Episode 8: What Boomer Leaders and Gen Z Workers Can Learn From Each Other

Katherine: Welcome to GenShift, the podcast where we explore how generations see the world and what happens when we actually listen to one another. I'm your host, Dr. Katherine Jeffery, a generational strategist and leadership consultant.

I created GenShift to open up real honest conversations about how generational differences show up daily in our work and how we can use them to work smarter together. Today's episode brings together Carol, a Baby Boomer and Valerie a Genzer. Their relationship began in the workplace, but it's grown into something that bridges age, experience, and perspective.

We'll talk about how they've learned from each other, how they communicate across differences and what they both wish other generations understood. Now, before we dive into their story, let's set the scene.

 For baby boomers. They were born between 1946 and 1964, an era of post-war, rebuilding, social change, and expanding opportunity.

They value loyalty, hard work, and steady progress. Many boomers built their identity through career longevity and commitment. For Gen Z, they were born between 1996 and 2012. Gen Z has never known life without technology. They've grown up surrounded by global connection, constant information, and very rapid change.

They value authenticity, inclusivity and wellbeing. And they're redefining success to include balance and purpose, not just achievement.

When these two generations meet, it can feel like two different operating systems trying to connect, but when they do connect, the combination of Boomer wisdom and Gen Z, adaptability can create something truly remarkable.

 So, Carol and Valerie, so glad to have you both here today. I just wanna start, just tell us a little bit about who you are and what you're up to.

Carol Wagner: Okay. I'll jump in. So I recently retired. I was the head of it varied, but learning talent development depending on the time at a large company. And I moved then to Colorado after I retired and I am enjoying very much being in the mountains. But it's really nice to say connected with the folks that I worked with.

Valerie, it's delightful to see you again. 

Valerie Hebenstreit: Yeah. And you, Carol? So Valerie Haven Strike, I am a specialist in learning and development. So I actually started working with Carol as an intern. I think that was four years ago now. And I am based in Chicago, Illinois. I am a 1999 baby, so I'm still a 19 hundreds genzer.

Just for some context there. 

Katherine: That's perfect. And what does that mean to you, Valerie, when you say that? 

Valerie Hebenstreit: I think the term is Zillennial, so I identify with the cuspers a little bit. Ah, but yeah. 

Katherine: Excellent. Alright. you said Valerie, you were an intern for Carol. Tell us how you all got connected and how that happened and what your first impressions of each other were.

Carol Wagner: Ooh. I wanna jump in and tell you that I hired her as an intern and she was a rock rockstar. And then I called her up nervously and said, hey, it's been going really well and I don't want you to have to answer on the spot, but would you think about whether you could make enough time to juggle your schoolwork and some part-time hours, however many you want, but we would love to keep that relationship going.

And she said...

Valerie Hebenstreit: Yes. 

Carol Wagner: And she said, I don't even need to think about it. Yes, because we really were already doing very cool things. And so she did continue through the school year, on a part-time basis, and then we very wisely scooped her up upon graduation and she came on full time. 

Valerie Hebenstreit: Yeah, I would say that.

I didn't know it at the time, but it was a big turning point for me in my life. I was getting my master's in human Resources in Champaign at the University of Illinois, and part of that was you had to complete a summer internship and I was already doing one through the school, so I wasn't like really looking, but I was exploring my options.

And that's when I heard from Carol and the recruitment team and I really liked Carol's approach. It was very, I want to develop you. I want you to do what you're interested in, not just, take coffee orders and do what I tell you. And so I think that was just so eyeopening to me for that to be my first real adult job out of college when I did transition into full-time.

And yeah, it really led me to where I am today. 

Katherine: Now, I tell people a lot like, 86% of Gen Zs say the number one reason they'll accept your job offer is because you're telling them from day one how you're gonna grow and develop them. 

So it sounds like Carol hit a home run there with you.

Carol Wagner: Yes. Yeah. I'm wired that way. It wouldn't have occurred to me not to do that. So I guess it was a good match from the start, but I don't think I recognized how unique what we had developed was until the end of the internship. Valerie said she got together with a bunch of her other, colleagues, classmates and they were comparing notes and she talked to me the next time with big eyes and said, these people are like sitting in cubicles, filing things and and you've got me presenting in front of the top senior leaders and helping you do like major things.

And I said of course. This is how you're going to learn and grow and do all of that. So I think we just both were very fortunate out of the gate to have had that opportunity. Yeah. 

Katherine: Yeah. 'cause you love to develop people and Valerie loves to be developed. 

Valerie Hebenstreit: I think just from day one there was like a trust there that I feel like a lot of my generation kind of craves. We want people to believe in us and know that even though we don't have as much experience, that we can bring, critical skills to the workplace. 

Carol Wagner: And you did.

Katherine: And she still does. 

Carol Wagner: And she well now for somebody else, but Yes, that's right. 

Katherine: Still does, that's while you're sitting on the side of a mountain. 

Carol Wagner: Yes. 

Katherine: All right. So Carol, let me ask you a question. Yes. Like you've, obviously throughout the years, you know your career, you've had different people on your team, you've supervised different people.

So first how big was your team and then having a Genzer on that team, how was that different for you? 

Carol Wagner: That's a really key question because Valerie expanded my team. And I had one direct report at the time, and then Valerie as an intern, and then her as a direct report , where we were working as a holding company.

They're quite lean, particularly in the HR space. And so I did not have a particularly large team at that point.

Katherine: And then how has having a Gen Z or on your team been different than maybe people you've had in the past? 

Carol Wagner: Absolutely. So I would say the big area that we needed to work through was technology.

Not only is my generation not quite as organic, it's just not intuitive for us. We didn't grow up with it, but I seem to have a particularly Amish kind of perspective on things. And so Valerie may have had to do a lot more in that regard than maybe she bargained for.

For example, we started to work together and she immediately started using teams messaging for everything.

Nobody else in my generation was using teams messaging. So that was, okay, I get it. I gotta get on the bandwagon and modernize, the way I communicate a little bit.

And was that pre COVID? We connected up during COVID. Yeah. 

Katherine: Okay. During COVID. So that's before Teams was a huge deal, right?

That it is now. Yes. Everybody has teams now. Yeah. 

Carol Wagner: That's fair. And I think in terms of the technology piece, one of the funny, but cringe-worthy stories is that we interviewed Valerie and she confessed after we hired her that she wasn't sure that we were a real company because our website was so outdated.

And so she was thinking, I don't know about and so you gotta be careful, right? And I was just so floored by the fact, that it's possible that generation seeing something like dinosaur was suddenly, we have to be careful.

This could be a scam situation. We have upgraded fabulous, not only because of what Valerie said, we knew it was time, but let's just say that might have pushed us a little bit faster. 

Katherine: That's brilliant. Valerie, you wanna add anything to that? 

Valerie Hebenstreit: Yeah, I would just add with technology, I think there were learning opportunities for both of us of where can we streamline, where can we help each other out and how can we communicate our preferences.

So if Carol doesn't, really like to use teams messaging, if there's a better way to reach her, like I can adapt to that. And it's about, just being open with each other and communicating that instead of getting frustrated and not saying anything and holding it in.

Carol Wagner: I agree. One of the things that I did in the beginning. I don't take any credit for this being as brilliant as it turned out to be. It was just desperation because of my understanding of what might be some real differences in how will we work well together, is, I asked Valerie almost day one.

Tell me about how you like to learn. And tell me about how you like to get feedback. She was very candid with me and I was like, okay, because I didn't expect some of her responses. They would've been different than my peers. I think that helped as well. So we helped each other get through that time in an interesting way.

Katherine: I love that. And Valerie, what were your answers to those questions? 

Valerie Hebenstreit: Do you remember? I'm trying to think back. I know like a big thing for Carol and I, she is very extroverted and I'm very introverted. So when it came to feedback or even just like decisions and questions, Carol would be like extroverting and, thoughts.

Just coming out her and I'd be like wait, what about, this and this? Or she would ask me something and she would give me time to think about it. Because she knew that I need more time to process internally. And I think that also got into how I like to receive feedback, which is in the moment, maybe not in front of everybody, pretty quickly after a presentation or a project instead of just doing your mid-year and your year end.

I think this is true based on what I know about Gen Z is we want that continuous feedback discussion. But Carol also knows to ask, are you open to feedback right now? Not just to bombard you with it because she is a trained coach. 

Katherine: That's good. So even though you want it in the moment, sometimes you might not be quite ready for it.

And so she was wise enough to know to ask you if you were ready for it. 

Valerie Hebenstreit: Exactly. 

Katherine: And I've heard Gen Zers talk about it. They want feedback. It's an ongoing, casual conversation. 

And to your point I've heard them say, if you wait until my quarterly review to give me feedback, you wasted a whole month when I could have done better on this.

That whole idea of honesty in the relationship really suffers from that.

Carol Wagner: Agreed. I did get teased at some point because once I recognize somebody I'm working with is an introvert and I do know now to give you something in advance to let you ponder it, as opposed to some of the colleagues who are on the spot, just let's solution right here. The introvert's like it's pots and pans clinging in my head, go away.

But to have this space and the time to go through something is one thing. But to also understand that folks wired like me sometimes have so many ideas in my head. I can't process them as well internally. And so I was teased for saying, okay, I need to extrovert from it because then they know that's not a conclusion because an introvert's already coming out with, they've processed it.

And then when they tell you, that's their conclusion. For me, I'm just thinking through and sometimes people would be like, wait out loud.

Katherine: That's good. Because the introvert's processing internally and you're like out here. Yeah, that's right. Did that work for you, Valerie? 

Valerie Hebenstreit: It took a lot of getting used to at first, but it really has been just invaluable to me and working with a lot of extroverts now and being able to flex a little bit and being able to have those discussions on the spot.

So yeah, I think we made it work. 

Carol Wagner: Yes, we did. We did. I would catch myself and then, give her that. Why don't you think about that? And we could talk about it later, but it did take some adjusting I think on both our parts.

But Katherine, something else popped in my head in terms of, key differences and things.

And we joked about technology, which is very obvious, right? But one of the other things for me was the expectation, of the younger generation about how they might prioritize a more rapid promotion opportunity. Than someone of my generation. And so I had to do a little educating and convincing with senior leadership when it became apparent that this person had so much value to add and we should promote.

And I would say five to 10 years ago, the company would not have been as receptive as quickly. So I think as an organization, we're starting to learn what the next generation needs. And then when we became a little wiser about that, as we're teaching, we have a leader is coach program that we teach.

And I would say to folks, hey, the old command and control stuff, it doesn't work. And oh, by the way, this next generation, they're not gonna put up with it. You know how I knew that because I took one of Katherine Jeffery's workshops and then also of course, every day it just was a proving ground about how that's not how these things go.

So that was a big aha for me. Not that it was inappropriate, it was just unexpected. Because you're dealing with colleagues of a comparable age for so long, somebody newer comes along with a completely different worldview, and guess what? Folks, we don't wanna stick around if y'all are gonna be playing games with us. We are bringing a lot of value to the marketplace and we can go somewhere else.

So, that was an important lesson for me as well as I think for the company. 

Valerie Hebenstreit: Yeah, I think that was great to touch on. I really do feel like Gen Z is breaking down that hierarchy piece of the workplace.

And not in a way that's oh, I'm entitled to anything. Like, they want to learn and to do the work and to build their skillset. But if there's anything that's this has been this way because it's always been this way, I think we're gonna question it. Which I think it's great.

Katherine: Carol, did anything about Valerie's approach to communication or her approach to work surprise you?

Carol Wagner: I don't know if this is a generational thing or if this is just a Valerie thing, but this young lady just worked her tail off and I think when you talk to many people of my generation, you get this, oh, those younger people, they just blah, blah, blah, blah, blah. It's nonsense because my parents' generation said it about us.

And as Vale was saying, you just keep perpetuating this nonsense without checking it out. You have to be curious. You have to talk about things. You have to be willing to learn, be willing to be open. And I think if either of us weren't, we wouldn't have had, I mean we, we were a, what did you used to call us?

Our mighty little team or something that was Yeah, mighty was small. Yeah, mighty. But at some point, the other person who had reported to me was promoted to another role, and it was just the two of us. And people would comment all the time about. The quality and the amount of work they came out of.

And they're like, oh, you have a team and no it's two of us. And so for me to dispel the myth and because I was so proud of how well she was doing and because she was doing so well and people knew what I was always wanting to go, yeah, let's stop with this nonsense about the younger generation doesn't really wanna work.

They don't wanna break a sweat, all of this. 'Cause she worked very hard and in ways so much smarter. Again, some of it being the technology that she was able to leverage that I was like, oh, you just did that and half the time I would've because of this. Can you teach me that so yeah.

Katherine: It's so good. She's teaching you technology. ,

Carol Wagner: I'm sorry, Valerie. Okay. I wasn't a quick learner on that topic. 

Katherine: What was that like for you, Valerie?

Valerie Hebenstreit: That's a good question. Being a learning and development person and training, I feel like I did have some of the tools to be able to like, slow down and come at it from the perspective of if I wasn't just so used to this, 'cause this had been here, like you said, I never knew a life without it, what would it be like for me?

So I tried to take that perspective when I was walking through those sorts of things. But to be candid, there are some times where it's difficult. Yeah. And don't necessarily know how to teach something that's just so intuitive to you. 

Katherine: Totally. And Carol, one thing that you said that struck me is you're talking about how hard she works.

But she did it differently. So what felt different to each of you? Ooh

Carol Wagner: I'm stumped a little bit. I don't know how to break that down.

Valerie Hebenstreit: The first phrase that pops into my head is working smarter, not harder. And how we can look at process and continuously improve it. Our company's big on like lean training and doing 80 20.

And so I think having that mindset and looking at a process and seeing how can we streamline this using technology or now there's a lot more tools in the world. Yeah I think I tried to go into it with how can I make this easier for myself, for others. And I think that my generation is recognizing that more hours of work doesn't necessarily mean that you're working harder or that the end product is better.

Katherine: And did you all ever have kind of a clash around, a typical boomer mindset might be, I need to see your butt in the seat, right? I need to see you doing your job versus what has now become it's much more results oriented. Doesn't matter how long it takes you to do it, I just need you to get this done.

Valerie Hebenstreit: I think I got very lucky with Carol in many ways that she wasn't butt in seat, and again, it was during COVID, so it was during, working remotely. And even when we started to shift back into like hybrid and in person, she was very flexible, which is something I valued a lot. 

Carol Wagner: I think, again, I was fortunate that I'm just wired that way, but also really quickly, Valerie showed the value that she could provide and to me, I wanna see the output. I don't care if you did it at 10 o'clock at night with your cat in your lap. It doesn't matter. We used to get.

So hung up on that for many years. I worked for people who they'd walk around at a quarter to five to make sure you were sitting in your seat. Really. I could be completely checked out. My butt in my seat doesn't necessitate quality work. And so her work product was so great so quickly that again, I was already predisposed to be that way, but then it was just, it was a beautiful thing. It was challenging, obviously during the pandemic to find creative ways to stay in communication. And one of one of the things that we did was we worked together out of my house with both our dogs. So I think that's a Gen Z type thing. Don't you think? 

Katherine: That's incredible. Did you like that, Valerie?

Valerie Hebenstreit: I did. It was just fun.

Yeah. Which is something that I think is very valuable to my generation. And it was different. Different way of thinking about work. 

Katherine: Yeah. And what was it like, being invited into Carol's home and, just seeing more of her life? 

Valerie Hebenstreit: I think it helped bridge that generational gap to see

we are both the same in a lot of ways, even though we, have that gap in age. We're both dog parents, we both, you know, like to go and grab a coffee and, I think when I was entering the workforce fresh out of college, no one really tells you what to expect.

And you're with all these people in suits and they're so buttoned up and they know what they're talking about and it's really intimidating. But then to break down those walls and be like, okay, we all get imposter syndrome sometimes, we all are humans and we all have struggles, we all have families and, things going on outside of work, it was just really beneficial for me to see that.

Katherine: I love that. All right, Carol, can you share a moment when you realized that you were like, oh, like this Genzer Valerie, she's teaching me things. 

Carol Wagner: Oh, there were many of those moments. Mm-hmm. So some of it, as we talked about is technology, because I was really pretty in the dark ages.

But I think a lot of it is also what Valerie mentioned a little bit ago about process. My style is more to I'll just put this thing on my back and I'll just drag it until I get it done and it may not be pretty or it doesn't have a form. And she brought structure to the work that we did in a way that at first was not so easy for me, but I came to appreciate very much because I could see the value in my adapting to doing it that way.

That we did get a lot done a lot more quickly as opposed to me being all over the place and knowing I'd hit the finish line, but maybe not as quickly or as pretty.

Valerie Hebenstreit: Yeah, I don't know about a specific 'cause like you said, it was just like daily things that we were managing. And I don't know if this is a generational thing, but Carol is very like big picture, very strategic thinker, which I think had just to do with how she's programmed, but also her experience, her wisdom.

And I, on the other hand, I'm very detail oriented and very analytical. And so we took our strengths and we balanced them out to leverage those to our advantage as a team for that shared learning and development. So when there were times where I was getting really bogged down in the details, I think Carol would remind me let's look at the big picture where we wanna be in the future state.

And then if there were times when Carol was extroverting all over the place, I can maybe reign her in a little bit and think, okay, but how are we actually gonna do all this? So yeah, I think we were able to balance each other out there. Yeah. 

Katherine: That's awesome. So it's really each of you, your own emotional intelligence and saying, okay, this is who I am, this is what I'm bringing to the table and this is what we're bringing together.

'Cause you're so different, you could have really irritated each other, but instead you turn those strengths into a compliment and I've seen you in action, right? You're a great. Team that flows very well together. 

Carol Wagner: Thank you.

And I only resonate with everything that Valerie said because I have over the years, and also teaching Myers-Briggs a lot. You see this, you see these people, ones this, ones that, and they don't value and respect what the other one's bringing to the table, and nothing organically forces them to have to understand and flex and adjust and work together.

Whereas you had these two women who had a mountain of work with expectations going all the way up to the CEO. We did not have the luxury of going you're annoying and I don't know how to work with you. It was really early on, we just had to start, oh, you're an introvert. I'm an extrovert.

Oh, you want this in private? Oh, you want this and that. Like we had to figure all those things out fairly quickly and just honoring and respecting where the other one was coming from. And so together then we became a pretty strong team. 

Valerie Hebenstreit: And what I like about, like some of the MBTI Myers break stuff is bleeding into this, but I think it's applicable still is that it's not about changing who you are or what your preferences are.

It really is just learning how to flex and adapt to others' styles. 

Carol Wagner: When I teach the workshops and say, if you're listening in Italian and I'm speaking in Greek, we're not gonna be able to understand each other. And so it's in the moment, I'm not trying to change who you are, but in the moment if I can't respect where you're coming from and see how it strengthens my approach, so yes we did that and we did that early on.

And I think that's another reason. Yeah. 

Katherine: Valerie, what was that like for you? You're coming in, there's lots of pressure, right? It's not a small job. It's not a small company. And you're both in charge of this huge area of the company and from what Carol says, it sounds like you had to learn pretty quickly to work well together and to operate somewhat seamlessly 'cause you were reporting to, the CEO. So what was that like for you as a Gen Z? You're coming in, you're working under this boomer, there's all this stuff you gotta do and learn like a really quick, growth curve, really? 

Valerie Hebenstreit: I like the challenge. It was overwhelming. You can say that now.

I think Carol and I are both people that get very emotionally involved, especially in our type of work. So that was also difficult. But at the same time it was like that much more meaningful when we did, have successes.

And when we were able to help, people that are within the local businesses or, within the organization. It is a very unique experience, I think being on the kind of team we were on for the Holdings organization. It provided me so much fast-paced development that I don't know if I could have gotten that anywhere else.

Katherine: Does that feed your soul like fast paced development? That's like amazing. 

Valerie Hebenstreit: Yeah. And if it didn't, I don't think I would have been in the same place for so long. And that kind of brings me to like the point, I know a lot of people talk about with loyalty to companies when it comes to generations.

And I tend to disagree. So I know a lot of people think Gen Z likes to job hop and maybe it's just me, but I don't think they, they want a job hop just to job hop. They're really looking for the values they want from the organization and to be fulfilled and, to feel like they have purpose.

Carol Wagner: You are reminding me of, I forgot about this. I don't remember the chronology how long Valerie had been in the role, but there was an opportunity to potentially have her become an HR generalist as opposed to saying in a learning development role. And there was some pressure, it was encouragement and yet from more senior folks saying she's so young in career.

Does she really want to limit her options now? And maybe she should go and do this. And so then I felt compelled to go and talk to her about that. And I was so impressed with the clarity that she had. Of No, I'm an l and d person. And if my options aren't as vast as they might be, being an HR generalist, I'm okay with that because this is where my passion is.

This is where my skills are developing and that's okay. And so I had to keep running interference going. You older generation person keep insisting that you are wiser and because this is where she needs to go, but she's telling us that's not where her heart is. And guess what? If you insist on that, we're gonna lose her.

And then everybody was like okay, if you think, and so now she has. Remained clear and true to her purpose and stayed there and continuing to add value in that role and really shining. But it was a really interesting time for me, for somebody of my generation to be going, wait a minute, why are you not listening to these younger people?

They're not stupid. They know what they want. And yes, I hear , my life's wisdom, my life's experience. So what it's not respecting and honoring who this person is. It's not somebody young who says, I don't really know where I wanna go. This is somebody who says, I have found my path and I'm going to stay on it.

And I was, really proud of her for that, for sticking to her guns. Even though I'm sure there was a little bit of quaking in her boots going, these people are telling me I need to do this, and maybe I'm being silly by not listening. But she was very clear. So there. 

Katherine: Valerie, how did all that hit you? What was that process like for you? 

Valerie Hebenstreit: Yeah, I think it is, hard ' 'cause I want to listen to my gut, but when you do have people who are older telling you like, you should be on this path. It's hard right? To, say, oh, maybe I should. But I think that gets at what I've seen with my generation and what I've felt is that it's less about, climbing some sort of corporate ladder or making decisions because maybe you'll get more pay or you'll become more senior.

It's less about that and more about I want the work-life balance. I want the flexibility, I want to enjoy my role. It's life first, not work first for me. 

Katherine: Yes. I think that's so good. Yeah.

Valerie, you wrap that up with basically you work to live, right? Where Carol's mantra would've been, I live to work.

Carol Wagner: Yeah. Here's a quick illumination on that.

My father, who was, I don't know, 93, I think when he said this to me, I was switching jobs and he asked me why, and I said because I didn't really enjoy that work anymore. He was aghast, Dolly, it's tough out there. What are you, this, his mindset from his generation is you did not leave a job for any reason other than they, closed down and laid everybody off, or you messed up and they fired you. This notion of leaving a job because it didn't fit well anymore. Think about that for me to him versus her, to me it's it's mind-boggling. So that was a really interesting thing to reflect on is yes, you stayed there and you worked hard unless the place closed down.

Katherine: Yeah. It's such a different world. Okay. Valerie, this one's for you. Did you have any assumptions about baby boomers before you met Carol? 

Carol Wagner: I wanna hear this one. 

Valerie Hebenstreit: I don't think I had anything beyond what we've talked about. Which is they, don't want to learn new technology or mostly their assumptions about Gen Z that, we don't, work hard or maybe we're lazy or too sensitive. But yeah, I wasn't like, oh man, I have to work with a boomer. I was just happy to have the opportunity.

Katherine: So you weren't walking around with an hashtag okay. Boomer sweatshirt? 

Valerie Hebenstreit: Oh, no, I was not. Thankfully.

Katherine: Generational differences show up everywhere in workplaces, classrooms, and even around the dinner table. Too often they lead to frustration instead of connection. That's why I created the gen shift dialogue deck with thoughtful questions for every generation Traditionalist, Boomers, Gen X millennials, Gen Z and Gen Alpha.

It's a simple tool that helps groups move beyond stereotypes into meaningful conversations. It works with teams, students, and families alike, and the deck is just the beginning. As a generational strategist and leadership consultant, I work with organizations to turn generational differences into strengths.

Through keynote talks, workshops, and long-term consulting, I help leaders understand what drives each generation and how to bring out the best in all of them. When we learn to listen and lead across generations, teams are more innovative, inclusive, and effective. Discover the tools and training that build generational intelligence.

Explore the GenShift dialogue deck and my services@katherinejeffery.com. Start bridging the gap today.

And then Valerie, what have you learned from Carol that's shaped how you think about your career or even leadership? 

Valerie Hebenstreit: Oh, like everything I'm listening to myself talk today and I'm like, this is all things that, like Carol told me at one point.

But. I've learned more just how to listen with curiosity and how to ask, questions that matter. And how much there really is that is unsaid. And how like sometimes you have to over communicate even if it's uncomfortable.

 Katherine: What do you mean by that?

Valerie Hebenstreit: I guess for me being an introvert, having a little bit of social anxiety, I'm very non-confrontational. But Carol was like, okay let's just talk about this. 

And like having her do that, and then being like, okay, like we resolved it, like everything's okay. It was almost like exposure therapy in a way.

Like I, I needed that so that I could go forward and have those conversations. And I found that when there were misunderstandings, it would've been more helpful if we would've just communicated like upfront about it. And so I think now I can really anticipate where challenges might come up and I can be proactive about it.

Katherine: And how do you feel about conflict after working with a boomer? Boomers tend to not, get stressed out about conflict. It's just something you have to deal with when you're rubbing shoulders with somebody else. And so how did maybe even your perception of conflict change or your understanding of it?

Valerie Hebenstreit: Yeah. I think. Over the past few years being in, the workforce, I've seen how it's necessary. It doesn't always have to be bad or like hostile. It's something that kind of has to happen in order for you to come to the right decision sometimes in order for you to have like productive conversations.

And while I still don't like it, I think I've gotten better about how I go into those situations how I respond. And even in my personal life, it's been really helpful for me to be able to have those conversations without getting overly emotional or overwhelmed.

Carol Wagner: I'm remembering Valerie, that early, early conversation when I said to you, tell me about your learning style. Tell me how you'd like to get feedback. I don't remember your exact words, but there was definitely something along the lines of more carrot, not stick. And that stayed with me really early on.

I didn't know if it was you personally, but there was this sense of I wasn't going to walk on eggshells or I wasn't going to avoid hard conversations, but I was probably more intentional and mindful

going into a conversation so that I could give you the input I needed you to have, but do it in a way that I knew that you could hear. And what is fun for me to hear right now is that for you, okay, might have been uncomfortable or tentative, but then you saw proof that you could go into a challenging situation and have to arm wrestle a little bit, and then come out the other side with a better outcome and stronger.

And it wasn't personal. And I think maybe you just needed to experience that a couple times to go okay, I could do this. 'Cause to be fair, I think the first little bit there was the deer in the headlights kinda look, I would get a fair amount, but we were your first job. Yes, you had some other things in and out of school, but in terms of being done with school and going into the beginning of your career, and so I was always remembering.

This is new and we have to, we'll get there, but we can't club you over the head with it because that's not gonna be good for anybody. Yeah. So I think you, you helped me understand how to show up for you in terms of giving you feedback and then you were brave and then you got the hang of it and it all worked out, right?

Valerie Hebenstreit: Yeah. I think there is this transition that not enough people talk about between when you graduate from college and enter the workforce. And when you're in those, like in between years, like a lot of people talk about going from high school to college, but it's this like really big turning point I think for a lot of people where they're learning how to adjust and there's a lot of things that you just have to go through in order to get to, a point where you're, used to a lot of those things and it's just, there's so much so many learning opportunities. Yeah. So many. 

Katherine: And Carol, it sounds like you naturally have a coaching mindset. Yes. So if I am a Boomer or a Gen Xer and I have Azer on my team and we know they, they like to be coached, but I don't really have a coaching mindset.

What are some things, some practical things you can tell me that I could work on? And Valerie, then I want to hear what you have to say about the advice she's giving. Okay. As a Genzer. Okay. 

Carol Wagner: I would say first and foremost, be curious. Don't make assumptions. And if you can start with that premise, then you're gonna have an easier time all the way through.

Because when we talk about having a coaching mindset. If you are genuinely curious, the appropriate questions will come up organically. People are like, oh, I don't know what to ask them. That's because you're trying to follow some script or somebody else's advice. But if you're genuinely curious about, okay, Valerie, so how do you like to learn?

How do you like to get feedback? And I come in and I don't start with an assumption of she's younger and she'll just have to learn from me, from my style. That might not have worked very well. So I think that's my first thought is be curious and don't make assumptions, because I'll tell you, if you want to recruit and develop high potential talent, this next generation, really that's what they're looking for.

Valerie Hebenstreit: And to build off of that, what I liked about Carol and the coaching mindset is that she asked questions in a way where I was coming to my own conclusion. She wasn't leading the witness. And I think that helped me a lot. Again, there's that trust there where she knows that I have the answers or I have the capability to get to that point.

And she was just there to help guide me through it. 

Carol Wagner: To be fair, as an extrovert, I had to bite my tongue a lot.

Katherine: But that's good for you to say Carol, because I think a lot of people from older generations, we have to learn to do that 'cause we're so absolutely quick. Absolutely. Wanna give advice, we wanna share our experience and so biting our tongue and allowing them to get there.

But we're still there with them. 

Carol Wagner: And I, oh, I like what you just said because really. I would say, and Valerie, tell me if, and be honest, tell me if this felt that way to you. But in my mind, I felt like this was a partnership. Yes, I was her boss. Yes, she was quite a bit younger than me, but we were a team and I felt like it was a partnership.

And so I think because of that, there wasn't any of this other stuff that I think comes up in those kinds of relationships. But yes, it is true. I did have to bite my tongue a fair amount because A, I wanted her to come to her own conclusion. 'Cause we all know how much more powerful it is. I could tell her what to do.

She's a good soldier. She'll go do it. But gosh, when she has to wrestle with it a little bit and say, this is why I am coming this way, she owns it. And that's a whole different amount of momentum for her to go and do it. Yep. So I think that was helpful. 

Katherine: So good. That was so good.

Okay. This is for Valerie. How do you balance bringing new ideas while still respecting the experience of someone like Carol? 

Valerie Hebenstreit: I think, again, like I was lucky that Carol was very open-minded to new ideas, but I learned that you can't always just have a great, wonderful idea if you don't have anything to back it up with the why, what's in it for me? Maybe is there any sort of like data that can show how this will help improve our business outcomes?

And I always went into it whether I was, presenting something to Carol or to some of my other colleagues that were more senior. I had to think, and Carol really taught me how to do this, was okay, what questions are they gonna ask me and how can I come already prepared to answer all of those questions?

What are gonna be their pain points? Like I wanted to expect the unexpected almost. 

Katherine: Yeah. And often Gen Z will say they just want more data, right? They just want more data. And so for you to learn to go in prepared, but also knowing that, you might have to shift and adjust.

That's a great skill to learn. And Carol, were you trying to teach that? 

Carol Wagner: There were many things I was teaching intentionally, and there were many things that I think I'm hearing now, maybe just because of who I am, the role I had, the kinda work we did, we weren't in the finance organization where all of that data and all of that analysis is just obvious and needed in our kind of role.

We're in an engineering centric organization and they love their data and so you couldn't get away from it. But a lot of what we had to do was give them a sufficient amount of data to be able to get on the same page and then start to be able to talk about the human dynamic, which often got lost in some of those conversations.

And so we had really unique roles in a way and it was really interesting to watch how all of that unfolded. 

Can either of you think of a time when a misunderstanding between you turned into a learning moment?

Valerie Hebenstreit: I have a silly one. Okay. Go. That I remember. And I think actually Katherine, we may have talked about this in one of your workshops that I found something that like Carol did or just folks from the older generations is, they'll put, when they're sending you an email, they'll put the headline and the subject line.

But my thought is always okay, the request is gonna be the body of an email. So there would be sometimes when Carol would email me and the request was in the subject, but I wouldn't really look at that. I would look at the body and I would be like, I would have no idea how to interpret what she was saying. She wasn't. 

Carol Wagner: Oh, that's interesting. You know what, I did not know that, and I absolutely did that all the time. 'Cause to me, all right, I this way, when you go to open the thing where we're going. Yeah. And just didn't really focus on that and in the body of it going, I don't know what she's asking.

Oh, interesting. 

Valerie Hebenstreit: Yeah, so I kinda just had to train myself. I was like, okay, I have to look at the subject line first, which is not a bad way to do things,

Katherine: Yeah. It makes it easy to find that email later, right? Is right there in the subject line. 

Carol Wagner: It's funny because I was schooled on that by my old boss who said to me, you write great emails, but you tend to keep the same subject line as we go down this thread.

But for me, maybe the subject has changed mid-body of the email, but you just keep resending.

This is interesting. I never thought about, that's why I do that, Valerie. Oh, I'm gonna pay attention to that more now. Thank you. 

Katherine: So Valerie, we talked about how you preferred feedback from Carol, but was there ever, moments where you were giving Carol feedback and how did she want to receive that feedback?

Valerie Hebenstreit: I think it was an interesting dynamic because she was my supervisor, but there were moments like when we were having those feedback discussions where she would say, hey, if there's any feedback you have for me, I'm open to it and you can share that with me. And I thought that was almost mind blowing to me.

I was like, oh, I could do that. So I think that's just like another thing that really made, like Carol said, our working relationship was really a partnership. And there was ways where I think there was almost that reverse mentoring in a way where I could say, and then again, I came down a lot of like technology or process-based things where I could say, oh, maybe if we did this in this way, I think I did eventually get her on teams.

You did? And yeah, I think that was really great just to hear.

Carol Wagner: I'm getting very sentimental now, ladies. 

Katherine: She's gonna wanna go back to work. Valerie, Carol, what was that like for you when you asked Valerie? Hey, is there any feedback you have for me?

And she's yeah, actually there is. What was that like?

Carol Wagner: It didn't happen early on, I think there was still this nervousness about you're my boss and I'm younger and I'm new and all of that. But I think, again, we've said this a couple times and maybe that's a really important fair point, is there was just proof of concept fairly quickly.

So she knew I wasn't just blowing smoke and just saying that to say it 'cause it was what you say, but that I really genuinely meant it and was open to it and knew that there were areas that I could strengthen and that she had those skills. And so I think we just tentatively I said it, she's you mean it, let me float it.

Oh, she didn't get mad like it seemed to work. I think we just incrementally sorted that out. But for me knowing, and I don't wanna harp on the technology too much, but it's just the most obvious pinpoint that is an area that I'm not as strong. And she clearly was. And so I was always, Hey, I don't know if I'm going to get as good as you are, but I need to be better than where I am, and can you help me with that?

And she was delightful. And again, a learning professional who likes to teach people things. And so when I made it comfortable for her so that she knew I genuinely meant it, then I think it clicked and it wasn't really ever a thing again. 

Valerie Hebenstreit: Yeah. It's not just a one and done. I think it took a few times.

Katherine: Yeah. And I love that you guys are being honest about that. It wasn't easy at the beginning, like you actually had to put some effort into it. You had to learn more about who you are. You had to learn more about this other person, but you stuck with it and you both saw potential and strength in the other person.

And it turned out incredibly well. 

Carol Wagner: The joke back at the ranch was always, I used to say Valerie was my favorite on paper. And so literally from the get go, we had this great relationship with U of I with their master's in HR program, which is the top one in the country and in our backyard.

So we developed a relationship with the director and we started to get this book of resumes and one of my colleagues went through them and I went through them where we specifically did it blindly and then came back with our little short stack. And I came in with a few and he came in with a few, and I just said immediately, Valerie's my favorite on paper.

'Cause we hadn't talked to her yet. And that was it. Here we go all these years later. Yeah. When you have that attraction, you're compelled to somebody that they have. And then we talked to her and she was just all eager and excited and had all this that she wanted to bring to the table.

It was just so easy to perpetuate that it, yes, it was challenging sometimes, but the end goal was what we were accomplishing together was amazing. I think about it now. Oh, exhausting. It was sometimes at the amount and quality of work that we produced, just the two of us, that's, that was the impetus for us to wanna do it better together.

Katherine: Love it. What strengths do you see in each other's generation that other people might overlook? 

Carol Wagner: Ooh.

At the risk of repeating myself, I think one of the things that struck me was being able to really quickly disabuse a lot of people of the notion that this younger generation just doesn't wanna work hard, and that they just want all the benefits and they, all of this kind of thing. And that's nonsense now.

Yeah. Are there people out there that do that? Sure. But there are people in my generation that do that too. So it's not a generational thing per se. And I don't like that mantra's kind of been put over the Gen Zs and we disproved it really quickly. Valerie really got everybody's attention because they kept saying, oh, this young person is doing this.

And, and I had to nudge you a little bit to get up and do some presentations in front of some big players early on, because it's intimidating. You're an introvert, you're new, this is your first job. All of those things. It's not like I shoved her in the spotlight the first week, but it was important to me to showcase her as soon as she was mostly comfortable.

She was never gonna be completely comfortable, but mostly comfortable so that they could also start to go, oh, look at that. So this whole thing about that generation not wanting to work hard or just only wanting all the goodies is nonsense. And Valerie helped us disprove that through the whole company.

And it was really fun to watch. And it's to her credit that she showed up the way that she did. I think those that come behind her have her to thank. 

Katherine: Yes. It's to her credit and to her generation's credit, she's changing the script. Yeah. Yeah. Changed that narrative.

That's right. 

Valerie Hebenstreit: I would say for me, and something that actually, Katherine, your training really helped me understand was that for boomers or for other generations, there's so much historical context that really informed their values that they hold even to this day. And so just to think about that is, someone might say something I don't agree with or might have a different value, but I'm not gonna.

Dismiss it and, say, okay, boomer, I'm gonna be, try to really understand like what happened in their life and what was going on when they were growing up to make them, think and act that way. And, how can you approach an issue or have a conversation in a way where it's not putting a blame on anyone and actually, trying to see it from their perspective.

And so I think that's what I've learned about the other generations and, and of boomers in particular.

Katherine: I love that. And really going back to what Carol said at the very beginning, you're like holding that sense of curiosity. Yeah. Like instead of making assumptions and oh yeah, okay, boomer whatever.

No, you're actually like, oh, she has a story too and there's a reason she's showing up this way, and how can I learn more about that so I can understand her instead of judge her? 

Valerie Hebenstreit: Yeah. And I think it took a little bit of like teasing of my generation to be like, oh, I don't want that. I don't, why would I tease other generations when, like I, I don't like being generalized or put into a box just because I'm Gen Z.

Katherine: Yeah. So applying that same way you feel to them. Yeah. That's really good. It's very mature. How has your relationship changed the way each of you view your own generation?

Carol Wagner: What's popping to mind is just because there were many of my generation where we worked and watching how we, we developed a robust intern program. And how I brought Valerie in and watching how some of the others brought them in. I wanted to just go, oh, you're, you really need to kinda meet them where they are and learn about them.

And so there was an aha about, we as a generation did generalize a lot of these things and shouldn't do that. And so being able to talk to colleagues about why our partnership worked so well and it was just, I think, surprising to me to see that people would still dig their heels in sometimes about those I'm a more senior level and they're younger and they don't know anything and all that.

You're missing the boat here. There's a lot of horsepower here. And if you support them. To learn more, they're gonna be able to teach you as much as you teach them. So I was a little frustrated with my generation for a minute there, I must admit, and then had the opportunity to enlighten people a little bit.

And I think it was just more them seeing what we did and how we did it and going, oh, that seems to go pretty well. What'd you do? And then being able to talk about it and them saying, oh, I didn't show up that way in the beginning, and maybe I should have and I can fix it now. So I think my honest answer is that I was a little frustrated because they were doing the things that we all naturally do, but don't have to.  

Katherine: Very well.

Yeah. Valerie, what about you? 

Valerie Hebenstreit: I would say even with what we've been talking about today, up until like recently I just didn't realize how much change my generation was capable of. And it does make me proud to be a Gen Z. I think there was a few moments early on where I was like, oh, gen Z we're like iPad kids, even though that's like a little bit younger than me.

But I've really come to respect a lot about my generation. And something that, like working with Carol helped me learn was that like, whether you're Gen Z Boomer or any of the generations, like you can actually have a lot of the same values and belief systems and you can care about the same things.

And so that was just another thing that I learned from our interactions that was like really eye-opening for me. 

Katherine: And I love, you brought up the term reverse mentoring a little bit ago, right? And I often build on that and call it co-mentoring. Oh, so it's the boomer mentoring, the z the Zs mentoring that boomer right back.

And that's really what ended up happening with the two of you. And sometimes the most powerful moments in our relationships are when you actually realize it's not about advice, but it's actually about shared growth. And I think that's so much of what you both are bringing to this conversation and to each other's lives and to the workplace.

And I just feel so inspired listening to you. It's really. It's pretty incredible because I hear a lot of the other stories, on a day-to-day basis, the frustrations. And so you two, turn that tension into teamwork. You can't really put a price on that.

So if each of you could describe your relationship in one word, Ooh, what would it be and why? 

Carol Wagner: Ooh. All right.

So if I'm only relegated to one, I would say impactful. If I can have another, I would say meaningful. Impactful because of all the things that we've said where we really showed up for each other and heard each other and took the time and didn't make assumptions and stayed curious. Again, part of it is because how each of us are wired, and part of it is because of the daunting amount and quality of work that we needed to produce.

So it's you could decide you don't wanna do it like this, but it's gonna be bad. So I think impactful was just because we really produced. Some good things together in a relationship that other people might've thought, how's that gonna work? She's however old, and she's however old, and she's been working forever and she's new and then meaningful because of, I think to leverage what Valerie said about shared values.

We had so much about how we see the world and how we want things to go and how we wanna grow and improve. But I think if you're in the kind of work where you genuinely wanna help other people and support them, then that becomes at the forefront about how you work together. And it's incredibly meaningful. 

Valerie Hebenstreit: So my word is hats because I feel like we both wore many hats.

So like Carol not only being my boss, but she was also like my biggest champion, like just from what you've heard today. So my biggest champion to others, she was my coach, my like unofficial mentor. She was my friend. And so I think yeah, I think that is like the best way I can describe it all in, in one word.

Katherine: How you feeling? Carol? Got some tears there. I got 

Carol Wagner: to cry actually. And I said to Valerie when we were working together many times, I said to her, I don't know what it is about you and about our relationship. But I would get, I would often get emotional and she'd look at me like, what's your story? Near tears?

Sometimes part of it is because I was just so proud of her and so pleased for her. But I don't know. There's something about who she is that I just. It's very dear to me, and so thank you for that because introverts don't always tell you everything they're thinking. So now I have it on tape, babe. Sorry! 

Katherine: That's right. Look out Valerie. Yeah. 

Carol Wagner: Thank you for 

Katherine: that. 

Carol Wagner: Yeah. Katherine I don't know if you were anticipating this was gonna be all the conflicting things between the generations and now it's become like a love letter. I don't know, 

Katherine: because that's what can happen, right? When the generation turn that frustration into curiosity, it, there's such beautiful things that can come out of it.

And so this whole interview, if you watch the cycle of the interview, it's like just growing to this point, yeah. 

Carol Wagner: Thank you. Thank you for the opportunity for us to tell this story because I do really hope that it helps some other people think about that. Just don't make assumptions.

Be curious. There's just such great talent there that you just don't wanna overlook. Yes. 

Katherine: And I have no doubt it's going to help people. And one of the things I love about the story between you two is how it proves that mentorship doesn't just belong to one generation. 

It belongs to anyone who's willing to listen, stay curious, and grow.

Right? Which are the three main things you all have talked about today. Those are the things that have really mattered and have built this bridge between you that is very strong and very solid. 

So I wanna thank you both so much for your time, your inspiration, your story, and the fact that you were willing to work together to create something beautiful.

And now, we get to share it with the world, which is really exciting to me.

 So if today's episode sparked something for you, check out our other GenShift conversations with Traditionalist Boomers, Gen Xers, Millennials, and Gen Z voices, all exploring how we can better connect across the years.

Katherine: Thanks for listening to GenShift. Keep listening, keep learning, and keep leading with empathy.

And if you gain something from this conversation, don't forget to subscribe and share and help others build bridges across the generational divide.