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Episode 93

Leadership Tips For A Multigenerational Workforce

Kathryn Landis
Founder and CEO of Kathryn Landis Consulting

Ever wondered how to get Baby Boomers, Gen Xers, Millennials and Gen Z to collaborate effectively? In the latest episode of Leader Generation, Tessa Burg chats with Kathryn Landis about the unique challenges and opportunities of multiple generations working side by side.


“I know leaders are probably thinking, ‘I don’t have time for this,’ but you also don’t have time for turnover or quiet quitting, which has also become a trend.”


Kathryn explains how understanding and empathy can help bridge generational gaps, creating a more inclusive and productive workplace. She shares practical tips for marketing and business leaders on adapting their management styles to create a workplace culture that accommodates diverse working styles and enhances communication across all age groups.

For those in leadership roles, this conversation offers ideas on creating environments where all generations can thrive, innovate and drive business success. Don’t miss this opportunity to learn how to build a stronger, more dynamic team!

Topics In This Episode:

  • Challenges of multiple generations in the workplace
  • Differences in work expectations and loyalty
  • Impact of remote work on generational dynamics
  • Communication norms and misunderstandings
  • Empathy as a key to intergenerational collaboration
  • Intentionality in leadership and engagement
  • Preparing younger generations for the workforce
  • Investing in early career development
  • Tools and resources for effective team management

Watch the Live Recording

Full Episode Transcripts

Tessa Burg: Hello and welcome to another episode of Leader Generation, brought to you by Mod Op. I’m your host Tessa Burg, and today I am joined by Kathryn Landis. She’s the CEO and founder of Kathryn Landis Consulting, and an adjunct professor of leadership at NYU. I’m super excited to have her as a guest. She spends her time helping leaders get to that next level. Kathryn, thanks so much for joining us.

Kathryn Landis: Thanks for having me Tessa. So excited to be here.

Tessa Burg: So we were talking before we got on the air, that the topic in which you have dedicated a lot of time, and expertise, and research, is of specific interest to us, especially as marketers who spend a lot of time in B2B. We deal with companies that are selling physically, that are selling online, but it’s really a lot based on relationship. And the same can be true for consumer brands. You know, why someone buys your product as a consumer, and why someone buys your product’s business has a lot to do with value alignment. And the topic is, multiple generations in the workplace, and how they operate together. They collaborate and teamwork. So this is something we see day in and day out. So really looking forward to diving in. Before we get started, tell us a little bit about you and your background.

Kathryn Landis: Well, thank you Tessa. I started my career in sales. I worked in B2B sales for about 10 years, and then pivoted to marketing. I led several B2B marketing teams at American Express, and at one point I had a really bad leader. And it made my life miserable, changed my career trajectory and made me realize, probably something I would’ve gotten to anyway, was that what I really wanna do, is help leaders be better. And I wanna help teams become more efficient and effective. So I went back to school at Columbia University and studied executive organizational coaching. Opened up my own business about five years ago, and been teaching at NYU ever since. So I feel very fortunate. There’s an old saying, you know, turning lemons into lemonade, that really led me to where I am today.

Tessa Burg: Oh, that is so funny. That has a lot to do with, very similar to my career trajectory as well. And how I got into marketing, was I was in IT and development, really felt like we were under-utilizing the data, and I was fascinated by how marketers consumed, thought about it, and really built in these layers of empathy for the audience. And I felt like at the time, and this is obviously a long time ago, but where IT and engineering sat was so disconnected from the customer. So, it’s interesting that your career change came out of empathy, and wanting to be there to help make the experience better, whether that be for teams or customers and consumers. And that kind of leads us into what’s really important when we talk about multiple generations at work and teamwork. And you mentioned that it’s important to start with empathy. So tell us, what are the generations, what are the different generations that we’re seeing right now show up at the workplace?

Kathryn Landis: Yep. Well we have the baby boomers, many of which are starting to retire, right? They’re about 59 and 68 right now. And I like to use famous people as examples. So think of Barack Obama and Meryl Streep. Then we have our Gen X folks, they’re about 43 to 58 right now. Think Elon Musk and Jennifer Lopez. And then we have our millennials. They’re about 27 to 42 think Mark Zuckerberg and Serena Williams. Followed by Gen Z, which is all in the news right now. You know, they’re around up to age 26. So think about Billy Eilish and Greta Thunberg.

Tessa Burg: I really love celebrity comparisons. That really helps ground you on who we’re talking about. And there’s even the examples you gave, such massive differences in personalities, and their approach. So why is it important for us to have these discussions about multiple generations at work?

Kathryn Landis: And I talk to a lot of leaders, and most of the folks I work with are senior leaders. You know, they are baby boomers, they are Gen X, or older millennials, and they are just baffled by younger millennials and Gen Z. They do not understand where they’re coming from. They are just shocked at some of the things that happen in the workplace. You know, things like sharing salary information. You know, I had one leader ask, can we stop that? No, you can’t. You know, and I also teach at a master’s program at NYU. And so I hear from my Gen-Z students and younger millennials, who have a completely different outlook on work and life. I mean, I had a student last semester tell me, Professor Landis, I just really wanna find a great job where I can stay there for six months. Like six months was the optimal longevity. I came into the workplace when five years was the minimum you wanted to stay. You know, if you stayed two years, it kind of looks strange. But more importantly as an employer, you’re not making your return on your investment after six months. And so there’s just a whole different outlook on working to live and living to work. And these, it’s creating tension in the workplace. And so, it’s on top of mind for a lot of people, and that’s really why I started to focus more and more on it. And you know, writing articles for Harvard Business Review, and you know, different blogs on my website, because it’s been such a topic, it’s such a headache for all parties involved.

Tessa Burg: So when you say things like that, like someone’s outlook is six months, my initial reaction is, well they, they need to change. That is terrible. And I know, I’m just saying I know this is wrong, because my initial knee jerk is like, oh my gosh, we’re gonna invest in training this person, and then they’re just gonna bounce. They don’t, doesn’t seem to be an appreciation for what companies invest in their teams and employees, if you’re only planning on staying there for six months. So what do you say to older leaders? Like, I guess my question is, who has to change in this equation, the younger generations or the older generations?

Kathryn Landis: I think it’s building empathy on both sides. You know, for the older generations realizing where Gen-Z is coming from, in the sense that they’ve, you know, lost trust more or less in, you know, government and institutions. They experienced COVID, and seeing so many people get laid off, and that social isolation and that remote school. So, they don’t have the same attachment or loyalty to a company, right? They are more willing to move if they’re not happy. And most Gen-Z, I think it’s upwards of 90% either are an entrepreneur, or have a side hustle or they want to have a side hustle. So they’re not in it to work for a real man. You know, getting that corporate job is not the same goal as it was maybe for you and I coming out of school.

Tessa Burg: So when we think about, you know, building up that empathy, and they have or want to have a side hustle. Do we feel like this is because they’re young and they can take those risks? Or does there seem to be a high level of understanding of what it requires to operate a side hustle that can fund your life?

Kathryn Landis: I think it’s a mixed bag. I think it’s hard to say one way or another. But in general, I think Gen-Z is really motivated by, and what I’ve observed, very motivated by purpose and meaning. Is what they’re doing meaningful? Do they see the impact of their work? Do they feel like their voice is heard, and they can make meaning of what they’re doing every day? Which is more difficult when you’re working from home, right? And they’ve worked in a remote environment in school, you know, the first two years on the job, perhaps they are fully remote or hybrid. And so that means that they haven’t had the same interpersonal connections that, you know, older generations may have had. And they are missing out on flexing those muscles, on getting some of that mentorship that you just hear when you’re in the office. And some of that is the fault of the older generations. You know, I was working with a senior partner of an advertising agency who was telling me, her day isn’t any different when she’s in the office or when she’s at home, working from home. And that is a big problem, because she’s directly contributing to the organizational culture. She was telling me, how she takes her phone and is like texting or emailing to and from, getting coffee, you know, walking in the hallways, going to the bathroom, she’s tethered to her devices. And what she needs to be doing is, thinking about how can I make my time in the office meaningful, so that I can have those connections with younger employees so that they see the benefits of– because people aren’t gonna wanna come in, people are not gonna start having that level of engagement that employers are seeking, unless you are connecting with them, right? And if the leaders aren’t doing it themselves, and think it’s gonna happen organically, it’s not, you have to be more intentional about it, now than ever before.

Tessa Burg: So on one lens we could look at Gen-Z and say, they’re being naive and they don’t know what it takes, and they’re gonna try these side hustles or switch jobs after six months and then they’re gonna learn that, that’s just not the way the world works. On the other hand, what I love about what they’re doing, is they are taking risks, they’re figuring things out for themselves, and they’re gonna come out with some really strong skills and discipline having tried it. And I’m sure a lot will succeed, especially with so many tools now being available to build a true business without a lot of resources. And maybe the optimist in me says, you’re gonna get a higher quality entry-level person who has a side hustle, who has explored their own strengths and passions, and they’re coming to work as a different, more well-rounded person. At the same time, we as leaders have to take responsibility, that just because we can operate the same, that we already had those life experiences, it almost felt like we have to be the ones making a little bit more of a change to make space for those people coming in to build the experiences they need. And it’s not necessarily the training, it’s the environment that they’re working in. And you know, personally I have seen remote work be very beneficial for myself and for cost reasons. And it’s hard to say like why we would have a physical office. But is there a space to get creative about the different environments, where we can still sort of have the benefits of, you know what, I work really well this way, and this is good for our business, especially businesses like ours that have a lot of offices across the country. And for a lot of our clients, we have a lot of large clients, multiple offices. And create space for more multi-generation collaboration.

Kathryn Landis: You have to be much more intentional. And I know leaders out there are probably thinking, I don’t have time for this, but you’d also don’t have time not to invest in it. Because the opportunity cost is just too high to have turnout. Or quiet quitting, which has also become, you know, a trend as well, right? Where you’re just not working. And I wrote an article about it, and I’ll ask you to put in the show notes. The idea is that, you know, because some of the younger generations haven’t had those interpersonal conflicts, they don’t know how to handle it, they just shut down. And so helping them help themselves.

Tessa Burg: Mhm. Yeah, I love that. It’s funny, there’s a parallel to this in a conversation we’re having on AI, where we’re recognizing that, when you use AI tools, you are able to do more on your own. And it feels very conversational. You know, like if I’m using ChatGPT as almost an assistant, and I’m starting to brainstorm with, what is a bot, is that taking away from the time I’m collaborating with people. And this, our prediction is, there’s gonna be this pendulum switch to, it truly is not, the quality, like what you get out of ChatGPT, what you can get out of AI tools is sometimes the kernel, the inspiration, you can automate remedial tasks. But when you need to elevate strategically, and really start thinking about where do we deliver higher value? Where do we start to measure and organize differently? That’s a person-to-person. That’s creativity in order to truly innovate. And I feel like the same thing is true here. In order to truly help people feel, included, and involved, and collaborate, you can’t just do it digitally. Like there has to be some element of people physically coming together. Do you agree with that, or do you think you could be just as effective remote or online as you can in physical spaces?

Kathryn Landis: I think you have to be, you have to work a lot harder, a lot harder to be as effective in person as remote in terms of collaboration. I’ve seen it done, I’ve done it before, but you have to really be tap dancing, to make sure you get that level of engagement that inherently happens and when you are in person.

Tessa Burg: That is interesting. So what have been some of your observations as to, when companies decide to be more intentional or invest, like what are they seeing that says to them, okay, as a leader, I need to take a step back, and I need to be more intentional about how I spend my time, whether it’s online or in the office.

Kathryn Landis: A big, you know, indicator, unfortunately it’s a lagging indicator. Our, you know, employee engagement scores. When they are low, and it’s low because of, you know, particular generations. They’re starting to slice the data that way. You know, when they are having high turnover, or they are hiring people that just don’t work out. You know, some of the things that people don’t talk about as often, is what are the working norms in the organization? You know, if you expect employees to be there from nine to seven, say that on the interview. You know, what I also hear from, you know, leaders is that, it is just implied. You know, I’m joining, I’m hiring for a top-tier law firm in New York City, what do you think, we’re not gonna work 12 hour days? Like that’s just how it is. But I think being more explicit and making sure that you are hiring the candidates that are gonna be a fit for your organization, and being very clear about who are those employees that are just like in marketing your ideal customer profile, your ideal employee profile, and seeing how you can get closer to that. I also think that, you know, with every generation people freak out. So for all the thoughts are happening about Gen-Z, you could insert millennial, and there’s lots of articles about, you know, the rise of millennials and how millennials are going to disrupt the workforce. And we’ll never get, it’ll never be the same again. You know? Yeah, the workplace changed, but we’re still here, right? So, you know, let’s also think about what are the benefits that Gen-Z is bringing. And maybe some of that is work-life balance. You know, maybe some of that is taking better care of yourself, introducing mental health needs that, you know, a lot of times the older generations never recognized, never acknowledged and kept moving through.

Tessa Burg: Mhm. It’s funny you say, in some of those conversations you can insert the word millennial. I’ll never forget when some study came out, that said millennials multitasking is the reason that they’re entitled and terrible workers. And at the time I was the only millennial in the department. And so everybody was like, because you had a computer and you chatted on it, and did all these things, now you’re completely ineffective, but think you should be promoted tomorrow. Like I don’t think that. And we have a company chat, like you all have chat and you are all using it. So I don’t know why my use of it is so different. But it was really funny the way people reacted to a study and started to project immediately. And I was at a talk soon after that where, an older gentleman, who was the founder of a company, I wanna say it was an AMA event. And he read all of these headlines, and everyone in the audience was rolling their eyes like, that’s right, that’s what’s happening now. And then at the end of reading these headlines, he said, that’s from a hundred years ago. He’s like, if there’s one thing you all have to learn, is that the challenges we are facing today, we’ve already faced and solved. And don’t take the information you see right now, as the only time this truth has occurred. Look at how this truth has occurred in the past, in order to find a path forward. But I think it’s like very true in the generations. While there are clear differences in values, the way in which you approach it, through empathy, through trying to understand and evolve, is the same. Like the need for empathy and evolution, is still the requirement for progress, creativity and moving forward. But what are some of the obstacles to that? Like what are some of the differences that people just can’t seem to get over? What do you see actually blocking that progress?

Kathryn Landis: I think it’s, I think people don’t talk about talking at work. And what I mean by that is, how do we wanna communicate? You know, and what is appropriate levels of communication? It sounds so basic, but I had a leader tell me that, you know, she was checking in on progress on a deliverable, and her employee sent her back like the emoji of someone painting their nails. Which I guess that means like, oh that was easy, already done. Like, but that leader was like, what is this? Totally unprofessional, I don’t get it. And so, that’s one extreme. But also, you know, understanding what’s the right time and place to bring up issues. I had another leader that was telling me last week that someone had an issue with one of the policies and so they sent an email, and CC’d the entire board of directors and the entire c-suite to it. And just went from, you know, escalated from A to Z. But you know, they felt like their voice needed to be heard and that was the way that you went about doing it. And when they spoke to the person about it, they had no idea that maybe wasn’t the most effective way to go about it. They hadn’t even approached their direct manager about it. And so, I’m giving you some real life examples where, you know, just being cognizant, and talking about, okay, what is productive communication at work? What’s unproductive communication at work? And what do we wanna change about the way that we work with our peers, our direct reports, our leaders? And coming to those agreements can be so powerful. You can do this in a couple hours, and really set the stage, you know, for the next six months to a year, until you have someone, you know, significant number of new people you might need to, you know, re-adjust. But working norms are more important than ever before. Particularly because, we’re running so fast and technology enables us to be always on, which is also a choice, for working in those working norms as well.

Tessa Burg: So if the listeners are thinking themselves, I’ve seen some of these real life examples play out, I understand that, we need to do a better job creating working norms. Where do they start? Like who needs to have buy-in, who’s actually documenting or setting these working norms, and what’s the best way to communicate that out and validate that it’s landed. Especially in multi-office, large company, remote work environments.

Kathryn Landis: I mean, ideally you would start with your direct team, right? You would talk about, you know, what is unproductive and productive communication at work. You would talk about, you know, what’s the worst team and the best team you’ve ever been a part of. Getting people to start visualizing what the differences are. And it doesn’t have to be just at work. It could be at school project, it could be your softball league. Everyone’s been on a bad team, and all of the negative feelings that go with that. And everyone’s been on a great team, right? When they feel like one plus one is equal to three. So getting everyone’s perspective on, how do we get to be the best team? How do we need to communicate with each other? It’s so important to, I would say, do it as a collaboration versus just telling someone, because people bristle at expectations. Ugh, that’s another thing from corporate. Ugh, leadership just telling me I have to do it this way. But if they come together, right, and they’re making agreements about things, that can really transform your organization. And it’s hard to start really broad, but you can train the trainer and try to even go down to the micro level, because people will be the most engaged. Why? Their relationship with their direct manager, and that they have a best friend at work. So start small.

Tessa Burg: I love that, because you highlighted that there is this mistrust of like big corporate machines or things coming down from somewhere, where they don’t feel they have a voice or they don’t feel they have an impact. So if I’m sitting here right now, and I’m even a manager of a few people, I can start to make a difference today, just by starting to get that feedback and starting to set norms on my small team and potentially create bright spots that do start to ripple through the organization. As opposed to being like, we need our CEO to come out and make some big statement. Like it’s just not gonna land the same, because no one and the Gen-Z generation had any input. They might not even understand why that statement’s being made, where it’s coming from, how to apply it to their life. But starting micro, and having conversations and listening first, will allow them, the managers first to understand and build that empathy. But two to start from a place of shared values, not differences.

Kathryn Landis: Yeah. And that’s change benefit 101, right? Getting people’s thoughts, and buy-in, and excitement for the change. And so, for generations that do not appreciate top-down communication, right? And just being force fed decisions, right? You certainly don’t wanna do that with your working norms and how you’re gonna work together.

Tessa Burg: Mhm.

Kathryn Landis: It’s like almost exasperating the issue. And I would say it’s almost like the Wizard of Oz behind the curtain, but that outdates me. Because I realized from one of my classes at NYU that people haven’t watched the Wizard of Oz. It’s like, I am really, am I really that old? I can’t use that reference anymore?

Tessa Burg: That’s funny. My kids have watched The Wizard of Oz. I love that movie. There’s so many good lessons in it. But, so, when I’m thinking about the older generations have to do work, we have to take responsibility, you have to create these places of empathy. When I am saying older, meaning like older millennials, Gen-X, boomers, is there any responsibility or anything that people entering the workforce should start thinking about now? Or how can they, I have a, my youngest sister is going to be a junior in college, and she’s always asking like, what should she be doing to prepare for entering the workforce? Like what advice are you giving to them?

Kathryn Landis: It’s a great question and I think a lot of times folks that are entering the workforce haven’t had professional conversations before. You’d be shocked how much I have to coach up my students to network, which is like this shock, horror, scariest thing they’ve ever done. Which really is just a conversation. And so to the extent that younger generations can dip their toe into talking to a friend of their parents that might have a, you know, a role that they might be interested in, or you know, just flexing their muscles of getting face time and having conversations with people that are in the workforce. It can really go a long way to making feel more comfortable when they do start at work, and they do have, you know, communication in a more professional environment. So you’re not starting from scratch.

Tessa Burg: Yeah, I love that. Good, that makes me feel good about some of the things I’ve been telling her. I do feel like the same way I appreciate a lot of Gen-Zs, want to have a side hustle and become entrepreneurs. There’s no substitute for real experience. And so there’s no substitute for having those types of conversations and leading with curiosity. And one thing I’ve observed about the Gen-Z generation, and even when I am in a group with my sister and her friends, is their FOMO is extreme. There’s an approach to conversation from what might I be missing or what am I missing for me, and not, I am super curious about what could be happening in this moment, what could be happening with this person. And I think having professional conversations can start to help move from, you know, just a younger mindset of FOMO to leading with curiosity, and wondering and learning through, the what’s possible, and not, the what I missed.

Kathryn Landis: Mhm, or what I should be doing.

Tessa Burg: Yeah.

Kathryn Landis: What do I wanna do? You know, what seems interesting to me and what can I learn about the paths forward, that get me excited?

Tessa Burg: Yeah, and it’s, I think, you know, social media has changed wiring for the younger generation so much. It’s just another piece that we have to start to give the younger generation something to be curious about, and letting go of the should and missed. Because it is very, very overwhelming. And we’re also the same people who created the platforms that do that. So it’s, you know, accepting that responsibility and thinking about, what could be exciting in those experiences, and mutually beneficial.

Kathryn Landis: Mhm. I mean, I will say I have been working with several companies who are investing in their Gen-Z employees and helping them with, you know, early career fundamentals, where we are helping them learn key skills, how do you network internally? How do you manage up? Things that you don’t learn at university or in a trade school, but are incredibly important. And then coupling that with group coaching, because then they feel like they have a cohort, that people that they’re learning together, and they can apply it on the job. And that can be incredibly effective to help Gen-Z, leapfrog, you know, some of the, I was gonna say missed opportunities, but I don’t wanna rub in the FOMO. Some of the,

Tessa Burg: Yeah.

Kathryn Landis: you know, experiences that, you know, correlate with being in person.

Tessa Burg: That is great advice. Actually this whole conversation has been very rich, with insights and opportunities to take some very accessible next steps. If the listeners want to learn more from you or contact you, what’s the best way to reach you?

Kathryn Landis: You can reach out to me on my website, kathrynlandisconsulting.com. I would ask you to follow me on LinkedIn. I have a blog that comes out every other week on LinkedIn as well, where I’m talking about the real topics that marketing leaders like yourselves are thinking about. And sharing, you know, what’s happening, what advice and actions they’re taking. I also have a quiz that might be useful for you all to help you measure how effective is your team. Because there’s six conditions of a highly effective team and if you have those six conditions, you’re 80% likely, that contributes to 80% of your effectiveness. So that might also be interesting for your listeners as well. So a few different call to actions if you will, but depending upon how interested you are, happy to make all this available.

Tessa Burg: That’s awesome. And that’s a really useful tool. So as you start to have these micro conversations and look at, you know, where can we start small and build. Being able to measure it using a tool, is always really helpful.

Kathryn Landis: Yeah.

Tessa Burg: Yeah, so thank you Kathryn, really appreciate you being here today. I hope you enjoyed it.

Kathryn Landis: Thank you for the opportunity. I could talk a long time about this topic, so, I appreciate the time and look forward to hearing from some of your listeners.

Tessa Burg: Awesome. And if you want to hear more episodes from Leader Generation, you can find them at modop.com That’s modop.com This episode will be posted there along with the links, and the show note, and the transcripts. And then, until next time. Have a great week.

Kathryn Landis

Founder and CEO of Kathryn Landis Consulting
Kathryn Landis

Kathryn is the Founder and CEO of Kathryn Landis Consulting, a global executive and team coaching firm dedicated to helping leaders empower and inspire teams, and become the best version of themselves in work and life. Her insights and strategies have gained recognition in prestigious publications such as the Harvard Business Review, Forbes, and Fast Company, further establishing her reputation as a highly sought-after expert in her field. Follow her on LinkedIn and subscribe to her newsletter: Your Future, Your Work.