With baby boomers retiring and Gen Z launching their careers, the landscape of employment is shifting. How will Gen X managers differ from the baby boomers who preceded them? How will a prospective Gen Z hire make a decision about their first employment offer? Because each generation brings specific life experiences and perspectives to the workplace, generational trends can be useful to your recruitment efforts—if approached correctly.

Kim Lear is a researcher and expert in generational theory. She’s written about generational wealth transfer and retirement trends, and she was the head researcher for the book Gen Z @ Work. As the founder of Inlay Insights—a generational research and public speaking firm—Lear has spent her career unpacking and demystifying what happens when people across different generations work together.

At the October 2022 SchoolCEO Conference, we invited Lear to speak on how each generation has impacted—or is impacting—the workplace. Afterward, we sat down with her to further discuss what her research might mean for school leaders like you.

What do school leaders need to understand about generational theory?

To begin, generational theory is rooted in sociology, not psychology. But both schools of thought are equally important, especially for leaders. Psychology is looking at who you are as an individual—your unique brain, your relationship to your parents, the way you practice religion. On the other hand, sociology contextualizes the individual’s experience by exploring broader macro trends.

Essentially, generational theory deals with demographic shifts and evolving cultural norms. We aren’t trying to capture the story of one person; we’re trying to capture the story of a shared society. We’re trying to understand why something that would’ve been wildly taboo 20 years ago is totally acceptable today. We’re also trying to see the world through the eyes of a different generation. We’re asking: If I were born into a different time, would I see this differently?

And because of the unique events and experiences of each generation, we see different behavioral trends in each population. And I want to make this clear: These are trends, not traits. That’s why I’m so upfront about the difference between psychology and sociology. Generational theory is not a psychological tool—and if people try to apply it that way, the whole conversation goes off the rails.

Just like any other form of diversity, it can be genuinely beneficial to understand the differences between generations—but it can also become really counterproductive. For example, you can’t sit in front of someone and say: Oh, you’re 27. Okay. I’m going to bring out a different script. Leaders have to understand individuals, know their motivations, and know what type of feedback inspires them. But when we aren’t focused on the individual—when we’re looking instead to make recommendations based on broader trends—that’s where generational framing is the most beneficial.

What are the most important things to know about each generation?

Baby boomers, the largest generation in American history, came of age with the bull market of the ‘60s behind them. As they grew up, the world was looking at baby boomers, saying: If anyone’s going to challenge the status quo, it’s you and it’s now. There was this momentum of optimism and idealism that really shaped the youth culture of the 1960s and early 1970s.

Gen X was heavily impacted by the emergence of 24-hour media, which started when CNN came on the air in 1980. Suddenly, these institutions that were built by traditionalists and improved upon by baby boomers were all being called into question by 12-year-olds watching TV in their living rooms. It was with Gen X that we started to see a real rise in skepticism.

Next, there’s millennials. I still have clients who think millennials are 12—but some of us are 40 now. We drive minivans and live in the suburbs. Millennials were there at the dawn of social media, when it was ad-free and adult-free. We were the first ones to question what the megaphone of social media was for and how to use our collective voice.

Then, these questions were inherited by Gen Z, born roughly between 1996 to 2010. When I’m in Gen Z focus groups, I tell them that 50 years from now, a historian will write about the events and conditions shaping their generation. When I ask them what they think those historians will write about, they mention Trump’s presidency, the Women’s March, TikTok, school shootings, climate change, the Black Lives Matter movement, the pandemic. Our current moment is the backdrop for their formative years.

What should we expect to see from Gen Z as they continue to enter the workforce?

As Gen Z has grown up, our culture has been abandoning an obsession with convenience and replacing it with a focus on optimization. Just to be clear about the difference between those terms, convenience is about involving little trouble or effort. To optimize something is to make it as effective, perfect, or useful as possible.

When we think about the future of workplaces—and the future of education—a lot is going to change as Gen Z comes in with different expectations for how to make their work environments more effective, perfect, and useful. How do we review our processes, procedures, and norms in order to really consider how something can be more optimal?

We should also expect to provide this new workforce with the training and refinement they’ll need in order to get stakeholders on their side and bring their ideas to fruition. So many good ideas fall through the cracks because they’re not in the right wrapping paper, but we shouldn’t write off Gen Z’s ideas just because they have a different style of communicating with authority. One of the roles of great leaders over these next five to 10 years will be to help young people figure out how to package their ideas so that innovation can actually happen.

Another takeaway for leaders trying to recruit young teachers is that Gen Zers tend to be very close with their Gen X parents. They’re highly influential over one another’s decision making. When you make an offer to a Gen Z teacher, they’re taking that offer and showing it to their number-one influencers: Mom and Dad. So it’s important to recognize that those parents may have different questions. Young candidates may want to know about learning and development, PTO policies, and community. But their parents may be wondering: What’s the dental plan?

Baby boomers are retiring in droves. What effect do you expect Gen X to have on leadership positions?

Again, one of the hallmark characteristics of Gen X is skepticism. That skepticism lends itself to a fairly specific style of communication: honest, direct, and unfiltered. So as Gen Xers move into management roles, especially executive positions, we’re starting to see a real focus on transparency and radical candor.

I remember coming head-to-head with this style of communication very early on in my career during a meeting with David Stillman, my then-boss and now mentor. He could be the poster child for Gen X. But I didn’t really know that going into the meeting.

I went into David’s office, and I’m not two seconds into my first idea before he stops me and says, What kind of research do we need in order to get this done? Can we run this in-house? Do we have to meet up with an outside market research firm? What void is this filling in the marketplace?

In that very brief interaction with David, I learned something critical about communicating with him. I would need to be able to anticipate and prepare for his skepticism. Eventually, this would become my most productive working relationship. No one vets my material with a more precise eye than David—but I have to be open to that type of feedback.

And because the Gen X ethos is one of skepticism—since they’re slower to accept and quicker to question the traditional ways of doing things—they tend to be more adaptable. Education, on the other hand, is an industry rooted in tradition. But now, we have a generation stepping into leadership positions that respects tradition, but isn’t going to sacrifice innovation for the sake of it.

What can a generational lens illuminate for educators specifically?

One thing I think educators should be aware of is how each generation does or does not take risks. I’ve heard folks say that schools need to innovate and empower their people to take necessary risks in order to keep up with where society is headed. But how do you do that?

I was at an event recently, and the speaker before me was talking about young people and their risk aversion. They were saying we should tell emerging young leaders: If you take a risk, what’s the worst that can happen? You fall down, you dust yourself off, you pick yourself up. And I actually really disagreed with that take. There is something that genuinely feels out of touch with that response—especially for younger millennials and Gen Z, who have grown up in a highly documented environment. When you tell young people that it’s no big deal to fail, you have to remember they grew up in an environment where small mistakes can have lasting impacts.

Instead, I think it’s better to recognize where we are now and say, I know that taking risks can be scary. It should be scary. How can I help you properly vet this idea? That way we can go through the fact-finding stage together to figure out what is most likely to work. That pertains to small things, too, like figuring out how to help a student or structure a lesson.

The other thing to remember is that there would obviously be more risk aversion in education. It’s not because people are scared—it’s because people really, really care. They understand that the price of failure in education is very high.

You’ve said before that this new generation of teachers is asking different questions than those who came before them. What did you mean by that?

There has been lots of research done around mortality salience, which has to do with how large groups of people behave after they’ve been faced with the prospect of death or illness. We’ve found that when large groups of people have a collective moment of introspection, they begin to ask questions like: What do I really want to do? How do I want to spend my time? What legacies do I want to leave?

The last big moment of mortality salience was after 9/11, right when the oldest millennials were first entering the workforce. That’s when we started having this conversation about meaning at work. Millennials wanted to understand why their jobs mattered. Now, we’re in a very similar time with COVID, but I think the top-line question for this new generation of teachers is different. Now, the question is: What am I willing to sacrifice for my job? Is it my wellbeing? Is it my family? Is it my balance?

Leaders in education should be asking themselves: What support systems can we put in place? When it comes to recruiting teachers, leaders will have to think through how to balance work differently and how to support their people. I’m not talking about giving them access to a meditation app—it has to be a systemic thing.

As you work to reenvision what supports are available, you might find yourself thinking: Why the heck am I doing this? When I came in, no one did this for me. This is very natural—we often think that someone else can’t have what we have unless they went through what we went through.

To leaders with that mindset, I would ask: Do you lead exactly how you were led? For most people, the answer is probably no. Good leaders adapt to what is needed today, and they adapt to the circumstances of the moment. Generational hazing doesn’t have to always be a part of our cultural narrative. Progress happens when there are enough leaders who genuinely want to create something better for the next generation.

Originally published as "Turning Tides: A Q&A with Kim Lear" in the Winter 2023 edition of SchoolCEO Magazine.