Becoming a Perennial Leader

As a school leader, it’s your responsibility to create a culture that works for employees of any generation.

By Melissa Hite Last Updated: October 21, 2024

BECOMING A
PERENNIAL
LEADER

Making your district a great place
to work for employees of any generation

by Melissa Hite Last Updated: Oct 14, 2024

Right now, in your schools, you most likely have employees from all four working generations: baby boomers, Gen X, millennials and Gen Z. These generations each bring unique perspectives to the table—perspectives that are all crucial to the success of your school district. 

Generations aren’t destiny, but understanding how each generation operates in the workplace can help you know and serve your staff better. “I would never say, ‘This person’s a millennial, so they will behave like this, or you should treat them like that.’ That is not the approach to me,” says Lindsey Pollak, New York Times bestselling author of The Remix: How to Lead and Succeed in the Multigenerational Workplace. “Understanding generational differences is about understanding potential expectations and experiences that someone may or may not have.” 

As a school leader, it’s your responsibility to create an environment that works for employees of any age. Here are just a few guidelines for successfully leading a staff that spans generations.

Who's in what generation?

Who are today's superintendents, principals and teachers? Of course, the answer is more complicated than their age—but knowing what generations your employees fall into can help you craft a culture that works for all of them.

Superintendents

In just the last decade, the mantle of school leadership has—for the most part—passed from one generation to the next. According to research from AASA, the average superintendent in 2014 was a baby boomer; today, the average superintendent is a 50-year-old Gen Xer. The vast majority of superintendents now—85%—are between the ages of 41 and 60, making them either Gen Xers or older millennials. Just 10% are baby boomers or older.

And while younger generations are beginning to assume school leadership roles, they're still sparsely represented in the superintendency. Only 4% of today's superintendents are under 40.

Principals

There is less data available on the specific ages of school principals. But according to 2021 data from the National Center for Education Statistics (NCES), less than one-third of public school principals were millennials or Gen Zers. The average principal is 49 years old, a member of Gen X.

Teachers

In our own 2023 study "What Teachers Want," we surveyed over 1,000 teachers from across all 50 states. Our findings, which were consistent with data from NCES, revealed that the average teacher is about 43 years old—right on the cusp between Gen X and millennials. While Gen Xers made up the highest percentage of our sample at 43%, millennials followed close behind at 37%. Baby boomers accounted for 14% of teachers; Gen Z, just 7%.

It's important to remember that what's true on a national scale may not be true for your district. According to former superintendent Mark White, the author of 5-Gen Leadership: Leading 5 Generations in Schools in the 2020s, "Superintendents need to look at their own staff and see where they are." (For a refresher on different generations and their preferences, click here.)

Seek out perspectives from all generations.
To create a culture that works for people of all ages, you have to listen to people of all ages. “Any leader has to have a multigenerational network of people,” says Pollak. “As a superintendent, you don’t want every advisor and voice in your ear to be someone of your generation. You really want to be meeting with and listening to the voices of everybody.” After all, diversity of perspective always leads to stronger, more informed decisions. 

This approach comes with a multitude of benefits—the first being the elimination of assumptions. No matter what generation you personally fall into, it’s likely you’re making assumptions about people in other age groups, even if you don’t mean to. 

“I think the core mistake is to assume that somebody else is just like you were at their age,” Pollak tells SchoolCEO. “If you’re a Gen Xer, you might assume that because you wanted to follow a very straight career trajectory—teacher to assistant principal to principal to administrator to superintendent—your younger staff members also want to follow that trajectory. But that’s not always true.” The reverse applies as well. “Younger people assume that older people once wanted what they want now,” she explains. “We really only know our own experiences.”

The best way to clear up these misunderstandings? There’s no shortcut—you just have to talk. “You have to hear directly from the people you’re trying to involve,” says Pollak. “As a consultant, sometimes I get asked, ‘What do Gen Z employees want?’ And I’ll say, ‘Have you asked them?’” 

As an added bonus, intentionally seeking out input from your employees will show them that you value their thoughts. Research from Gallup has found that employees of all generations are more engaged when they feel their opinions count at work. But this is perhaps especially true of millennials and Gen Zers—partially due to the family dynamics they experienced as children. 

An illustration of some flowers in a pressed floral layout

“Studies show that millennials and Gen Zers have grown up having a much more important role in their families’ decision-making processes,” explains former superintendent Mark White, author of 5-Gen Leadership: Leading 5 Generations in Schools in the 2020s. In fact, according to a 2019 report from the National Retail Federation, Gen Zers have been more involved in family purchases than their parents were as kids. So it makes sense that, as employees, they value being consulted on high-level decisions. 

But having conversations with employees of all ages won’t just make them feel good—it will also strengthen your leadership. By involving people of all generations in important conversations, you’re more likely to catch blind spots you might otherwise miss. “I’m a big fan of reverse mentoring, where an older leader has regular meetings with a younger employee to say, ‘What do you think? What am I not understanding here?’” says Pollak. Inviting this kind of input from people outside your own generation will make you a better thinker and leader.

Make expectations crystal clear.
In a multigenerational work environment like your school district, there are a lot of different expectations floating around—and potentially clashing. That’s why it’s critical for you as a leader to clearly lay out what you expect from your employees and what they can expect from you.

Take dress code, for example. If you simply tell your teachers or principals to “dress professionally,” a baby boomer might show up in a business suit, while a millennial might don jeans and a nice shirt. It’s up to you to set specific standards and communicate them. “Clear is kind,” says Pollak. “Most people say they’d rather have a clear policy that they don’t like than one that’s vague.”

"Any leader has to have a multigenerational network of people. As a superintendent, you don't want every advisor and voice in your ear to be someone of your generation. You really want to be meeting with and listening to the voices of everybody."

When it comes to setting those standards, don’t forget to take different perspectives on the issue into account. Like we said before, it’s crucial to get input from all generations. If younger teachers (or older ones!) are interested in a different dress code, consider why your current policy is in place and whether it should change. But no matter what you decide, be sure to tell your employees exactly what you consider appropriate. “If you’re clear, honest and transparent, people really will appreciate that, even if they don’t get their exact needs met,” says Pollak.

Establishing clear expectations also means letting your staff members know what they can expect from you and your leadership. In our 2023 study “What Teachers Want,” teachers of all generations ranked “leadership” as a top priority in their job searches. “We’re all more similar than we are different when it comes to these big concepts like leadership, culture and purpose, but we often have different interpretations of those words,” says Pollak. Everybody wants to follow a strong leader—but perceptions of what a strong leader looks like may shift from generation to generation. 

A painterly illustration of a close up of a flower


So Pollak recommends being as upfront as possible about your own leadership style. “It’s an act of generosity to tell people your style and how to work for you,” she says. “If you’re a very hands-on superintendent, some people might like that, and some people might not. But either way, they’ll respect that you’re honest about it.” Again—clear is kind. “People respect a leader who says who they are and tells people what they need,” says Pollak.

Combine the best parts of the past with the present.
As new generations enter your schools—whether as employees or as students—you may find yourself torn between two extremes. On the one hand, there’s the stability (or perhaps stagnation) of “what we’ve always done,” and on the other, the progress (and risk) that comes with change. The trick is to live somewhere between those extremes, to blend the strengths of the past with the new best practices of the present.

This is the core idea of Pollak’s book The Remix. “A remix starts with a classic song, something that was considered good,” she tells SchoolCEO. “You don’t throw that song away—there’s a lot of value in it! But it might need some updating because there are new things that we know now.” The same is true in your schools. Keep what’s always worked, but update those strategies for the modern day. “I had a college professor once ask me if he shouldn’t teach the periodic table of elements because kids today can’t handle it,” Pollak explains. “And I said, ‘No, I’m saying that maybe the way you’ve taught it for 35 years could use some refreshing.’”

Take, for example, the traditional teacher evaluation model. Across all industries—not just education—younger employees report anxiety and discomfort around job evaluations. According to a study from human resources firm TriNet, 62% of millennial employees say they’ve been “blindsided” by performance reviews, and nearly half say performance reviews make them feel they can’t do anything right. “It’s a bigger deal for the younger teachers because they want to do it right,” says White. “They’re not used to hanging out there on a limb—they’re used to having people coaching them all the way, like their parents have done.”

So should you stop evaluating teacher performance altogether? Of course not. And in fact, your younger teachers wouldn’t want you to. While some Gen Xers and baby boomers mistake younger employees’ discomfort with evaluations as an unwillingness to receive constructive criticism, millennials and Gen Zers actually want more feedback. In fact, the same TriNet survey found that 85% of millennial workers expressed a desire for more frequent conversations about their performance. Another survey from the Center of Generational Kinetics found that Gen Z employees prefer to receive feedback as often as weekly.

It’s just like teaching the periodic table. You don’t need to change the substance of your district’s teacher evaluations, but you may need to change your approach. White recommends moving from a cold, clinical evaluation mindset to more of a coaching mindset. The key difference between the two is the existence of a strong relationship between teacher and evaluator. 

“Young people want coaching; they want face-to-face interaction. The idea of going into an evaluation without a relationship with the evaluator is terrifying for a lot of them,” says White. “We need to give them prompt feedback, and we need to have a conversation, not just sit across the desk and tell them how they scored.” Having more frequent conversations about performance with a leader they trust will set those younger teachers up to thrive.

Not sure whether a practice needs “remixing”? Be sure to ask a multigenerational group for their thoughts. “If you want to take something that has always worked and rethink it, you’ve got to have fresh voices there to help you think through those ideas,” says Pollak.

Be a perennial leader.
In 2016, tech entrepreneur Gina Pell coined a term for a whole new generational group: the “perennials.” Perennials, she said, are “ever-blooming, relevant people of all ages who live in the present time, know what’s happening in the world, stay current with technology, and have friends of all ages.” And according to Pollak, all leaders should work to become perennials. “You are the age you are, and there’s nothing you can do about it,” she says. “But you can develop a perennial mindset.”

perennials

(noun)

"ever-blooming, relevant people of all ages who live in the present time, know what's happening in the world, stay current with technology, and have friends of all ages"

So how, as a school leader, do you become a perennial? It has to do with that remixing—valuing and upholding the good parts of your district’s past while bringing it into the present. “You have to know your district’s history, talk about it, share it and keep it alive,” says Pollak. “But you also have to keep up with the times. You realize that you need a website, a social media presence, an app, whatever it is—because times change.” The trick is to always have both angles in mind, no matter your age.

 Luckily, a school district is one of the best places to come into contact with people of all generations—from baby boomers all the way down to emerging Gen Alphas. “At any age, you can appreciate and listen to people of all generations—and what better environment to do that than a school system?” Pollak says. “That’s the most important quality of any perennial—that appreciation for all ages and the value that they bring.”