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Executive Leadership Podcast #182: Coaching the Millennial in the Middle

April 7, 2022
Executive Leadership Podcast #182: Coaching the Millennial in the Middle

The millennial generation is now in leadership positions reporting to a Gen X’er or baby boomer and leading a Gen Z’er. Today Perry and Chris talk about how these Gen Y leaders can succeed.

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Perry Holley:    Welcome to The Maxwell Executive Leadership Podcast, where our goal is to help you increase your reputation as a leader, increase your ability to influence others, and increase your ability to fully engage your team to deliver remarkable results. I am Perry Holley, a Maxwell Leadership facilitator and coach.

Chris Goede:     And I’m Chris Goede, executive vice president with Maxwell Leadership. Welcome, and thank you for joining. You want to learn more about our 5 Levels of Leadership? It’s the methodology that we believe sets the common language for all organizational culture, maybe even our 360 Degree Leader content, another great content piece for leadership teams. Maybe you just want to even leave us a question or comment. We absolutely love that. And it helps Perry when it comes to creating some new content. And just our last episode had one that we responded to. Please visit And there, you can fill out a form, leave us a question or thought and our team will get back to you with that. Well, today’s topic is titled Coaching the Millennial in the Middle.

Perry Holley:    Oh yeah.

Chris Goede:     This is something that, at first, when I saw the title, I was like, “Say what?” I had to reread it again. What’s going on here? What are you thinking?

Perry Holley:    Well, I was doing some research for a keynote I’m giving in a month or so. But somebody had reached out and said, “The millennial generation is now in leadership at all levels of leadership in the organization. And they are reporting up to either a Gen-Xer or a baby boomer, they’re still hanging around.” Did I say that like-

Chris Goede:     Yeah, you’re still here.

Perry Holley:    I’m still here. And they’re leading a Gen Z person. And so it’s really interesting. They said, “Our millennial leaders have some very interesting dynamics when it comes to leading up, down and across.” So we’ve talked here in the past. We’ve done some podcast. I think we imported a millennial to do that podcast, if you can find that.

Chris Goede:     Yes, we did.

Perry Holley:    That was nice.

Chris Goede:     That was great.

Perry Holley:    We’ve talked about how to lead a millennial. But today I thought we would talk about how you can lead as a millennial when you have this multi-generational thing around you, above you, beside you and below you.

Chris Goede:     Yeah. Let’s first set the stage of these generational gaps. I don’t know about you, but I get confused. And I don’t know if it’s denial, which one I want to be in or I don’t want to be in. I was born in the wrong year. So just to kind of set the stage, the baby boomers, I’ll just give you some ages. They range between 58 and 76. So we got about 18 year gap there. Those are the baby boomers.

Perry Holley:    Yep. The new look at that now is they kind of call it kind of baby boomer one and baby boomer two. The baby boomer one, from roughly 1946 to ’54. They would be now around age 68 to 76. The reason they divide this is that it really is, what influenced the generation the most? So millennial obviously around the millennia, the changing of the millennia would be a big piece of that. But a baby boomer one would be affected by a Vietnam war and the draft and some other things that were there that the baby boomer 2, ’55 to 1964, roughly aged now 58 to 67, weren’t affected by that. So that would be me. I would be in that group that I wasn’t in the draft or anything like that. But some of the older in that would be baby boomer were affected by that.

Chris Goede:     That’s good. That’s good.

Perry Holley:    So go on.

Chris Goede:     So that’s baby boomer. The Gen X is born between 1965 and 1980. So roughly, they would be 42 to 57. So that’s me. So I’m the Gen X. Gen Y or what you just mentioned, the millennials were born from 1981 to 1996. Now ages, roughly 26 to 41. And then the next one is Gen Z, which is born from 1997 to 2012. Now ages 10 to 25.

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Perry Holley:    And if anybody’s interested, they have gone back to name what’s now from 2012 to now, which would be age 10 or so and down, they’re calling it Gen A. And it’s kind of going to always be, I think the Gen A is going to always represent the newest generation coming up. So whatever that is. But I think about how we would demonstrate the challenge right now, is that if the millennials, what they’re facing now is that you report to me and your son reports to you. And that kind of sets the dynamics in play. But notable differences between my generation, your generation and your son’s generation, the millennial leader needs to be skilled at leading up and leading down based on the differences and the influences of a way that a generation sees things. And there are some notable differences in these, is why I think this company asked me to do a keynote on that. But it’s very interesting, I think.

Chris Goede:     And it’s relevant because I think, not only this organization, but many organizations have multiple generations inside their organization. So this is happening. And I would love to be in the audience when you do that keynote because I’m sure you’ll have some fun with the different generations and how they’ll look.

Perry Holley:    I asked them. I really asked this because I thought, “You’re going to ask a baby boomer with some gray hair. Okay. A lot of gray hair. I’m going to come and talk to your millennials about leading. Is that going to be okay? I’m doing a generational talk from where I am in the march. Is that okay?” And they said, “Oh yeah. Yeah.”

Chris Goede:     That’s awesome. So let’s talk about this leading up. We talked about leading up and leading down, two principles that, for us, are core to our 360 Degree Leader that John has put together in two core, and there is the leading up and leading down. So let’s talk about leading up first. So we’re going to look at this and we’re going to say, okay, the millennial leader is reporting to a baby boomer or even to maybe a Gen X, the two that are above him. And so, the first difference that I think about when I think about your leadership style, I’m just kidding. When I think about the baby boomer or maybe a stereotype that generation has and how they like to lead is that it’s very authoritative. “Hey, I’m going to tell you to do this. You go do that.” And there are no conversations about it. Where the millennial, we know this, they want to have their voices heard versus being told. So can you speak a little bit more to that?

Perry Holley:    Yeah. There’s potential for tension here if you have a boss that is more of an older generation, more command and control, perhaps, or that authoritative. We would coach the millennial leader, as we talk about leading up, it’s not your job to fix your boss. It’s your job to add value to your boss and to the organization. So I would coach the millennial leader leading up to another generation to look for opportunities to lighten that leader’s load, to provide insights, provide helpful insights for the leader’s mission. Figure out what’s important to your leader. What are they trying to accomplish? And then have a voice, if not that people don’t want to have your voice. The baby boomer, Gen X, may be used to hearing their own voice. But if your attitude is not, I’m not trying to fix you or change you, I’m trying to help you. And I want to add value to you. And I want to lighten your load by bringing insights to you. I think most leaders receive that pretty well.

Chris Goede:     Yeah. So when I think about this, the challenge that comes to mind, and people talk about this, success versus significance role. The baby boomer boss is being driven by the success, period. To where our millennials, or even in the middle in this situation, are going to be driven by significance. And that’s a big difference. And so, we need to remember that these younger generations are looking for that, for the purpose behind what you’re doing and meaning.

That’s why I think it’s also key in this particular quick sentence and statement here is that the team members that are in that millennial, if you’re leading them, that they understand why what they’re doing is tied to the bigger purpose of where they’re at and how they’re making a difference while, again, the older generation is thinking about the metrics and the financial success behind it from a success standpoint.

Perry Holley:    No, it’s a very good distinction. And I think we would coach the millennial leader to fully understand for your organization, and it could be for the entire organization or your boss’s organization, what are the mission, vision, values of the organization and the person you’re working for and with? And then how do you align your personal purpose and vision for what you’re trying to accomplish with that? If you find it’s, again, totally disarray, maybe you’re in the wrong place. But mostly what I found is, I’ve worked for some organizations. I know what they’re trying to accomplish. And I know trying to find my role in that. And how does it fulfill the purpose in me for what’s my why?

And so I think most millennials can figure out that based on what this organization’s trying to do, you wouldn’t have joined it if you didn’t believe in what they were trying to do. So what are they trying to do? And how does that align with my personal view of me and my purpose? You could also add value to your boss and the organization by helping make the link between what the organization stands for and how to be good for the world. A lot of baby boomers, we’re just thinking, like you said, we’re trying to figure out how to win and get the revenue or the quota. Get whatever’s done. The millennial may be thinking, we can do all that and still be good for the world, and be a bigger purpose than just making the success, being significant, as you said. I think that’s a great value add that we talk about being for. And that was one of our content pieces that I think this is really a great place for a millennial to make a lot of difference.

Chris Goede:     I agree. The other thing that comes to mind is the millennials seem to have more of a focus on the work, life balance.

Perry Holley:    The what?

Chris Goede:     Yeah, exactly. Where the baby boomers may not have that. Do you see that?

Perry Holley:    Yeah. Definitely something the millennial leader needs to consider, deciding how much they’re going to work. We would coach the millennial leader to help the baby boomer boss or the Gen X boss to focus on outcomes and results versus just the hours worked. I’ll tell you, from my generation, it might have been considered an eight to five, an eight to six, or 40 hour week or a 50 hour week. We were busy all the time. But maybe not busy doing what?

Chris Goede:     Not productive.

Perry Holley:    Yeah. Busyness doesn’t equal productivity. So I think what a millennial could bring to the mix is helping the baby boomer boss to focus on outcomes. Are we accomplishing what we said we’re going to accomplish? Are we producing the results we said we would produce? Why do hours matter in that? And can we have more balance? Most baby boomer bosses, and bosses in general, know the difference between activity and productivity. So I think the great question is, busy doing what? And help your boss to see that.

Chris Goede:     That’s good. So let’s shift now. Let’s go from leading up to leading down to other millennials or Gen Z teammates. And some of the things will be very similar, and they’ll apply. Gen Z teammates will want to have a voice.

Perry Holley:    I think yes. And because you know how that feels as a millennial, you want to include their voice in your planning, include their voice in your vision setting, include their voice in making the plans for how we’re going to do work.

Chris Goede:     Yeah. And so as a millennial leading a Gen Z teammate, they’ll want to also find purpose.

Perry Holley:    Exactly. And since that’s a big deal for the millennial, you can get them to help you define your why, the why for your organization, for your team. And then in the midst of that, helping them connect it to their why. I think it’s a beautiful thing. It’s actually more consistent than the leading up. The Gen Y and Z have some similarities in this area.

Chris Goede:     Yeah. And then the last one here, Gen Z teammates will want to have work, life balance.

Perry Holley:    What? Yes. I think that’s interesting how the COVID and working remotely and a lot of things have changed how people see that. But I think a millennial boss can help. You can help each other find ways to work and also serve your families. In my generation coming up, we probably drove to office buildings and we stayed there for long hours at a time. And now there are different ways of working. So I think as a millennial boss, you have a great insight into that. And your Gen Z teammates may have some other ways to look at that. How do we do that?

Chris Goede:     That’s right. Yeah.

Perry Holley:    I think if you’re a millennial leader, if you picked up an authoritative communication style, we would coach you to develop more of that empathetic communication style to help connect with the younger generation. I think some of the millennials have been in leadership now for years, and it’s not something that’s just happened. But most young teammates don’t respond well. I’m noticing that the generations coming along now, they don’t respond well to being told what to do. They want to be inspired. They want to be empowered and they want to feel like they matter, and that what they do matters. And so finding that purpose. But I’ll let you have the last word as you wrap it up.

Chris Goede:     Well, when I think about the conversation around millennials, it makes me smile because I’m like, you understand every generation has different ways they want to be led. It goes back to our core principle of everyone deserves to be led well. And we need to make sure that everyone is led how they want to be led, no matter the generation. And we do have this diversity of generations in our workforce right now. I think you and I were talking about one of our manufacturing partners that we have, there’s four or five different generations in that workforce. So this is going on. And it’s going to draw us to make sure that we really understand that we learn about our team. We learn about our individuals so that we can inclusively lead them.

One of the things I’m really excited about as an enterprise is that we’re bringing on thought leaders as part of our world. And Tim Elmore, I just last night had dinner with Tim. We were talking about some of the things going on in organizational cultures and things being said by different up and coming team leaders that are in that different, whether it’s millennial, Gen Y, whatever. And we were kind of laughing. And then we’d come back and we’re like, “Well, we did these crazy things.” But I say that to say, we were talking about this generational diversity. And we were coming out with some content on that about the diversity and the generations inside, and how do we lead them? And how do we connect them? What does that look like? And so, if you’re interested in that, just a quick reminder, go back to the And there, you can just request more information about that. Just maybe think about that as we were talking through this today.

Perry Holley:    Well, he is an expert for sure. Anything Tim Elmore, you should grab that. And he has been working on the inter-generational spaces for years. He knows this cold. So great. I hadn’t even thought about the Tim stuff. So good insights, Chris. Thank you. And just as a reminder, if you’d like to learn more about, as Chris said, The 5 Levels of Leadership or 360 Leader, if you’d like to leave a question or a comment. We love hearing from you. If you would like to download the learner guide for this episode, you can do all that at And we love hearing from you. We’re always grateful that you would spend this time with us. That’s all today from The Maxwell Executive Leadership Podcast.

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