Author Smiley Poswolsky: Leading Different Generations in the Workplace

Gene Marks (00:00)

Hey, everybody. Did you know there are six generations now working in the workplace? Going all the way from Boomers all the way down to Generation Alpha. I am speaking to a workplace professional and expert. His name is Adam "Smiley" Poswolsky. He covers all of this, talks about it, and writes about it. He will be sharing some advice on managing all the different generations, dealing with remote work, performance reviews, giving feedback, and other thoughts for business owners and HR and people managers to make sure that their workers are getting the most attention as possible, make sure that they're retaining them, and attracting the best people. So, let's get to our conversation now with Adam. I think you'll really enjoy it.

Announcer (00:40)

Welcome to THRIVE, a Paychex Business Podcast. Your blueprint for navigating everything from people to policies to profits. And now your host, Gene Marks.

Gene Marks (00:52)

We're talking about attracting and retaining and managing, you know, workers in today's workforce. Four generations of workers, I think, are in the workforce. Some people can argue there's even more than four because they break the millennials out, like, into two. So, Smiley, first of all, thank you so much for joining. I'm really glad that you are here. Talk to me a little bit about the workforce in 2025 with all these generations. What's your perception of today's workforce?

Smiley Poswolsky (01:22)

Yeah, the word I would use is probably challenging. Really, to make sure that we are paying attention to what I would call as many as six different generations at work. Even if you're not seeing six generations on your team or even in your office or remotely or hybrid every single day, in terms of the people that we're interacting with, that might be customers, clients, next gen talent that are coming into the pipeline and people that might be retiring or still using our services. Right. We have to pay attention to six different generations at work. So that goes everywhere. From Gen Alpha. I'll walk through, yeah. Gen Alpha. So, this would be a generation, you could call them the AI generation, born after 2010. They do not know a world without ChatGPT. If you can imagine that. Gen Zers. Igen, the smartphone generation. This is a generation born after 1997. 1997 to 2010. This is a generation that does not know the world without the iPhone. I call them the swipe right generation. Like it used to be that you could double click, like that's what we did, but that's too much work now. Swipe right. Right. I can swipe right. I can get an Uber, a car, hotel, food delivered, a date. Doesn't work, didn't work so well for me, it works for some people. And then those Gen Zers get to work, get to their job, and they expect that they're going to get promoted in, you know, three weeks, like, swipe right. Or like, I should probably be running this place, be the CEO, like it's your third week, swipe right. Then we have the Millennials. I myself am part of this fine generation. I'm an elder Millennial. So, Millennials are born early 80s to 1996. 1981 is usually what you hear as the cutoff. I was born in '83, so I call us the Oregon Trail generation. So, this is a generation that understands technology, right? We had AOL and send messenger, early email, but like, you know, when we grew up, like if you made plans with someone to meet up at 7 p.m. and they weren't there, like you got stood up, you're going home. Like, they're not like, oh, I can't find you on Google Maps, my Uber is late. Like, you're going home, right? Unless you both have a pager or something, which I'm not sure why you both have a pager. And then we have Gen X, born 1965-1980. You know, I think we can like give a, give a clap. I know we're on a podcast here, but we can give a clap to Gen X. Gen X gets no love. I guarantee if you go to any business conference anywhere in the world, there is not one session that says Gen X anywhere in the title. So, I think we need to start talking more about investing in our mid-career talent, often tasked with the brutal responsibility of managing either Millennials or Gen Zers and leading them. And then we have Baby Boomers, right, often 1946 to 1964, who I think we often treat as if they're already at the door, as if they're just kind of waiting out the clock, waiting for retirement. When these are the people that have built our institutions, our organizations, our companies, and have much wisdom and knowledge to give. And we actually even have people from the Silent Generation, the Greatest Generation, working later and later into their lives, either out of financial necessity or because they love their job or if they're not working, we're still serving them in terms of customers or clients in our products. So, we have to pay attention to what all of these people want, which is, I'm not saying is easy, but I think it's important to just kind of break down, like not everyone looks the same and not everyone wants the same things. And while we often only talk about younger folks, in the workplace, which is important to kind of pay attention to the trends of where things are headed, it's also important that we consider everyone. So that's why I think like we often think that workplace culture is changing so quickly. It is because we're evolving to the needs of a rapidly changing workforce. It's not like it used to be.

Gene Marks (05:15)

I fit the demographic right now of today's average business owner. So, I have 10 employees. I'm Gen X because I was born in 1965. We, as a Gen Xer and a Baby Boomer, according to the Small Business Administration other data, half of small business owners are over the age of 50. More than half actually. In fact like the average small business owner's age now is 56 to 57 years old. So, there's those Gen Xers and Boomers that are out there running the businesses, but they still have to deal, you know, they've got to employ people and deal with different generations. Sometimes I tell you, Smiley, I hear it from my own clients, you know, like they don't even want to hire younger kids anymore. Like they would, they would rather just focus on hiring older millennials like yourself or people that are Gen Xers because they just, they can't deal. You know, are they, are they wrong by having that attitude?

Smiley Poswolsky (06:17)

I understand their sentiment, I can identify with where that's coming from. But it's not a sustainable, long-term business strategy for reasons that are pretty obvious, right? Like you're going to need young people either to work for you or to understand where your customer segment is headed. Right? Like these represent the future of our companies. Especially if you get over 10, 20, 30, 50 people, 100 people and you don't have these folks on your team, you're not going to be relevant to the competitor and the competitor is going to beat you out by either attracting that next gen talent or solving your customers problems better because you're not in their head and not understanding where they're going. So, it's a yes and. It's not like we say, you know, the kind of the metaphor that I often use is that it's a seesaw because often what happens when we start talking about next gen talent is like, people be like Smiley, these young people, they want to work three days a week, they want to work two hours a day, they want kombucha on tap in the office, they want ball pits, they don't even want to work, they just want to be on their phone all day. So that's the one hand, right? I'm not saying we do all of those things, but on the other hand, we can’t have the perspective that, you know, in my day, this is what we did. Pay your dues, kind of, you know, you don't get to give feedback, you don't get to share your ideas until you're five years in, 10 years in, and you've worked your way up the ladder, kind of, you know, mind, you know, just pay your dues, take a seat, that person's going to be out the door. And they might be a phenomenal employee, but we just haven't tapped into that expertise. We haven't met them where they are. So, the, the metaphor is the seesaw. It's meeting them somewhere in the middle. It's not giving someone a promotion on their third day. It's not putting kombucha on tap in the office. But it's also not ignoring them. It's also meeting them where they are in terms of their language, in terms of the speed of the world that they grew up in. Like, this is important to remember. Like the swipe right thing I use, and it's kind of a joke, but if we put ourselves in the shoes of someone who grew up in a world where they could get literally anything at their fingertips, of course when they get to the workplace they're going to be a little bit confused and frustrated, but it's our job to kind of explain, yeah, that's not quite how things happen here and I can't solve that. It's your third day, it's your third week. But I want to help, I want you to be a part of solving that. I do care about what you're saying. I'm listening. So, the kind of metaphor, and another metaphor I often use is like, no longer is it the traditional, like, you're the boss, you're the supervisor, you're the manager. It's much more you're the coach, you're the peer learner, you're the mentor, you're the guide. Right? So, these people, Gen Zers, will often, they be looking for their team, their manager, their supervisor to provide kind of personal growth as well as professional growth. It used to be that you expected your workplace to provide professional growth, new skills, new trainings, you kind of work your way up the ladder. You go to a conference, you kind of get your titles higher and higher, your salary higher and higher, and one day you retire. Simply not relevant, approachable, accessible for many young people. So, they are actually increasingly looking for personal growth at work, this sense of how to be an adult, how to navigate an overwhelming, rapidly evolving world. Just think about the changes that have happened in the workplace in the last five years in terms of remote work, in terms of the pandemic, hybrid, AI, globalization, technology, how things are changing so quickly. They are looking for their team, their company, their culture to provide that personal growth as well. How do you navigate this? And some people will say, like, Smiley, but, like, I'm not their father. Like, they have a dad. I'm their boss. I'm not your mother. I'm not your therapist. Like, go talk to your mother. Like, I'm your boss. I pay you to do a job. I get that. But if when someone comes to us on Monday morning with their entire life story, the date that they went on on Saturday, what's happening on TikTok or Instagram, and instead of rolling our eyes and being like, oh, my God, please leave me alone, if I have to talk to this person one more time, we simply take a deep breath and we say, tell me more. What's on your mind? How can I support you? I can't solve all those problems, but I am interested in having the conversation. It's possible. Not always. It's possible that that person is going to do incredible work for us. Incredible work.

Gene Marks (11:05)

You know, we focus on the younger generations. You said that at the beginning of this conversation. And yet you yourself just said, I mean, the Millennials themselves. You're an older millennial. I mean, Millennials are like in their 40s. You know, I mean, it's a... They're no longer like these young kids that everybody makes fun of. And in fact, not only are they no longer young kids, but fewer people make fun of them because, well, we have Gen Z and Gen A to make fun of now. But this is a generation right now, your generation, that's now in management. And in fact, there are a lot of people in their late 30s, early 40s that are starting businesses or buying their own businesses. You know, what advice do you have for Millennials? Forget about old guys like me, but if you're in a management position and you are dealing with this Gen Alpha, Gen Zers, talk to me about advice that you give to your Millennial-age clients, your age, to deal with generations that are younger than them.

Smiley Poswolsky (12:03)

Yeah, I think, you know, the main word I would use is listening. And I think that this is the key for management, regardless of age, but especially for Millennials who are often managing both down and up. So, you often, I often hear this a lot. You have Millennials in their late 30s, in their early 40s, who are managing, you know, 23-year-olds, but they're also managing people in their 50s, right? Their late 40s, their 50s. And the key there is to understand your place, to understand and kind of have empathy for where people are and to be a really great listener and to kind of understand where people are coming from. And not to come in like you know the place and that you know the right answer, but you come in with that sense of humility, that sense of empathy, that sense of I'm a learner more than a manager. And I think that that's what makes a great leader today. I think that there's this big shift that's happened and I think the Millennial generation is actually like a perfect, is perfectly emblematic of this, but how purpose has kind of shifted in the workplace. So, I think when I came up in the workplace and this is kind of, you know, I graduated college 2005, but most of my generation joined the workforce, entered the workforce post-recession. Right. Right 2008, looking for jobs, financial crisis, very overwhelming time. And there was this big kind of, you know, all about aligning your passion with the work. Right. So, it was all about the do what you love. If you think of the Steve Jobs famous commencement speech, follow your passion and you'll never work a day in your life, this kind of mantra. And the whole idea of the mission of the organization and aligning yourself with the mission of the organization, and that was like kind of this obsession around meaning and finding meaningful work and purpose in work. I think that that has shifted over time to people understanding... And if you talk to Gen Zers about this, they're like, I don't need meaning from my job, necessarily. I need meaning from my life.

Gene Marks (14:06)

Right.

Smiley Poswolsky (14:07)

So, it's almost less that you have the work-life integration that Millennials were looking for. Like, I want to follow my purpose, find my passion in the work, work for the company that is most aligned with who I am, perfectly aligned. Which, let's be honest, if you get far in your career, you know that that's very hard to find and that the reason something is called a job and not a vacation is because it's often you have to make sacrifices. And even if you love your job or love your organization, it's not going to be that perfect. But that younger people are actually finding some of that purpose outside of the workplace and they're looking for that work life, almost not separation but a little bit of the work-life separation, that they can kind of do a job that supports them and that the purpose just isn't at the organizational level, it's at the individual level. So, it's this pendulum shift of where it was all about the organization's mission, which is still important, of course. If we don't have a strong mission and strategy and values that people can align with, where are we headed? Right? But we also need to pay attention now to the personal mission, the personal values, who that person is. This is something that I think in the corporate arena, this is not where we've excelled. We kind of were like, oh, let's finally focus on the corporate mission. The mission statement. I guarantee if you go to any mission statement somewhere on the website, it's, we're changing the world. Look at our assets under management, our global impact, our reach. We're amazing. You should wear a vest with our logo on it. Right?

Gene Marks (15:35)

You should.

Smiley Poswolsky (15:36)

You want the swag? You want the swag, don't you? And a young person is like, actually, I want to pick up my daughter at 2 o' clock on Tuesday. I'm going to miss that meeting. Or like, I want an extra day of work from home. Like that's what purpose means to them. And this is like a very big shift, a very big shift. And that purpose is kind of understanding the personal as well.

Gene Marks (16:01)

I'm going to throw out some different trends that's going on in the workplace now and I want to get your hot takes on these trends, what you think. And the first one has to do very much with what you were just talking about. Having purpose in your life or not being completely married to your company. It's not like your entire life. I just wrote a piece, I write every week for the Guardian and I wrote a piece just this past week on a trend called polyworking and polyworking, and again, not, not to put you on the spot or for people that are, that are listening, watching means this growing trend, particularly among Millennials, not as much so much with Gen Z and Gen A, but growing there too is people having more than one job. You know, I mean they work their full-time job or maybe it's a 30-hour to 40-hour week job and then they have another week, which kind of speaks to what people are looking for. You know, they view a job as a, not an ends to a means, but a means to an end, you know, like something they're using. So, what are your thoughts on that from an employer's perspective. You know, if I, if I hire an employee and they do, maybe they have a part-time job somewhere else or maybe they got a side gig on Etsy or they're selling on Amazon, they're doing polyworking. Is that a problem for me as an employer or do you think that's just the reality of today's workplace?

Smiley Poswolsky (17:12)

I think it's the reality of today's work. In terms of the average... The stat that I used to quote all the time is the average Millennial is going to have 20 different jobs in their lifetime.

Gene Marks (17:22)

Yeah, right.

Smiley Poswolsky (17:24)

Just basically based on the nature of... Not necessarily... That doesn't mean just because they want to quit their job. It's actually the market, the job market. A job will become obsolete. AI will make it obsolete or change the job. The job will be, you know, shipped somewhere else or somebody else could do it in a different place for cheaper. Whatever it is. That somebody has to constantly be agile, adapting, experimenting, trying new things. So, I think the old perspective would be like, this person isn't loyal to me. The new perspective might be like, how could the, what the, this person is doing outside of here make them even better at their job in here? Like we don't own them, we don't kind of have that like the corporate loyalty thing has shifted. Like you hear a lot of about boomerang talent, right? Where people will, hey, you did a great job here. If you want to, you know, you're trying to do something else, you want to leave, you're welcome to come back. Now if the person wasn't a good performer, cool. Bye. There's the door. See ya. But if they were great and they're leaving and they're taking a two-to-three-year break, maybe they're starting a company on the side, they're going to work somewhere else, they might come back with even better skills and more experience and they might even more importantly recommend their friend to work at the company who's even just as good as them. So, I think it's much more fluid. Now what the key piece that we have to talk about as well is expectations. Now it's, it's one thing to say, oh yeah, sure, you can have four jobs if you're getting your job done, but if you're not getting your core job done and your responsibilities and your JD, you know, your PD, like you're not checking those boxes, then we have a problem. So, if the expectations and communication align, that's where it's it comes down to communication, clear expectations, setting those expectations. If those things are being checked, then yeah, if someone needs to do something on the side to support their family or to support who they are and their purpose, then that's great. That actually could make them a higher performer for you.

Gene Marks (19:19)

Okay, I'm going to throw a curveball at you only because it's current events. There are a lot of layoffs going on right now in the federal government, as we all know. I have quite a few clients actually that view this as an opportunity. These are smaller businesses because they're like, wow, we've been desperate for talent over the past however many years and now there might be some talent now because people are getting laid off from federal jobs. Curious on your take. If you're, for business owners that are looking to hire people out of the federal workforce because you're a workplace expert, you know, are there any specific considerations that they should be making or do you think that if you're bringing somebody on from a government job as it is, do they have a, you know, a different way of working or different, you know, priorities or anything that an employer, particularly a small and mid-sized employer should maybe keeping into consideration when they start interviewing people coming from that place?

Smiley Poswolsky (20:19)

So, I used to work for the federal government, actually. I started my career in Washington.

Gene Marks (20:23)

FBI?

Smiley Poswolsky (20:24)

I can't talk about that.

Gene Marks (20:27)

You could tell us, but then you'd have to kill us.

Smiley Poswolsky (20:29)

Exactly. No, not the FBI, but I did work for the, for the federal government for a couple of years. And in my experience, the people there, I mean, the federal government employs millions of people. It's so vast. But the majority of people there are really driven by that impact, by that sense of service. Right. There's a real sense of serving something greater than yourself. And that could be for people that are working in healthcare, that are working, you know, in research, that are working in benefits, that are working in whatever. Right. That there really is a sense that you're, you're a servant, you're a public servant. A lot of people use that terminology. So, I think that if I was hiring from someone from the federal government, you know, I'd really kind of try to tap into that sense of duty, that sense of service, that sense. These are people that have a mission higher than themselves, a higher purpose, which is the exact type of employee that you want.

Gene Marks (21:26)

What a great answer. It's a great answer. It's a great answer. All right, I got two more questions for you, and I'll let you go. You're awesome, Smiley, this is, it's great stuff. Obviously, we have a lot more that we could talk about, but in your latest book, The Workplace Belonging Toolkit, you talk about inclusion and why that's so important. Obviously, you know, DEI, diversity, equity, and inclusion has been a hot topic and a controversial topic over the past few years. Talk to me a little bit about, and again, we have small and mid-size people that are watching and listening to this. What do you mean by inclusion as you write about in your book? How does that interface with all the different talk, positive and negative about DEI, and what should small and mid-size employers be considering when you talk about inclusion?

Smiley Poswolsky (22:12)

Yeah, like the key piece that I care about is that everyone is able to show up and do their best work. Right. That they feel seen and heard. And to me, the data that I look at is disengagement, right, the Gallup data, I'm sure you're familiar with that. Nearly 70% of Americans are disengaged at their jobs. One-fifth are so disengaged they're actively undermining their co-workers' work. So, we're paying people to mess things up for us, for our shareholders, for the bottom line, for us as CEOs or leaders, as executives. We have people on our team who are like, let me give you a salary to make my job harder and to make my company suffer. Like that makes no sense. So, when I think of inclusion, I think of less of kind of, you know, the politics around it and more of how do we give everyone a place where they can show up and do their best work. Right. Two-thirds of workers are disconnected from their coworkers. 40% don't trust their coworkers. Half feel a sense of burnout. Two-thirds are afraid about losing their jobs due to AI. So what I care about is creating an environment, a culture where people feel included. That to me is what it's all about. The other pieces that come, well, not so easy, but the other pieces that come are more complicated and nuanced and are often actually require a little bit more deep dive and can't be kind of solved by just saying this letter, that letter, whatever. But the big, that's why I kind of, the big picture framing, that's how I think about it. How do you do that? I think you start small. You start, I think a lot of times people kind of have this like, you know, belonging is this intimidating thing. I think it starts by how you show up every day, how you talk about yourself, how you share your story as a leader, how you start your team meetings, your check-ins. Do we go right into the agenda? Okay, it's Monday. Here we go. Here's our report. Here's our quarterly numbers. Where are we going? Or do we say, how was your weekend? Do a personal check-in. Where are people at? How are you feeling today? What's happening? Did anything happen in your family this weekend? Is there anything we should know about? And people say, well, some people like, well, Smiley, I got people on my team, or maybe even I don't want to share. I got, I want to get right to work. I got my family I can share with. I can have a beer with my best friend after work. I got a therapist. I'm good. That person can just say, skip, pass, no thank you. Not today. I'm good. But they don't get to create the culture where other people don't get to share. Because even taking that one minute, two minutes at the start of a meeting for someone to share what's happening, maybe their kid is sick, their mother's in the hospital, something's going on for them. That might be the unlock where you're like, oh my gosh, I had no idea that this person was going through that. I might be building a deeper relationship with that person, or even better, a deeper relationship with a with a key client or customer just because you ask those questions or connect on a deeper level. So, yeah, that doesn't completely create a culture of belonging, but I think it starts there. And I try to, in my talks and in my work, make this as practical as possible. I want to give people practical tools that they can do. They require zero budget, they require energy and time and intention, but $0 to create a culture of connection at work. I just actually released a guide last week, 70 Ways to Connect at Work. It's 70 practical tools. Things that you can do in a meeting, things that you can do in an existing meeting, at a team retreat, at an off-site with your direct reports to build a sense of connection. And you might not do all of them, but to pick one or two, or say, hey, next week I'm going to work on this one. That's the whole idea here. I'm trying to make this as practical and actionable as possible.

Gene Marks (26:08)

Final question and an observation. And again, maybe I'm putting words in your mouth, but I am getting the vibe that you're not the biggest fan of remote work when it comes to building that workplace culture. Talk to me a little bit about this trend and talk to me about what advice you give to your clients as they're kind of grappling with remote work and work from home policies.

Smiley Poswolsky (26:28)

To me it's an, it's a yes and, and it's not a one-size-fits-all answer. And I apologize because I know that's like, well, Smiley, give me the, give me the band aid, give me the, you know, four days a week in-person, one day a week remote, three days a week in-person. It's, but it's, I don't think it's that simple. It depends on what people are doing. It depends on the nature of the organization, the company, what we do. Like I have friends that run restaurants, like that is an in-person job. I have friends that run factories or manufacturing like you got to be there, like we're building something. But I also have people, friends that run companies that they have access to engineers and talent in four different countries, right? They got someone in Argentina, someone in Ireland, someone in Vietnam, someone in California, someone in Detroit. That's a remote company. So, the key is that we build connection wherever people are working for. Where they're, excuse me, wherever people are working from. Hybrid work is not just the policy, it's a purpose. It's how do we connect in the future of work. The nature of this is that in order to have access to the top talent, it is going to be impossible for most companies to have people come in five days a week, no matter what, depending on what the company is. But just because someone is coming in doesn't mean we're you know, just having connection because they're at a water cooler. That doesn't just happen. We have to create a culture of connection in the office, remote, and hybrid and everywhere in between. Right. So just so we just because people are saying Wednesday is the in-person day, that doesn't de facto mean that because people are actually in the office, they're connecting. Now it's probably better that they're there than all at home, but we need to actually be intentional about making the office and in-person time worth it and designing for human connection wherever people are working for.

Gene Marks (28:27)

Adam "Smiley" Poswolsky is a workplace expert and the author of a bunch of books. His latest is The Workplace Belonging Toolkit. Adam, how can we find you?

Smiley Poswolsky (28:38)

You can check out my website, smileyposwolsky.com I'm also on LinkedIn at Adam "Smiley" Poswolsky.

Gene Marks (28:44)

Very good. And I called you Adam, and I should have called you, Smiley, because that's what you like to go with.

Smiley Poswolsky (28:47)

It's all good.

Gene Marks (28:48)

It's all good. and you're all good, as well. Thank you very much for your time. Great advice. We'd love to have you back. We have covered just a small fraction of the questions I wanted to ask you, but very, very valuable stuff. So, thank you so much, Smiley.

Smiley Poswolsky (29:01)

Thank you, Gene. Thanks, Paychex, for having me.

Gene Marks (29:04)

Do you have a topic or a guest that you would like to hear on THRIVE? Please let us know. Visit payx.me/thrivetopics and send us your ideas or matters of interest. Also, if your business is looking to simplify your HR, payroll, benefits, or insurance services, see how Paychex can help. Visit the resource hub at paychecks.com/worx. That's W-O-R-X. Paychex can help manage those complexities while you focus on all the ways you want your business to thrive. I'm your host, Gene Marks, and thanks for joining us. Till next time, take care.

Smiley Poswolsky (29:38)

This podcast is property of Paychex Incorporated 2025. All rights reserved.