Finally! Expert Shares Secrets to Working with Younger Generations

In this episode of Great Talent, Great Business, Rob Levin sits down with Jon Sheppard to dive into the realities of generational differences in the workplace. They explore how each generation brings unique strengths, challenges, and expectations—and why these differences sometimes create tension. 

Key Takeaway: 

One of the biggest takeaways from this episode is that generational clashes in the workplace are often fueled by assumptions rather than real conflicts. Each generation has different values, communication styles, and work expectations, but these differences don’t have to be a source of frustration. When we take the time to understand where others are coming from—rather than judging or resisting change—we open the door to stronger collaboration, more effective communication, and a workplace culture that benefits from diverse perspectives. Embracing these differences isn’t just about avoiding tension; it’s about unlocking new ideas, innovation, and growth. 

Questions I ask Jon:  

•[01:53] What is generationality and when did you identify it? 

•[05:13] Is the pandemic the main reason for generational issues at work? 

•[07:24] Give examples of generational conflict in the workplace. 

•[10:16] Is setting expectations a big part of solving generational issues? 

•[12:00] Is this issue prevalent with fewer generations at work? 

•[14:02] Is the "lazy" stereotype about younger generations accurate? 

•[15:40] How can businesses turn generational challenges into opportunities? 

•[18:08] Should businesses ask younger generations what they want? 

•[20:13] What do younger generations offer that older generations do not? 

•[22:55] What does "work-life rhythm" mean for different generations? 

 

More About Jon Sheppard:  

Check out J.Sheppard Associates. 

Connect with Jon on LinkedIn. 

 

More About Rob Levin  & WorkBetterNow: 

Like this show? Click on over and subscribe to our YouTube channel! 

Follow Rob Levin on Linkedin. 

Visit WorkBetterNow.com 

  

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Episode Transcript

Jon Sheppard (00:00):
All the pandemic did, Rob, was, kind of speed things up. We find ourselves in a place, you talk about five generations, you talk about the traditionalist, people that are 75 plus right now, and then you talk about the Boomers, the Gen Xers, the Millennials, and the Gen Zers.

Rob Levin (00:02):
Jon when did you first understand or identified generationality concept? And actually, what is it?
And what I found was they all had a different need set and we'll get back to that later. But the thing I really found was they were all generationally judgmental about the others. They all disliked the other generations for various reasons, and it started kind of got me thinking like, you should be looking for the best in everybody.
So she said to me, Jon, I don't mean to offend you, but I don't hear any recruiters talking like this. Nevermind somebody your age. And it struck a chord in me; so I started really bringing it out in people. And I came to realize very quickly, Rob, that each group of people had different things that they needed to address in their personal lives in their professional lives and it really is something now I talk about the generationality of work.
You've got a recipe for either really moving ahead in a new way or a recipe for disaster, depending on where you are.
There's a different way to do it now, and you don't accept that you don't like that, but there are very productive people who do it a different way and it's not only with hybrid work It's just the way that people communicate whether it's in person and email versus text and instant messaging and things along those lines.
I'm like that you did. I'm like, how old are you? 28. I'm like, and you're bitching about the 19 year old. And he said, you betcha. And that led me to believe, Rob, that this is an issue that's never going away.
And, I have other businesses now trying to reach out to me and talk to their people about this. It's really about communication and it's about accountability. So for the boomers and the older gen extras, they're used to doing business one way. If they have a piece of work that somebody that reports to them needs to do, generally somebody younger, they're going to call them, they're going to email them and they expect instantaneous attention.
Take an email I sent you and work on it from 5:30 until midnight and give it back to me at one in the morning. Even if that might have been the request from the client, you should have had a conversation with you people earlier about, listen, just get back to me and acknowledge my email, or my call and that will talk first thing in the morning.
You don't serve your brand by saying, oh i'm doing this and this is the way I want it. I have an interesting story that i'll tell you later about first year associates in big law and what i'm telling them it's it's a little eye opening. So
And in fact, I talk about this all the time about this concept I learned about from a great professor in school called mutual mystification. Nobody really knows we're doing or what the expectations are. And it's I think is I think it's just a matter of simply setting the expectations. Like I expect that if you get something at, five o'clock or what, during the business hour, during the business day, even if it's at the end, I'm not expecting you necessarily to stay later, but I am expecting you to reply saying, Hey, I'm on it or whatever the, or, and I do expect you to get back to clients within X number of hours or X number of days.
Jon, is this an issue? Let's say with a company that only has two or three generations in the workforce, is it an issue to the same extent? What have you seen?
And, it's not only with businesses that are, call it across four or five generations. It's really the core four, but even I see it with Millennials and Gen Z type companies. The Millennials are having a hard time talking with Gen Z because the Millennials came up in the time of Oh, we're going to have an open workplace space.
So Jon, I'm going to ask you like a, I guess a challenging question in a way. I do speaking, I got a book coming out. One of the things I talk about is literally just citing statistics. On Gen Z and a little bit of Millennials, too, on how a lot of them are, there's this lazy girl job concept, or quiet quitting, or I'm just going to do the minimum.
I did a real on LinkedIn and Instagram. I wanna meet the other 24% of employers. So yeah, all the stereotypes could hold true. Yes, the answer is a yes and no. Like, all the stereotypes may hold true. But at the end of the day, you're looking for people that fit your business. Whether you're a law firm or another kind of business.

Jon Sheppard (00:16):
The short answer is everything's always an opportunity.
every other year for a two year term to voice the concerns of the associate ranks in the firm that goes a long way. Yes, it goes a long way. It doesn't cost you any money, right? And you may learn something if you're an enlightened You know second half of your career partner sitting on the management committee.
I said, yeah, but you got to look back. Okay, like you don't get off you know cheap where they just tell you things and because it's expected things are expected of you too so a firm that puts an associate on the management committee they get it
What are you doing? You spend all this money on law school. You graduated from a top school, you're working at a top firm. But you're sitting on the Upper East Side in New York City or in Brooklyn in your Lululemons or your Adidas sweatpants thumbing your nose at the man because you're working in your living room three or four days a week.

Rob Levin (00:20):
And by the way, this works even in a company that's totally remote. It's it, to me, it's just a matter of, mingling, being a part of the, being a part of the company taking part of whatever a company might be doing in a remote environment. We do, we, we had like literally a remote holiday party, South America, North America, we had everybody on, very cool.
And if they disengage, then it's on them. But if you handle it the right way, say, listen, keep coming at me. You may have 20 ideas. Okay. If we use one that makes us money, I promise to promote you.
And he changed the world, Steve Jobs, people like that. Now you have AI coming along. It's very much like the old Louis Armstrong song, I see babies cry, watch them grow. They'll learn much more than I'll ever know. And I say to myself, what a wonderful world.

Jon Sheppard (00:23):
Yeah, I, I hate the term work life balance. And I use the phrase work, work life rhythm. Work life rhythm is how does your job fit into the rest of your life?
And the people are saying the two and a half younger generations saying, if you don't let me do it this way here, I'm going to go over there. And for the first time in maybe a generation, they have other options because firms, companies are figuring out. That the old way of doing things, although very successful and very profitable is starting to fade.
And if you just extend yourself a little, like you don't even have to believe all of it. Like you don't have to be a new age. I believe in everybody. Just extend yourself again, stay focused on what you're doing. What you're doing is trying to get the best result in the business that you're running or the firm you work for, and that's your customers and your clients.
Really appreciate it. Listen, thanks for having me on. Really appreciate it. Yeah, yeah. This well exceeded my expectations, which were high to begin with. Jon, where can people find out more about you and J Sheppard Associates? Uh, you can get me directly at jsheppard, spelled J S H E P P A R D at jsheppardassociates.