobs.

I was a director training for the AMA. I was on the HR development group for Brunswick. They were nice gigs. But again, after the third one, I just said that if I can get one client, one client, I’ll give this a go and I got a client.

Paula Edgar: I love it. That all led you to thinking about, I’m guessing, communication, connections within the space, and maybe that’s what the generational piece out of the–

Chris De Santis: Ah, no, the generational piece came 15 years into this.

Paula Edgar: Okay.

Chris De Santis: When I came off, I had to say, “What do I have on offer that they might want to buy?” In the sense that as a contract person, I knew that I didn’t want a job. I wanted to have consulting work so I had to find contracting gigs, which I fell into right away.

My background in improvisation was very helpful because what I learned to do is whenever I was at an interview for one of these training gigs, I would just mimic whoever was the decision maker, not in an overt fashion.

Paula Edgar: I was like, “What do you mean?”

Chris De Santis: Not overtly mimic, but their style. I would say if they were a polished or present other than I would do, they were more of a, “Let’s ask a lot of questions,” or if they were frenetic, I would quietly mimic a little bit of who they are so that they would then think, “Oh, I like this guy,” because I’m mirroring them, I’m mirroring. So I, get these nice gigs and they eventually accumulated into enough work.

To your point, fast forward 15 years later, I’m now running a school for new consultants at one of these accounting firms in the suburbs, very big accounting firm, no longer there.

I was what you’d call the headmaster and I made sure these 300 kids who came in every three weeks got through the program and did it well. This was a great gig for a while. Then all of a sudden these kids were bitching and moaning and I’m going, “What the heck?” First I thought it was the British because they bitch about everything. But it turns out it’s just young people didn’t like the program the way it was run.

I was a little taken aback because I’m thinking, “I would never have told me that. I thought this was strange.” Around the same time, I ran into an article in the HBR by Strauss and Howe, they wrote a wonderful book called Generations, which I then read, but they had this whole thing on this generational theory that they had.

Their theory was one of a cycle. There are four generations that keep repeating. I’m not necessarily buying into that, but I did really like the notion of difference about the young. At that moment is when I started reading about it, and I’ve read every book, I don’t know every book, I probably read 70 of these books between now and when I wrote my own.

To your point, because this really fits the Paula, this is why you should be listening to Paula, is you say, “Where is your niche?” I tried to find within that my niche on the generational discussion as it relates to the workplace alone and not in a way that indicts anybody but recognizes first and foremost that we each have a skewed perspective of the other based on how our narrative turned us into who we are.

Paula Edgar: So Chris and I are both speakers for LCLD, Leadership Council on Legal Diversity. When I first saw you speak, I was like, well, first of all, before that, people were like, “Chris De Santis is going to speak.” I was like, “Oh, it’s Chris De Santis, okay, all right.”

I sat there, and number one, I get excited, to your point earlier, when the presenter is excited about the stuff. You weren’t just excited, you had so much nuance about the different generations that I remember being riveted.

I will say the highest form of flattery that I can give any speaker is when I sit through the same presentation over and over again because I love it. I have seen you speak three times, and I can tell you, to people I’m like, “Oh, I already know what she’s going to say. I gotta go do that.” This one, I’m like, “What is he going to say now?” So I have with me your book.

Chris De Santis: Oh, my God.

Paula Edgar: Which is Why I Find You Irritating, which I just love as a title anyway. It’s fascinating. I’m not finished yet. Actually, I want to get an audiobook because maybe a part of my Gen X in this is I have ADHD and the way that I navigate content is I can focus if I can read it and hear it at the same time. Oftentimes, I will read out loud so that I am actually ingesting information. But tell me, what do we have? Is it six generations in the workplace right now?

Chris De Santis: First of all, that would be child labor.

Paula Edgar: I know.

Chris De Santis: It’s a different country we’re in now.

Paula Edgar: Okay, my bad. I’m not good at math, but whatever number it is, we have a lot of them.

Chris De Santis: I think it’s four. Yeah, four is probably the safest bet. Boomers, Gen X, millennials, and Gen Z. Clearly, there could be traditionalists but they’d have to be more emeritus in their role.

Paula Edgar: Right, yeah, they’re just chilling, hanging out and being like, “Yeah.”

Chris De Santis: Exactly.

Paula Edgar: What are some of the traits of each of these?

Chris De Santis: Yes, it’s a very large question, because one of the things about all of this, and this is more for your listeners because you’re familiar with this, is that there are perceptual differences because we see them as different than us in some way, but when we see them as different, we don’t see them as better, we see them as worse.

I always find that very interesting. We never say, “Wow, they’re so much better than us.” No, there’s a problem with them. You see what I’m saying? By the way, that’s being said of us as well.

Paula Edgar: I know, because we’re eccentric. We have to be the best and then everybody else has to fall in line.

Chris De Santis: Exactly. There’s that thing going on. You gotta get rid of the perceptual differences which is a big part of this, because so many people play into this notion that we are so different, and I don’t agree with that.

I think we are somewhat different, and I think one of the differentiating factors of who we are, one of them, is how we were raised. How we were raised plays into our narrative of who we are.

I’m a boomer. I was raised in the world where my parents told me what to do, and that world was consistent in every aspect of my life. Now we live in a world where children are engaged in a dialogue, and the parents really question what they should do with them, and then move to a conclusion that they both agree upon. You see what I’m saying?

Paula Edgar: I do. I’m like, “You’re right.”

Chris De Santis: Yes, you’re doing that. I know you’re doing that. I know you’re doing that.

Paula Edgar: Should we take that class? Don’t you want to? All that engagement.

Chris De Santis: Exactly, and by the way, I think you’re giving them something that you didn’t get. You’re giving them eight, the attention you would have liked to have, and you would have liked to have been engaged with your parents, in the conversations that we didn’t have. You’re much younger than me. You’re probably like a late millennial or something like that.

Paula Edgar: I am a strong Gen-Xer.

Chris De Santis: Oh, you’re an Xer. Okay.

Paula Edgar: We are the most resilient of them all.

Chris De Santis: You’re the best. I think your generation is the most interesting because you are the most self-sufficient. You just figure it out, figure it out.

Paula Edgar: Yes, we didn’t have cell phones and now we do and we could do all the things on them. But I never thought about those strengths because it was just what our experience is until you laid it out the way that you did.

There was a part in your presentation where you talked about, I think it was Gen X because I probably paid attention to that more, that we grew up with the, “Do you know where your children are?” I was like, “Oh, my God, I’m traumatized. That’s why. I thought I wouldn’t be missing.”

Chris De Santis: Exactly. Your milk cartons. “Oh, you’re on a milk carton, oh my, oh my.” By the way, the recollection of that is scary and I’m going to protect my child. I’m not going to let you out of my sight. You’ve got to have a phone on you. I’ve got to know where you are. This tracing technology that some parents use on their own kids, and the kids don’t mind. Which I find crazy.

Paula Edgar: Yeah. I am some parent. That doesn’t even sound like I know where you are at all times, you’re walking down the street, aren’t you? I know because I can see you. Anyway.

Chris De Santis: That’s exactly right. But again, it’s an expression of love.

Paula Edgar: Yeah.

Chris De Santis: But if they’re not our kids, we blame them for not being us. That’s the problem. Any young person listening to me, your challenge at work is they don’t see you as you, they see you as younger reflections of who they were and you’re not acting like you should.

Paula Edgar: Hmm. Yeah, there is a lot of conversation when I go into, I work at a lot of law firms and there are a lot of conversations around the associates not aligning, not getting in line in terms of what they’re expected to do, and not in just the work, but even responsiveness, engagement, and communication verbally and non-verbal.

So you definitely see a lot of that. That’s why I think that this book is so important because it’s giving you, not just that perception piece, but if you know what their lens may be and what their experiences might be, then it can help you to get maybe what you want from them in a different way.

Chris De Santis: Absolutely.

Paula Edgar: Yeah, I love that.

Chris De Santis: Absolutely. I mean, part of the challenge is again, they are not nearly as comfortable with ambiguity because they have lived a life where everything has been explained.

You had insisted on explaining to your daughter or anyone, “This is why we’re doing it. This is what it’s about. This is what I mean by that.” By the way, you lived without any explanation.

Paula Edgar: I know.

Chris De Santis: You lived with that. You just figured it out again, figured it out, you see?

Paula Edgar: When I tell people that, when I was eight, I used to take the subway into Manhattan.

Chris De Santis: Oh, my God.

Paula Edgar: To meet my mother at the World Trade Center, and she would tell me, “Stand at the Sbarro or stand inside the Lerner’s department store and wait for me.” And I would, and there was nobody to track me.

Chris De Santis: Unbelievable.

Paula Edgar: And again, and I did. That resilience piece is really instilled because you gotta figure it out as long as you learn what you need to do. There’s definitely a conversation, I think that could be had based on the intersection of generations and culture. I come from an immigrant family from the Caribbean.

Chris De Santis: No, you’re absolutely right. Again, this is why the narrative of who you are determines who you are. It trumps your age group. Your age group, all that does is it contributes to the possibility of a common experience.

Because if I was born between these ages in the United States in the middle class, I experienced these things, I saw this on TV, I did this. But when you come from another country with a different, by the way, your parents saying different things relative to the other parents, you know what you have, the advantage you hold? The boomers like you because you think like they do because your message is probably more aligned with the old boomer messages of “You work really hard, do what you’re told. Listen to these people, you’ll move up.”

Paula Edgar: Yep. That’s exactly right. I have said in the work that I do in consulting, particularly, I work with a lot of white male partners at law firms, and we just connect. Maybe that explains maybe a lot of it. Also, I went to boarding schools and that gives me a little bit of an [inaudible].

Chris De Santis: Oh, no, no. That helps a lot too. You’re hitting on a couple of factors. One is of course, you accept the hierarchical model and say, “You got to do this, get a lay on all that,” and also, you are in the class as they are. You know their game.

Paula Edgar: Knowing their game, I think in the last maybe 10, 15 years, there was so much maligning of millennials. It was like, “Those millennials, they’ll roll your eyes and they don’t blah, blah, blah.” But what are some of the nuances that you see the most, I guess, in terms of workplaces? Let’s take the law because I know that well. Anything that jumps out that you hear about a lot?

Chris De Santis: Well, again, with the millennials, we heard early on that they want a trophy for everything, they’re really bad with feedback, blah, blah, blah, blah, blah, which again is not fair because they look at it through this lens of the self-esteem movement.

That was foisted upon these young people. No kid said, “I need another trophy,” the adult insists on giving you trophies. But when you have this acceptance of these participation awards, the removal of scoring on teams, it makes the young appear, “You can’t do this, you can’t suck it up as it were, you can’t figure this out,” which is very unfair.

I think what’s nuanced about the millennials is, first of all, I do think they want to play well with you. I think they’re very collaborative in their desires, but they have to understand what the rules are.

This is a mistake both that we make for the millennials and now Gen Z. We don’t tell them the rules, we only tell them, inform them, of rules after they break them. Then it’s like, “What are you doing? Why are you doing that? Why did you send me an email when you could have walked in here? Well, why didn’t you tell me that was your desire and then I would have done otherwise? I just do what I do.”

My point in this is we’ve got to start elevating some of the rules because they are different. I’ll tell you the other thing is we come from the old model that we want to move right up to the top. I’m not convinced in any way that the top is the sole direction.

In fact, I like the Deloitte model of a lattice. In fact, some of the research is showing that, I just read in The Economist, I think they call it The Crab Model. The crab means they move across this way. Yeah, you go sideways, you try different things because what it does, it gets you from being bored of what you’re doing, you learn new things, you broaden your scope of what you know, which makes you more promotable as well, and it creates greater stickiness because you’re perceived as more conscientious relative to the organization. Those are things.

So we have to design for that, but we don’t design for that, we just blame the person who doesn’t want to go after that.

Paula Edgar: Right, yes because we are living with the unsaid rules that we just know to follow, and they are like, “How can I follow if I don’t know what the rules are, especially if they’re unsaid?”

Chris De Santis: Remember, the children of video games as an example, they want to know how to get to the next level. You can’t just tell them, “Well, just work hard, work hard.” I will say this for the people listening at home, I believe we’re in a transactional model of work.

A transaction is, “What can I get from you? I will give in return, the transaction between us.” I came from the model of the covenant. If I work hard, there is a promise of employment or better things for me later on. Deferred reward, deferred reward. I don’t think these young people live in a deferred reward world.

Paula Edgar: Yeah, nor do they want to, I think. They’re like, “Even if this is what you have, that’s not what we want.” When people started seeing before the pandemic that people were jumping from job to job in two years, it was like, “Oh, they’re so flighty.” But I think that’s going to be more of the model that you continue to see because they want to continually be engaged.

Right now, you can get information at your fingertips. You don’t ever have to be bored. You’re the space where you’re like, “Okay, well, I’m just doing the same thing over and over again. I’m filing the TPS report. Nobody’s going to stay doing that.”

Chris De Santis: No, no, no, no. You know what they’re looking for? Because, again, we come from a space where a job probably ran 15 to 20 years, and anyone who had a job under five was a job hopper. They’re a job hopper.

But to your point, what they’re looking for in the conclusion is a narrative identity. This is what the emerging adult is experiencing. They’re trying to say, “Who can I be?” This is why what you do is so important, Paula. It’s not just naming who you are, but deciding what is important to you, then what do you pursue relative to that, and then strive to find situations where that exists.

In the sense that you are a life coach, I hate to say life coach because I don’t know if that’s really, but you are helping them in their life because you’re saying, “What is your identity? What is the story that you tell of yourself and what is the story you want to promote as a consequence of telling that?” That is your ticket, that’s your ticket.

Paula Edgar: Yes, when I talk about the concept of branding to groups that have different rules and responsibilities of ages, oftentimes the questions I will get from folks who are older than me will be, “What if I don’t want to do anything on the internet? How do I do what you’re talking about with people?”

That’s what we were just saying, where is that golden thing I can go get, but I don’t want to use this tool, you’re telling me to do that, I don’t want to do that. Teaching or trying to encourage that fluency is really challenging with folks who are like, “Nah, I’m good. I’ve made it. I’ve made it already here.” How can I do what you want me to do within the what I’ve got and what I want to do?

Chris De Santis: I have a theory on that is one of the things you might add to your repertoire, which is robust, by the way, robust, because, this is for your viewer audience, I saw what she did was she was able to take these people that were very self-conscious of saying who they were, and that made them very assertive in the span of about 45 minutes.

This is a very, very, very great trait and very great talent to do this. I think enough layer here is to say, “What is your stage of life?” Because that’s a conversation you should have.

For instance, some of these young people are still finding who their narrative identity is. That’s its own brand and saying, “Here’s what I’m seeking. This is where I want to be better at.”

Others have arrived at the stage saying, “Okay, I’ve now arrived, now how do I announce to the world my expertise because I have arrived and where do I spend that?” Then there’s us at the farther end of this who are just saying, “Look, I am known. I am known. In that sense, do I need to have the same mechanisms that they need relative to where they are?”

It’s about what mechanisms are most appropriate to where you are in the stage of life. This is why you reduce resistance because then you would say, “Well, you are known in this community, and this has maybe 1,000 people which know you, that’s great. Did you want to know more than that? Or do you want to know a younger crowd?” The question then becomes the breath of knowing.

Paula Edgar: Yeah. No, I love that. One of the ways, I am like, “You know what, if we always do what we’ve always done, we always get what we get.” Fine, that’s fine. I’m good with that. I’m like, “Okay, and if you’re good with that, I’m good with that.” It’s if you want more, then what do you need to do?

Chris De Santis: That’s exactly right. By the way, I thought you were spot on with the audience and saying, “Where are they in their careers? What do you need now?” Because then after they get to that, I mean, you should cycle in throughout their lives. That’s how I would view this.

Paula Edgar: Oh, yes. Personal branding is a journey. It’s never a destination because no matter where you are, you should be iterating, observing, and goal setting as to whatever you want next. Even when you are saying you want to retire, there’s a brand aspect in that. How do you want to sunset what you’ve been doing? Then how do you want to communicate what you’re not going to do anymore or what you want to do when you’re not doing this?

For me, the strategy sometimes I think sounds like it’s so robust. It’s really not, it’s just determining what it is so that I can help you to figure out how you want to do that.

Chris De Santis: It’s interesting, Paula, you should go after, I’m not to tell you how to, but there are programs now, there are programs at universities for retired CEOs and such that say, “Okay, what is your next life?” You would be so good in that environment because what you’d be saying to them is, “Okay, I get who you want to be. Now, how do we get that out there as to who you want to know this?” Oh, you’d be so good. You should go after [inaudible] CEO.

Paula Edgar: Listen to me, university people.

Chris De Santis: Exactly, no, I’m telling you because they’ll go on in their old models again because again, they were successful. The problem with success is it breeds the assumption that I know more than I actually do. It’s the illusion of knowledge.

Paula Edgar: Yes. Success can sometimes halt a growth mindset and make it fixed because you feel like you’ve gotten there. I’m always like, “The worst part you can do is to say you can’t learn any more or can’t do–”

My business tagline is engage your hustle. It’s like, “What else are you going to do?” Not that you gotta do everything all hard. It’s like, “What’s the next thing?” Never stop, never settle.

Chris De Santis: I like all that. I like that. I like that.

Paula Edgar: Fabulous. Another place in which the generations tend to be talked about differently is technology. What are some of your thoughts about that? Because I think I found that the kind of, “Oh, young folks, they embrace technology and older folks don’t,” is really not true in full.

There are definitely some people who are stagnant where they are, and stagnant where they are top and bottom. Or do you have any reflections on that technology piece when it comes to that?

Chris De Santis: Well, again, a myth about my generation is we are technology adverse. That’s not quite fair. What we are, we will leverage tech, we will take the time to learn something if we see there’s utility in learning it for what we are doing.

If you’ve already achieved mastery of something and somebody says, “Oh, you’ve got to go on TikTok,” you’re going, “Well, where does that fit? What is the gain here for me?” This is why I’m a big fan of reverse mentoring where somebody can explain to me how it can be leveraged and then I work with them say, “Oh, I see where this might have some utility and application.”

Although I am concerned about the young because we as humans are prone to social comparison, you know this, you compare ourselves to the other people who do what we do. Well, it’s just how humans are.

But they’re in this world where we used to be, I mean, I was in a class of 120 kids, and I wasn’t the bad-looking kid because that’s all I knew. Now they’re in a world, there are not 120 kids in their class, there are thousands of kids on the internet who everyone interacts with and now you’re not in the top 10% necessarily, you see what I’m saying? The pressure of social comparison.

Paula Edgar: I do, my daughter is a freshman in college, so yes, I do.

Chris De Santis: Right. This drives them to artificially compare themselves or to artificially inauthentically create who they are. I think it’s especially detrimental to young women.

Paula Edgar: Yeah, I would agree. Social media has, to your point, opened up horizons of seeing folks and not just people who are similar to you, but people who are where you may want to be, and then what you’re striving for, realistic or not, becomes very curated.

I would say social media is curated, it’s like a museum. You’re only going to see what people want you to see. I’m not going to go and say, “I’m taking a selfie on a day, I have a bad day.” To that end, then you think that everybody’s good day should be your every day.

Chris De Santis: Yes. It’s just not true to what’s real about us. This is why I would like them to embrace your strategy around creating an authentic brand as to who I am. The beauty of that in my book, I call this lopsidedness. We are particularly good at some things, but we have to admit we need others for other things.

By the way, the future is all teams. That’s my theory. It’s teams because the work, especially in law firms, in consulting, or in professional services is complex. There is no great person.

There’s a great coordinator or there’s a great facilitator, but there is no person that drives it all. Even Elon Musk, who positions himself as the genius of all geniuses, needs all those other people. He just doesn’t credit them, he doesn’t credit them.

Paula Edgar: That part. The pandemic, when it happened, there were so many people who thought, “How are we going to go forward? Because we can’t be interacting with each other the way–” Then all of a sudden, we were like we’re doing right now. We were on video screens, and surprise, surprise, work could get done even when you were at home.

That technological shift, I think, shook a lot of people to the core because it was like, “Oh. But we have always done it that way and we have to get back there.” Now we’re seeing that shift where people are like, “You’ve got to go back in the office.” I am of the, “I think you need to be in the office because I do feel like we need people with each other.” But I’m also of the, “I’d like to be in sweatpants and I don’t want to necessarily see you all the time.”

That shift from the pandemic and then this new shift we’re experiencing with AI, I think it’s shaking so many things up and you can see the discomfort, and not just folks who are older, but people who are younger as well who are like, “What do I do now? I’m very unsteady.”

Chris De Santis: Yeah. No. Well, going back to the hybrid workplace, it’s here. We didn’t collapse. Quite frankly, I think millennials were vindicated. They had said all along, “Why do I need to come in at 8:30? Nothing happens till 10:00.” They were vindicated like, “Ah, see, it works.”

But coming back to your point, knowing a person and learning, learning is not through what somebody just says, 70% of what we do is through observation of others. It’s observation. I’m in a meeting in a real room, I’m on a conference call, let’s say there’s somebody, the client says something stupid, nobody says the client says something stupid, but somebody rolls there to go, “Oh, wow.”

Everyone now knows that was a stupid thing. But we don’t say anything, but you see it. When you see it, these are cumulative. These little moments are cumulative. I think everyone does themselves a disservice for not coming in.

By the way, the new young Gen Z wants to come in. They like this work experience. They just want to have more flexibility around it and they want to be with somebody that is actually there for them when they are there.

Paula Edgar: Right, right. They don’t want to come into the office and no one else, the people who can actually help them are not there.

Chris De Santis: Are not there, are not there. You had mentioned one other thing after you had mentioned about the hybrid workplace.

Paula Edgar: AI.

Chris De Santis: AI, this is interesting. I have a theory. AI is a level playing ground. When I say level playing ground is who knows as much about AI as anybody? The youngest people in the room. They don’t know any less than the more senior people.

But in fact, they might even know something new because they’ve been cheating on this thing since it was available in grade school or high school. But the point being is what we’re going to see in my theory is because we have a hybrid workplace, because we have more remote workers, because you are not as tethered to the firm, you will see another round of the dot com boom where these young people will learn this technology and then start leaving in larger numbers in small groups and creating their own, creating their own versions.

Paula Edgar: Yeah, yeah, the “We can be free and do this better, faster, and for more money.”

Chris De Santis: Exactly. My other theory about this is firms have got to create because if all these kids have, not all of them, a lot of them have side hustles, you got to get them to surface what the side hustle is, if it’s a good one, invest in it.

Paula Edgar: Yeah. The narrow thinking and the silos of your expertise is no longer realistic at all. I don’t think it ever really was because people are so nuanced that a good inclusive organization, good inclusive leaders will want that piece to thrive because it’ll help people stay longer.

If you feel invested in, if you feel cared about, you’ll stay. When you leave, at least you won’t leave mad if you leave.

Chris De Santis: Right. What we’re not good at is we’re not measuring performance. If we’re not going to measure performance well, then we’re reluctant to give people space to do what they want to do on their own in addition to paying them. If we’re clear on the measurement of performance, then in fact, then you have the space you want or I don’t pay you as much for this, but I invest in some of that.

Paula Edgar: Yeah, yeah. When you talk about the measuring performance, it makes me think about feedback. I had your good friend and cubicle confidential, Mary Abbajay was on.

Chris De Santis: Oh, I love Mary.

Paula Edgar: Yes, and we talked about how feedback and good feedback is essential for people to grow. So many people will tell me, “Paula, I don’t want to say this thing to this person because they can’t hear me,” but really what I find is that it’s not they don’t want to, but they don’t know how.

They want to be like, “Here’s this red-line document. Take it in just all the things that I’ve imbued into it, but I don’t want to tell you what to actually do.” I think that’s probably one of the biggest challenges that I see with those generations and in the space because you can’t learn, to your point, with somebody being like, “Here’s this thing that’s different from what you gave me,” without saying. “This is why I made these changes.”

Chris De Santis: To your point, one of the problems we face is that we’ve become a little too tribal in the sense that, “Look, I’m afraid to say anything to you that might offend you.” In that sense, I don’t want to offend you.

We get into this disposition like you’re them, I’m me. My point, and to your point is, “Look, my gift is to make you a great lawyer, if that’s what my gift is.” Then I tell you, “Here’s how I would go about it.” Then I should be asking you, “What do you need from me to be a great lawyer? Because that’s what I want.”

Now, I’m going to make mistakes along the way. You have to be cognizant enough to tell me in a way that I can hear it, how I have not helped you. But at the same time, you have to be willing to listen to how I want to help you, even though it will feel harsh.

It’s not about the harshness of the event. It’s about how we have to see where we will make mistakes so we don’t make them again. Trust is so low in the country. In fact, the new young are the least trusting, but the most desirous of having trust. They want to trust. But how do I trust? What’s the evidence of trust? That’s why these conversations become so critical.

It’s saying to them, “Look, I’m here for you, but I have rules. These are how I play.” Because we are an economic engine, in that sense, so I have to conform to something. I say remove the curtain and explain everything and say, “This is what it’s about and we will be imperfect to each other until we start to trust and then we’ll accept that we are imperfect.”

Paula Edgar: Oh, imperfect to each other is such a perfect way, I think of just talking about how things are right now. Everybody wants to be perfect for themselves, and maybe [inaudible] that way, but if we can understand that, number one, we are all interdependent on each other, we can’t do this without each other, whether or not we like each other or not, but that imperfection can help us to, number one, become, I call it champion apologizers, “I am so good at apologizing. Ooh, I made a mistake.” I’m like, “Guess what? I made a mistake, I’m going to learn from it and try my best not to do it again.”

If people just did that a little bit more and were really authentic in it, we would move along a lot further. We may not agree, but we would do it better. We would do it better.

Chris De Santis: To your point, Paula, the people in power should be saying, “Oh, these are the mistakes I’ve made to get here. These are the failures I’ve had.” Because, look, if I’m a young person and you’re a big shot up there and I’m thinking, “Wow, I could never be that,” “Oh no, I’ve made a mistake. My world’s over,” we all have made a mistake, we only get to where we are because we don’t make the same mistake.

Paula Edgar: That’s a quotable right there. Absolutely. My financial advisor says that she goes, “You want to make different financial mistakes, not the same ones.”

Chris De Santis: Exactly.

Paula Edgar: That is fantastic. I knew that this conversation was going to go quickly. Number one, you were welcome to come on my podcast at any time and talk about whatever you want. But I’m going to ask you two questions that I ask everybody as we close.

One is this, with now our new shared understanding of a personal brand, what is an aspect of your brand, and a view of your brand, the ethos of Chris that you will never compromise on?

Chris De Santis: Ah, okay. That’s an interesting question because it’s hard, but at the same time, I think where I would not compromise is I get asked to say things certain ways. Do you ever get asked that?

Paula Edgar: Oh, I do.

Chris De Santis: Right? We want to say it this way. I will push back and say, “Look, I will make the point that I believe in, in a way that is favorable to you, but if I don’t believe in the point, I will be absent of making it. I will not condemn it. I mean, I won’t say this is wrong. It will be absent in—” In that sense, I won’t say what I can’t, I don’t also believe.

Paula Edgar: I love it. Yeah, it’s a values piece. Yeah, I get asked all the time, particularly just connecting what we just talked about, which is like the hybrid workplace, people are like, “Just go in and be a cheerleader for going back in the office.” I’m like, “But I’m not a cheerleader for going back.” I’m not going to say don’t do it. But I will say that there are benefits to both and give the argument as opposed to saying, “You must go in five days a week and cartwheel to work.

Chris De Santis: Exactly. If they want to shill, then hire a shill.

Paula Edgar: Or pay me a lot more then.

Chris De Santis: I’ll use another name. I’ll use another name.

Paula Edgar: Exactly, there’s a [inaudible] for me to say a little bit more than that, just kidding. My face will tell the difference anyway. Even if I said it, I was like, “You don’t believe me, my face is telling you.”

Okay, the final question I have is, Branding Room Only is a take on the phrase standing room only because I’m clever.

Chris De Santis: Yeah, you are, and she is.

Paula Edgar: I want to ask you, what is the unique skill or experience about you that would have a room full of people with standing room only to experience?

Chris De Santis: Yeah, it’s again, I think I tend to fall back on humor when I think I can, but again, because of my improvisation and the nature of who I am, I tend to be a tad spontaneous.

When I make a speech, I don’t have the speech, I have the scaffolding. I will say, “Okay, this is what I want to get at.” But in the moment, I might digress or I might come back and go, “So I’m willing to step out and then step in.” Now does that play out 100% of the time? Not always, but it plays more than not.

Paula Edgar: That’s sort of the magic. I think you just hit the nail on the head as to why I like to watch you and then done it over and over again, it’s because it is not the same. There are some speakers I’ve seen where I’m like, “Okay, I know the joke about the bird is coming up,” but [inaudible] supposed to, and similar to you, I do, I have four pieces that I want to include, but I want the experience to be from them, from me, and what has happened at this time.

Adult learners need to feel fully heard and fairly treated. That means that if I’m like the same thing that everybody, it doesn’t resonate for most because I’m not actually honoring who they are.

Chris De Santis: Well, I knew that was true of you. You know how I knew it was true of you? Because when you spoke, you asked them things. By the way, when they could say just anything, there was never a guarantee that they were going to answer in the manner that you wanted, but you went with the flow. That tells you a lot about the presenter.

It says, “Okay, this person is confident in the message they’re giving. In the same way, they also want to play and recognize the needs and wants of the people in front of them.” That’s magic.

Paula Edgar: Yes, well, that’s a beautiful way to end our conversation. Chris, I love this. This is fantastic. As I mentioned, you are a Branding Room Only VIP from now on, and everybody, go out and tell all of your friends and that person who annoys the hell out of you at work to listen to this podcast. We’ll see you all next time on Branding Room Only. Bye