Navigating Generational Differences in the Workplace, with Katherine Jeffrey

Announcer: 

Welcome to The Lawyerist Podcast, a series of discussions with entrepreneurs and innovators about building a successful law practice in today’s challenging and constantly changing legal market. Lawyerist supports attorneys, building client-centered, and future-oriented small law firms through community, content, and coaching both online and through the Lawyerist Lab. And now from the team that brought you The Small Firm Roadmap and your podcast hosts 

Stephanie Everett (00:35): 

Hi, I’m Stephanie Everett. 

Jennifer Whigham (00:36): 

And I’m Jennifer Whigham. And this is episode 466 of the Lawyerist Podcast, part of the Legal Talk Network. Today, Stephanie talks with Katherine Jeffrey about generational gaps. 

Stephanie Everett (00:46): 

Today’s podcast is brought to you by Posh Virtual Receptionists, Postali, & LawPay. We wouldn’t be able to do our show without their support, so stay tuned, tell you a little bit more about them later on. 

Jennifer Whigham (00:56): 

So Stephanie, this topic is really interesting to me because it comes up a lot in our lab community, and I think just a lot in the business world in general. So I’m curious, how did this conversation go? What did it feel like? 

Stephanie Everett (01:09): 

Yeah, I mean, I think Katherine has so much cool knowledge and how she frames up the issue, so I’ll let everybody listen to that. But I think it’s one of those topics that when you see it, I see it a lot too. And at first I thought, oh, generational gaps. Is this really relevant? Are we really doing a show about this? But then I heard Katherine speak a couple months ago, which is how we got her on the show. And I’ll say, so earlier today I was on a coaching call with some lobsters and an issue came up with one of their associates and we were talking through what the issue was, and at the end, one of the partners was just these millennials, that’s how they are. And I was like, aha. I just kind of jumped on it, but I was like, yeah, you say that, but actually some of this behavior of what you’re seeing can be explained and the differences, it’s not that this person is bad, it’s not that this person is showing up to work, that they have a different experience growing up, which is impacting how they work today, which is exactly what, and Katherine, we get into all the specifics. 

(02:18): 

And so I think if people will just give themselves a little grace and say, okay, this is something maybe I have been approaching the conversation the wrong way. I think there’s a lot to be learned from this as leaders. And now, ever since I first met Katherine, like I said a couple of months ago, I’ve been fascinated with this and I’ve been talking about it kind of nonstop. So I was obviously very excited to now have her on the show and be able to share this knowledge with everybody. 

Jennifer Whigham (02:45): 

That’s cool. I can’t wait to listen. And millennials, I think the oldest millennial is maybe 42 at this point. So as a catchall, I don’t know. I’m on the cusp. I’m on the cusp of Gen X and millennials, so I never know where I fit. 

Stephanie Everett (03:00): 

She says that you’re xennials. 

Jennifer Whigham (03:02): 

Oh, we’re xennials. Okay. I’ll take it. I’ll be on that sometimes. I always grew up thinking Gen X, but then it changed. But regardless, I’m really interested in this conversation, so let’s go ahead and listen to you and Katherine. 

Katherine Jeffrey (03:18): 

I am Katherine Jeffrey, and I’m a generational strategist and really enjoy working with companies and organizations, helping them build bridges across that generational divide and really work towards a better way forward together. 

Stephanie Everett (03:36): 

I love that. And I’m sure we’ll talk about this, but I heard you speak a few months ago now, and everything you said has just stayed with me. I’ve probably repeated your bathroom example like a hundred times since then, so we will for sure have to get into that. So I’m so happy to have you here with me today. And maybe just to tee this off, could you just define what is a generational strategist? 

Katherine Jeffrey (04:01): 

Yeah, I mean, really I think a lot of companies just, we look at all these areas of diversity, and I think that this space between the generations is often overlooked, and it’s one of the biggest issues in diversity right now. And I think it’s something that deserves a lot of attention. And I think I had a millennial say to me about a year ago, this is one of the most important topics of our time. I mean, it’s causing a lot of tension. And if we can bring people together, I mean the difference we can make is huge. In fact, there was one study done that found that when you have a team with only a 10 year age span, so that’s one generation represented, they will meet or exceed expectations 35% at the time. You expand that to 25 years of age or more, make it a multi-generational team, and those teams will meet or exceed expectations 73% of the time. I mean, that’s more than double when we’re all working well together. So I think it’s worth the investment and I think there’s great things to happen as a result. 

Stephanie Everett (05:09): 

Well, let’s kick it off and define, as I understand it, we have more generations showing up in our workspace today than ever before. Am I right about that? 

Katherine Jeffrey (05:20): 

Correct. Five generations. 

Stephanie Everett (05:22): 

Okay. So let’s just put some words around it. So what are the current five generations as we have them today? 

Katherine Jeffrey (05:29): 

Yes, we have the traditionalists. So they were born between 1925 and 1945. And then you have the baby boomers who were born between 1946 and 1964. And then you have Gen X, which is where I fall, and we were born between 65 and 80. And then you have millennials who are 81 to 95, and then Gen Z who is 96 to about 2012. And then there’s a lot of millennials out there who are like, I’m a millennial, but I’m not really a millennial. And they often identify as a xenniall, which is spelled with an X, and then ennial, and they’re kind of half gen X, half millennial, and they’re kind of right on that cusp between Gen X and millennial. 

Stephanie Everett (06:15): 

Everybody wants to be a Gen Xer. 

Katherine Jeffrey (06:18): 

I mean. Right. 

Stephanie Everett (06:21): 

So I know we’ve all heard these terms and we’ve all read studies or even just quotes about generational differences, and it feels like sometimes it’s an excuse, it’s a label, right? Oh, we’re calling out something as a generational difference, but that’s just a label for why someone’s lazy or doesn’t work hard or that seems to be how it forms in our mind. And what was so impactful when I heard you speak was that you really explained there’s actual reasons why we show up differently based on our generation. So I wonder if you could unpack that a little bit for us, because to me that was just so helpful to say, oh, this isn’t just a label. It’s like this is a real thing we should know. 

Katherine Jeffrey (07:09): 

And I kind of think of it as when you have the generational conversation, you’re looking through a filter that helps us understand how the world has changed over time. Therefore people and the things they value and the ways they communicate have also changed. I think one of the things we talked about that day was even if we go back to the baby boomers and we think about many boomers grew up in a small house and they had one bathroom, and I think the average number of kids in a boomer family was like 3.7. And you’ll hear a lot of boomers say, I had five siblings, I had seven siblings. They had typically had very large families, and again, they had one bathroom. So boomers learned at an early age that conflict was just a thing. And if you have these five siblings, you guys share a bathroom with them, you’re learning how to navigate different personalities, you’re learning how to care about different personalities, and conflict is just a part of your day. 

(08:14): 

Boomers also learned how to sacrifice at a very young age. They started working at a young age because they were doing things on behalf of the larger family, trying to move the family forward. And then if you jump well, if we stop next, you’ve got Gen X, and we were known as the latchkey kid generation. We would come home from school and we’d have a key tied around our neck. And that’s illegal in many states today. If you’re under 12, we would do our homework, we would make dinner, we would babysit our younger siblings. So for Gen X, you kind of figure things out on your own and you learn how to navigate this world. And Gen X also has a huge priority on relationships. They were very important because they needed all of these outside relationships to function because the divorce rate had tripled at that point in time. 

(09:10): 

So many more women were in the workplace, and then you get to the millennials, and for them it was a huge priority for their parents to really listen to them. Many boomers grew up with children were to be seen and not heard. So they bring that into the workplace. That’s how the boss interacts with the employee. I’m paying you to do a job. I don’t need to hear from you. I just need to know you’re doing your job. When at the same time they said, I’m not going to raise my kids that way because I had parents who really didn’t care about my feelings. And so many millennials grew up coming home from school and sitting down at the dinner table and having back and forth friend to friend conversations with their parents. And so millennials are actually the first generation to call their parents their friends. 

(10:04): 

And if we get into leadership at some point, if you think about the hierarchy that used to exist, it’s getting greatly flattened out. And that’s one of the big reasons because you’re no longer, just because you’re older than me doesn’t mean I have to respect you. It actually means that I’m probably going to get along with you pretty well and you’re my friend. It’s, it’s a different mindset. And then with our Gen Zs, if you think about the average number of kids in a Gen Z family, it’s about 1.7. So you have a lot of only children. Most Gen Zs have their own bedroom. They have their own bathroom. They’ve spent a lot of time in front of their screen. So when they think about conflict, they’re like, I don’t do conflict. In fact, now my parent is not just my friend, their parent is their best friend. 

(11:01): 

So it changes things. And then what we do is we expect Gen Zers to enter the workplace and interact on a social level in the same way that a baby boomer or a Gen Xer would. And we’re like, figure this out. Have these don’t how to interact with our clients. What’s wrong with you? And they’re going, yeah, but I don’t do it that way. That doesn’t make sense to me. And we have to help them understand why older generations communicate the way they do and value the things they value. And I think I gave the example of the pizza company where all the older managers were really frustrated with the Gen Zers because the Gen Zers didn’t want to pick up the phone and take an order for a pizza. And they’re like, why are they doing this? And well, how many times has a Genzer ever answered a phone and didn’t know who was on the other end? 

(12:00): 

Right? Never. That’s never happened for them. And add to that, many of ’em don’t even answer the phone. They prefer to text and those kinds of things. And sometimes we take for granted skills that we think younger generations should just intuit and know when in reality we actually have to offer them training and opportunity to understand how the world at large operates, and not just from their perspective of the way the world’s been since they were growing up, but they don’t have a context for the world of Gen Xer grew up in, it doesn’t even translate for them. Right? 

Stephanie Everett (12:37): 

Yeah. I mean, it makes so much sense when you say it. And when I was with you, you had us all sitting by our generation, so it was like we were all five were represented in the room, and as we went around and each generation gave a report of how do you like to communicate? If somebody wants to get ahold of you, what are they going to do? And it was so interesting as you started with those traditionalists and it kept going around and you just saw it shift and you knew what was coming. It was like by the time we got to the younger generations, they were like, why would you call me and why would you just call me out of the blue? If you need to talk to me, you should send me a message that says, we need to talk about this thing. And that was one of those light bulb moments for me on our team, because I was like, I’ll walk into your office or I’ll just, Hey, let’s chat. And never really realizing that that would be so odd to them that they would be offended by that. How rude of you to just show up or just call me and not tell me the agenda? I was like, oh, yeah, that’s super interesting. I just didn’t think of it. 

Katherine Jeffrey (13:38): 

Right. Why would you? Yeah. 

Stephanie Everett (13:42): 

Yeah. So it’s really practical things about the way we were raised and how we interacted with our parents that are now translating into the workplace. And if we’re not aware and not realizing it, we don’t know how this is impacting our workplace. 

Katherine Jeffrey (13:57): 

Yes, absolutely. Absolutely. I mean, even if you just think of when you write someone an email, how is that interpreted? Right? Many younger generations will say, yeah, my boomer boss sent me an email and it’s a book, right? It’s so long. And then they don’t even read it. And the boomer’s like, what do you mean you’re not reading it? I just gave you this gift. I gave you all this context. And then they’ll say that Gen X emails are really bossy and rude. And they’ll say, they just tell me what to do and bullet points. And sometimes in the subject line it’s just instructions like, go do this, get this done. Because Gen X is very efficiency minded, and for younger generations, emails are simply a place where you document important information. It’s not a way to have a back and forth conversation. And then they also don’t answer emails right away. 

(14:51): 

They typically, they’re waiting to respond to you until they gather all the information that’s necessary, because in their mind, it’s a waste of time to send you another email. Not only does it waste their time, but it wastes your time. And often the Xer and Boomer, it’s like, wow, you really aren’t into this project, are you? Or they start to think that they’re not really a team player because they’re not responding right away, which feels important to an X boomer. I need to know you received it. I need to know you’re on it. And younger generations just have a very different perspective. And so if we never talk about those things and figure out how to work through them together, it doesn’t mean one side always has to be the one that changes, but we have to be able to have the conversations so that we can figure out a way forward where we’re not creating these negative narratives about somebody, or we’re assuming the worst, but rather understanding, no, we’re all working towards the same goals, but we have different ways of getting there now. 

Stephanie Everett (15:52): 

Yeah, makes sense. Well, let’s take a quick break and hear from our sponsors and we come back. We’re going to dig into some of the more specifics now that we have this information, what we should do with it. 

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Stephanie Everett (18:21): 

We’re back and we’ve just really set out and started to understand. And I love that bathroom example as I mentioned, because it made so much sense to me, like, oh yeah, if you had to wake up every day and negotiate when you can brush your teeth, and when you get bathroom space, of course you’re going to approach the workspace differently from someone who just has never shared a bathroom in their life. And I think I have a friend who works on the college campus and the kids, they can’t believe that you’d have to live in a dorm room and share a bathroom. A lot of students are choosing to just go to, they want to go to apartments, they don’t want to live with someone in that shared experience. They’re like, why would I do that? So it seems to me, so this is good for us to know. It’s not just they’re weird, it’s that they grew up in a different set of circumstances. But as employers now, it means we have to approach our teams differently. And it might mean we have to train differently. I suppose we have to assume our team members are coming to us with a different skillset, not the one that I came to work with. And so how do you start to help us unpack what does that actually look like? What do we need to be doing differently that we might just otherwise assumed was the case? 

Katherine Jeffrey (19:36): 

Yes, I love that. I often talk to companies about the three Cs and the first C. If you think about the core three Cs built on top of each other, the core C is care. Because a lot of boomers will say, but Katherine, I don’t care. They’re like, you leave your feelings at the door, you’re here to do a job. I don’t care. But if you don’t care about younger generations and care about them as holistic people, they’re just not going to stick around. That’s becoming increasingly important. So they want to know, do you see me as a unique person? And then they want to know, do you actually care about people and the planet? They want to work for organizations where their values are in alignment. And those are some pretty high values for younger generations. And then you’ll hear a lot from them, the words authenticity and transparency. 

(20:36): 

So is my boss, is my CEO, are they actually authentic and transparent? Are they people that I can actually trust or am I working around people that I don’t necessarily agree with or feel safe with? The second C is curiosity. I think a lot of this started with how millennials were parented, right? Their parents wanted to hear their opinions, they wanted to hear their feelings. And so one of the quickest ways to discourage a millennials to not listen to anything they have to say, and they don’t believe you have to do everything they tell you to do, that’s not it, but they definitely want to be heard. So under curiosity, do I feel safe sharing my thoughts and feelings? And then are they actually heard? Are they respected? Is something done with them? Not every time, but sometimes, right? And then 86% of Gen Zers say the number one reason they’ll accept a job offer is if you tell them how you’re going to grow and develop them. 

(21:38): 

And so growth and development and nurturing that curiosity about their personal future is huge. A lot of them will-millennials and Zs will talk about career mapping, gen Xers and boomers. They’re like, well, I wanted to do this, so I figured out how to get there. Well, younger generations are saying, no, I want you to help me figure out how to get there. If you’re my boss, Stephanie, I want you to bring it up in our meetings. I want you to make sure I’m on track towards my goals. And that communicates to me that you care about me as a person and you’re helping me get where I want to go. And then the third one is just collaboration. Are my values aligned? Is my intergenerational team actually fulfilling a greater purpose? And I think sometimes a real practical thing under this one is pulling apart the values and the mission of your company and thinking about the words that are used, and do they translate across the generational lines? 

(22:46): 

Is every generation going to get behind it? A perfect example, I just got done doing some focus groups for a large company and their corporate survey, their scores have gone down around the question of ethical behavior of managers. So of course they’re like, oh my gosh, what’s happening? What’s going on? Well, what it was is younger generations are now translating ethics and ethical behavior is, are you treating me with respect? Is the tone in the email appropriate? So it’s the same word, but it has a different meaning. And so sometimes we have to pull those words out and even create intergenerational groups to talk through it. What does this mean? Do you value this? Is this going to motivate you? And then there’s also, if you think about collaboration, you have to think about generational bias within your organization. I always give the example of we say things like hashtag OK boomer, or, oh, you’re such a millennial. 

(23:54): 

We laugh about these things. We think they’re funny. But what we don’t realize is it actually impacts how people show up on our teams and our workplace. And I always ask groups that I’m with, I say, how many of you would make those same comments in any other area of diversity who would look at me today and say, oh, you’re such a woman. You wouldn’t dream of saying that in today’s workplace. But we say it about an entire generation of millennials, and quite honestly, they are so tired of it, right? They’re like, stop saying that about me. And so we have to be aware of what we believe, what our personal biases are, and then how’s that filtering down throughout the organization? I had one CEO, she was a boomer. She used to come into her workplace pretty regularly. She’d step out into their kind of common space and she’d say, I need a millennial. 

(24:53): 

And what she was really saying is, I’m a little bit embarrassed. I need some help with technology. Can someone please come help me? So reluctantly, a millennial would get up, they’d go help her, and eventually they started leaving her company and she’s like, I don’t know what’s going on. She didn’t have a bad attitude towards her millennials. She just was like, what’s happening? And one of ’em finally looked at her and said, we bring a lot more to this organization than just our skills with technology, but that is the only thing you ever call us out for. So even by her trying to hide her own embarrassment, she was isolating an entire generation so much that they didn’t want to work for her anymore. And so we have to be aware of these things and create spaces for every generation so that they can do their best work. 

Stephanie Everett (25:51): 

I love that framework. And I’ll say when we were in the room seated by generations, and you said that, and I remember you said, would you ever say you’re being such a woman right now? And everybody was just like, it was a room full of women. So of course we were like, that’s offensive. But it was one of the Gen Zs, and I just saw her eyes popped, and you had just explained to us that Gen Z really cares about inclusivity, and this is one of their core values that they have been raised with. And I just saw her face like, oh, when I say, okay, boomer, it’s the same. And I was like, yeah, wow. That was so impactful to have that reframing of how we’re showing up and not even realizing that we’re not being inclusive if we alienate or if we call out people based on these generational differences. 

Katherine Jeffrey (26:41): 

That’s huge. 

Stephanie Everett (26:43): 

Huge. I know. It’s like let that sink in. The relationship with our parents was so interesting. And one of the other things you shared with us, I think it was millennials, but you’ll correct me about which generation the parent might come and say to the kids, I’ve been offered a job, should we move across the country? Like the older generations, the dad’s going to come home and say, pack your bags, everybody. We’re headed to Utah. There’s no family discussion about that. But as we get into the younger generations, that shifts and now the kids become part of the conversation and decision-making process. I don’t want to leave my friends. I don’t want to change schools. How dare you. I would give up more money because I want to stay here. So we have different relationships with our parents, and I think sometimes the parents get a bad rap. 

(27:39): 

I’ve heard them getting made fun of a lot. Like, oh, the parents show up to work now. Or the parents want to know. I have a friend who’s in a admissions office at the law school, and she’s like, I have parents coming to talk to me about why their kid isn’t getting job interviews. And she’s like, law students, not high schoolers, law students, right? Oh, yes. In our mind, we think you’re in law school. You should be out there doing this. But what’s interesting to me that some companies you’re working with are taking that concept and actually embracing it and saying, let’s lean in and let’s make the parents part of the conversation. So I wonder if you could just chat about that. I just found this super fascinating. 

Katherine Jeffrey (28:19): 

Yeah. First I wanted to say that parents are now showing up at job interviews on top of that, and I know there’s a law firm I worked with where they literally had a parent show up for the first week of work, right? 

Stephanie Everett (28:34): 

Yeah. 

Katherine Jeffrey (28:35): 

It’s real. It’s out there. So LinkedIn had a bring your parent to Workday. Sometimes companies are sending out newsletters to parents, and they’re actually finding that to be a win-win because now they get to promote their company to the parent, but then they also, that parent sits down with their Gen Z and says, Hey, look at all these amazing things your company is doing. So Gen X and Gen Z, because Xers are the parents of Zs typically, and they have a huge impact on one another, very influential back and forth because they even have matching tattoos. A lot of X parents have tattoos that match one on their kid. So there’s definitely a stronger bond there. 

Stephanie Everett (29:28): 

Yeah. So I think it’s interesting because it’s not only are we thinking about how our employees are showing up, but this is like how do we actually embrace this relationship with the parents and get them involved? I mean, I’m sure there’s a lot of listening right now that it never occurred to them to have a bring your parent to Workday or that they should do a newsletter or even a report home. Like, Hey, here’s the skillset your kid might need to work on in their profession. That’s new to a lot of us, but yet some companies are experimenting with it and finding some success. 

Katherine Jeffrey (30:03): 

Yep, absolutely. 

Stephanie Everett (30:05): 

Any other examples of something that is just different that you’re seeing that people are doing that maybe we’re not thinking of that we should be? 

Katherine Jeffrey (30:13): 

Yeah, I think another thing to think about is this idea of co-mentoring. So if I’m a Gen Xer and I’m mentoring a GenZ that GenZ has just as much to teach me about the way the world is turning, where we’re headed. And this is the first time in history that younger generations are teaching older generations about the way the world works. And so if we’re not creating that kind of like, yeah, your voice matters. My voice matters, let’s learn from each other. I mean, that’s culture changing. I would also say think about your leadership team or your board. And while if it’s just Xers and Boomers making all the decisions about how you’re going to move forward or how you’re even going to respond to reviews about your organization online, even if Zs or younger millennials maybe aren’t ready to be on a board, invite them into conversations. 

(31:19): 

Get their perspective. Allow them to share with the whole team. Because if you don’t listen to them, you’re just going to fall further and further behind. And if you’re not letting them craft some of your responses to the outside world, you’re probably going to miss, like we talked about earlier, certain words that mean certain things to different generations. So getting those perspectives from everyone I think is really, really important. And then thinking about just feedback. I think when millennials came into the workforce, everybody was giving them a hard time. They wanted more feedback. Well, of course they did. They actually talked back and forth with their parents. And so a constant thing I hear all the time is millennials really, they expect feedback to go into directions. They don’t just want to hear from you. They actually want to share what they think about you and how things are going. 

(32:16): 

And they want to work on the relationship. It’s not this, I’m going to be disrespectful and you need to listen to me. It’s why don’t we learn from each other so we can both grow. And for them, it doesn’t even make sense that you wouldn’t want to hear what they have to say. And I would also say, think about the size of your team. Younger generations seem to be requiring more relational support. And so if you’re managing 30 people, that’s probably way too many. A lot of people are saying six to seven people is a good size team because it takes a lot of back and forth. And even Gen Zs, they’ll say, I want feedback in real time. I want to know if I’m doing it right, doing it wrong. I want to make sure I’m on the right track. They don’t want to mess up, they don’t want to fail, and they expect to have somebody who’s there and accessible for them. And it’s not that they’re not capable. Again, they’ve just had a lot of interactions with people who have had more wisdom and they would like to continue that. So those are some things that pop to the top of my mind. 

Stephanie Everett (33:28): 

Yeah, there’s so much, and I just am so appreciative of you getting the conversation started for us. I know we could learn so much more, but if anybody just takes anything away from this conversation, I think it’s just that knowledge. And remember the bathroom, I can’t tell you. I’m telling you hundreds of people, and every time I repeat that bathroom story, they’re just like, oh, I get it now. One bathroom. One bathroom for the whole family versus your own bathroom. And it’s like, okay, that explains so much. But it really does. 

Katherine Jeffrey (34:02): 

I love it. 

Stephanie Everett (34:03): 

Well, thank you so much for being here with us. We’ll make sure if people want to learn more about you and the work you’re doing, we’ll have all those links in the show notes because I think we’ve just started to scratch the surface and there’s a lot more work we all need to do to figure out how this is going to work and how we bring these new generations in. And like you said, really learn from them because they have a lot to offer. So thank you Katherine, for being with me today. 

Katherine Jeffrey (34:27): 

Yes, thanks for having me, Stephanie. 

Announcer: 

The Lawyerist Podcast is edited by Britany Felix. Are you ready to implement the ideas we discuss here into your practice? Wondering what to do next? Here are your first two steps. First. If you haven’t read The Small Firm Roadmap yet, grab the first chapter for free at Lawyerist.com/book. Looking for help beyond the book? Let’s chat about whether our coaching communities, are right for you. Head to Lawyerist.com/community/lab to schedule a 10-minute call with our team to learn more. The views expressed by the participants are their own and are not endorsed by Legal Talk Network. Nothing said in this podcast is legal advice for you.