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Field Trip: Five Generations at Work


Ian? He’s of Generation X. Erin is squarely in the Millennial camp. Today on Field Trip, they explore the differences between the five different generations currently represented in the labor force: Traditionalists, Baby Boomers, Generation X, Millennials, and Generation Z.

  • Why understanding the characteristics of each will help administrators and district leaders communicate better and tap the strengths that each generation brings
  • How to foster intergenerational collaboration and “reverse mentoring”
  • Why this all matters to school culture and how it impacts hiring and retention

This interview with Ian Halperin, Executive Director of Community Relations at Wylie ISD and Erin McCann, Director of Communications and Public Relations at Crandall ISD is one that every education leader should hear.


Don’t Miss:
Field Guide: “Recruiting Millennial Teachers” — How to effectively market your school district to young prospective teachers, plus strategies for enriching your applicant pool through online recruiting.

Full Transcript  

There are five generations with people in the workforce today: Traditionalists, Baby boomers, Gen X, Millennials, and Generation Z… How are they different? More importantly, what does it mean for schools?

IAN HALPERIN: It’s everything from recruiting teachers. It’s how the school board members interact with each other because you may have different generations on your school board. Your superintendent and your cabinet may be of different generations. So it’s really an issue that covers all areas of education.

What do school leaders need to keep in mind when communicating with parents of a certain age? Should principals work with older teachers in different ways than teachers in their 20’s?

ERIN MCCANN: You’ve got to keep in mind who that person is, what their learning style is like and how you’re going to coach them. Are they someone that desperately needs that face to face, that regular ongoing feedback? Or is it more just kind of the quick check in, “Hey, looks good. Think about improving this. You know, I respect the work that you’re doing”?

From Frontline Education, this is Field Trip.

ERIN MCCANN: And just remember that millennials are about more than avocado toast.

RYAN ESTES: No matter how good it is.

ERIN MCCANN: No matter how good it is.

* * *

Today my guests are Ian Halperin and Erin McCann. Ian works at Wylie Independent School District, just outside of Dallas, Texas, as the Executive Director of Communications and Community Relations. Erin is the Director of Communications at Crandall ISD, also near Dallas. Although they work in different districts, they know each other well. And here’s something really important to our topic today: Erin is a millennial. She’s been working in school PR for about 4½ years. Ian is a bit older, he’s been in school PR for more like 20 years, and he’s part of Generation X.

RYAN ESTES:     Well, we are talking today about cross generational communication and I’m curious, Ian, I know that you have been a mentor to Erin for a while. What differences have the two have you seen in how you communicate?


ERIN MCCANN: I’m a lot cooler than Ian.

IAN HALPERIN: Yes. Yeah. I tend to talk in full sentences and use all my vowels and punctuation, unlike some of my younger friends who abbreviate and things I don’t understand. It’s not a huge difference. I think a lot of it is subtle. I joke about the punctuation and the emojis, but they’re really just tools. And so whether you communicate in formal AP style or in emojis and other icons, it’s really just a style. I think the challenge is meshing those styles to make sure that however you’re communicating, whoever you’re communicating to, you’re meeting them where they are.

ERIN MCCANN: I think this is a really interesting time in the professional world, because you do have so many different generations, and I know that we’ll get into that a little bit. You mentioned, you mentioned that Ian has been a mentor to me and he has, he’s been a mentor and a friend for many years before I was even formally working in school PR. But almost equally, I’ve served as a reverse mentor, because what you have is people who have been doing this job for a long time. What they have on their side is experience and the knowledge of what has worked traditionally and what has not worked. And what you’ve got with some of the younger generations is not that wealth of experience, but a certain level of energy. And school PR particularly, and definitely education, requires a lot of energy to be effective.

So at least in my friendship with Ian, sometimes he might be just a little bit beaten down, and I’m like, “No, no, no, look at it this way,” and coming in from a different angle. Whereas for me, when I’m going to Ian, it’s more, “Hey, I’ve got this issue, I have this idea, but you’ve done this before. Is there a better way to get there?” And so that’s where I see the generational gap is, how our friendship benefits the other person, if that makes any sense at all.

I asked Ian and Erin, in a professional world like education, some people might wonder why this issue even needs our time at all. I mean, sure, they both work in district communications offices. It might make sense to think through how to send out information in the best way to reach people – are we using the right media? Are we using language people understand?

But really? Do principals need to keep generational differences in mind? Do superintendents? Do teachers? And Ian said, absolutely – this issue matters in ways that may not be obvious, all across a district.

IAN HALPERIN: We quickly realized that it’s more than that. It’s everything from recruiting teachers. It’s how the school board members interact with each other, because you may have different generations on your school board, your superintendent and your cabinet may be a of different generations. So it’s really an issue that covers all areas of education. And so we’ve really worked hard to kind of expand that. Again, it’s about having the messaging and getting to make sure it’s falling on the right people’s ears.

ERIN MCCANN: Well, and I think it’s about feedback and growth as well, especially when we talk about our internal audiences. If you’ve got a principal who’s looking to grow their staff, or maybe you’ve got a superintendent, maybe a new superintendent who was working with cabinet members of different generations, how do you help each one of your employees reach their potential? How do they need to hear that information? How can you coach them up? Different generations need to hear that information in different ways.

RYAN ESTES: Let’s imagine a scenario where you have several different generations and they’re not able to connect as effectively as they would like to. What are some of the downstream negative effects that one could expect to see there?

ERIN MCCANN: Well, I know some of the research shows, talking about some of our older generations, the traditionalists and the Greatest Generation, and they’re not so much in the workforce anymore, but they’re still around. And then your baby boomers, who are still the people leading your districts. For those older generations, it’s really about respect. You know, “I’ve been in this career a long time. I’ve seen more things happen in the world, and you should respect me because I’m in this role.” Whereas with some of your younger generations, that respect has to be earned. It’s not just given because you’ve been there the longest. No one retires from the same place that they started as an 18 year old and is given a pocket watch after 35 years. That almost never happens anymore.

RYAN ESTES: Let’s dig a little bit more into those different generations, then. You already mentioned a couple of them. You have those who were born earlier in the 20th century, fought in World War II, the ones whom Tom, Tom Brokaw called the Greatest Generation. Then you have the baby boomers born after the war, through the mid-sixties. You have Generation X, and I’ll raise my hand there, right at the tail end. You have a millennials, born roughly between the early eighties and mid-nineties. And then, Generation Z, those born after 1995. Those dates and labels might shift a little bit depending on where you look, but I think people will know who we’re talking about. Can you give just a brief snapshot, paint a picture of each one of these?

IAN HALPERIN: Well, sure. One of the things that we talk a lot about is where do they get their news from? That’s an important thing for us, being in communications. Look at those older generations, they are used to turning on the TV news and listening to a respected anchor. And that’s the person they trust. And if it comes from them, it’s absolute truth. They’re not looking for multiple points of view. They’re just looking for the point of view that reassures theirs. And on the opposite end of the spectrum, you’ve got Generation Z and, and even Gen Y where they’re going to find the news source that fits their beliefs. There are enough people out there, and you can define news stories as anything from a mommy blogger to a website, to a Facebook page, to a guy with a microphone. I mean, today, you’re our news source. Where you choose to get your news really varies by generation.

ERIN MCCANN: And the younger generations, you know, it is the rise of the citizen journalist. And what’s good about that is that you don’t have to wait for your hourly news cycle and hope that that’s going to turn over tomorrow. It’s kind of ongoing. But on the opposite end of that is, journalists aren’t trained the way that they used to be, where you really take your time investigating a story and you get a balanced story, because it’s the immediacy and the need to get the information out there as quickly as possible. So sometimes you don’t get the other side of it. And that’s really the risk that we’re running into, going to how our younger generations are getting their news sources is just, “What is the most immediate information in front of me?” I can tell you that the first thing I do in the morning before I even get out of bed, I scroll through my Twitter feed to see if anything important happened while I was sleeping, and I check my email account, and that’s before my feet hit the floor. So if it’s on Twitter, I’m sort of interpreting it as factual news, when in fact there’s nothing saying that it actually is. So that’s sort of a risk that you run into.

RYAN ESTES: That strikes me as dangerous to consider everything on Twitter—

ERIN MCCANN: Very dangerous!

Where people get news might be a big difference between generations, but it’s not the only one. I asked Ian and Erin: for those in educational leadership, what is the most important generational difference to be aware of?

IAN HALPERIN: I think it depends on your role within the organization. For Erin and I, being the communications people, then obviously yes, that’s important. But for a principal, a school board member, that may not be the most important thing you need to look at. Erin talked about the idea of respect, and we talk a lot about that here in Wylie. There’s a certain amount of respect that older generations feel they have because they’re there, because they did the job that you’re doing. They have the experience, they have the knowledge and young people just don’t buy into that anymore. Respect is something that’s earned. It’s something that has to be earned daily. They feel like they have respect just for being born. They come into that classroom and they want respect just because they’re there. And even on the teacher’s side, that may not be the case. They may not respect their students the way they need to. You know, every generation has its values, and so you have to tap into that. It really just comes back to you. What is your role within the district? And how are you going to use that to identify those different groups and work within them?

ERIN MCCANN: I think we do see that a lot with our students, too, particularly our high school students that are coming into their own and they’re not quite adults, they very nearly are. There’s this constant rhetoric of, “I need respect, I need respect, I deserve respect. This person didn’t respect me.” And that is, as Ian said, something that we see a lot with some of our younger generations. And you mentioned all of the generations earlier, but the newest one, these are actually our kids that are not even in high school yet, they’re casually calling Generation Alpha. And these are the kids that I believe were born after 2010 and I apologize, I don’t have that number in front of me.

I looked it up – Generation Alpha is made up of those born between 2010 and 2025.

ERIN MCCANN: But we actually found that, because when we started talking about all of this in presenting on these topics, I’m like, “What is my daughter going to be? She was born in 2013. Who is this kid and what is that going to look like when she’s an adult?”

IAN HALPERIN: She’s going to rule the world. She is totally going to rule the world.

RYAN ESTES: Let’s look a little bit at how these differences play out in schools. I’m sure this matters both in how leaders interact with parents and the community in roles like those that you have, as well as how they interact with employees. And let’s start with parents and the community. What do we need to keep in mind about cross generational communication in this area?

ERIN MCCANN: I think it’s reaching parents where they are. And again, we’re looking at this from a school PR communications standpoint, because that’s the work that we do. But I think this is beneficial for everyone, regardless of their role. How do you get information to your parents? In the old days, you know, when Ian started in school PR, the old days—

IAN HALPERIN:  Stone tablets and smoke signals.

ERIN MCCANN: When you were etching things in stone, there was a lot of printed information being sent out. It was the rise of the print shop and lots of newsletters, things like that. And as we’ve seen technology increase, almost everything has gone digital, which is great because it’s more immediate, but you do run the risk of missing some of those generations who don’t prefer to get their information — I was thinking about some of the things that I wanted to talk about with you today and I was thinking about the traditionalists, the oldest generation that we still have alive and who that is.

My 90 year old grandparents are of the Greatest Generation. They’re obviously not still in the workforce, but they are active in our school communities. So when we as school districts go out and say, “We’re hoping to sell a bond and we’ve got to start these presentations,” you would be crazy to overlook your senior citizen communities. And they’re not going to get on Facebook. They are not going to wait for an email blast to get that information. You have to go out and physically find them. And that’s the best way to communicate with them, either with that printed material or physically being present in front of them.

IAN HALPERIN: We were talking earlier about snow days, you know, your kids still have snow days. And when I first started, you had two ways. You had the call tree to take care of staff, which is on a phone. And then as a communications person, I had a list of secret codes and phone numbers to call the TV stations. We were going to delay school, you’d have to watch your name crawl across the bottom, right? But now, with the information systems we have and the mass distribution systems we have, I can send an email to 20,000 people and make 15,000 calls in under five minutes. So on my flowchart, traditional media is the last thing I call.

ERIN MCCANN: Exactly the same for me.

IAN HALPERIN: And of course we’re a W, so in the metroplex we’re going to be the last thing, it’s going to be noon before our name gets up. But again, it’s utilizing that. We also talk a lot about sphere of influence with social media. Most communities are going to have the local paper that is read by the diehard people, kind of like Erin was saying, the grandparents. But I have more people on my Facebook page in a day than they have total circulation. So it is one of my methods, but it’s certainly not the only method.

RYAN ESTES: What about internally? I’m sure that a Generation X principal, for example, would interact differently with, say, a veteran teacher who is 20 years older than he or she would with a new teacher who might be a millennial. How does all this play out when we think about inside the school or inside the district relationships?

ERIN MCCANN: Well, I kind of think about it in terms of coaching and feedback. Your younger generations actually mirror some of the eldest generations, which we found very interesting in the fact that they like lots of feedback. I’m a millennial, I’m an old millennial, which I might mention, we didn’t define that. There are two kinds of millennials. Either you remember The Oregon Trail as a game or you don’t remember The Oregon Trail. I’m an old millennial. But my boss is a Gen X, so we’re not that far apart in age. I’d say, actually I’m not going to say in case she listens to this podcast and I get the number wrong. We’re just not that far apart in age. But even in the way that we communicate, she might send a quick text to me about something that she needs to address, and that text is one plain sentence. Whereas my response back would probably be a lot more flowery with lots and lots of details. So I might think that she’s mad at me or that I haven’t done something, but all I have to do is walk down to her office and have that conversation in person, and everything’s fine. So going back to your original question about the principal and the different teachers, you’ve got to keep in mind who that person is, what their learning style is like and how you’re going to coach them. Are they someone that desperately needs that face to face, that regular ongoing feedback? Or is it more of the quick check in? “Hey, looks good. Think about improving this. I respect the work that you’re doing”?

RYAN ESTES: That’s really interesting, what you just said, because those are some of the aspects of how we communicate that oftentimes, you know, Myers-Briggs or the DISC profile or other personality tests get at, rather than necessarily being generational divides. Do you see overlap there as well?

ERIN MCCANN: I think you definitely have certain personality types regardless of your age or your generation. But then you also see a lot of this bracketing by the era in which you grew up, which makes sense because certain things that go on in the world influence your life and influence the way that you need to interact with people.

IAN HALPERIN: And that’s part of the thing that we caution people on is, yes, you can bracket people and yes, there are individual styles, but don’t stereotype. It’s like anything else. No one wants to be grouped in and we kind of make fun of, any day you can look on your Facebook feed and see “The top 10 things millennials don’t want you to know,” or “Are baby boomers ruining the world?” There’s lots of tongue in cheek clickbait things to get you out there with those terms. And so we need to kind of rise above that, especially if you’re a supervisor or a principal administrator, and not get too caught up in that, because there are always going to be individuals within those groups. Like you talked about the DISC survey, those kinds of things, it’s good to have that information because that way you can really reach in and know who you’re talking to, know what drives them, what motivates them, and therefore hopefully be a better boss to them and have them be a better employee in return.

ERIN MCCANN: And just remember that millennials are about more than avocado toast.

RYAN ESTES: No matter how good it is.

ERIN MCCANN: No matter how good it is!

RYAN ESTES: What would you say are the wider, the broader implications of all of this on things like hiring or leadership development or even teacher evaluations? What I’m trying to do is get at, as we think generational differences, where are the specific areas and how does it play out in some of these really important facets of the job that a principal might face, or that a department head might face in a school district?

IAN HALPERIN: Well, I think you still have to have a basic understanding. They say that millennials want more feedback from their managers, and they want it on a more regular basis. They’re not content with the once-a-year evaluations. And I know that’s difficult because the education system, you’ve got evaluation tools at pretty much every state requires, but that doesn’t mean you can’t have the casual conversation every six weeks, every four weeks. Especially with a newer teacher or a newer employee, because of the way they get their news and information, they’re used to immediate feedback. And if you’re not providing that to them, they’re going to be frustrated. On the other side, like Erin said, working somewhere for 35 years and getting a watch, I think those days are gone, and really in any age group.

I’m kind of minority. I’ve worked really three places in the time I’ve been out of college. I think that’s because I chose the places well. But they’re really there to see, “What can I get out of this job? What kind of experience can I get? Is there a potential for me to grow? Do they respect me as a person and as a professional? If not, then you know what? I’m going to move on.” And more times than not, it may be to a whole ‘nother career. They’re not afraid to jump careers like people of other generations would never do so.

RYAN ESTES: So in this day and age, when many places are having a hard time finding enough teachers to fill vacancies in a school district, what is the action step there? How can we take this information and use it in order to retain people, in order to attract people, in order to make sure that we’ve got the best teaching workforce?

ERIN MCCANN: Well, I think that this is a very clear message to school districts and to all businesses, honestly, even outside of K12, about having a strong work culture. We know companies that do that incredibly well. Southwest Airlines has been nominated worldwide for their strong culture. There are some other ones I could throw out there too, but they probably didn’t pay for advertising so we won’t give them that shout out. But Ian talked a little bit about your millennials and your Gen Z and the need for feedback. It’s not just feedback and ongoing growth, but also, we’re starting to see studies about how younger professionals are extremely cause-oriented and how they’ll gravitate to career paths and to jobs where money is a part of it. It’s part of the reason — because you all have to pay your bills and support your families — but they don’t necessarily take a job or leave a job because of the financial component. That’s just one piece.

There’s a great meme out there that people love to share when they’re dissatisfied in their career, talking about how people don’t leave jobs, they leave bosses. And I do think to some degree that is true, because if you’ve got a strong work culture, if you value your employees, if you make them feel valued, and if you’re finding continual areas for them to grow as professionals, they’re more likely to stay and to buy into that same culture, which then helps with your teacher retention and your recruitment and so on and so forth.

RYAN ESTES: What about collaboration? That’s a buzz word, right? We hear that all the time. I use that quite a bit. How do you foster intergenerational collaboration?

IAN HALPERIN: Well, I think Erin touched on it earlier. As much as I was a mentor to her, she certainly has been a mentor to me. And they call it reverse mentoring, which I’m not really sure why, it’s still the same function. You want to be effective, I think just about everybody wants to be good in their job, and the reality is, there are five generations working together and I don’t think that’s going to change for a long time. So if you’re going to be successful at whatever level you’re at or whatever career you’re in, you’ve got to figure out how to do that. And so seek out someone at work, maybe a team member, maybe someone teaching the same subject. For me, it was someone in the same profession, and they talk about hiring for your weakness. When I have the opportunity to hire, I’m certainly going to look toward someone who brings a different skill set.

I can lay out a newsletter and run a mimeograph machine pretty well. I need the Twitter person, the 140 character master. So you’ve got to look toward those things because none of this is going to change. This is not a fad. The generational thing is going to continue and the distance between them is only going to grow as people live longer, as people start working earlier. Our workforce is going to be more diverse. This could be a whole ‘nother discussion, but you even talk about culturally, there are lots of workshops that are done on communicating cross-culturally. And really generational is really just a culture, so all of these rules really still apply.

RYAN ESTES: Erin, that idea of a reverse mentor — and I’m assuming the reverse comes in where you have a younger person pouring into an older person — what is that like for you, being in this mentoring relationship? What do you, as the younger party, get out of that?

ERIN MCCANN: I like to say that I taught Ian to use emojis in his texts, but that’s not really true. It just makes for a great pity laugh when you’re doing a presentation. I think when you mentor, regardless of who the person is or how old they are or they are not, sharing knowledge and a wealth of knowledge and expertise is equally as gratifying to the person sharing it as the person benefiting from it, because you start to feel as though you have something credible that someone else can benefit from. It’s also building friendships and collaboration. In school PR, many of us are in unique positions where we have a very small staff or maybe are a team of one, and so your colleagues really are not people who work for the same district as you. They are people who are all over the state or all over the country.

And so when I run into a problem, depending on what that issue is, I’ve got a list of people I can call. I know if I’ve got a question about a public information request, Ian is going to be my first call, because he knows that law backwards and forwards. And so I would say he benefits from our friendship because he knows that he’s got this information that he can share when somebody needs some help. And it would be the same thing for me. The information just looks a little bit different, whether it’s a new technology or a new way of looking at something or maybe even calling him to task on an inappropriate social media response, whatever that looks like.

IAN HALPERIN: She taught me hashtags. It wasn’t emojis, it was hashtags.

RYAN ESTES: And then as we think about working with students, what are the kinds of generational differences that are really important to keep in mind for staff, whether they be certified or noncertified in a district?

ERIN MCCANN: I think one of the biggest things that I’ve seen in working with high school students and then young staff, because there’s not really a huge age difference in those two groups, is the lack of privacy and how they’re fine with that. They have never lived without social media accounts, not in their mature life. Probably middle school forward. And I know I was late in college when I got my first social media account. So anything that I would have said or done or posted in middle school and high school and early college, there is no digital footprint for that.

RYAN ESTES: Thank goodness, right?

ERIN MCCANN: Thank goodness! And so some of the, I hate to say younger kids, because I think it sounds disparaging and I don’t mean that, but some of our younger professionals and high school students don’t have a great concept yet of how that digital footprint can follow them.

And so they’ll basically put anything online except how much money they make. That was a really weird anomaly that we found in the research is, they are still quite private about how much money they’ll make. They’ll talk about how much money they owe, but how much money they make they still keep that to themselves. I think we’re just at the tipping point of seeing the long term ramifications, where we’re going to see, you know, new politicians that everything exists online. This is a turning point, in my opinion, about what that’s going to do.

RYAN ESTES: Let’s do a little reflection here. I’d love to hear from both of you on this. What would you say is the most important takeaway when thinking about how different generations communicate within the world of education?

IAN HALPERIN: I think for me, it’s that they want to be appreciated. They want to know that their feedback is valued and listened to. Whatever generation you’re talking to, they just want to know that their opinion is valued, that their work is valued and that they’re part of the organization. Everything else is sort of secondary. Because if they don’t feel that, then any efforts you do are going to be wasted.

ERIN MCCANN: I kind of feel like a cop out, but I kind of want to agree with Ian on that. In some of the research that we did, it talked about a lot of the disconnect with generations. It was not that they couldn’t get on board with the same ideas, but that they went about it different ways. So one group might desperately need to do trust exercises to build rapport, and then another group absolutely thought it was a gigantic waste of time. If you can get everybody in the room and you can figure out the different ways that everyone needs to communicate with each other, that then you can get to the end goal in the most productive way possible.

RYAN ESTES: As you look at your respective school districts, Wylie and Crandall, are there specific action steps that you or your districts have taken in order to better facilitate this kind of cross generational communication and better working relationships between the generations?

IAN HALPERIN: Yeah, Erin came and we presented to my staff—

RYAN ESTES: Tell me about that.

IAN HALPERIN: Well, it was actually because we presented somewhere else and a principal said, “You’ve got to have them come and do it for our staff, because this is important stuff.” Again, I think it’s no different than dealing with any other situation where you’re not reaching your audience. Whether it’s because of a language barrier, whether it’s because of a technology barrier, this is really just another example of making an effort to reach people where they are and respecting their opinion and what they bring to the table. It just happens to be talking about age. And so if you think about it in that context, then it’s really not as abstract. It’s just another situation where we’ve got to do a better job of making sure we reach our audiences, whether that’s internal or external.

ERIN MCCANN: Right. I agree. As professional communicators, that is our job, is to find out where everyone is, what they know, what they need to know, and how we can get it there. So if we can figure out how to get everybody on the same page and figure out the best way to connect with each one of those audiences, we have a much better chance as a school district of successfully getting our messages out.

RYAN ESTES: We have been speaking with Ian Halperin from Wylie ISD and Erin McCann at Crandall ISD in Texas. Ian and Erin, thank you both for taking the time to speak with me today.

IAN HALPERIN: Well, thank you Ryan. We appreciate it.

ERIN MCCANN: Thank you for having us.

Why do we put together this podcast? It’s simple: at Frontline Education, we’re passionate about education. We regularly publish new stories about leaders in K12 who are doing amazing things. So if you liked this one, click on that subscribe button and make sure you don’t miss any of them.

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For Frontline Education, I’m Ryan Estes. Thanks for listening, and have a great day.