Leading the Multigenerational Workplace | On Connection

Transcript

Transcripts are generated by machine learning, so typos may be present.

Emma Rose:  Hello, and welcome back to On Connection. There are now up to five generations working together in organizations, making today’s workforce the most age-diverse in history. Yet only six percent of organizations believe their leaders are equipped to manage this dynamic effectively. Millennials are now the largest workforce segment. Gen Z is reshaping expectations around flexibility and the purpose of work, and generations that are later in their careers are retiring later and later. 

The leadership challenge isn’t just about navigating age differences. It’s about fostering cultures of communication and adaptability, turning that diversity into a strategic advantage rather than a liability. While these differences can lead to conflict and misunderstanding, they can also create novel opportunities for innovation and high performance. Some of the most common places people observe the challenges of generational difference include fragmentation in expectations and norms around communication, increasing interpersonal friction, and slowing decision-making, varying views on how and where we should work, which we see in the remote, hybrid, in-office debate, and the challenge of aligning expectations around the use of digital collaboration tools, differing developmental needs, creating a need for adaptable approaches to both management and feedback, expectations around work ethic and productivity, along with seemingly different values of the role of work in the context of our lives. 

Generational labels are generalizations, tools for pattern recognition, and a way to organize what we observe. Human beings evolved to make meaning out of information fast and with as little cognitive load as possible. Social categorizing creates a sense of predictability and order that is far less exhausting than deeply individuating every person we meet. We also form emotional attachments to those categories. This is a core aspect of social identity theory, which explains how people define their place in society through identification with groups, leading to in-group, out-group preferences and biases, which then boost self-esteem. These biases become the lens through which we judge or assess others, and this happens largely unconsciously. We may form them through our personal experience, or we get handed those beliefs through cultural messaging or the stories other people tell. This cognitive process does have its benefits, of course. 

Generational categories help us explain common attitudes, values, and behaviors that emerge from shared experience and context. They help organizations leverage data to anticipate shifts in expectations that impact things like talent attraction, development, and retention. They’re helpful ways to segment data for market and consumer research, and they can help with adapting communication and leadership strategies to different populations. They are not, however, universal truths. Anytime these labels become a way to place blame or perpetuate disconnection and misunderstanding, they’ve lost their value. 

Today, thirty-six point eight percent of Boomers and thirty-nine point seven percent of Gen Zs report age discrimination at work. Generational stereotypes like Boomers are resistant to change or Gen Z lacks resilience amplify friction and erode trust, limiting collaboration and performance. To cultivate an aligned and high-functioning organization, leaders need to create spaces of mutual respect and connection, even where values or perspectives may differ. 

In today’s episode, I’m joined by Mickey and Robin to explore this challenge and offer a different mindset that can better support those in leadership positions and beyond in collaborating more effectively across age bands. It will come as no surprise that this requires a level of self-awareness and willingness to be curious about the individuals you’re working with, seeing generational assumptions as perhaps helpful tools or data, but not the full picture of what motivates or shapes a person. These same ideas apply whether we’re talking about generational biases or broad judgments about whole teams or business units in an organization that lead to siloed behavior and increased friction in cross-functional efforts. We have to constantly check our assumptions and amend the stories we tell about others if we want dynamics to improve. 

We do have a few resources in the show notes for you, including a generational profiles document that you’ll hear us referring to throughout the episode. Because we each can represent three generations, Boomers, Gen X, and Millennials, we spend the majority of our time talking about those groups with a light touch on Gen Z. We recognize that many of you may have Gen Z employees that are central to your management challenges, so take a look at the summary information in the document for that population and consider asking them questions similar to those that we offer in this episode. 

As always, we’d love to hear about the challenges that you’re up against or topics you’d love us to explore. So please feel free to send us a note at onconnection@conversant.com. And without further ado, let’s get into the conversation. Hello, hello. Welcome back to On Connection. I’m joined by Mickey and Robin once again. We haven’t actually had a recording together in a while.

Robin:  I was gonna say, it feels like it’s been a long time.

Emma Rose:  Long time. I actually don’t think we’ve done a recording since The 10 Laws. Really? Holy moly. I know. So for those of you listening, if you haven’t checked out our video series on The 10 Laws, it’s The 10 Laws of High Performance Collaboration, and Mickey and Robin were both very involved contributors in that. So please do check it out. We’ll link it below. But anyway, now we’re here again. We are gathered here today to talk about multi-generational workforces and all the different challenges that may arise for leaders and employees in those workplaces. And, we are a multi-generational crew here. That was sort of one of the initial ideas of having this podcast. We had a very, very early on conversation about this topic, when we started the podcast, it was maybe episode two or something, and it’s been four years. So the world has changed in four years, and we might have some different things to say about it now, but it does seem to continue to be something that’s on the minds of the people that we meet and work with. So I’d like to start by just naming what is it that you see as some of the core challenges that you’re hearing from leaders in the environments where we get to engage with them, and, maybe some examples of some of the things that they’re grappling with. Robin, do you wanna start?

Robin:  Well, I’ve been in a lot of executive rooms over the last six months, probably more than that, but over the last six months in particular, this does seem to be a question that comes up frequently. How do you handle the different generations? How do you handle the different generations’ perspectives? How do you motivate the younger generation? That question comes up very often. I was at a networking dinner not that long ago where the guy sitting across from me was like, “What is with the millennials?” was the way he opened the conversation. So I think there is just an ongoing discussion around how… What does the workforce look like today?

Robin:  It is different four years later — five years post-COVID, and the impact that that had on each generation, I think, is slightly different, and then how we bring that into the workplace, I think, does impact the way that we work together and collaborate and influence one another.

Emma Rose:  What about you, Mickey?

Mickey:  Well, in particular, if I’m looking at what’s recent, I’m involved in executive succession conversations in a few different organizations at this time, and almost all of them have got a template of potential successors for these senior positions, and they have things like ready now, ready in an emergency, ready in one to three years, ready in three to five years. Well, the really savvy places are then going, “Well, what are we doing with them in that three years to have them be ready?” And what I’m seeing is there used to be templates for that. Well, these are the four things they need to learn and how they need to learn them, and if they do that successfully, they’ll be ready in three years to be the next CFO or whatever role they’re targeting. And what they’re running into is there actually isn’t a standard developmental path, and people are talking about generationally how that’s different.

Mickey:  Like, getting somebody in different generations to actually advance — it’s not working like, “All God’s children, this is the recipe.” And so that’s where I’ve been hearing about generational issues: the learning solutions don’t automatically apply across the generations. I think it’s been interesting to have to look at how, developmentally, we may have to connect with people in different ways in order for them to advance. So it’s an interesting question, and it’s showed up as a repetitive issue in these different organizations.

Emma Rose:  Yeah, I think, what comes up for me about that that I have noticed is that what people need in order to succeed may be different, whether that’s a developmental track or even just stepping into the things that they’re already accountable to. I spend time both in senior leader rooms, and with some more emerging leaders. So I’ve been in coaching conversations recently with people that are more mid-career, early career, or more senior, and I think all of them have this challenge about how do I help my team be successful, especially when there’s all these different needs it seems like they walk in with. And some of that does get put into these generational buckets or labels. And I think in some ways, the generational labels help make sense of what’s going on for those people, but in a lot of ways they also hurt just seeing that individual for what they need. One of the core challenges I’ve heard from people also is this, how am I supposed to spend enough time with each individual person that I understand what they need? And is that really my problem, or do they just need to step into what the organization is asking of them or step into a standard for performance?

Robin:  One of the things on that that I’m just sitting here wondering about listening to the two of you, and this is not a case for back to office, so what I’m about to say could sound like that.

Robin:  It is not, ’cause I think there’s a lot of value in hybrid work or remote work. However, I would say Mickey and I probably, for the vast majority of our careers, did not actually have a remote work alternative.

Emma Rose:  Option.

Robin:  Was not, was just not even a possibility.

Robin:  And so some of that connection, you got just walking in the hall. Like, it was a, it was just a lot more available to you. And Mickey, even when you started talking about the, what people need, my recollection was that so many of the nine-box exercises or whatever you were doing for succession planning was a lot about technical skills, what additional technical skill or technical experience that people need. And what I hear more today is more on the leadership skills — the social skills or the strategic skills — which I think is what makes some of that planning a lot more difficult because it’s not like, hey, they just need to go and, and have a P&L, that they’re responsible for for the next three years. It’s actually something else that’s missing for, some of the folks. They have the technical skill.

Robin:  They don’t have some of the leadership skills because they haven’t been in rooms with people.

Robin:  I was with a group two weeks ago, really large financial institution. There were people in that room who have worked closely together for five years who had never met.

Robin:  Because they’ve gone so far to remote work, right? And so I wonder, again, this is not, advocating for it, but I think as we start talking about some of the generational differences, how we work has also changed pretty dramatically over the last, decade.

Emma Rose:  Yeah. Well, and I think one of the things that I’ve noticed in particularly the Millennial and Gen Z space, and then now, this is a producer question. Guy, what, what’s the, what’s the Gen Alpha is below Gen Z?

Robin:  That is the very uncreative name they are calling it, yes.

Emma Rose:  Okay. All right.

Robin:  Like Gen X or Gen Z was creative? I don’t know. Gen X had something.

Robin:  Gen Z and Gen Alpha both are… Anyway, I’m not in this episode.

Emma Rose:  Okay. But there’s another generation coming up, right? And that they’re also being shaped by how the world is currently playing out. But something I’ve noticed is related to the remote work piece and related to other things that people generalize about the younger generations is, I think some of the complaint I hear is that they don’t know what they want, or they don’t, they don’t know how to develop the same work ethic that we expect. They aren’t as focused as we expect. But circumstantially, one of the things that that generation has gone through is a whole lot less structure and a whole lot more choice in the options, right, of what your work day-to-day looks like. And so I think that has more people considering how do I find a job that serves my life on a day-to-day basis, feeling the way I need it to feel to feel good, rather than just fulfillment from a purpose or from meaning alone. There’s a lot more practical need that I think is starting to come up for people. And when I hear this complaint — I was actually having a coaching conversation with somebody a week ago about a Gen Z employee that they’re struggling with around work ethic and accountability — they’re remote, and so not having the same oversight into what they’re spending their time on on a day-to-day basis, and all that you experience is it seems like they take a lot more time to do the things. Well, this is probably their first or second job out of college. They were part of the generation that was remote during that educational experience, not in a fully structured environment. And so they’ve been left largely to their own devices to develop some of that discipline or the day-to-day understanding of what they need to succeed. And if you can think back to when you were 21 or 22, that’s not a given.

Emma Rose:  Like, we didn’t just, take a pill at some point and suddenly we were really responsible about our work ethic. You learn that so much, but people don’t have the experience of getting to be in an office where they’re learning that from other people or there’s this structure holding them to it. But to move away from some of the Gen Z and younger space and to kinda play with this thing about how does it feel and what is the value or maybe waste, as we would say, of the labels or the generalizations, do you mind if I, if I test something out with you both? Okay, so we’ll start with the Boomer. So the Baby Boomers, 46 to 64. That covers the years 1946 to 1964. So we pulled what AI, through some prompting and spending a lot of time with it, getting some research on all these generational differences and everything, what AI would say the core purposes, things that they care about, concerns, things they’re worried about, and circumstances are that shape each of the generations. So I’m gonna read you what AI has said about your generation, Mr. Boomer, over here.

Mickey:  Oh, okay.

Emma Rose:  Okay. So for Baby Boomers: your core purposes are defined by hard work, loyalty, and leaving a legacy, and you thrive on teamwork and structured career goals. Hold please for a reaction until I finish. Your concerns are about retirement readiness and financial anxiety, as well as worry about being perceived as outdated or a burden. And circumstances: grew through post-World War II expansion, civil rights, and employer loyalty. 2024 to ’25 data shows Boomers working past retirement are doing so for financial and identity reasons. So if we pause there, how did it feel, me telling you about you?il I finish. Your concerns are about retirement readiness and that that stirs financial anxiety, worry about being perceived as outdated or a burden. And then circumstances grew through post-World War II expansion, civil rights, and employer loyalty. 2024 to ’25 data shows that Boomers working past retirement are doing so for financial and identity reasons. So if we pause there, how did it feel, me telling you about you?

Mickey:  Like some of it was personally resonant and some of it was not.

Emma Rose:  Okay. And what were the things that felt personally resonant to you?

Mickey:  Well, I’ll start at the bottom at the concerns. You know, the worry about being related to as outdated, beyond your expiration date. You know, that’s very rarely conscious for me.

Mickey:  Pardon me, I’m laughing because I was making an inappropriate stroke of the microphone.

Robin:  Just trying to help.

Mickey:  Yeah, thanks.

Emma Rose:  We caught him. We caught him.

Robin:  Help you keep a promise that you made.

Mickey:  That’s right. So that’s true. You know, that there’s something that’s rarely conscious about it — but when you just said it, it really resonated. I don’t wanna be seen as outdated. The other thing that did resonate is the issue about legacy, about wanting to create and impact something that endures.

Mickey:  You know, that’s definitely true. Loyalty, I don’t often think in the terms of that word. So the way it resonates for me is something like time-tested, battle-tested relationships.

Emma Rose:  Okay.

Mickey:  Like, what really resonates for me is the relationships that last for 15, 25, 35, 40 years, where you know you’ve been through enough together that you’ve seen beautiful and ugly, you’ve seen happy and sad, and brilliance and idiocy.

Mickey:  So there’s something about the sticking with a relationship that feels true to me through good times and bad. And if you wanna call that loyalty, but sometimes loyalty to me has a kind of a thoughtless expectation that I don’t like. The thing that did not resonate for me i- is What was that about structured goals? It was like

Emma Rose:  Yeah, thriving on teamwork and structured career goals.

Mickey:  The teamwork’s true. I mean, the sense of community — I just think it’s the source of energy, as far as I’m concerned. But I’ve never had structured career goals. My career only makes sense in reverse, if I look back through it.

Mickey:  ‘Cause what I was absolutely certain about in high school and going into college is I was gonna be an attorney, a successful litigator.

Mickey:  Never happened. And all the things that I lived my way to were like voyages of discovery. So I did not have some structured career goal thing. If I look at the other circumstances that really impacted me, I would say the Vietnam War was absolutely huge.

Mickey:  Because up to that time, it felt like whoever was in authority, I automatically trusted. But my experience going through that time was that all these people in authority don’t know any better what to do than the rest of us. It felt like there was no “let me just look up and trust whoever’s older and smarter than me.” I was just looking for who’s in charge that I can learn from and respect and support. So I would say that impacted me deeply — moving from assuming the wisdom of authority to learning to think for myself. That was a huge impact.

Emma Rose:  Yeah. Robin, what did you hear of yourself in what he just said, even though you are Gen X, correct?

Robin:  Well, it’s interesting because one of the things that Mickey, what you were saying about loyalty — I have a deep sense of loyalty. I don’t know if that’s generational. It’s just in my DNA. My family has a deep commitment to being loyal, and I’ve stuck with jobs way longer than a lot of folks in my generation, although I think that’s actually pretty common.

Robin:  Similarly, my career only makes sense in reverse. If you’d asked me, from where I started, whether I’d end up here — this was not foreseeable. There was just not any possibility of that. And definitely working in community resonates with me. I’ve mostly worked in jobs where I’ve been with other people, and when I had my own solo coaching practice, those were some of the loneliest years of my life — probably the least satisfying part of my career. So that definitely resonates.

Emma Rose:  Did you learn anything new about him, listening to him there?

Robin:  Well, the thing about loyalty was really fascinating to me listening to him talk about that ’cause I would’ve been like a hell yes on that for you, just having watched. And so to hear the way that you sort of parsed that apart was fascinating to me, and I see it, but I would’ve just been like, “Well, check the box yes on loyalty.”

Mickey:  I think it’s just because I get concerned about how loyalty is interpreted from people from different vantage points.

Mickey:  So the way you just spoke about it, I am a hell yes. But I hear people get concerned about this assumption of loyalty.

Mickey:  Like, the test is your faithfulness to me —

Emma Rose:  Which is really a form of power over another person.

Mickey:  Yeah, that’s right. So I just get worried about what it triggers — including multigenerationally. I guess what I was triggered by is I don’t want the assumption of loyalty.

Mickey:  I think there’s something earned, and I was clumsily trying to say that how that’s earned is over time being able to stay with each other through good times and bad.

Mickey:  In fact, some of the mistakes I’ve made in my career are staying “loyal” too long without examining whether something wasn’t what it could or should be. I waited too long to deal with performance issues. So I guess I just want loyalty as a commitment and not as an assumption.

Emma Rose:  Yeah.

Robin:  I also thought this, the thing that you said about the Vietnam War, my dad served in Vietnam, and he doesn’t like to talk about it, so I don’t know that much about his experience there. But your sort of point of view of really entrusting authority up until that point and then having a realization that, yeah, they don’t know what the hell they’re doing either, is, was really interesting. And I think it’s telling about even the way that you are with leaders today, right? Around the, leaders that we deal with that, they want to think they have all the answers, and you being one to very quickly help them remember that it’s probably impossible for them to have all the answers.

Emma Rose:  Well, we’re gonna move on to you next, but I’m gonna do a little transparent facilitation for the listeners so they know what we’re doing here. ‘Cause the whole point is, yeah, there’s all these labels. Some of it might be true and resonate with an individual, or it might help you make sense of a group of people that you’re trying to grapple with. But the seeking out these points of connectivity or new understanding about a person is part of what has them feel like they have a place in whatever the space is that you’re in. So organizationally, othering and labeling, void of some of the curiosity, likely isn’t helping your case if you’re struggling with some of this multi-generational management. Robyn, okay, so Gen X is 1965 to 1980. Purposes: seek autonomy, work/life balance in bridging roles. Concerns, burnout from dual caregiving and career, feel overlooked in favor of Boomers and younger generations. And then circumstances, raised amid economic upheaval, rising divorce rate, and an early technology wave. Surveys show high stress, slower promotions, and mixed support. What of that resonates with you or does not?

Robin:  Well, I think the overlooked comes from being the first generation of the latchkey kid, and I was a latchkey kid. I didn’t feel overlooked as a kid, but I get that overlooked thing because I think what we’ve been seeing as a result of Boomers retiring later is that a lot of There’s been less upward mobility — there’s been no places for the, Gen X’s to go inside organizations, right? So you see a lot more mobility and job hopping, I think, among Gen X than you did Boomers ’cause you have to go someplace else if you wanna get a promotion.

Emma Rose:  Less upward mobility.

Mickey:  Oh, that’s interesting.

Robin:  And that was really part of what I grew up believing, is that salary compression would be real — that I would reach a point in every organization where I have to leave in order to get to whatever the next thing is ’cause there is not a next thing here. And so that was just what I believed about work. I have been here 15 years now, so, we’ve been able to break some of that here at Conversant, but, my jobs before that were definitely part of that pattern.

Robin:  The burnout thing is a real thing. It’s really interesting because, and we’ll, I know we’ll talk about this in a minute, Millennials talk about it as wellbeing, and you will hear my generation, and myself included, we only talk about it as burnout.

Robin:  I think we’re after the same thing, but it’s really interesting, the language. Like, wellbeing is not a phrase that you hear come out of my mouth most days, but you will hear me talk about, burnout and what that feels like.

Robin:  And not very many solutions to it, by the way.

Robin:  There was something that you said, though, that I was like, “I don’t even know what that means.”

Emma Rose:  Bridging roles?

Robin:  Yeah, I wasn’t sure what that meant.

Emma Rose:  Well, we’d have to look it up. But I would imagine it’s about how one role gets you to where you wanna go, or maybe thinking more into the future, or beyond your current role.

Robin:  Maybe.

Mickey:  I actually think it refers to the different roles you play in your life.

Emma Rose:  Or more beyond your role

Robin:  Oh, okay.

Mickey:  Like, you’re a mother, and you’re an engineer, and you’re a friend. How do you have all those roles get cared for?

Robin:  I think what has changed is that some of that around bridging roles — really, when I was younger in particular, there were not very many women in leadership. This bridging role was very real.o this bridging role So I remember having a very distinct conversation with a colleague when, the kids were little, and I was working in a director role, and I said, “I have to leave ’cause I have to take the kids to the doctor.” And he said, “Oh, my wife does that.” And I said, “Right, I am the wife.” Right?

Robin:  And so there was this whole tension around it. I don’t think it happens the same way now.

Robin:  Right? But it was like, “What do you mean you have to leave to go do this thing?” The gender roles were so concrete in that moment in time, which doesn’t show up in these generational profiles, but I think was true.p in here, but I think was true.

Robin:  So if that’s what that means — for me, it doesn’t resonate quite as much, because I’m very lucky about the sandwich situation. My parents are quite healthy.

Robin:  And so I haven’t had to deal with that. I imagine it’s on the horizon, and my dear sister is much closer geographically to our parents and is also a medical professional, so she’ll likely deal with much more of that than I will. So I don’t think about it as much.

Emma Rose:  What did you s- hear of yourself or learn new about Robyn in that?

Mickey:  Well, it makes so much sense, I’m surprised it felt new. But when you said that about living in an environment where the, what people sometime pejoratively call job hopping, ’cause I noticed I’ve had lots of times I look at resumes and I’m going, “That person was only there a year and a half, and then they were only there three years, and then they were only there ” You know, what bad thing does that say about that person? You gave me a different perspective there. Because it’s true that Baby Boomers have stayed at work longer relative to previous generations, and I just hadn’t considered that that’s one of the ingredients in all that job mobility — that in order to progress, you’ve gotta go where there’s not a ceiling. That really struck me.

Emma Rose:  Well, and it’s another example of how a generation impacts another generation, right? That we don’t all live in a vacuum. It’s not like millennials decided to be millennial-esque on their own — void of circumstance.

Robin:  Are you sure? No, I’m kidding.

Emma Rose:  But it is — it goes hand-in-hand with the thing that when we see a flaw in our relationships with other people, we tend to blame character.

Emma Rose:  But they personally would blame circumstance for whatever that breakdown was. And I think the same goes across generational boundaries too, that some of this conversation we’re in, and some of it is meant to be funny and flippant, but it comes from a real place of frustration and friction, which of course happens when you have any group of people that has a diversity of perspective or values or experience. But the sort of blaming for the way that they occur probably, yeah, again, isn’t helping your case very much. Yes?

Mickey:  I would love it if you would include the research you did with your well-prompted AI in the show notes.

Mickey:  ‘Cause I think it’s really a concise look at these generational differences, and each person can look at those and see for myself and the generation I’m in, what resonates, what doesn’t.

Mickey:  What might I think now about other generations I wouldn’t have thought before. So I think what you put together was really, really good. And I wanna make sure we have space to actually discuss, well, what can bridge those generations in order to create more value and less waste?

Mickey:  And I, so I just think people would enjoy looking at that.

Emma Rose:  Yeah, absolutely. We’ll include that in the show notes. I would encourage you to look at your own profile, see how much it resonates, and whether there’s anything new to learn. if someone were to understand you, and your motivations around work and your work life. And then I would also go right to the one that you tend to judge the most,

Robin:  Before we go to the millennial, which I’m guessing is where you’re headed — what did you learn from either one of us about the generational perspective?

Emma Rose:  Well, I think for one, there are these world and environmental circumstances that shape how people approach work, what they value at work, and then what you are, how you’re dec- making decisions in your life. I think that that’s something that millennial, myself, I resonate with. And it seems true across both of you. I think the financial anxiety thing is also true, and it shows up in the millennial one too, and I can speak to that personally. And the thing about, of course, finding meaning and purpose in what you’re doing or what you’re leaving behind, I think that makes a lot of sense and then of course bridges into what people do generalize about millennials is them seeking meaning at work. But I think that, the thing that came up for me about that was a curiosity of whether, how much of that is also age-related? And would you, however many years from now when you’re looking at retirement or whatnot, would you also be pretty concerned about the legacy that you’re leaving? And I likely would bet that I would feel the same way. You know what I mean? I don’t know that that, I don’t know how much it motivates us, but

Robin:  I was gonna say something flippant: I don’t really give a shit about you people, so

Emma Rose:  Well, you sure don’t act like it.

Mickey:  Thank you for being so successful at pretending you care.

Emma Rose:  That’s so nice of you.

Robin:  I’m kidding.

Emma Rose:  So that whole personal camaraderie and community at work — absolutely. I think that connection at work and all of that, absolutely. And I just see a lot of humanness in all of what we’re talking about. I don’t, I don’t necessarily feel that it falls just on generational linesat all, which is sort of the point of what we’re talking about. To just quickly move through the millennial one so that I’m also an active participant. So millennials, years 1981 to ’96. Purpose, seek the trifecta of money, meaning, and well-being. Thrive on feedback, career development, and purposeful work. Concerns, financial strain from debt, housing, and retirement. Prone to burnout when purpose or manager support is lacking. And then circumstances, experience the Great Recession, social media, and then remote work normalization. Yeah, I resonate with all of it. When I read it, I was like, “Oh, well that’s, fairly accurate actually for me.” The thing that is interesting, in reading this that had me actually feel like, oh, you got something right there, that I wasn’t even necessarily conscious of or would be able to articulate myself or would generalize to my whole generation is this thing about prone to burnout when purpose or manager support is lacking. And I wonder coming out of that then what you think has shaped your own development that’s unique to your generation. You know, you said this about these varying needs are on, across generations for succession planning purposes, but do you not feel like purpose and manager support was integral to your success, or what, what’s different for you?

Robin:  Well, what I was just thinking is this actually explains a couple of things.

Emma Rose:  About me specifically, or?

Robin:  Yes, we’ll deal with that later. Just kidding.

Robin:  No, about them needing manager support. If you think about it logically, it’s most likely that a millennial will report to somebody in that chain is probably a Gen X or a Boomer, probably. They may report to another millennial, but let’s just go with, in the way that the organizations are structured and how long people have been there, that there’s a likelihood of that. And both of our generations have a lot of value in autonomy.

Robin:  And so that manager support — I didn’t get a lot of that ever. It was a lot of, “Do your job.”

Robin:  “Go do the things.”

Robin:  “Go do the things, do them on time, do them well.” And if you did that, then you got more opportunity, and so that’s sort of what that looked like. The most coaching I got was when I had a manager who was terrible at all the people things, and he sort of saw that I was pretty good at it, and he was like, “Hey, why don’t you start doing all the onboarding?”

Robin:  If that’s support, that’s what it was. But there was no manual. There’s just, “Hey, we have five new people coming. Can you figure out how to get them up to speed and part of the team?”

Robin:  And so this idea of manager support — when it’s not what you experienced, you might just miss that other people need it to a different degree.

Emma Rose:  To a different degree, yeah.

Robin:  Or have a different expectation of it.

Robin:  ‘Cause I sort of assume, and I, this is not just me, I think it’s humans in general, I assume that my expectations are your expectations, that the way I expect the world to go, you have the same ones because we haven’t talked about them.

Emma Rose:  Right, and I think that’s actually probably the biggest breakdown when it comes to whatever people wanna call the challenge — whether it’s multi-generational collaboration or workplace management. It is this thing about I assume you see the world the same way I door that you have the same expectations or understanding about expectations around work, and that that’s not necessarily true.

Robin:  And then I don’t get real curious about, “Wait, you, what are your expectations? What would be helpful for you? What do you need?” Versus, “Here’s what I need.” And also, what do I need, and what am I able to provide, right? And, how do we find a place where those come together?

Mickey:  I think there’s a place that if people can be conscious about when they arrive at that place, then you can pivot to the kind of curiosity you’re talking about.

Mickey:  I think it’s really important, especially for leaders in positions of power and influence to notice the moment that they’re relating to other people like, “You shouldn’t be this way.”

Emma Rose:  Right.

Mickey:  ‘Cause that’s the real raw way it shows up is, “I shouldn’t have to deal with this from you. You shouldn’t care about this,” or, “What’s wrong with you that you huh, huh?” So this whole spirit of you shouldn’t beif you can catch having that feeling, that perspective, that’s the time to stop and take a breath and say, “Wait a minute. Where am I expecting people to be like me and who’s not is somehow invalid?” I- it’s a, it’s an important area of noticing, of awareness.

Mickey:  Before I go further down that, I want to back up to something I thought was interesting as you were taking us through these generational profiles.

Mickey:  I think it’d be great, and you could do this even virtually, to deal with the understanding that the answer to lack of intimacy can’t just be getting everybody back to the office.e saying. It’d be really interesting to host conversations where you ask people, “What are the most impactful events in your life that somehow shape who you are today?”

Mickey:  ‘Cause when I look back at that period — people who aren’t old enough to remember this, look it up, but Kent State was a huge issue — where there were people killed on campus, and it led to this uproar all over the place. I was at Tulane University, which is a real conservative spot in the countryand yet people took over the university center, burned down the ROTC building. It was just incredible. So if I just look at the reaction to Kent State, the Democratic Convention in 1968which was an incredible mess, but I’m wondering for you or for somebody el- what are the couple of those in your life that really impact who you are?

Emma Rose:  One of the things I’ve thought about in this conversation is I wonder what generational generalizations there might be about how people respond to the stress of an environmental or economic event, you know? Sociopolitical, whatever, just stress in the macro environment, and if that has any impact on how people relate to some of these things. But another question, I think that about life events that shaped you, one that sounds so basic, but I don’t think we ask each other enough, and I wonder if some of it is ’cause people in managerial positions are afraid to ask it, is what do you value or expect out of work?

Robin:  I’ve actually had this conversation with a few leaders, and they all get so nervous about asking that question, because they say, “What if they answer something I can’t do?”

Emma Rose:  I can’t do, yeah, that’s what I was thinking.

Robin:  I can’t do or I’m unwilling to do.

Robin:  It’s like, well, and what I’ve said to them is, “That not asking doesn’t make the expectation go away.”

Robin:  “It’s still there, and now it’s just being unmet, unintentionally as opposed to an intentional conversation that says, ‘I hear you. I can’t do that. What else could we do together?'”

Robin:  Which is a different kind of conversation. But they feel like any question has to be met with a yes or a no, as opposed to recognizing there might be some other alternatives between those two polar opposites.

Emma Rose:  Well, in looking at the long game of it just sounds like what we would call an easier moment to address — if it’s going to keep impacting how that person shows up. And also with these younger generationss that are trying to find a spot that aligns with what they want out of work, I would imagine having that conversation earlier just helps make sure that you have the right people on your team, and that they have the opportunity to make the choices they need. I think it’s actually an empowering conversation to have if it’s had in the right way, but I understand the fear around it.

Mickey:  I want to say something explicit that I think would naturally, Robin, be inside of what you were just saying. I want to point to something because I think it could be useful to some of our listeners.eners. ‘Cause I’ve heard this a lot too, where people in senior positions are go- they don’t wanna ask the question for fear that they’re not able to respond to it affirmatively. And when that comes up, what I recommend to people, the starting place is exactly what Robin said. Well, first, the expectations are still there and impacting the relationship no matter what, so that’s my starting place is exactly where you started. And then I say to them, “May I give you some suggestions about how to manage the conversation?”

Mickey:  And as y’all know, I don’t like to coach into a lack of request for our coaching, so that means I want them to say, “Yes, I’d be interested.” And then I’ll say, “Okay, here’s what you do: whatever they say,ur first response is not yes or no to that. The first response is, ‘Can you tell me what makes that important to you?'”

Mickey:  “And what’s important about that?” You want to get into, as deep as you can, what they’re trying to take care of — what getting that request met would actually help. Because that’s where you start to see as you were pointing to, “Well, what, what else could we do? What are other possibilities?” So I think the curiosity that’s the antidote to you shouldn’t beis really important, and it can’t be handled in just one question. What do you want, and let me tell you whether or not I can give it.

Emma Rose:  Well, and especially when that assumes everybody is very, very clear and locked into their definition of what they want instead of recognizing there’s room for influence. We’ve talked abouttalked about in the whole remote versus hybrid versus in-office debate, that your work setup is a method, and what’s the method that’s going to achieve the purpose or the results that you are setting out to or committed to as an organization or as a team? And I think the same goes as an individual. Like, what, what do I want out of my life o- or my work life experience? And then I might be attached to a method in my head until I have conversations with other people, and I learn that there might be other options available, right? That I don’t think that people are as locked in as they might seem, and even if they are, it doesn’t mean that having a conversation couldn’t help move that into a more valuable space, whether that’s them realizing, “Oh yeah, you really do feel that strongly about it, and we can’t give it to you.” You now have your agency back, you know? But being able to explore that rather than assume that it’s as extreme as I think most people do, that there really is a rift that’s gonna arise from that. And then going into this thing about curiosity, which you’re saying right here, whose job is it to be curious in these situations, would you say?

Mickey:  Well, my first response is whoever notices the lack of curiosity. Anyone at any place in the system can actually shift from, “This shouldn’t be” to, “Let me understand what this is about.” And then I’m gonna m- move this to Robin ’cause you mentioned this before we started. Perhaps the most influential person in being curious is who’s got the most power.

Robin:  Yeah, because I think it’s really hard actually. So, just put myself back to being 21, 22, right, and having a different point of view than, than my manager or boss at the time. The curiosity is hard It’s harder to come by ’cause there’s so much a feeling that you have to prove yourself.

Robin:  Right? And so curiosity, I think in too many places still feels like uncertainty.

Robin:  And so, how do we, as the more senior folks in the hierarchy — and all organizations have some sort of structure associated with them, even if that’s become kind of a dirty word.her day.

Robin:  And it’s our responsibility to actually create the places for people to speak into that judgment that they’re holding onto, and for us to get curious about it. ‘Cause I think if we just meet judgment with judgment, we know where that’s going, which is no place fast.

Robin:  And so if I can be the one that catches the, “Would they just do their damn job?” And replace it with some curiosity about what makes that hard, what’s actually happening, what’s different, what’s a different perspective than the one that I have, I think it opens up way more windows in terms of our ability to collaborate and work together. And if you are the person that has, positional authority in an organization, if somebody comes to you with curiosity, to take it, however inelegantly it may be delivered, as curiosity and not as, s- some sort of judgment or being, interrogated. And so I think people sometimes get this wrong, right, where somebody in an organization comes with a question, and I take it as somehow being judgmental or, quest- questioning me or questioning my, the decisions I’ve madeas opposed to what if I just listened for the curiosity inside of the question, and what if I offered curiosity in as many moments as I can find it?

Mickey:  Yeah, I think it’s important when you look from The view of how somebody with position power can impact this multi-generational situation — I think it’s important also to think of what are efficient ways of doing that.

Mickey:  And I’ve seen a few examples that I thought were really good. Y’all know we care a lot about Martin Lindstrom’s work, and we’ve had the opportunity to be connected with him over the years. And the book he wrotecalled The Ministry of Common Sense, and Winters, who’s the CEO at Standard Charter Bank, about they’re trying to take waste out of the system. So they started this place where people could send in, where do you see us doing things that don’t make sense? Where do you see frustration? Where do you see it’s difficult to get the right thing done? And it was enormously successful ’cause people had this place to put things, and then the senior people there, their job was to get back to them and say what they learned from them about it, and which things they could act on and by when. But it ended up being a, a process that was more efficient, where people felt that.

Mickey:  I’ve also seen more really senior executives, CEOs in several places, start to use one of the current apps in these very large sessions with thousands of people, saying, “What questions are on your minds?”nd?” And instead of having this ancient idea of you pre-program the questions and make sure they’re only the ones that I want to answer, really let people voice those, and the software will automatically prioritize something that’s come up multiple times.

Mickey:  And people see it all happen. They see the sorting going on, and you get to respond and genuinely be curious about, “Well, what has you ask that? What would make that better from your point of view?”

Mickey:  So I think doing some things that allow the spirit of curiosity between position power and everyone else in the system to be efficient is important, as well as moment to moment, whoever you’re with, can you care about what it’s like for them, rather than just comparing them to what you think it should be like for them?

Emma Rose:  Right. Well, and I think that sort of the fundamental principle underlying a lot of what we’re recommending is if you are noticing a place where there’s a wall you keep running up against, or there’se’s some chronic frustration with a person based on a generational profile or a group of people based on a generational profile, that when you notice, that’s an opportunity to lead. So whether you have power or not, that’s an opportunity for you to step into that and get curious about, “What’s going on here that I could lean into and f- and understand better and see if there’s an opportunity to navigate it in a different way than we have tried?” Or, do you wanna defer that power to somebody else and say, “Fine, that’s not my problem,” and that’s your choice. But I think the people that do have hierarchical power have a responsibility for what they’re perpetuating culturally in an organization and what stories are being perpetuated and how valuable those really are.

Robin:  I think there’s two quick things inside of that that are maybe easy to remember and hard to executebut easy to at least hold in your head. The first is: we say all the time, “Where you get resistance, do research.” And so thisesearch.” And so this really is an opportunity for, what research is there to do. And the other is, I think most of us try the same thing over and over and over again.

Robin:  And we think it’s the other person’s problem that they didn’t get it, and we don’t look at, okay, so You’ve tried to inspire the other generation the way youu want to be inspired, right?

Robin:  And you haven’t really looked at what inspires them, what actually calls them as an individual — not just as a generation, but as an individual. And so many of us try to do it the way we have in the pastt was done for us or the way we’d like as opposed to really thinking about it from the other person’s perspective. And so it’s really a do some research on, well, what would inspire them? What would what is in their way?

Robin:  And then it might take you doing it different than how it was done for you or how you would like it.

Mickey:  Yeah, I’d love to see those kind of questions become institutionalized in systems. Again, I think of efficiency as well as effectiveness.

Mickey:  Like, onboarding could include those kind of questions.

Mickey:  And, and then checking in with somebody after their first three months or six months where we’re asking those exact questions. It would be so illuminating, and a lot of organizations have those check-ins anyway, but they’re not asking that.

Mickey:  And I think, what do you find important about your work?

Mickey:  What about your work does energize you? Is there any contribution you have to make that you don’t think we’re taking advantage of?

Mickey:  You know, just really delving into what has that person feel connected to work.

Mickey:  And it brings me back to a couple things that we know in our bones. One of them is that across all these generations, one of the things we notice is people want meaningful work — and there’s something about whether you call it purposeful or meaningfulor, “I wanna make a contribution I’m proud to make,” if you look across all those profilesthey all have some- something of thatin there.

Emma Rose:  Or they want to know that they made a meaningful difference in their work

Mickey:  So the question about what holds us together across generations is really interesting, and that’s why I would love to see some major organization where people in power are funding one of these big off-sites.

Mickey:  And I see time taken on some things that are just fun, but I wouldn’t say are very meaningful.

Mickey:  What if one of these annual off-sites, you created this event that you call Generations of Intelligence?

Mickey:  And you had people get into their different generations and come up with: What is it that’s true about your generation that it’d be great for everybody else to know? And what do you have to give that you would love the rest of us to get?

Emma Rose:  Yeah. Yeah.

Mickey:  And I think it would be terrific to do that. It would be energizing, it would be fun, and it would also be valuable, ’cause there are generations of intelligence here, not just generations of difference. We could make each other smarter.

Emma Rose:  Well, and right now, a lot of the conversation is happening about a generation that’s not in the room rather than with that generation. And I do think that’s an important switch — we know that there’ss a lot that you can gain if you actually are harvesting the wisdom across those differences. And just to name the very practical challenge that we know that there are these trends in the number of people that middle managers are now responsible for in terms of their development and their accountabilities, and it might feel daunting to go, “Okay, I now have to go ask all of these people and have this whole conversation one at a time.” Maybe focus on the one you have the hardest challenge with, and trust that by investing that time, it’s actually gonna save you a lot of friction and wasted time, in the future. So we think it’s a worthwhile experiment. In the show notes, we are going to include those generational profiles in case it’s something of curiosity for you. It does have a Gen Z one in there for those of you that are primarily worried about that generation who is not represented on this podcast. Just a couple things that stand out in that one really quickly, that they demand authenticity, inclusion, purpose-driven roles, and stability, prioritize mental health and structured support via mentorship, mentorship, anxiety over job security, cost of living, climate change, AI, blah, blah, blah, isolation, and they grew up in tur- global turbulence, pandemic, rapid automation, prefer structured office environments for mentorship and community. So some of this is, challenge your assumptions potentially, and then also don’t take these profiles as a given. Go and talk to that particular individual that you’re concerned with, their performance and their buy-in and their ability to be successful in your work environment. One thing I will also just c- start closing with also is, what the intersecting purposes are that AI pulled. So a desire for meaningful work, like you said. Every generation wants to feel their work matters, whether that’s leaving a legacy, driving innovation, or contributing to a bigger purpose. Growth and development. Continuous learning is universally valued, though the format differs, so formal training versus microlearning versus mentorship. That’s where the method may shift to achieve the end. Respect and recognition. All generations want acknowledgement for their contributions, even if the style of recognition varies. So a lot of this, again, is just deeply human, and we have to remember that, and I think catch when some of those explanations come up that make us feel disempowered by whatever the rift is. ‘Cause there’s so much of it that I think we hear that’s sort of a playing victim to whatever the circumstance is around generational differences instead of, “Oh, well, what is there to be curious about, and what could we learn from it?” closing thoughts from either of you or advice to those that are s- currently focused on this challenge?

Mickey:  Well, just listening to you then, what occurs to me is, as y’all know, I have a lot of respect for Marcus Buckingham, and his newest book that’s coming out in the spring is Designing Love In. So it’ss about how you have people love their work and customers love working with your company. place, and how do you design that in? And one of the things he talks about is, critical process redesign, which I think is funny. It’s CPR. But I’m wondering, where do the things that you were just talking aboutwhere do they show up in the natural processes of work? Whether it is, like we said earlier, onboarding or, people who do reviews in certain kind of routine ways, I would just like to see the sensitivity to what’s it like for people at work and how do you connect to what really matters to them to be in the standard routines of our work rather than just a response to breakdown.

Robin:  I think the thing that’s on my mind as we sort of close out is just a word of caution. I think a lot of us don’t love the generational labels that get put on us for a variety of reasons. It doesn’t feel exactly like me. It doesn’t fit me exactly. And I think the reason we use them is it is a speed thing. It’s easier. It’s faster to just put a group of people into this category.

Robin:  For me, the thing I try to always remember is that all of us have purposes, concerns, and circumstances, and the circumstances aren’t just the ones of this moment. They’re all the ones in my life that have gotten me to this moment. And yes, I have a whole set of Gen X circumstances that shaped me — at a lot of people that are my, in my age experience similarities in those circumstances, but they’re not identical, and the same is true for millennials, and the same is true for Boomers, and the same is true for Gen Z, right? That they have all We’ve They’ve had world circumstances that had similarities that caused them to see the world a particular way, but they each had individual circumstances that might have been radically different. So to be careful about overgeneralizations and assumptions about the age of somebody, and so therefore, they must be X because they are in this generation.

Emma Rose:  Yeah. We all want to be seen — not generalized or labeled — so try to think about how that feels to you, right?

Emma Rose:  And then go and see if you can give that gift to other people, and it has been known to potentially move mountains. We’d love to hear from you.

Robin:  I know, but I’m such a stereotypical Gen X that it’s hard.

Emma Rose:  And sometimes that’s true, too. Well, thank you for tuning in. If you have thoughts, concerns, or questions about this topic or others, please reach out, and we’d love to engage with that in the future. But until then, take care, and thank you very much, Mikki and Robin. Goodbye.

Robin:  Thank you. Bye! Leave us a review. Your feedback helps others discover the show and join the conversation. And lastly, share this episode with someone who would love it as much as you did. This episode was produced by Guy Connolly. Original artwork is by Dana Buckingham, and music is by Cast of Characters. Special thanks to Conversant’s extended community who inspire the continued evolution of our work and stand with us in our commitment to change leadership, business, and the world through conversation. You can learn more about Conversant at www.conversant.com. On Connection is created and produced by the members of Conversant. Awakening the world to the power and joy of authentic human connection, we set a new standard for leadership that produces meaningful, enduring impact. Until next time.