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Episode 12:

Conquering the Generation Gap – Quarterly Recap

Jeremy Clopton and Heath Alloway


Heath Alloway and Jeremy Clopton come together for their second quarterly recap in episode 12, and the focus of their conversation is viewing people as people, rather than generations. They talk about the misperceptions that can get generalized to entire generations, the nearly generic buzzword that “millennials” has become, and how important it is to integrate the ideas and values of every generation in your firm to ensure its success.

About the Guest

Jeremy Clopton and Heath Alloway are your hosts for The Upstream Leader Podcast.
Jeremy and Heath pic

Highlights / Transcript

Hello, and welcome to The Upstream Leader podcast. I’m Heath Alloway, your host for this episode. And one of the promises that Jeremy and I made when we started on this journey was to have some recap conversations—what we’re hearing across profession, some of the top issues, different opportunities that we’re seeing—and help provide some thoughts and guidance to firms.

And today, one of the things that Jeremy and I have been hearing a lot is that thought around leading multi-generational teams, and how to address those generational gaps. Some of the common examples I’ve heard are, “the millennials or the younger generation, they maybe don’t want to put in the time, or they don’t want to work as hard as we do.” And then on the flip side of that, I’ve heard some up-and-comers, maybe new partners, and the comments of, “Well, some of our partners, more experienced partners, they’re stuck in their ways, and maybe they don’t want to change.”

So how do we start to change this mindset? And my first thought is, I think there’s a lot of times there are misconceptions on how we define some of these terms, especially “millennials.” And so Jeremy, to lead us off, let’s just set the foundation at how do you define those different generations?

Heath, that’s such a good question. And it’s interesting, we’re sitting here across the table from one another, recording, and we’re in two different generations—though we’re only a few years apart in age. So it’s important to do this so that we have an understanding, and let’s just go with the basics: The most common definitions over the years. Anyone born 1945 or before is a traditionalist; those born between 1946 and 1964 are your baby boomers; 1965 to somewhere around 1979, or 80 are going to be Gen X; and you’ve got 1980 to 1995 is Gen Y or the millennials; and then 1996 on to let’s call it maybe 2012 at this point, are going to be your Gen Z.

So we’ve got five definitions in the workforce. There are still some firms that truly do have all five of those generations. But you asked at the start of this, “What are we hearing?” and what I’m still hearing is “millennials, millennials, millennials.” And it’s so funny to me, because millennial is now this catch-all phrase, it seems like, for individuals that are young in their careers—which means young in life. I had the opportunity to speak at a convocation to open a college a couple years ago, their opening convocation. And I asked everyone—we were talking about generations—asked everyone in the audience, “if you’ve ever been called a millennial to stand up,” the whole auditorium stood up. And I said, “Now, great. If you were born between 1980 and 1995, I want you to stay standing.” And this auditorium of a few thousand students all sat down with the exception of four.

So here we’ve got an auditorium of thousands that have been called millennials, referred to as millennials, and four that are actually millennials. So I should probably disclose: I’m a millennial. I think I heard the phrase the other day “geriatric millennial,” which I don’t necessarily care for, but I’m a millennial. I was born at the very beginning of that, as I understand it. You’re Gen X, you were born at the tail end of that. So we’re different generations, but we’re not that different in how we approach the professional life, which I think is really important in this context. Would you agree?

Absolutely, Jeremy. And yeah, I look back, you know, some of the things you and I have talked about just the different phases of life. And that made me kind of take a walk down memory lane and some of my own experiences and what I learned and, you know, as I reflected, I don’t think there was ever a time that I didn’t care, or I didn’t want to do well. Sometimes it was just a lack of maybe coaching, or a lack of understanding of what it meant to be successful. And I have multiple examples of that.

And then one example I will share: I had a team member once, she was with our firm, and she was pretty early in her career. And in her first I think week and a half, there were certain things that happened. And in fact, one meeting, I think she actually fell asleep in the meeting. And her direct supervisor, we had conversations about this. But she had a lot of potential, she had a lot of skills, and I think he just took some open conversations with her and now she’s still with the firm. She’s doing amazing things. And that is just one example.

And as you talked about those different levels of generations, it’s kind of crazy to think about, that sometimes that next generation of partners, they are actually even millennials. And if we don’t have the faith and the hope of some of our professionals, you know, they’re the future of your firm. So what are some key things? What are things that we can look for? What are things that we can do to really help bridge that gap, and help some of our maybe, experienced partners, better understand some of those different seasons of life? And then vice versa? How can some of our up-and-comers, what can they do? How can they be more impactful? And how can they help the firm as well?

One of the things we’ve got to do across the board, is we’ve got to stop talking about individual people as generations. An individual person is not a generation. They may have certain characteristics that you might say are, you know, millennial in nature, or you know, Gen X in nature. I’ve got friends that are in their younger 30s that are as traditionalist as traditionalist gets. And I’ve got some folks that I know that are near retirement, post-retirement, that have that mindset of a traditional millennial, and they’re a bit more progressive, and, you know, trying to, you know, new things all the time.

What’s really important is we start off by recognizing there isn’t a single firm, there isn’t a single organization, that hired the generation. You hired an individual. They may have different characteristics, but we’ve got to stop painting with this broad brush, because in so many situations, I hear firms or organizations say, “Oh, this generation doesn’t want to work hard, or you know, they just aren’t open to change.” But if you really press someone and say, really, it’s everyone at that level, if you press a young person, and you say, “Really, nobody at the partner level is open to new ideas?” they’ll almost always come back to, “Well, no, it’s really just one or two.” And the same thing is true when you’re asking the leaders of the firm, and when you hear somebody say, “Well, you know, they’re just really not, they’re not accountable, they don’t work hard.” And you say, “Oh, well, you’ve got a whole bunch of people then, that you really got to, you probably need to replace if that’s the case.” And they’ll say, “Well, actually, it was really just as one person that worked on this one job, this one time for me.”

When pressed, we recognize that we almost take the easy way out and say, “Well, it’s just that generation or that group of people,” when in all actuality, it was an experience with an individual that really led to this. So that’s the very first thing that I would say we’ve got to do, is we’ve got to step back and say, “We’re not working with a generation, we are working with individuals.”

Now. There’s two different approaches here. Those that are most experienced have learned a ton in their career. I don’t ever want to discount that. Young professionals should never discount that. Because it’s absolutely critical, everything that they’ve learned. The more we’ve learned, though, the easier it is to forget what we didn’t know when we were early on. And sometimes those questions that get asked, or those new ideas that sound just so obscure and off the wall and uneducated—it isn’t because someone maybe is just trying to rock the boat or they’re not trying. It’s because they don’t have thirty years of experience under their belt. They are still learning all of that. So we forget when we learned what we’ve learned, and frankly, there’s probably a lot that we’ve learned that we’ve forgotten along the way.

So from a leader standpoint, we’ve got to recognize, where are those ideas coming from, and that sometimes challenging the way that we’ve always done it is really good, because someone that is younger, without as much experience, that’s a different generation, brings a different perspective. And it could be that challenging of the status quo or challenging the way that we’ve always done it from a place of natural curiosity, and wanting to improve, that helps us make changes to move us forward.

Right. Kind of goes back to the innovation concepts of getting a broad audience and in different backgrounds.

Well, Jeremy, one of the things that I’ve seen as well: You think of expectations, whenever you bring on a new employee, whether you know, they’re their first one to four years, whatever the number may be. And we get so honed in on certain KPIs that maybe they don’t understand the bigger picture—they don’t understand the impact that they’re having on their firm, or they don’t understand what it takes to be a successful firm. So I think just opening that dialogue between experienced partners, and then, you know, those up-and-comers, I think that can be pretty impactful as well.

What role does coaching play in all of this? Because it, it goes back to your examples we talked about, if you keep doing the same thing over and over, well, have you actually had a discussion with that person? And what kind of coaching and advice and candid conversations have you had? So what role does coaching play in all of this as well?

Coaching plays a significant role, and it really is a recognition that coaching is different now than it probably was ten, twenty, thirty, forty years ago. More and more managing partners that we’re talking with are recognizing the value in coaching, and really putting more emphasis on it than there ever has been in the past—which I think is important.

What we need to be doing in the coaching area is helping the younger professionals learn to communicate new ideas in a productive manner. That’s one of the very first things that I would always encourage a leader to coach a young professional to do. Too often, in not only in our profession—I think we have a great profession, by the way, I love our profession—but in our profession, and many others, young professionals are often coached to first figure out how to do the technical things really well, and temper the excitement until three, five years down the road.

Instead of that, I would encourage leaders out there: Coach your young professionals on how to tactfully and productively share new ideas. One of the things that that’s going to require is you to help them understand the bigger picture. Heath I know, something that you and I talk about a lot is how many times we hear a firm say “They just don’t understand how the firm works,” right? “They don’t understand the basics of running an accounting firm.” Well, sure they don’t, they’re two years out of college.


They’ve just figured out how to do auditing or tax or consulting—they’re still learning that. There isn’t a course in university that I’m aware of that says “Hey, by the way, here’s how a public accounting firm runs and is profitable.” So one of my favorite books on this—there’s also a TED talk—Daniel Pink is the author, and it’s called Drive. And it really goes to three things: autonomy, mastery, and purpose. In my experience, we too often forget to help individuals understand their purpose, and instead, they become task takers.

It’s part of being bigger than just themselves.


And I think that open dialogue on what does make a firm successful.

And Jeremy, one thing that came up in a previous episode was the topic that we all as humans have emotion. And it’s not just about generational differences—that emotion piece, it is universal. And you know, no matter where you’re at in your career, you’re still trying to get, you know, from where you’re at, a certain point, to another point. And each professional, each person, we’re processing that through our own lens, our own experiences.

So one of the things if I were going to give advice to maybe some of our listeners that are earlier in their career, I would lean towards also understanding the ability to take some of that constructive feedback. So listen to the more experienced partners, the more experienced professionals—we can learn a lot from that. And just having that open dialogue, I think, can make a big difference.

And I would say for that younger professional—one of my favorite approaches comes from the world of improv, which for anybody that knows me, is a bit comical because I am terrified of going to an improv show that I might ever get called on. So that idea of improv, actually—I’m not a fan of. But I love the idea of “Yes, and.” And if you really want to help the firm and showcase your ideas and your perspectives, I would encourage you—whether you’re a young, professional or experienced professional, it really doesn’t matter—acknowledge the success and everything that got you to where you are and got the firm to where it is, and then build on that. “Yes, that’s the way we’ve always done it, and yes, we’ve seen all of this great success. And I think we can make it even better doing this.”

Too often, the rub isn’t the fact that it’s a different generation, it’s the fact that somebody wants to come in and propose a new idea without acknowledging the past and all of the effort that came in. I’ve seen that be one of the big, you know, rubs generationally, and across the generations. But I’ve seen experienced partners come into a firm, direct admit partner come in—

—A hundred percent.

—They try to change things, and it’s the same rub except at that point it’s, “Oh, well it’s the new person. How dare they come in with new ideas?” When it’s a younger person, it’s “How dare that generation.” It’s challenging us. We’ve got to figure out how do we challenge each other productively to grow forward.

And Jeremy, I think you know, a couple things we’ve hit on throughout. And we talked a little bit about this in our previous episode, but around that thought of capacity and recruiting and retention. And this goes back to, I think there’s a misconception of what it truly means to be in our profession. And I think that education piece for our younger professionals—it’s critical. Because whenever I step back and look at it, you know, I think you look at the last year and a half. I think many firms, they upped their game, they stepped up in a lot of ways. They helped their clients through probably some of the most challenging times that they’ve ever faced. And to me, that’s pretty powerful, pretty rewarding. Not only that, they’re being strategic advisors. They’re helping bring solutions. And they’re really focused on helping others. And that’s, that’s powerful to me.

Not only that, we work in a profession that is… very professional, without a, you know, with a lack of better terms. And there’s a lot of great opportunities. So I think if we can communicate that from our partners to the different generations, I think it helps with that recruiting, and it helps with retention. Help tell that story of what it means to be within your firm. And I think that can in a lot of ways, alleviate the different generations and put them on the same page. So just a few thoughts on bridging that gap.

And in doing that, I would add—we’ve got to remove the focus on metrics. Too often, the story is told that it’s a great profession, because you can make all this money. And don’t get me wrong—I don’t know anybody that’s going to say “No, I, you know, pay me less to do the same thing.” But it’s not all about the salary. Yes, salary is important. I’ve heard some, you know, I’ve heard some people say, “Oh, well, this generation doesn’t really care about getting paid.” No. Everybody does care in some capacity about making enough money. But when you’re making enough money that it isn’t the issue, that’s when you’ve really got to highlight everything else in our profession.

Like you said, we as a profession have helped so many organizations, so many companies, so many nonprofits over the past eighteen months, navigate so much uncertainty and come out on maybe not a better place, but a better place than it could have been without it. And there’s always going to be a need for an accountant. Now, I don’t care where technology goes—and you know that I’m a huge proponent of technology and emerging technology—there is still always going to be a need for accountants that care about their clients, and helping them grow. That’s the story we want to tell. I mean, I’ve got young kids, I would definitely say, “If you want to go into a great profession, where you’ll always be in demand, you can make a difference for others, become an accountant.” You have young kids, would you?

A hundred percent. And in fact, I’m already working with them and helping point them in that direction. Not too hard, though—I’ll let them figure that out along the way.

So do you have any personal experiences—I know I took that walk down memory lane—I will never forget, and I’m sure that Doug Adams, the head pro at the golf course I was working at, at the time, he’s probably not listening in to today’s episode. But there were a couple of things that just were very simple. And this may sound funny, but I would wear—keep in mind I was 21, maybe 20 years old—I would wear my golf shoes, and I worked in the pro shop. Well, I had my spikes, and they weren’t probably, you know, polished. And he spent a little time with just the observations or perceptions of our members. At the time, my mindset was, “I don’t want to spend $180 for a new pair of shop shoes.” In his mind, it was the perception of our members and the bigger impact. And little things like that, just, you know, those coaching moments really stuck with me. So do you have any maybe personal experiences throughout your career? Maybe I’ll open up and share one or two of mine as well. But do you have any experiences that have really impacted you on this topic?

I think one more recently—I was actually working with a firm, and they were really struggling with accountability—or at least that’s what they thought it was. And we talked about it, and you know, the leadership was saying, “Hey, you know, our young people just aren’t accountable, and you know, they used the generational terminology, and said, “They just aren’t accountable.” So I said, “Okay, well let me go and talk to them.”

So I had the opportunity to talk with their associates and their seniors and said, “I hear there’s some challenges around accountability.” And they said “No, really, there’s not, you know, we get everything done.” So I go back to the partner group, and I said, “All right, they don’t think there’s a challenge with accountability here.” And they said, “Well, we expect that they’re going to get it done immediately when we give it to them. So by Tuesday, and they don’t get it done till Thursday.” So I said, “Okay, well, let me go back and talk to them.” I said, “It sounds like you’re not getting things done as quickly as you’re being asked.” And they said, “Well, that’s not true at all.” They said, “Hey, we want you to get this done. So we did.” All of that—

—Communication gap.


Goes back to what we talked about.

Yeah! It was all, you know, disguised as, “Oh, well, this generation is not accountable.” And what it came down to is there wasn’t effective delegation, because there wasn’t effective communication.

So for young professionals out there in particular: I want to speak to you on this one. If someone delegates something to you without a deadline or an expectation as to what your next steps are when you get back to them, when you get it done—do yourself a favor and ask.


Get a deadline. Know what their expectations are. Clarify those expectations. And if you get pushback that’s saying, “Well, I shouldn’t have to micromanage you.” – “Look, I’m not asking you to micromanage me. I want to make sure I meet your expectations and I can hold myself accountable. To do that, I have to know what it is that you want.” That will alleviate some of the generational noise that’s out there in that regard.

Jeremy from having a team of roughly twenty in my past career, you know—one of the things that we would always coach and talk to our people about this, whenever we were first hiring them, because sometimes, you know, someone’s hungry, maybe it comes across the wrong way—was always setting the expectation. Even in the interview process, about career path, career progression, ‘cause if you’re not setting that expectation, having that open dialogue, three months, or six months in, they could be knocking at your door asking when their next role is or next promotion.

But also you flip that maybe in their seat, they view that as, they’re hungry, they’re trying to take that next step. So I think that just going back to the open dialogue and coaching, it can be so powerful.

Let me add on to something on that, because I think it’s so important what you just said that they’ve got that hunger, and they’re going to come knocking on your door: That’s a good thing. I think way too many people attribute that to a young professional. I remember one of the very first times I spoke about the generations, and I’ve led multi-generational training in accounting firms, and outside of accounting firms. This was in manufacturing. And this gentleman said, “I just don’t understand. I had somebody interviewing for an internship, and he said, ‘once I get through the internship, how long till I can get hired full time? And then once I get on full time, what does the path of my first promotion look like?’ Because I couldn’t believe he had the audacity to ask that.” And I said, “But you’ve got somebody who is so invested in getting their career going and growing, why is that a bad thing?”

That would be one of my questions.

Oh, yeah! And I’d much rather have someone that comes in with that hunger, that desire, that initiative, rather than somebody that comes in and says, “Tell me exactly what to do, so that I can clock out at five o’clock”

A hundred percent, Jeremy.

Just like any discussion we have, in any of our podcast episodes, we always like to leave our guests with maybe one or two resources that can really help them in their journey. So any thoughts from your end on resources? I know there’s probably a ton out there on this, on this topic, any thoughts on resources that could help our listeners?

From a resource standpoint, when it comes to the generations ,often what you’re talking about employee engagement. It really isn’t as much on there. I think one of my favorite books of all time in this is Haydn Shaw’s Sticking Points. It’s a really great book, just pinpointing—it’s a little bit older, so it doesn’t get into Gen Z, I think it stops with Gen Y, the millennials—but what it does, is it just helps you understand how everything gets shifted, and it gets shaped as far as their perspectives, and why maybe a traditionalist might have a different perspective than Gen X. I think it’s important though, to remember, just because we’re different generations doesn’t mean we have to have completely different beliefs. You and I are just a few years apart in age—we’re different generations, because we’re both right on the edge—but we’re pretty similar when it comes to, you know, our professional and personal beliefs. So it isn’t all about the generations.

Yeah. I don’t know if this is a resource, but it’s more of a thought of, whenever you are having those conversations, of just taking a moment pausing and the thought of empathy and perspective, put yourself in their shoes. And I think that that’s a powerful exercise to go back when you were entering the workforce, or maybe you’re ten years into your career—whatever it may be. Just taking that pause and taking, you know, putting yourself in their shoes, that can be, you know, pretty powerful when trying to bridge that gap.

And my other thing, I’d say this is gonna be a strange resource to throw out there. But if you do have children, even looking at them as a resource—and I’ll share an example. This is, I’m going to put myself on the spot here. But just a couple days ago, I was at my kid’s gymnastics class. And my four year old son looked up in the middle of class and I was texting someone. And in front of everyone, he said, “Dad, put your phone down and watch me!” So it’s just little things, like, we can learn from all generations. And he’s right, I should have been more engaged with what was going on there than what I was doing. So I’m a big believer that we can learn a lot from our children as well. And not only from that aspect, but just that power of why and questioning—always wanting to know what, you know, why we do certain things the way that we do. And it’s not out of ill intent. It’s just out of curiosity or fear of the unknown and trying to learn and learn more and continue to improve. So, I think a little different approach to that question. So Jeremy, give us your your closing thoughts.

Yeah, and that goes back to understanding purpose. And one thing to remember for everyone—we’ve talked about this from the generational aspect, I’d ask you to shift your thinking. You’re not leading—don’t think of it as leading the multigenerational team—think of it as leading a multi-perspective team. And every effective team needs multiple perspectives.

Every firm has to have multiple generations as well, by the way. If you’re going to have sustainability and longevity and you’re going to maintain independence, you’ve got to have that next generation. So this has been going on, by the way, for a long time. This generational topic is not new. Now that there’s podcasts and social media and everything out there—there’s just more talk about it. This has been going on. It happened with Gen Z, with Gen Y, it’s gonna happen with Gen Z, it happened with Gen X, it happened with the boomers. This isn’t anything new. We’ve got to have multiple generations. But more importantly than that, we need multiple perspectives to be as effective as possible.

And really, as we wind up this episode, that’s a lot of what we’re doing on this podcast—is trying to bring in multiple perspectives. Some that are inside of our industry, some that are outside of our industry—and really give you multiple perspectives that can help you become the best leader that you can be. So with that: Heath, thanks for leading the conversation today and everyone that’s listening, thanks so much for joining us. We appreciate having you on The Upstream Leader and look forward to talking with you in another episode soon. Have a good day!



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