Kim Lear: Understanding & Decoding Generations

Generational researcher and keynote speaker Kim Lear shares how you can better understand and communicate across the generations that make up your school community.

By SchoolCEO Last Updated: December 13, 2023


Generational researcher Kim Lear re-joins SchoolCEO on the podcast to discuss how you can better understand and communicate with the different generations that make up your school community—from students to teachers to parents to members within the community. Learn about the key events and cultural shifts that have shaped each generation along with their communication preferences.

Join this conversation and learn about:

- Understanding the societal events and cultural moods that shape each generation’s values and perspectives (00:06:21)

- How baby boomers are aging differently with more vibrancy, energy and tech adoption (00:11:44)

- The rise of skepticism and desire for transparency among Gen X (00:14:39)

- How overwhelmed and anxious millennial parents feel about “doing what’s right” for their kids (00:18:23)

- Communication preferences for reaching different generations (00:27:55)

- Delivering feedback that motivates (instead of paralyzes) (00:42:00)

- Being clear about desired outcomes when gathering input to avoid mismatched expectations (00:35:11)

- Fostering mentor relationships by spotting potential and proving yourself as a mentee (00:46:57)

- And so much more

About Kim Lear:

Kim Lear is a writer and researcher who explores how emerging trends impact the future of our workforce and marketplace. She is known for her ability to use a mix of data, storytelling, humor, and actionable takeaways to discuss the trends that most impact the bottom line of organizations. Previously, Kim was the content director at a research firm dedicated to generational and Millennials trends. Her undergrad research is around Baby Boomers and longevity. Her post-grad work is around Millennials and social media networks.

Kim has written whitepapers on the topics of generational wealth transfer in the finance sector, retirement trends in the hospitality industry, and Gen Z’s impact on higher education.

A researcher to the very core, Kim employs eye-opening statistics to accentuate her points and mixes them with stories and case studies to make her message come alive.  She is a sought-after expert and has been featured on NPR as well as national publications such as The Wall Street Journal, The Huffington Post, USA Today, TIME Magazine and more. Kim is currently in her fifth year of a longitudinal study on leadership.

You can follow Kim Lear on X/Twitter @KimLear or subscribe to her exceptional newsletter "Kids These Days."

Follow SchoolCEO on LinkedIn or X/Twitter @school_ceo

Subscribe to SchoolCEO at for research, stories, and strategies for leading your schools. And if you have a story you’d like to share, email us at


Kim Lear (Guest) (Intro Quote): Leaders really have to consider, am I delivering this feedback in a way that is going to motivate this person to improvement, or am I delivering this feedback in a way that's going to paralyze them? And what we often found with young workers is their decision to leave. An organization can often be pinpointed to like a first performance review where if their leader gives them some constructive or possibly negative criticism, which is fine, that's all part of learning. But if they leave that meeting feeling like maybe I was wrong, maybe I am not good at this, maybe I don't have what it takes compared to leaving having some clear next steps about how to improve, I think that that is one of the key pieces because people need feedback all the time. It's the only way to get better. But delivering that in a way that makes people want to work harder for you instead of disengage is tricky but so imperative.

Tyler Vawser (Host): I'm Tyler Vawser, part of the SchoolCEO team here at Apptegy. We publish original perspectives and research that helps school leaders build a strong identity for their schools. Along the way, we have conversations with superintendents and other K12 leaders, marketing experts, and more to help you brand and market your schools in a highly competitive environment. Published quarterly, in print and online, SchoolCEO is the only magazine focused on marketing in K12 public education, and this is SchoolCEO Conversations marketing for school leaders.If you haven't been before, SchoolCEO Conference is a one of a kind experience. Unlike other conferences that tease a single keynote speaker and make you walk through vendor booths and breakout sessions and keep waiting for the good stuff, SchoolCEO brings three of the highest quality keynote speakers back to back to back. And today I bring one of our crowd favorites, Kim Lear, onto the podcast. Kim brings clarity to what many of us experience every day as we work together, teach students, and work to reach our communities, namely, that different generations see the world differently. In our conversation, you'll get words and frameworks for better understanding yourself and your colleagues. Based on Kim Lear's research, my personal hope is that this conversation will unlock new perspectives as you reach your broader school community. 

And just a quick note, this is the third and final part of our series on Generations. First, we had Andrew McPeak talk about reaching Gen Z students. Second, we had Dr. Pete Hannigan and Samantha Cook talk about their working relationships as Superintendent and Communications Director and how they're reaching different generations within their school community. And here we listen to Kim Lear talk about generational research.

Kim Lear is the founder of InLay Insights, a research firm and think tank focused on demographic shifts and cultural evolution. Her work and her talks explore the generational trends shaping the future and how you can better work across generational lines. Kim has keynoted for Apptegy, American Express, Disney, Deloitte, LinkedIn, and so many more. Kim's work has been featured on NPR as well as national publications such as SchoolCEO Magazine, the Wall Street Journal, the Huffington Post, Time Magazine, and more. Since 2020, she and her team have conducted two research projects exploring the future of work in uncertain times. The first, a 200 interview pandemic time capsule, provided insight into quarantine work from home and the quote unquote new normal. The second 100 person interview series focused on the great resignation and tried to uncover why people leave their jobs, where they went, and what, if anything, we can do to entice them to stay. In this conversation, Kim and I discuss the most important things to know about each generation, especially for school leaders. Things like how to support Gen Z students, how we can improve one on one communication between generations, how to develop better mentor relationships, and so much more.

Let's join the conversation.

Tyler Vawser (Host): All right. Well, Kim Lear, welcome back to Schoolceo.

Kim Lear (Guest): ThAnk you so much for having me.

Tyler Vawser: You've been a keynote speaker at SchoolCEO conference three times. You've been interviewed for the magazine, but this is your first time on the podcast.

Kim Lear: I know. I feel like this is the real kind of cherry on top, so I'm grateful to be here.

Tyler Vawser: Usually you and I are chatting briefly on stage before you come up and give a talk, and then we kind of pass each other on stage as you're leaving and I'm coming back. And so I'm selfishly looking forward to actually getting more of your time instead of just chatting for five minutes and giving your introduction, getting to chat for the better part of an hour here. So thanks for agreeing to come on.

Kim Lear: Yes, thanks for having me.

Tyler Vawser: Well, this is part of a miniseries within our season two, and we're really looking at different generations and how we can better approach communication and influence and working relationships. And so Andrew McPeak was on talking about Generation Z and how leaders can support their students and help them develop those soft skills and get them ready for real life. And then we also had Superintendent Pete Hannigan and his Communications Director, Samantha Cook talk about their working relationship as a Gen X and a millennial, and then also how they're trying to reach different parts of their community. So today we get to hear from you. You're really the expert in all things generations and you're going to bring a lot of your experience and your opinion, but also the research that you bring to bear, I think, is the part that SchoolCEO has leaned on you so heavily for.

Kim Lear: Happy to.

Tyler Vawser:  Well, let's jump in. School leaders, in particular superintendents, are having to work and reach so many different stakeholders. And I think this is a real challenge for any school. But in particular, the leader is that it's not just students, it's students and teachers and staff and also parents and also community members. And so I'm curious if you can just kind of start at a high level by telling us how your research can help leaders understand those different stakeholders and the generations within that group.

Kim Lear: Yeah, I think that one reason why I love this topic, and one reason why I feel like people within education just have a natural understanding of it is because it really does do a good job of giving us a framework to explore where we've been and how we got to where we are and where we may go from here. And so from these generational lenses, we can understand shifting societal norms and values. We can understand why we can do something today, and it's totally acceptable. But if we did it 20 years ago, it would have been wildly taboo. And those things, the way that norms and values evolve, it's not totally random, right? 

There's moods change and priorities evolve, and those shifts can create some of those changes about how a new generation steps into adulthood with the different framework and different tools and different cultural expectations. And people within education, again, a reason I think that they inherently just understand this topic is because they see it all the time. I mean, you talk to a teacher who's been teaching for 35 years, and they can tell you immediately about with their students over your career, what is the same, right. Of course there's going to be so many things about students that are the same, and then what do you feel like is so different? And that is a generational conversation. That's inherently what it is. And so this lens matters because, one, it gives us some language to help us describe the reality of what we're seeing. And just in that language, it can be really powerful so that we can actually move to action once we have that. And it matters the same way that all forms of diversity matter. Right. 

It allows people to ask that empathetic question of, if I were born into a different time, would I see this differently? And it's just a simple, elegant question that I think changes our focus when we do have some differences or misunderstandings with people, it allows us to approach that more in a spirit of curiosity instead of judgment. And when you think about building a great school culture, a great community culture, that's what it's built on is curiosity and wanting to understand where another person is coming from. And so I think that's where these generational framings and understandings can be the most helpful.

Tyler Vawser:  Yeah. When we get feedback after the conference, everyone loves your talk. And I think a lot of times it's not just that they're understanding a different generation, but they're understanding their own generation. They're able to put some labels and words and frames around their own experience. And I think people come to a talk like yours and they're thinking, I want to learn about the generation below me or above me because I don't like how they do things and I want to figure out how to tweak them, but they actually are more self reflective by the end of it. Go, you know what? There's some things in me that I didn't realize, like maybe I'm this way because of this event that happened in my teenage years, or these shifts were starting to take place when I was really starting to think about who I am as a person. And so I love that about generational research is that we often come to it imagining we're going to learn about someone that's different, but we often learn just as much about ourselves.

Kim Lear: And I think that's the most disarming piece about the topic of generations. When it's done right. Is that. Again, not only do people usually come in being like, I want to hear about these other generations, they actually usually come in being like, great, I'm going to arm myself with how to fight these other. Because they're not working as hard as I am, or they won't change or whatever. And people almost come in armed, ready to get tools to kind of win arguments with someone they work with or someone in their community, but I do think that it is in that moment of reflection, I think it's always valuable for people to know that they probably bug people sometimes too.

Tyler Vawser: That's right. Well, before we continue the conversation, I think it's important to kind of pause and ask what are the most important things to know about each of these generations.

Kim Lear: Yeah. So forgive me. For those of you who are listening and have seen me present, I am going to give a quick refresher because I think it's important, which is that these generational labels, this whole topic is really rooted in sociology, not psychology. But both schools of thought are equally important, especially for leaders, where psychology, it studies who you are as an individual, and it's your brain and your relationship to your parents, the way you practice religion, where sociology. We are looking at these broader macro trends, these demographic shifts and evolving cultural norms. And so I think even when we begin kind of the categorization and looking at what would be the most important, I think it's just critical to have that framing, that, of course, people are still individual people. Right? And so this is really meant almost as another layer to understand culture and shifts and those types of things.

So for baby boomers, and I decided to just focus in on the things that are perhaps the most relevant at this moment for all of you who are listening, because there's so much that we can go into about the history of the baby boomers, the legacy of scarcity of the 1970s, the legacy of 60s activism. We could go in a million directions. But in terms of something that's happening with baby boomers right now, I think that the way that they are aging is just so profoundly different from what we saw with their parents. And the story that we collectively share about what it means to get older is just no longer in step with the way that baby boomers are actually aging. In so many pockets in America, that gap between health span and lifespan is really beginning to shrink quite a bit. And so you have people late in life filled with vitality and vibrancy and energy and a hunger for innovation and a hunger for change. And we've seen this for a long time. I mean, baby boomers were, even before the pandemic, showing some real rapid tech adoption. And then during the pandemic, it just accelerated dramatically. There were, and there continue to be a lot of baby boomers who are still in the workforce. And so they started working from home. And a lot of these technologies that initially, some of them were slow to adopt, then they did, and then you don't go back, and then you're empowered by your new skills. And so there's the tech adoption piece. There's also know I do work in economic development. And one of the things that we look at is the cities that kind of fight for high end retirement dollars. And it used to be that, like Naples and Palm beach and Palm Springs were all fighting with each other. And now they're competing with Austin, Texas, Raleigh Durham. We see some movement to Madison, Wisconsin, as baby boomer retirees want to go to places with better art and better music, more walkability, more access to higher education.

And so I think that this real reframing about what it means to age in this country is one of the most urgent things with baby boomers, because they're not oftentimes being communicated to in the right way, because we all still are stuck in this idea of what it means to age, and it is not how they're doing it. And so that's one piece that we can go into more, if you'd like, with baby boomers, Gen X. I do think that actually the events and conditions that shape Gen Xers are still, almost still need to be looked at because it's had such a profound impact on communication styles. But their formative years, one of the major things that happened when they were teenagers was the emergence of 24 hours media. It was the emergence of 24 hours news. This was 1980. Ted Turner put CNN on the air. And now that we have news coming at us every second of every day, and that's the norm, it's almost hard to remember what a transformation that really was in the early 1980s. 

And so you got these institutions that were built by traditionalists and improved upon by baby boomers, all kind of wobbling and crumbling in front of their twelve year old eyes. And so we go through this phase in history where it's WorldCom and Enron and organized religion, sports, politics, and we started to see a real rise in skepticism at this time. By the time the average Gen Xer was about 20 years old, they had watched 23,000 hours of television and they couldn't binge watch commercials or fast forward anything. And so they were really constantly being sold to. And advertising then doesn't have the same regulation as it does today. So this was also like the Wild west of advertising. 

The joke that I've told at Apptegy before, but it still makes me laugh, is when I'm in focus groups with Gen Xers and we talk about those early ads, I'm always surprised by how many of them still talk about the AB roller, which was this contraption that promised users a smoke and hot body, but it broke your back and was recalled and there was just all these weird things. So that skepticism really does remain such a steady piece with Gen Xers. One of the research areas that we focus on now is looking at Gen Xers ascension into the C suite, because the average age of a C-Suite executive in America is 56. And that's how old Gen Xers turned two years ago. And one of the things that we see is as Gen Xers move into that seat, these trends of radical candor, hyper transparency, these types of things come with them as part of that skepticism, of this kind of hunger for this honest, direct, unfiltered style of communication. And so I think that we're going to continue to see that just impact our whole society as Gen Xers become more and more in charge.

Tyler Vawser:  That part's interesting to me because when I think of transparency or openness or radical candor, I think of a generation younger than Gen X. Right, millennials, or even like Gen Z. So that's interesting that maybe it starts there. And as they move into leadership positions, they're actually the ones that are implementing something that is going to filter into other generations. Is that the right way of thinking about it?

Kim Lear: Yes, but part of it is because even the author of Grit, the author of the book Radical Candor, these are all Gen Xers.

Tyler Vawser: Yeah, I haven't thought about it like that.

Kim Lear: Yeah, because there's always a bit of a lag between when the idea is introduced and when it is adopted. And so you're right that I think a lot of millennials ended up adopting that because they grew up with some of that language. And for the ones who are fortunate enough to have really good mentors, they were taught some of those skills. But the ideas, those were very kind of. Of that Gen X Zeitgeist, of that mood. It is from that generation where those ideas originated. So, yeah, it is an interesting piece. So I think that's a big one with Gen X. We can also, later on, if you'd like, there's things going on with their life stage, but I think we can probably do that in other questions.

And then with millennials, it's an interesting time as they have become parents. I think one of the things that has been really interesting to watch with millennial parenting, I'll talk about specifically, is that the idea of parenting just really changed. I mean, the pressure of it, what a parent owes to a child, what the community owes to the parent, those are really pieces that have been explored for, I think, a lot of different reasons. So there's a lot that we can go into with millennials, especially because this life stage shift into parenting has been so interesting to watch. And so I think one of them, just on the parenting perspective, because I know for a lot of schools, this really is your generation of parents right now. One is that how lost a lot of millennial parents really feel. And you think about how one thing that we all have in common when we become parents is like, we just have absolutely no idea, really what we're doing. And so every generation of parents, when they step into this life stage, are really hungry for advice and really hungry for expertise. And so you look at, like, in the 1950s, there were many years during that entire Decade where the number one bestselling book was the Bible, and number two was Dr. Spock. And so there was a real uniformity in what we thought about child rearing. And a lot of people could just kind of move in that direction where, with the dispersion of expertise, particularly for millennial parents, there is this bombardment, there is this confusion, and there is this insatiable hunger to do what is right for your kids in an environment where it feels increasingly difficult to know really what that is. 

And I bring this up because, especially when I speak with teachers, they're like, the demands of these parents, the involvement of these parents is so overwhelming. There are times when it's like, it impedes my ability to really do my job as an educator. And I think just to even have a little bit of that framing of where some of that anxious energy, where that frenetic energy is coming from is from this feeling of bombardment overwhelm, lack of true expertise, as millennials kind of try to figure out the right way to do this in a world that it feels there's a lot more pressure to do it right. And so I think those are some of the things going on with millennials. And the other piece that we always look at is the generation that was there at the dawn of social media, and that first generation to really experiment with collective leverage, that ability to influence and be influenced. And that influence is a piece that we still study that's also impacted parenting in a lot of ways.

Tyler Vawser:  Yeah, that's interesting, because we are always wanting more parent involvement. But then there's a tipping point where it goes way too much, and then you've got the helicopter parents, the bulldozer parents, all of that.

Kim Lear: Right. You're right, though. But you're right, because there is that other side of, like. And I think that parents deal with the overwhelm in different ways, where I think, for some, it can feel so paralyzing, where that's where you do see some of that disengagement. And then I think, for some, that's that kind of frenetic energy that can begin happening because it jumps them into an almost place of fight or flight or something. So I think that could be part of it. And part of the disengagement, which, again, we can talk about a little bit later, is millennial families are also generationally unique, where it's so many dual income households and so that changes our communities also a lot of single parents. So right now, America has more children growing up in single parent households than anywhere else in the world. And so that also changes things when we consider school engagement and advocacy and that kind of thing. And then Gen Z, my we, I think that, again, this one can go all over.

So I'll try to keep it concise, which is that social media, of course, has had a profound impact on Gen Z in a really different way, because the social media that millennials grew up with, it was ad free, it was adult free, the technology was too new, and the users were too young to know that they were for sale. So it was really this haven for the youth experience. There were these explosions of creativity at that time. It was a very idealistic time in the history of technology, where Gen Z grew up with much more sophisticated algorithms that curated their experience with it, which changed the conversation, which changed their youth culture in a profound way. 

And so when we think about the role of schools, the role of families, it is just this constant push and pull about how much tech do we bring in, how much tech do we keep out. Bullying has obviously had just a completely different meaning if it can't be left in the physical doors of a playground or something. And so we look at all of that media literacy, vetting sources, all of these things are just such, some of the main issues that I think Gen Zers are dealing with. And this really optimized technology, this technology, we look at where artificial intelligence is and where it's going, and we look at the ways in which these algorithms are really built now to be more perfect, more useful, more effective. And that just changes baseline expectations, expectations about how to learn, how to work, how to produce. And so I think Gen Z is really going to end up guiding us in a really interesting direction about how to properly leverage the technology that, for better or for worse, really fell into their laps during this porous time.

[Break Music In]

Tyler Vawser:  Coming back for more but first, SchoolCEO Conversations is powered by Apptegy.

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Now back to the conversation.

[Break Music Out]

Tyler Vawser: Now back to the conversation. It's interesting to think about Gen Z and then what we were saying about Gen X being skeptical, and some of what they started just now in the last five to ten years, kind of becoming, I don't know if mainstream is the right word, but more common. And so we have an obsession with novelty. So Gen Z is new and flashy. We're trying to understand it, but meanwhile, the real influence is coming from the Gen X generation and even millennials that are starting to move into leadership positions. But it's almost a little bit more hidden or not sneaky in a nefarious way, but just, they've been around for a while. People have been reaching for understanding for a while, but it's the new thing that we're all focused on. But I think sometimes we forget that the real influence is coming from the people in power, and we forgot to analyze them and what influenced them when they were teenagers or in college.

Kim Lear: Well, because I do get asked sometimes, can you come deliver a speech just on Gen Z? And twelve years ago, I was asked to come and do stuff like just on millennials, and I never have. I do not do any presentations that are on one generation because you can't understand the tech fatigue or apprehension from Gen Z without understanding the techno optimism of the mid 2000s. From millennials, these pendulums swing and we build off of each other's foundations. We rebel against them in different ways. And so it's a full story. There's no secret island where only Gen Zers live. We live together, and our relationship to culture is so symbiotic, it influences us and we influence it constantly. And so it needs to be put in that context and that broader framework.

Tyler Vawser:  Yeah, I think that's really helpful. It was after your last talk that I kind of thought the way for me, in my mind, as a shortcut of understanding different generations was like, take the birth year and add 15 years. And what was happening in that moment, because those are the influential teenage years. Right. So someone born in 1986, add 15 years, 2001, you have 9/11, you have the tech boom and bust, you've got all these different changes. Politics really gets wild. And so it's interesting to think about that versus just the birth year when a newborn baby is not going to be influenced the way that a 15 year old is by world event.

Kim Lear: Right, exactly. And generational theory, I mean, we're really specifically studying those formative years, meaning teenage years into young adulthood.

Tyler Vawser:  That's really helpful.  Well, let's talk a little bit about communication preferences. SchoolCEO, we're often focused on brand marketing culture. And so much of that comes down to communication, both at a high level, one way communication, and also two way dialogue, one on one conversation. So walking kind of back through what we just did, how do those generational differences impact communication preferences, in particular with external stakeholders? So not as much of like a working relationship, but say, a superintendent communicating to parents or even the broader community, maybe retirees that are within their district.

Kim Lear: Yeah, I would say for baby boomers, kind of along that line of a real misunderstanding about this life stage of aging and retirement communication that over indexes on nostalgia, sentimentality, things like that, I actually think can backfire. Rather, you're showcasing innovation and focusing on change can create more engagement. And here in Minnesota, in the Bloomington School District, I think they did a really good job with that of looking at what type of people do schools need to help grow for today's world? And I think initially there was a little bit of hesitation because people do feel nostalgic for their own education, the way they were educated, the way they remember it, which is never accurate, those types of things. And so I think sometimes the initial is like, okay, especially if we're going to be communicating to retirees who we want involved in a bond referendum or things like that.

Let's kind of focus on remember your schooling or when you were a young parent and had kids here. But instead I think it's like, just like you, we understand that the world has changed, which means education has to evolve. And that line of change and innovation adoption, I think that works for Gen X. It's two things. One is we have traditionally seen that just like hard numbers, even numbers without being built around a comprehensive narrative arc, still work better of like, what are the scores? What is the teacher to student ratio? You know what I mean? Just kind of going through the types of things that have always been used to combat skepticism, which was like objectivity. And so I think that is a piece that speaks to Gen X. The other one is just remembering that Gen X is the sandwich generation right now, caring for aging parents on one side and have school age children on the other. And so really, the best gift that you can give Gen Xers in terms of communication, is the gift of their time back. And so when thinking about communicating change, getting some enthusiasm, growing for some type of shift, it's a lot about in the communication that's sent out, prioritizing clarity over brevity, so that there's not these spirals of miscommunication. 

It's thinking about how to put something together in the most articulate way. And I think schools have done a great job of this, of then there's always places you can go to get more information. But I think kind of just providing those high level things for millennials, finding within, let's say, your parent population, the right people to advocate for your school. That peer to peer trust building has always been such a cornerstone for millennials. And I think that's a piece that can really be leveraged and then just real proactive communication. It was definitely during the millennial era where this idea that no news is good news completely went away. No news makes people concerned, confused, suspicious. And so I think the more proactive that schools can be about their communication, the better for millennials. 

And then Gen Z almost kind of growing on that peer to peer piece. One thing that's been really interesting is in this interview series that I did with Gen Z's who were embarking on their first internship, and we were talking about how they chose it and all that. And one of the things that came up over and over again was these day in the life videos that a lot of companies put together where just they hand their social media platforms over to their interns, and it's like just walk them through, like a day in the life. Like you get up, you brush your teeth, da da da, and then you go into work, and what do you actually do all day? And something about the authenticity of that, something about the peer to peer nature of that, and something about the ins and outs. Almost the opposite of Gen X, right, where Gen X, it's like, just give them their time back, just kind of focus on. There is something that seems to work really well with this youngest generation to come in about giving some real insight into the nitty gritty of the school, the experience, the student experience. So some ways to some communication tactics that we've seen work.

Tyler Vawser:  Yeah, that's really helpful. Schools are communicating all the time, so anytime there can be more guidance, not just on share information, but how to share information or how to be really intentional about how you're communicating that I think the better.

What about internally? So thinking about an organization for schools, teachers and staff, administrators, what can a superintendent do to really improve that trust and communication internally among the teachers and the staff?

Kim Lear: I will say that kind of in a funny way, I was with a large district recently and we were doing more of like a workshop thing. And so one of the questions that I had posed to this large group that they worked at at small tables was talk about some of your communication pet peeves. And a lot of the stuff that came up is like very low hanging fruit. So it is things. So I want to give some of those because sometimes it can feel like that recommendations can seem so lofty, but.

Tyler Vawser: Like, yeah, low hanging fruit.

Kim Lear: Yeah, low hanging fruit. A lot of the people said that there was just a ton of people who didn't know necessarily when to CC or BCC on an email. And so then you're CC'D on all of these emails that you actually do not need to be a part of. And it's like a tiny silly thing, but having some process around email communication, something like that, just so that people are not bogged down in a million emails that they do not need to be a part of in meetings, like having a clear agenda, so that there's an understanding of this is what we're going to be covering. This is the allotted time to cover this. And then these are the desired outcomes and a real management of expectations around desired outcomes. And an example that I would give is, I think, in such a great way. 

There are so many amazing superintendents who host a lot of these listening sessions with the school counselors, with teachers, just to make sure that they have this real on the ground insight into what's going on. I think where it can get sticky is that if the expectations around action is not clear, it can actually end up causing more friction. Because perhaps the top leadership, they're hosting these listening sessions because they want to understand concerns, they want to hear ideas that they can think about in future decisions. But some of the people who are talking during those listening sessions are expecting some very immediate action. And so then they can come back and be like, well, we told you all these things. We told you the things that we need or the things that aren't working and it's six months later and we still don't have it. So I think some of that is in that management of expectation a little bit.

Tyler Vawser:  Yeah, I think that's so important. If you're going to ask for feedback, tell them how you want the feedback to be used. Is the feedback going to be, we're going to make some changes next week or next year or. This is really just to kind of get inside of your minds. We're not planning to make any changes.

Kim Lear: Right.

Tyler Vawser:  But we still value your input.

Kim Lear: Absolutely. And then I think the other piece, and I see this in schools and I see this in hospitals, these are really the two places where I see it the most pronounced is the authenticity movement of people really bringing their whole selves into the workplace. And because schools and hospitals are two places where the work is so important, the emotions can run, know the people who work there care. So of course it makes sense that they're bringing everything that they've got into that door every day. And there was a great essay written by the organizational psychologist Adam Grant. 

This was a couple of years ago now where he was talking about authenticity, and he said, authenticity asks that we bring our whole self to work, and leadership demands that we bring our best selves. And I think that in schools, just in building these really strong cultures where you've got people pushing the same boulder over the same hill, people who are in each other's corner, I do think that there is something to play with there for leaders around that distinction between authentic self and best self and how that can be infused into a school culture.

Tyler Vawser:  Yeah. As a manager myself, I think probably 90% of issues fall somewhere in that phrase. Right. Best self versus real self. And it is a little bit of a double bind. Right. Because you do want people to be their whole selves. You want to really understand how they're thinking and not just put on a work face. But on the other hand, things need to get done. It's got to be great. We've got to elevate our brand and the experience for our students. And so what can you do to do that and still be yourself? Right? Yeah, that's interesting.

Kim Lear: Well, and I think we learned a lot about that, actually, during the pandemic where I did 250 interviews throughout the pandemic, and when I talked to people about what their leaders have done for them that has helped them, hurt them, all these things, it was interesting that a lot of, I think the narrative was like, leaders should show a lot of vulnerability. We're all in this together, which that is still valuable. But a lot of people also talked in depth about their leaders who were like 1ft in front of the other, like Brick by brick. Just kind of that steadiness where when everything felt really volatile, to be able to come into work with a leader who felt real steady. And that's the emotional regulation, I think, of best self leadership.

Tyler Vawser: Yeah. There was an interesting moment, especially in those first couple of months, where it was like, the world's on fire. How do we focus on work and what's happening? And I remember having a conversation with my team and saying, take care of yourself. And the thing you can control is the work. Right now. You can't control what's happening across the world. You can't even control what you have to get a mask. And all of that's outside of your control. But when you're behind your laptop and you're at home, if you have that luxury, you get to control the quality there. Right? Not to minimize everything else that's happening, but let's own the thing that you can own while everything else is spinning out of.

Kim Lear:  Totally.

Tyler Vawser:  I think. I think that was helpful in some ways. Right. Doesn't solve everything, but at least reprioritize and feel some agency in that.

Kim Lear:  Exactly.

Tyler Vawser:  What about one on one communication? Kim, so much of our time is spent in those individual conversations between direct reports or coworkers and colleagues. What are some practical steps we can take to improve communication when it's different generations in a dialogue?

Kim Lear:  Yeah, I think in general, in those one on one conversations, this is still a place where I really like a lot of psychological tools that are used in a lot of workplaces. And so there's, like Myers Briggs and know there's all these ones which can help leaders know introversion and extroversion and fact finding, but all of those things. And so I still think that and for all of you leaders listening, you know this, in those one on one conversations, the leader really needs to understand not only who they are as a person and the type of communication that they are most responsive to, but to also really understand who is this person in front of me. And so there's limitations to where I think generational ideas can add the most value. But just in my learnings and working with a lot of organizations and a lot of schools, I think one that comes up quite a bit is when delivering feedback, especially delivering room for improvement, areas of opportunity, that kind of thing is that leaders really have to consider, am I delivering this feedback in a way that is going to motivate this person to improvement, or am I delivering this feedback in a way that's going to paralyze them. 

And what we often found with young workers is their decision to leave an organization can often be pinpointed to, like, a first performance review, where if their leader gives them some constructive or possibly negative criticism, which is fine, that's all part of learning. But if they leave that meeting feeling like, maybe I was wrong, maybe I am not good at this, maybe I don't have what it takes compared to leaving, having some clear next steps about how to improve, I think that that is one of the key pieces because people need feedback all the time. It's the only way to get better. But delivering that in a way that makes people want to work harder for you instead of disengage is tricky, but so imperative.

Tyler Vawser:  Yeah, that's really important. I think that's really insightful. And to maybe think more about that first meeting than all the subsequent ones and think about it like a continuing conversation.

Kim Lear: Yeah. So that would be one and then the other stuff on one on one communication that we don't have to go too far into because I think people really do know where it is, asking really good questions. I think Krista Tippett has a beautiful book about asking questions and that's one that I've used many times. And being an active listener, managing expectations appropriately, being clear is kind. I still think that that is just so true. There's some of those just evergreen tactics.

Tyler Vawser: Yeah, that's really helpful. Yeah, clear is kind. I think that relates to what you said earlier about emails and being copied on every email and do I really need to do this? I think so much of it, especially when it comes to ongoing working relationships. Right. Like a manager and A direct report is of course, that trust and empathy, but also just that expectation setting. And I think when I reflect on my own career as a manager, the times where I've been frustrated, it's because I haven't actually been clear and the other person hasn't been clear with what they're expecting. And so when you can just kind of say, like, hey, there's a gap here. Here's what I'm expecting. What are you thinking? How do we maybe can't close the gap all the way but get a little bit closer and then suddenly it's like, oh, well, no wonder we've both been banging our head against the wall. We were seeing different realities and now we have a shared expectation.

Kim Lear: Yes, that's such a good point. That's such a good point. And it kind of reminds me of another one, which is forever for 15 years that I have been doing this work and with organizations, so many managers, when I ask managers like your ideal employee, a lot of them will say something along the lines of like, I like people who bring me solutions, not just problems, which I think is great, but then what I often find, especially if you have a really green person, whether they came from outside the industry or they're young, they bring you a solution that won't work. Whatever it is, it's been tried before, a million times and it just doesn't work. Or there's not the budget for it or whatever it is, it's not a good solution. And there is no process or procedure developed to handle bad solutions. And so then the manager is like, no, this isn't good. This isn't going to work. And the young person is like, well, you told me to bring you solutions. I'm trying to bring you a solution. And so even to build something in, if you do want to create an environment of like, you come with solutions, not just problems, which I think is great, then it also has to be okay. The time has to exist to actually address bad solutions and use that as a training opportunity. But I know that when time is so limited, these things happen where it's like it's a bad solution and then that person is not going to bring you solutions anymore.

Tyler Vawser:  Yeah, we'll have to create a part two, which is a twelve hour episode about how to solve these issues. Those are tricky. I think those are like the ongoing things, right? Yeah. If anyone that's been in leadership understands exactly what Kim's talking about here.  What about mentoring and mentorships especially? That's usually going to be across generational lines because one person has experience in a career and is advising someone that's earlier in their career and has less experience. What advice do you have based on research about how to make those productive relationships?

Kim Lear:  Yeah, the biggest study that we did before the pandemic was around mentorship. And I'll just bullet points of some of the things that I think are the most helpful. The first is that a lot of people don't really know how to be good mentors. And what really makes someone a great mentor is if they can develop and perfect the skill of being able to spot and nurture potential, like seeing something in someone that they don't see in themselves and putting them in these stretch opportunities, which what that communicates to them is like, I know that you can do this even if the person has their own doubts. It's instilling confidence in the right candidates. I mean, a great mentor in a lot of ways is like a talent scout. 

You have to look and see who has the potential here to be great. And then let me pull that out of them, believe in them. It's sharing stories of not only your triumphs, but a lot of times it's answering questions for yourself of what would I have done differently than if I knew then what I know now. Right? And it's those kind of white spaces, those trip ups in our own stories where we find the most valuable mentorship lessons. So I think that's one. The other one for mentees is to recognize that the best mentors, again, are talent scouts. And so you, as the mentee, your job is to prove over and over again that you are worthy. That is, essentially. And the mentees who get the best Insight, the ones who have more impactful career trajectories, better opportunities, are the ones who really sit in the driver's seat of that relationship. And they do the right amount of research on the mentor so that they can write better questions that elicit better insight. They are respectful with that person's time. They try to add value in meaningful ways. And so it takes real time and intention. But when we look at the mentor relationships where it is so strong, where both people are learning and feeling valued, and this sharing of knowledge is really seamless, it's in those dynamics. And so I think that is just such a key piece of building that. And the other thing, and I would say this more maybe to younger listeners, is that mentor mentee relationships, it's not like boyfriend girlfriend, where it's like you have to ask, are you my boyfriend? It isn't like that. 

There are a lot of people where the word mentor is never said, it's never spoken. And so you don't need to worry, because I do talk to some young people where before they really put in the effort, they're like, well, I have to figure out if that person's really my mentor. And I'm like, you don't.

Tyler Vawser:  You don't have to label it for it to be valuable. You shouldn't.

Kim Lear:  You shouldn't. I think it's just moving forward with someone who inspires you, someone who you want to learn from and go for it. And you never need to make a formal announcement, but you just move into a place of action and value add to get the momentum of that relationship going.

Tyler Vawser:  Yeah, that's really interesting. Something that I've experienced and at Apptegy, we don't have formal feedback or performance reviews that are event based. It's much more continuous conversations and ongoing feedback. And even with the youngest generations, they're like, yeah, I don't want performance reviews, but also I want feedback. And when we get in these conversations, sometimes they're like, well, I haven't had any feedback for six months. It's like, yesterday we talked for 30 minutes about something, and the day before that, we talked for an hour. The day before that, we had a five minute. From my perspective, we're having feedback all the time, right? But there still is that desire at times to put a label on something, to say like they're flashing lights. This is now feedback in the same way that people are like, well, should I listen to this or not? Because I'm not sure if you're actually my mentor, but to kind of treat all things as good advice and treat anything like feedback and not worry so much about what category or label it.

Kim Lear:  Has on it, I love that. And I think that that even in some type of onboarding situation, or even if you have any all hands meetings or something like that, that could be said that in any culture of learning, you're learning all the time. Everything is feedback. Everything is an opportunity to learn something with or without a formal label on it.

Tyler Vawser:  Absolutely. One of our readers, and actually, someone that heard you speak at the last SchoolCEO conference, asked this question. And so this is Rachel from Colorado. She had know I've been noticing lately that an increasing number of my Gen Z students are struggling with purpose and motivation. Are there generational factors that are contributing to this struggle? And how can I, as the educator, speak to the issue in a way that connects with the way Gen Z students are inclined to think?

Kim Lear:  Yeah. Oh, my gosh, yeah. For the listeners. Tyler sent me this question before, and I've just been staring at it and thinking about it. So, Rachel, I think you're so not alone from a cultural perspective, a parent perspective, a teacher perspective. So, in answer to your question of, like, are there generational factors that are contributing to this struggle? I definitely think yes. One of the things that I hear quite a bit from young people who are participating in my research is this supreme sense of overwhelm, some of this helplessness, some disillusionment, things like that. And then I'll hear from managers, because the oldest, Gen Z, is about 26. A lot of them are in the workplace. And I'll hear from managers that they're like, they seem so overwhelmed, and what could possibly overwhelm them? They'll say it's like, whatever I've got aging parents and I've got kids, and I have more work responsibilities, and I can do it. Why are they overwhelmed? But I will say, when they tell me that they're overwhelmed, I do believe them. And I think the generational piece of that is that for most of their formative years, the average age that someone was getting a smartphone was eleven. And we really still do not know how this technology impacts a developing brain. And more research is coming out all the time. And I think that the research that's already available basically just crystallizes hunches that people already have. And so I think that that has to do with it. I think so much of the bombardment on social media, because the way that the algorithms work, it is overwhelmingly negative. 

A very interesting study going on right now has to do with the youth mood towards the economy, because on all objective measures, the economy is phenomenal, but the youth mood is incredibly negative. And so people are studying this disconnect between objective realities and subjective moods, and trying to look at what could be impacting this. And I think a lot of it is social media. So speak to the issue in a way that connects with Gen Z and the way that they think. I think for as much as we can, almost articulating back to them something that many of them do inherently know, which is that the amount of social media that they interact with is not healthy and is only going to contribute more to, just like you said, with these struggles with purpose and motivation.

And so, again, that sense of autonomy, kind of being in the driver's seat, I think there is a question to explore for parents, for teachers, for mentors around. What can you really control here to get yourself back in the driver's seat of your life, to put your foot back on the gas, for your ambitions and your dreams. And it's really simple things. I mean, there's one teacher out in Washington that for her morning homeroom class every day, that they can, she just has them go outside and no sunglasses or anything, and just face the sunlight. And she talks about, she played them part of this podcast with a neuroscientist who talks about the impacts of just that sunlight on your face early in the morning. So sometimes I think it's like when we can deliver these really bite sized, easy things to do, that they can be like, I can do that. I think it sounds like such a small thing in this bigger issue of motivation and driftlessness and restlessness. But to make it approachable for a really young person, I think these bite sized pieces of these are ways to get you back into the driver's seat of your life is just such a critical conversation to have.

Tyler Vawser: Yeah, I think that sense of agency is just so important. Yeah, absolutely.

Well, in the few minutes we have left, I think it'd be fun to kind of talk about these different kind of quips, or, for lack of a better phrase, Snide remarks that we all tend to make about different generations. Right. So everything from, like, oh, millennials are entitled, or young people don't work as hard to the other side where, like, well, the older generations are just stuck in their ways, or boomers don't understand how things are today. So I'm just kind of curious in those kind of drive by comments, what are some good, disarming ways to get all of us to think more openly and empathetically about people that are born in a different time and see things differently than we do?

Kim Lear:  Yeah, I think. Well, I'll do. The young people don't work these days like nobody wants to work because that one comes up quite a bit. And where I think that generational theory is helpful and just so fun is that it gives us these historical frameworks for evergreen narratives. And the older generation never really thought that the younger generation had a good work ethic. And there are a lot of historical examples of that. One that I give is that a client many years ago shared this with me is that he's a baby boomer. He works in finance, and from his earliest career memories, he has put in like 80 hours a week. That's what it was. But his dad grew up on a farm in northern Minnesota, and his dad went to his grave not thinking that his son had a good work ethic, because he's like, you work inside sitting down, and that doesn't seem like good work ethic. 

So it wasn't that long ago where the majority of American workers worked outside on farms, and then they worked in factories, and then they worked in offices, and one day they won't. And the way we work, our relationship to work is one that is constantly evolving. And so I think just having that framework allows us, again to just approach it instead of with such feeling of judgment, more of this feeling of curiosity. I also think that we just cannot underestimate the profound ways in which technology has impacted efficiencies. Right. And so this was many years, so long ago. I think this was with Accenture, where we put together these employee personas and showed them to leaders. And one of the employee personas was the person who's like, first one in, last one out eats lunch in front of their computer every day. And we showed that persona to older leaders, and they were like, that's our person. That's an amazing work ethic. And then when we showed that same persona to younger leaders, the responses were more varied. We heard a lot of, what is this person doing from 07:00 a.m. Until 07:00 p.m. Every single day. They can't even get up for lunch. They must not understand how to properly leverage technology. They must not know how to prioritize their work. Like, it felt more like, in some ways, like a time waste. And the British historian C. Northcott Parkinson, in 1955, he wrote Parkinson's Law, which is work expands to fill the time available for its completion. If we give people tons of time to do their work, that's how long they'll take. And if we constrict it, they can probably get around that same amount done in a shorter amount of time. And so I think that is one of the pieces that I would say just to. Just to have people look at the work ethic debate in some different ways around. Partly it's always been there, and partly technology really has changed a lot of how quickly we can get things done.

Tyler Vawser: Yeah, that's a good reframe on hours worked versus projects. Like, you can say, well, you're going to have the same amount of work regardless, but how you get it done, your time is. That's up to you. There's flexibility in that.

Kim Lear:  And I think a lot of leaders are working now on, like, how can I focus more on what gets done and obsess less about how it gets done?

Tyler Vawser: Yeah. In the last episode, actually, with Dr. Pete Hannigan, he talked about this as a superintendent, because you mentioned optimization, and I know you talk about this in your know, superintendents, they have a very difficult job, and the hours can stretch quite long. And so what he kind of realized, and he talks about this really openly at the end of the episode, is instead of going to every football game or every choir rehearsal late to show his presence, be more present during the typical nine to five, or for schools, right, the seven to three, be present in those hours and around the teachers and the students and the staff then, because that's actually more impactful than just kind of sitting in the bleachers at the football game. And I thought that was a really smart way, even at the leadership level, saying, there's a way to optimize my time and increase my impact without extending the work week. Exactly fits what you were saying.

Kim Lear:  Yes.

Tyler Vawser:  Good. Well, Kim Lear, thank you so much for joining me. I really enjoy you every time I get to chat with you. This is the longest conversation we've ever had because there's no conference, there's no audience that's waiting for me to stop talking and for you to start talking. So it's fun for me to be able to chat with you.

Kim Lear: Well, thank you. Thanks for having me and for everyone listening. Thank you for the amazing work that all of you do to raise a new generation of humans for a very interesting world. So thank you.

Tyler Vawser:  Awesome. Thank you, Kim. 

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