104: Boomers to Gen Z: The Leadership Skills Every Manager Needs Now w/ Gabby Rosely

If you’ve ever struggled to understand why different generations communicate, work, and clash so differently, this episode will give you a new lens on leadership.

In this conversation, Sean Patton sits down with Gabby Rosely, keynote speaker, leadership trainer, and host of The Gabby Rosely Podcast. Gabby stepped into leadership at just 21 years old, managing boomers, Gen X, millennials, and Gen Z simultaneously—an experience that shaped her expertise in multi-generational communication and leadership.

Together, Sean and Gabby unpack what it really takes to build trust, accountability, and strong culture across age groups. They explore the challenges of moving from individual performance to leadership, the difference between being nice and being kind as a leader, and how generational blind spots can quietly derail teams.

This episode is a must-listen for leaders, managers, and entrepreneurs who want to communicate better, retain top talent, and create workplaces where every generation can thrive.

Chapters

• 00:00 – Why Generations Clash at Work
• 02:00 – Stepping Into Leadership at 21
• 04:30 – From Individual Performer to Team Leader
• 07:30 – Leading by Example vs. Taking Charge
• 10:30 – Kind vs. Nice Leadership
• 14:00 – Blind Spots and Why Leaders Need Coaches
• 18:30 – Developing Leaders, Not Just Performers
• 22:30 – Understanding Boomers, Gen X, Millennials, and Gen Z
• 27:00 – Keeping Gen Z Engaged at Work
• 32:00 – Vision, Alignment, and Team Buy-In
• 35:30 – Leveraging Multi-Generational Strengths
• 40:00 – Culture Shifts and the Search for Structure
• 45:00 – Where to Connect with Gabby Rosely

Guest Links

• Gabby Rosely – LinkedIn: https://www.linkedin.com/in/gabbyrosely
  
  
• Gabby Rosely Podcast: https://podcasts.apple.com/us/podcast/the-gabby-rosely-podcast/id1681507089
• https://open.spotify.com/show/26HaB2hjLj0R1YrWLoHW5F?si=KKnhURrXSKi4tKkYEyYSxg&nd=1&dlsi=93bed0d235794479
• YouTube (Speaking Videos): https://www.youtube.com/@GabbyRosely
  
  

No Limit Leadership is the go-to podcast for growth-minded executives, middle managers, and team leaders who want more than surface-level leadership advice. Hosted by executive coach and former Special Forces commander Sean Patton, this show dives deep into modern leadership, self-leadership, and the real-world strategies that build high-performing teams. Whether you're focused on leadership development, building a coaching culture, improving leadership communication, or strengthening team accountability, each episode equips you with actionable insights to unlock leadership potential across your organization. From designing onboarding systems that retain talent to asking better questions that drive clarity and impact, No Limit Leadership helps you lead yourself first so you can lead others better. If you're ready to create a culture of ownership, resilience, and results, this leadership podcast is for you.

Transcript

Sean Patton (00:00)
If you've ever struggled to understand why different generations communicate the way they do, work the way they do, or clash the way they do, then this episode is going to unlock a whole new level of clarity for you. Because today I sit down with someone who has lived this challenge from the inside out, stepping into leadership at 21 years old, managing boomers, Gen X, millennials, and Gen Z all at once, and learning the hard way what actually builds trust, connection, and collaboration across generations. Since then, she's actually become an expert in the area of multi-generational communication.

This episode is packed with insights that will make you a better communicator, a better leader, and a better builder of culture starting today.

Sean Patton (00:49)
Welcome to the No Limit Leadership Podcast. am your host, Sean Patton, and I'm very excited to have Gabby Rosely today. She's a dynamic keynote speaker, a leadership trainer and host of the Gabby Rosely podcast. She's a rising voice in the world of multi-generational communication. She specializes in helping teams bridge the divide between boomers, Gen X, millennials, and Gen Z by teaching leaders how to communicate more effectively, build trust, and create cultures where every generation thrives. She speaks across the country on a multitude of topics.

And her work blends research, real world experience and deeply, a deeply human approach to leadership development. ⁓ Gabby and I met at some training and we hit it off right away. We both found out we had podcasts. We both found out we're speakers and I really loved what she had to say and I was very impressed. So I knew we had to have her on. So thanks for doing this.

Gabby Rosely (01:37)
Absolutely. Sean, thank you so much for having me and for the wonderful intro. feel like the energy is already up. So I'm excited for our conversation today.

Sean Patton (01:43)
Absolutely, that's what we do here. What was really interesting to me when we had our sort pre-interview call for this and I got to know you more is how you stepped into leadership management so early in life, immediately, and how that had a profound impact on you. what was that experience like, kind of like right out of college, like hopping right into...

leadership in a corporate environment.

Gabby Rosely (02:09)
man, my corporate position out of college was my first big leadership role.

But, ⁓ before I went to college, I started a swim program in my hometown and I ran that for three years while I was in college and I had a team of about eight instructors. So I was kind of dipping my toes in the leadership realm. But when I took on the corporate role, that was when I had, I had higher ups to answer to. And that's when I got really into the multi-generational stuff because I had boomers, Gen Xers, millennials, and other Gen Zers on my team. And I think the hardest part for me accepting that role at

21 years old was quote unquote proving myself to the people that I was leading and even the people that hired me that I could do the job that they hired me to do because I was so young. And although I had experienced that I could make sound really good if we're sitting across from each other on paper, it's like this girl just graduated college. She's 21 years old. How is she going to run this team? So I definitely had to overcome the initial barrier to entry with trust.

in other people that I was working with because a lot of people just didn't think I was qualified to do the job. And so I would say that that was my biggest challenge, but that also really prepared me to do all the things that I've done after leaving that position, which I'm sure we're going to talk lots about. ⁓ but it also built a lot of self-trust in me and my ability as a leader because I had everyone initially doubting me, which I think was, you know, I was forged by the fire. So that was, that was good, but it was definitely not easy while I was doing it. ⁓ but.

But yeah, that was probably the most difficult part.

Sean Patton (03:41)
You know, one of the things that I related to from your story was you were a, very accomplished swimmer, right? As you mentioned, swim too. So like you were a very accomplished athlete in an individual sport. I was a wrestler. Uh, and so also is that individual sport mentality. And, you know, there's some, I think some challenges when you come into, uh, you know, the performance, right? Like job performance, whatever, your performance comes down to you, your preparation, your action, I think it's some.

huge benefits in life to that. But when it comes to then stepping into leadership and sort of being like, it's all on me. I know you mentioned there was some challenges along with that transformation to that bigger team environment. What was that like?

Gabby Rosely (04:22)
Yeah. And I'm also curious to hear your take on this because as an individual sport athlete, I really do resonate with the performance pressure being placed on us by us. Also you've got coaches and teammates and stuff, but when you're on the wrestling mat, you're

in it for, you know, your own performance. And when I'm in the water, I'm in it for my own performance. And funny enough, I actually just joined a master's swim team. So I'm swimming again and ⁓ my God, it's so great. It's so awesome. I'm back to my roots and it feels so good. And yesterday in practice, it was so funny because we were doing this hard set and it was like a descending 100 set where you basically, you know, where you're at and you are the one who gets to choose how hard you push yourself as you get faster and faster. And I was you know, kind of swimming

Sean Patton (04:49)
Nice.

Gabby Rosely (05:07)
my own lane, I'm the only person that's making me do this is me. And, ⁓ but it's, but it's such a powerful, powerful understanding when, when you know that you're your biggest supporter and also your toughest critic. and I think that.

coming from that individual sport into leadership. I tried to use that same mentality where it's okay, I just got to put my head down and grind and I just got to push myself because I'm the only one at the end of the day who I have to really answer to. ⁓ when I lay my head on the pillow at night, but I think that that is.

equally as powerful as it is exhausting. And so I had to decondition myself from this mentality of do everything all on your own and tell everybody about, you know, the results after you've achieved it to, you have to integrate other people into this process. And the more that you communicate with the people that you're leading, the more that they trust you, the more that not only the culture has changed from the inside out,

But your performance as a leader is enhanced because you have multiple different perspectives. If you loop people into the conversation, whereas before I was trying to figure everything out on my own, cause I didn't want anybody to think I was weak. And I already had this placement of doubt on me and on my shoulders where I was like, okay, well, I definitely can't tell people that I'm struggling or that I need help because they're going to, you know, kind of like this corroborating belief where they already think I can't do it. so I had to decondition myself from that.

And I had a really, really, really great assistant manager that helped to create that space where I could talk things out with another person and slowly dip my toes into working together with people versus trying to do everything all by myself. but, but yeah, I'm, curious to hear your thoughts on that as an individual sport athlete also.

Sean Patton (06:47)
Yeah, it's, I love how you described that. It's right, it's kind of like a double-edged sword. And, you know, it's interesting that I found that a lot of things in life, when you get to sort of the extremes where you push yourself in these environments, you come up with a tool. It's almost like the stronger the tool is.

It's could be, it could be a force for good or force of evil, know, you get to it, you get, it gets something like in anything like that. So I guess the two examples for me would be yeah, wrestling, where it's all on you and then you sort of then maybe create that expectation. So then when I first got, and started working with teams, it was, what I found early on when I, I went for me was interesting. Cause I went from, ⁓ into West Point. So right into you know, the leadership crucible, right? And so it was very direct in terms of.

Gabby Rosely (07:09)
Absolutely.

Sean Patton (07:30)
in college and still on the wrestling team, but, that you're, we're going to like go directly at leadership. We're not going to have to beat around the bush a bit. and what was interesting in, this all the way through West point, even in my early officer years was I think the lesson that I took that was strong from, you know, sort of the good, the good side of that double edged sword was the leadership by example part, right? Like you push yourself, you show them what right. looks like

You show them what, you know, right training looks like. You show them what discipline looks like. You show them those things and then people come along, you know, ideally. And so like that was always a strength. it meant that like peer to peer leadership, like on a team was sort of a natural strength for me and where that, and that sort of worked for me through West Point. ⁓ and then where it sort of ran smack into,

The other side of that coin was when actually when I got to like ranger school and I got to be like an, an actual officer and I failed ranger school and had to start over, like one of the most brutal leadership training events in, schools in the army. And it was literally cause they said like, you're under these very stressful conditions, right? Like everyone's cold, wet, no one slept is hungry and like it's hungry and you're like trying to lead. Like what I didn't have is the ability to be like,

take over, but you do this, like really top down, be directive, and, take charge because it was always just like, well, if I just do the right thing, then everyone else is going to come in along. It's like, well, not always. Right. And so that was sort of double X or that I had to learn the other side of that to your point when you start, like when you're, you know, got to work for me, that same thing, when I got into the military, it was like,

Gabby Rosely (08:44)
Mm.

Yeah.

Sean Patton (09:04)
I had these sergeants being like, no, no, you need to like, and it's a little different because I was in infantry, but you need to grab them by the chin strap. like, listen here, mother, after like, your job. Be, take charge. When in charge, take charge. And that was something I had to kind of, you learn to turn that switch on.

Gabby Rosely (09:12)
Yeah

Yeah, I think that's so important to call out because I think that in this new paradigm of leadership, there's so much focus and I agree with a lot of it on emotionally intelligent leadership and leading by example and all of these things. Very, very, very important. But at the end of the day, a great leader is somebody who knows how to delegate and knows how to direct and knows how to encourage people. And sometimes that looks like a little bit of tough love of like, yeah, get your head in the freaking game and let's go. And then you got to do what you got to do. And I'm to make it very, very clear so that there's no room for

for

misunderstanding because I think that when we're always trying to reflect back to people and be a mirror and kind of like beat around the bush in that way, I think it works to an extent, but in a leadership position, we...

Choose our leaders so that we have someone to look up to. So we, so we have someone to give us direction. That's why leaders are chosen for their, for their positions. It's yes, to make leaders out of those that they lead, but it's also to be that leader for those leaders. And so it's like this, this interesting balance. And so I'm so glad that you called that out, especially with your background, from West Point and then now in entrepreneurship and coaching, because yeah, it's, it's just, it's so, so good.

Sean Patton (10:27)
Yeah. Well, you know, and when, when I'm hearing you say too, and as I think about it, you, you, you reflected back, like it's that there's also what we want from our leaders. And I see it with clients and things like that where it's setting clear standards and expectations. And then having the, you know, to use the military term, the intestinal fortitude or the courage to hold people accountable. And to your point, I see a lot of managers and leaders.

Yeah. Be so soft and like, we're, we're trying to get this together and you could do and all that. And then what happens is they avoid and, the words is coming to me and it's actually something that, ⁓ I've had to work on even my own life is like being kind, not nice. Hey, like nice, nice. Doesn't bring up nice. Doesn't bring up, when you see something going wrong or you just like kind of be like, you know, I'd really appreciate if you did this thing and maybe we could do that.

Gabby Rosely (11:06)
Mmm, so good.

Sean Patton (11:16)
And then you let it fester because what you're actually doing is, is avoiding itself. You're avoiding the discomfort of having that hard conversation and tell you're like, well, now we got to let you go. Here's HR and here's a performance pan later. Right? Like it's abdicating that responsibility of being kind, which is like, look, you're underperforming. You are not meeting standard. Here's what standard is. Here's where you're at and how are we going to fix this? And

If it doesn't, here's the consequence. to me, that's kind versus nice. and when I'm, I guess I'm interested in how you see that. And then also getting into your, your, your, expert opinion here, or what you're seeing in. Then we throw over the multi-generational lens on that as well and how different generations see that and how that plays out. like around that sort of area of.

how to handle and hold people accountable and being kind versus nice. Like how does that, how do you see that play out in your work?

Gabby Rosely (12:10)
Yeah. I just want to note on the kind versus nice, because I think that's an, ⁓ a very, very important distinction to make because I remember when I was in my management position, I wanted everybody to like me. So I wanted to be the nicest person, which oftentimes meant like, okay, I'm going to avoid the difficult thing that we should probably talk about, but I want you to like me so bad that I don't want to make you, ⁓ feels any type of way. So I was, I was falling into the nice trap versus the kind and directive leadership.

role that I was being called to fill the shoes of. And I think that, yeah, it always led to more friction in the long run because I was trying to smooth things over with these niceties and it just didn't end well. So I had to release that, that desire to be liked by everyone. And I had to...

fall deeper into this call to be a leader, which oftentimes means having the hard conversations and yeah, just doing the things that might cause a little bit of disruption in the niceties every now and then. But yeah, I think that now working from a scope of I'm building into leaders and I'm building into team members, but I'm not.

involved over a long period of time. kind of get a brief, whether it's a workshop or it's a four month coaching program, I get a brief little bird's eye view. and, usually it's, it's very, very, it's holistic, but I, I find a lot of leaders nowadays that don't know who to go to, to talk about the problems that they're having with their teams. So they're trying to figure everything out.

their own using only the set of experiences and knowledge and skills that they have. And they don't know where they could improve or where they're maybe missing the mark or where they're falling short or where they're stepping into niceties over kindness. They have blind spots and because leaders don't have people to talk these kinds of things out with unless you have a consultant or you have a coach, then they're falling short because of their blind spots. don't know what we don't know. ⁓

And, yeah, I think that across the generations as well, when we're trying to bridge the gaps, we have to know what the gaps are. And if we don't know what the gaps are, it's like, everything's great. Right. But, oftentimes there's the team members who, if the leader can't have the difficult conversation, the team member sure as hell isn't going to initiate the difficult conversation because it's just like not, that's not the standard. And so you don't know what you don't know. And even if your team members know it, maybe your leader doesn't know it because they haven't, they haven't bridged that gap.

They don't even know it's there. So I think blind spots are a really big thing. I see in the leaders that I work with and in the teams that I work with because ⁓ sometimes we just need that unbiased third party. Sometimes we need, we need that soundboard. Sometimes we need, we need a coach. I've got a coach, you've got a coach. We all need a coach, you know? So yeah.

Sean Patton (14:57)
Yeah, I think first of all, I agree with you. should get, everyone needs a coach. I told you all the time, like, you know, I have, I literally have four coaches. like, I tell you like a significant part of the money I make every month goes to other people to invest in myself because ultimately, right? Like where are our own limiting variable? And what I also see in what you said there is what I see is it with clients and companies as well is how

Yes, outside coaches should be there, but in an ideal sense, ideal structure, they're supplementary because what I see is a complete lack of expectation, don't if it's expectation, ability, a combination of leaders. think with the primary, how we judge great leaders is ultimately on the leaders they create. So what we have is we put leaders in management positions

Gabby Rosely (15:40)
Mm.

Sean Patton (15:44)
without the training, without the input to them, without the coaching so that they're prepared to turn around and build and develop the leaders underneath them. then you have this, you mentioned this skill gap, this mindset gap of like, now I'm an assistant manager, general manager, I'm a director. And now, yeah, I could lead salespeople, like I could help them hit KPIs and talk to them one-on-one, but...

Now I'm in charge of developing other leaders. How do I make other people great leaders and call out their blind spots? And it's like, well, where's that in their promotion? Or did you just promote them because they hit their revenue quota? Because those are different things.

Gabby Rosely (16:21)
Yeah,

absolutely. think perf, performance is only one, one of the tick marks that should be looked at when we're thinking about promoting someone to a leadership position. And I think what you're saying is really important too, because yes, outside coaching and outside consultancy is great, but it's supplemental and a lot of organizations aren't at that place right now. And I think that when we do have middle management,

that is now thrown into a role that they didn't have the training or the coaching to be able to prepare them to lead others and to delegate and to encourage and to support and then do all the other managerial things that they have to do. I think we really have to, we have to create that funnel so that from the top down, the leaders that are building into their leaders know exactly what it is that they're going to probably fall into a pit if they don't have the

important conversations before the role calls them there. So yeah, I think that the top down approach is very, very important. But, but I also think too, that when it comes to working with a team and leading a team, sometimes as leaders, we feel like we have to have everything figured out before we step into that role or, just as a leader, like, they expect me to know everything. Okay. A big part of leadership is humbling yourself enough to ask for feedback.

and asking for perspectives from people on your team, not because you don't know, but because you care enough about your team members to hear about what's actively moving through the team. What are the suggestions that they have? One of my favorite questions as a leader to ask those that you lead is if you are in my position, if you are a leader, you you got an issue or you have a problem. If you were in my position, what would you do? Like I really love to hear your opinion, not because I don't have my own, like I've got my own thoughts, but what would you do?

And then that creates a little bit of a sounding board in a way that you also validate and you encourage your people that you're leading to step into their leadership roles and to put on their leadership hats. I think that's a really beautiful place to look for a sounding board, not for everything and not all the time, right? Because yes, you are the leader and you're called to that position to make qualified decisions, but a great opportunity to help your team put on their leadership hats.

Sean Patton (18:33)
Yes, yes, absolutely. I'll double tap that like for sure. Because what you're really talking about there in my estimation is like you are, that's how you help people and coach people on how to think differently, right? Not what to think, but how to think. It's like what I love that question. If you were in my position, what would you do? Cause then one they might come up with and probably will. I had a lot of times come up with a better idea than you had. You know what? That's a great idea. We'll go with, we'll go with that.

Gabby Rosely (18:50)
Yes.

Sean Patton (19:00)
⁓ cause they're closer to the problem or you're like, ⁓ interesting. All right. Tell me how you came to that. And now you get a chance to develop. get to have a developmental conversation about how they're thinking about problems. They get an insight into how you think about problems and you start to close, as you mentioned, these, these gaps between, know, between the different levels and you, and you get to invest in your people. now as we, as we shoot that and we look at that,

Gabby Rosely (19:02)
Yes.

Sean Patton (19:26)
um, across generations, right? Um, maybe for people who have, you know, I would just because I haven't hear like for people who haven't studied generational theory, but I think a lot of people maybe have, but so I'm interested in this, like, what's your take on the different generations and maybe like, what is sort of what most people think of sort of stereotypically and if that's true or how that's true or, or not, you know,

Gabby Rosely (19:34)
Thank

Yeah, 1000%, this is my favorite thing to talk about. So basically, let's break down the major four. There are some silent generationers still in the workforce, but it's such a small percentage that we're gonna just focus on the main four, which are boomers, Gen Xers, millennials, and Gen Zers. So we'll start with boomers.

Basically the way that I summarize boomers, they really like context and they like tradition. So they value hierarchy, they value loyalty. We can go into post-World War II and the clear social roles that developed a generation of abundant and confident people in the workforce and loyal to the family unit and to the country and their social roles and all of that. But we'll just keep it at that, that baby boomers really do value tradition and they value context. They want to be in the loop.

And I think that a really, a misconception that's very prominent, especially with the younger generations, is that baby boomers are old fashioned and they're not with the times. they, you know, my gosh, they didn't grow up with technology. So how could we ever consult baby boomers about something that has to do primarily with, you know, an interface that's online? Like, no, we could never.

⁓ and so I think that that is a lot of lost wisdom and a lot of lost experience there because the traditional approach and the longevity of baby boomers and their careers, have so much to offer. If not just another kind of perspective to be able to create this, you know, whole, and I think that's so important. and I find that when I work with baby boomers, especially because I'm a Gen Z or that is so different for them. That is not how they grew up. Like.

seniority was oftentimes based on how long you were with the company. But now we've got millennials and Gen Z managers that come in. They've been with the company for four years versus the boomers who have been with the company for 40. And now they're in middle management roles or they're in, you know, C-suite executive positions. And it's like, what the hell, man. So having some patience around that and taking the time to break down those barriers, because it's not going to happen right away. And you got to, you got to be in the long game, especially with baby boomers, if you're a younger generational leader. And yeah, so.

So GenX, GenX is the sandwich generation and I really like GenX a lot. They're an interesting generation. They're very independent, primarily because they grew up in a time where skepticism was like at an all time high, know, okay, we can't really trust the government. We got a bunch of people getting laid off, economic recessions are like through the roof, a lot of instability, mom and dad are now in the workforce. So we got latchkey kids.

So we're just, creating this hyper independence in this generation, which now shows up in the way that they are at work. And so when we look at millennials and Gen Zers who really value collaboration, Gen X is like, can you send me an email and then leave me alone and let me do my job? So I think that one thing about Gen Xers that is really important to understand is that when they are given clear contributions, you have to trust them.

and let them do their job. And just because they're not communicating all the time with you doesn't mean that A, they're not doing their job or B, that they don't want to, but that's how they work oftentimes. So just having that like, maybe they prefer to do things in their office because that's how they work really hard versus be super active in this meeting or on this Zoom call.

It's just not what they're used to. They didn't even share with their parents because they were running around the neighborhood with their neighborhood friends versus sharing with their parents about their days at school because that's just not how they grew up. So really important to recognize about Gen X. And I think oftentimes, yeah, we think that they're mean or they're rude because they don't include emojis or exclamation points in their emails. No, they're very direct. They're direct.

So it's like, get to the point and move on because I'm busy and I got work to do. So if you, if you get an email that ends in a period from a Gen X or don't worry about it, like don't sweat it. Okay. yeah. So, so then millennials millennials, they're also generation Y. So millennials were a very, very confident generation as well. They grew up with technological advancement through the fricking roof.

⁓ You know now we got the dot-com boom so people are starting businesses in their parents garages and you can become an overnight millionaire essentially So they're very confident. They're like the cafeteria kids You can kind of do anything you want choose your college major choose your career path. Just a lot of optimism in this generation so so really important to recognize that Millennials have this this confidence and this optimism and in the workplace. They are relational creatures

So millennials really enjoy the collaboration and the dialogue because they were raised with an engaged discuss model versus a commando bay model that Gen X and baby boomers were raised with. So do as I say, because I said so, it's not like that for millennials and Gen Zers anymore. They're raised with a, do you have any questions? Let's talk about this, okay? In their education systems and at home. So really important to recognize that with millennials.

And I would say misconception from millennials is that, yeah, they care too much about the aesthetic of things. They're just really passionate and creative people. So I hear that a lot with the millennials. It's like, they just wanna talk too much. They care too much about the fluff and they'd rather sit around and chat and have coffee. Some of them definitely, but it's because they value relationships. And then Gen Z, which is my generation.

Gen Z is a very unique generation because of all of the craziness that has gone on since 1996 when that generational cohort begins. They're 1996 to 2012. So Gen Z, one thing to understand about this generation is that they are a very, they're a very anxious generation, but they are equally as much so a creative and entrepreneurial generation. So because Gen Z,

had smartphones introduced in 2010, which critically affected the social development and even brain chemistry and mental health of this generation with the constant comparison and noise and what's going on all the time. There is an always a feedback loop. So in the workplace, if they're not getting constant and instantaneous feedback in whatever degree, they feel like they're left in the dark and like they're doing something wrong.

Okay, so if you are a leader and you lead Gen X or Gen Z, I'm not telling you that you need to be like, oh my gosh, yes, you're doing so great all the time, but don't wait until your quarterly or your annual review to let them know that they're doing something right or wrong. Have the conversation when it happens because that instantaneous feedback is going to create the pattern repetition loop that Gen Z needs to be successful. And yeah, I will say that as much as you can,

foster their entrepreneurial spirit because Gen Z is the side hustle culture. It's like they saw some economic instability. see now it's the digital age. You can go into digital marketing and drop shipping and YouTube and make as much money as you want, really. It doesn't mean it's easy, but the more that you can make positions entrepreneurial in nature,

innovative for Gen Z, the more engaged you're going to keep them. So they're not disengaged. They just need your help leveraging their strengths and getting them plugged into the role ⁓ based on the way that you frame it and the opportunities that you give them. So a lot of people think Gen Z is disengaged. They're not disengaged, but they just need a little bit of help figuring out who they are and how to leverage their strengths in the role. So as a leader, that's your call to help them to do that.

Sean Patton (26:56)
Well, amazing, you know, overview there of and really hitting some, feel like the major points, the point about Gen Z being entrepreneurial. And when I hear that, because, you know, I see it too with the younger workers and of course, there's a blend, right? Like, you know, have like millennials bleeding into Gen Z and that sort of thing. And it's interesting because I'm Gen Y, like you mentioned. I'm like,

I feel like I have like half of that gen X, you know, I was a latchkey kid, but I was like a single mom. And it was like literally with a key around my neck, show up, you know, I, Hey, here's the instructions to put the pizza in the oven at seven. When I get home, you know, like that's how I grew up. Um, and, without technology, know, right? Like I remember when AOL intubation first hit and I was a junior high and we were like, you know, having to, so we pick up the phone, it would hang up the internet and all that stuff. Um,

So I resonate with sort of both of those. ⁓ and then, but the, the point about the, entrepreneurism that's sort of the digitalization and interconnectivity that we've have now with the younger generations, without say younger millennials into gen Z. that's what I see a lot of leaders or managers, especially older ones struggle with because they, they, they want to, I think it's, I think it is generally well-intentioned. It's just like, we want to be clear about here's your role. You're going to do.

these things, you know, one, two, three, four, five, six, you're to do these and that's a good job. And if you don't do the things you do that. And Jen's is like, yeah, I did that 30 minutes ago. Like nine board, you know, like, you know, and, and if they're not getting a chance to be creative and to solve problems and do multiple things, then, they get very, then they, do get disengaged because they're like, you know, I would say like, treat people like a cog in the machine. Like they're going to act like cogs in the machine, right? Like, so how do you foster and really explore that ability? So.

⁓ I'm interested, you know, one, how you see that now. And then I would also be interested in your take on as companies and businesses transform in the age of AI, and the speed of change and how that, like how that could be leveraged or utilized with, with the change in business.

Gabby Rosely (28:55)
Yeah, definitely. I think that great leaders are becoming more popular because I do think that the tools to become great leaders and to nurture the skill that a lot of us, feel like are born with has become a lot more widespread. And so there are a lot better tools out there for leaders to step into these roles. And I think it falls on leadership.

So when you are working with a Gen Z-er, I thoroughly believe that there should be, in the very beginning of the career, I don't know if it's in the hiring process or if it's immediately after they're hired, I do believe that we should have a it's a vision call with a Gen Z hire or a millennial hire, a Gen X hire or a boomer hire.

I think there should be a vision call and a part of that vision call should be referencing the strengths and kind of the skills that that Gen Zer brings to the table or any generation, let me just say. Because I think that...

When we know more about the person than how they're gonna fill the shoes of this role, then we have things to grab from when we notice, ⁓ maybe they're getting a little bit bored. Okay, well, this Gen Z-er, I'll use me as an example, says they really enjoy public speaking. Okay, well, we need somebody on this panel to talk at this upcoming webinar.

Well, maybe I'll see if this is something that they're interested in. So when you take mental notes, which starts with having the conversation and having that vision call with each of your new hires, then you've got a little bit of stuff behind the scenes you can work with in those situations. And I think also that when you see and notice that you've got disengaged team members,

⁓ You don't want to wait until that becomes louder than it'll whisper, it'll yell and then it'll scream. If you can catch it at the whisper, awesome.

And if you have, if you got to wait until the yells to be like, maybe I thought it was this, but now it's this catch it at the yell. Don't wait until it's a screen. Cause that's when they're quitting. That's when you're losing top talent. that's when you know, you're losing out on clients because now they don't have the same project manager on their, on their account. And it's just, you know, it's a mess. So, ⁓ so definitely listen for those whispers and open up the conversation more often, because I think that the new paradigm of leadership is going to be more so focused on.

the human being as a whole and how they can use their existing skillsets, experiences and strengths to fill the role. Yes, but also revolutionize the culture and, you know, contribute to the vision and to, to really pour in from a place of, okay, yes, I'm doing my job, but how can we grow together? Because engagement also falls on the leaders to involve every team member in the bigger picture, in the vision. Cause if you're, if, if you're not,

If you don't have team members that are plugged into the vision, no wonder they're disengaged because there's no reason other than they get their check and they're out of here. Okay, so let them leverage their strengths because that'll help them with their engagement and their role and then help them to feel plugged into and possibly even contribute to the vision so that they feel we.

We all want to have impact. We all want to have purpose. We're stepping into a new paradigm of leadership that is purpose driven, that is impact driven, and it looks different for each person. But when you open these conversations and plug them into the vision, then it becomes a lot more of a collaborative and collective working toward a goal, which is we were on teams, you know, even though we were individual sports, like heck yeah, I want to win states with my team. That's awesome if I win a title, but if we could win as a team, that's so bad ass, you know?

Sean Patton (32:17)
Yeah, no, totally. love the call out of like the vision call. And I think you articulated this, know, even better than I have, even the past of having this conversation, you know, cause I really, I've really framed it around like alignment. And so I love the, you've talked about like casting vision, but sometimes we don't even ask like, what are you here? Like, what do you want out of this? You know,

You know, do you want to just show up from nine to five and push paperwork and hit numbers and then like click the paycheck? Like most people don't. I would also say most of the jobs that involve that are going away. right. So like, what are you, is it development? Are you, what skills are you trying to bring? You mentioned bring to this, but I think also then like what, you know, what skills are you bringing? But what do you want to develop? Like maybe you're like, maybe you're like, I'm a great public speaker. Maybe like I'm awful at public speaking. I really need to work on it. Like, cool. How do we integrate that into?

If that's a goal for you, right? Or whatever, like these skill sets or flexibility is important or, know, some people like, well, I've got two young kids. Like I'll work my tail off for you and do whatever you need, but like, I need to be out here at four 30. Cause I got to pick it from daycare. Like that's what matters to me, you know? But like, and then if you can find a way to align, you know, I think it was in line. Like you mentioned the, I think of it as like aligning that personal goal and values with like company. So how do we say cool company needs, this, you want this.

Gabby Rosely (33:29)
Yes. ⁓

Sean Patton (33:34)
And once we get those things in a line and they're working together, now we've got engagement. And so that's why I've always framed it. And what I love, think if you could take that almost as a base and then take what you used, what you called out there, which is then also let's cast vision even further out and get them involved in co-creation of like, not just like, okay, what do you want? What do I want? Let's align sort of like level one, but the next level of what are we capable of?

Gabby Rosely (34:00)
Hmm. I love that. And I love alignment too. I feel like that is a really, really important word and a word I come back to often when I'm making decisions, when I'm going through struggle, when I feel, you know, mentally like I'm down or I'm physically not in the best shape. It's like alignment, alignment, alignment. I think about it in work. think about it in friendship. think about it in diet. I think about it in physical activity. Is this in alignment? Not just with, you know, what I think is right, but like where I want to go.

And I love that you broke it down in level one, level two, because yeah, we're at a breakthrough point right now where we're kind of transcending from the level one, which is a really great place to start, but it doesn't mean that we have to stop there. And just this whole idea of beyond high performance, meta performance. And yeah, so I love that call out.

Sean Patton (34:44)
When let's talk, you know, get maybe real practical here on a lot of people maybe are in these, you know, larger or medium sized companies and they are the millennial, maybe Gen X like area, like they're getting ready to move into like senior leadership in a company or, know, maybe they, they had a career and now they've started their own company. And so they're moving into like that senior level of ownership.

⁓ And they're going to have multiple workforces and age groups and things like that. Great awareness and call out on the different sort of generalizations for them. But what are some best practices or like what's, how do they ensure that they're leveraging the strengths of a multi-generational team to the best capacity?

Gabby Rosely (35:27)
The first thing that I would say, if you're stepping into a role where you're going to be leading the different generations is just taking inventory of your own assumptions first and foremost, before you actually start to get any real information is take inventory of your assumptions where it's like, okay, know, hey, I tend to gravitate towards working with the millennials because we get along a lot better. I tend to avoid meeting in person with a boomer because I know it's going to take three hours or whatever. So taking inventory of your own assumptions.

and also challenging yourself of like, well, where has this been proved wrong? Whether it's inside or outside your organization and exposing yourself to like, what is possible out there and maybe doing a little bit of case studies. That stuff is always interesting to me. Like research is always interesting. So you can find so much stuff on multi-generational teams on the internet nowadays. So doing a little bit of research is always helpful. Inventory, great place to start. Research, great place to go next.

And then it's real time conversations with the different groups on your team. And you can do it by department. You can do it by.

a shift, you know, depending on the industry that you're in, but having those real time conversations and giving a voice to each person. And ⁓ it doesn't have to be, you know, it's not this huge thing where it's like, I'm asking you to go on a retreat once a quarter with your whole team. If you can afford it, great. that. That's awesome. But, but no, it's, it's just being intentional. Maybe it's once a year, or you go through a sweep of new hires and you sit down and you ask some really, really important questions that are, Hey, what are your top three to five strengths?

How

does that reflect how you show up in your role? When do you get the best from you? When do you get the worst from you? What are some assumptions that people make about you or your generation? Open it up, start talking about the generational gaps in the cohorts. What are some assumptions that people make about you and your generation that you wish you could dispel right here, right now? What are your biggest fears when it comes to working with people that are a lot older or younger than you? These are conversations and they can be reflective. It doesn't even have to be a meeting.

Hey, I'm gonna give you this set of questions. You're gonna get curious. Here's your homework. And you come back and you look at the answers and then it's like, ooh, this deserves a conversation. I might wanna expand on this a little bit more. So I think it really just starts with genuine curiosity and humility.

Sean Patton (37:37)
Hmm. I love that point. you know, I love that strategy, especially when it comes to like team building and asking like, what are people, what assumptions people make about you? Oh, that's such a cool way to frame that. And, you know, I also think generations is one way we classify people, right. also where they're from their age, their age, where they're from, maybe ethnicity, whatever, right?

Cause you get someone who's from, I don't know, like a Latin American country or something. And you're like, well, most people assume that, you know, we've got 300, you know, I don't, making up, I'm just making a story up. Like we've got three generations at home and like, I, you know, eat this way. I do that thing. Like I don't do any of that. And it's like, it could be a, it could like a, it's a fun conversation and maybe like a fun, almost like icebreaker or share. Like what's something, what's an assumption people make about you on the surface level that is completely not true. And that's actually, now that I said that, that's probably something I'm to use in a workshop. do. I like, I think that's a pretty cool.

Gabby Rosely (38:09)
Yeah.

So good.

It's so good. yes, 1000%. I love the call out too, with different cultural ethnic backgrounds. Like, yeah, we, we're all, we're biased creatures. develop biases. we develop assumptions. That's how we survived. And you know, that's kind of this we're human beings. And so to be able to defuse some of those assumptions and get the elephant out from the closet and into the middle of the room, it's like, this is fun. And it's like exciting. And you're kind of on your toes because it's a little taboo. we don't really talk about this, but we should.

Sean Patton (38:28)
way to open up and break walls down.

Yeah. as we get close to wrapping, think, I just had this idea of we've talked and I think covered so much gold around leadership and business and people and interactions. So if we pulled out a bit to like, maybe, maybe culture, like just culture and specifically in America right now, um, one thing that I've seen or I've seen research on or called out, and I'm interested in maybe you're probably closer to it. So I'm interested in your take is

especially Jen alpha or young Gen Z maybe because of the chaos being drawn to or pulled to more almost like a full circle back to sort of like traditional things, traditional structure, traditional hierarchy where that's where that's religion, without social structure, without conservative belief, whatever that might be. Like there's almost this, like, I see that as something that's been called out as like,

starting to sort of have this upswell. And so I wondered if you could maybe speak to, is that all noise? Do you think that that's there? Maybe why that's there and how that might sort of, as we look forward, you know, impact us as a society and in the workspace in the next 10 years.

Gabby Rosely (40:03)
Absolutely. I always consider my dad always would bring up this image when we talked about anything, whether it was political or cultural or just anything agenda wise. Sometimes the pendulum swings too far to one end. And I think that's exactly where we got. And we're starting to see a swing back the other way, because you start to realize where it's like, whoa, whoa, whoa. You know, now I'm just going against all of like any piece of logic, you know, in some area where it's like this,

This

doesn't make any sense to me and I don't even know if I would sign myself up for this anymore. And so as we start to kind of take a step back and remove ourselves, because I think that when we start to...

define our identity by the things that we believe in and movements and the direction that things are going socially, politically, whatever, then it becomes very difficult to open your mind and remove yourself from the movement and the shifting goalpost that is always like, oh, we thought we were going here and now mob mentality. Oh, we're going here. Let's just get up and go. When you're able to, and I think a lot of people are kind of waking up because we thankfully live, yes, there's a lot of information and a lot of noise, but because we do still have free speech, let's pray.

to God that we continue to have that, people are waking up to what is going on and realizing, my God, like don't think I want to keep going in this direction. I don't think I want to shift to that goalpost. So coming out of it and removing yourself and the definition of who you are from the group or the things that you believe or even your hobbies or even, you know, maybe even, even your religion. Like you can find a lot of peace in that and you can find a lot of purpose and a lot of impact, but just removing yourself so that you don't fall into this like quote unquote cult mentality of anything, any group.

and really saying okay, is this direction that I wanna go? And I think a lot of people are waking up to that, yeah.

Sean Patton (41:47)
Yeah, it's an interesting place. feel we're at where.

there has been, and I think because there are some of maybe the traditional, like if we went back to, like you mentioned, the boomer structure, like everything in society was so defined. And then we started questioning, like, wait a minute, we should have more options or like people think differently. And that's awesome. We celebrate all these things and we create all these different opportunities. And then you get the internet or, and then you, you know, it's if you go to a high school with like 500 people and there's

there's five social groups or something. Right. And now you're you get in the real world and everyone's connected. You know, you get in the real world and like, Oh, there's a thousand and you go to a big city and there's 10,000. And then you go on the internet and you're like, there is infinite. And so you sort of like make all these different connections. get so scattered that, um, I feel like there's this sense almost among the younger generations of just like, it's so much noise and like, and to your point, like there's, there's so many it's

it gets to a point where it's like unwieldy in your own psyche of like, wait a minute, what is my role? What is, what, what is right and wrong and how do I know what's right and wrong? And, um, and what, and what do I really believe? And I love the fact that you sound like the, it was almost this pendulum back to like, uh, almost looking at and rediscovering as an individual, um, and questioning like, okay,

Gabby Rosely (42:48)
Yes.

Sean Patton (43:03)
where do I want to put myself? And I think there's that natural desire. mentioned that mom and like the tribal social mentality of just like, we're, we're bias creatures. Like we're tribal. Like we need to find a tribe and, ⁓ that, that aligns with us. And so I think it's really interesting to see society, how there's this longing and, and hopefully people end up in great tribes and not like you mentioned, like not extremist cult tribes or we don't have.

you know, a YouTube algorithm or something driving people to like this hole in the dark web where all of a sudden there are some extreme thing just because they're like, no one's because we have this sort of relativism around things like morality.

Gabby Rosely (43:41)
Yeah. And I love that you're talking about like this oversaturation of options. like, mean, I know I can resonate with that when I was choosing a college major. It's like, no, you know, nobody was telling me what the hell to do. I can be an archeologist or I could be a marketing major, or I could be a, you know,

be anything. So it's like, my God, like, well, and then it boils down to now you got the internet. Now you don't even have to go to college. So now I can be a YouTube star if I want to, but what kind of YouTube star? my gosh, I could be a gourmet chef or I could, you've got so many freaking niches. Like you've got people who literally have miniature little things where they'll make videos where they pretend like they're cooking with these miniature tools. that's a niche. there's infinite amount of niches. And so yeah, it's overwhelming.

So I think before you do any of the scouting of what's out there for me, and this is the advice that I would give to Jen Alpha or even young Jen's ears, before you do any scouting of what's out there, you got to ask what's in here. what do I enjoy? Reflect on your experiences or even your childhood likes and dislikes. If you want to get down deeper into the roots of where your heart might be calling you.

⁓ Or you know presently but like what is it that you like? What is it that you dislike? When do you feel like you're on ten? How do you when do you feel like you're you know, the best one at this skill in the room? When do you feel like you're the worst one at this just it all starts within so when things get too loud, I think that intuitively we have the spirit that guides us back within

And when the pendulum, yeah, it swings too far and we've been listening to too much noise and too much out here and people telling us what to do, we have a voice that calls us back within. And yeah, I think that's the best place that you have to go when you're making these kinds of decisions. And it doesn't always mean you're gonna get the answer right away, but that's where you should start, in my opinion.

Sean Patton (45:27)
And it's a great way to end it, right? Start inside and what lights you up? Where does your, I think trust, know, trusting your intuition is something feels wrong or it feels right. trust and explore that. ⁓ and so, yeah, that internal trust with yourself before you start, giving that a top authority away or just, ⁓ to the rest of the world, because yeah, you get out there and it's, it's.

It'll knock you a thousand different ways because there's an infinite possibility. great, um, great advice as we sort of move into, the next evolution of a brave new world. Um, man, Gabby, this has been an awesome and just like we sat next to each other at that workshop, I feel like we could just do this for hours, but, I really appreciate your time today. And we're of course going to put some links and stuff like that, but

where, should people primarily go if they want to connect with, with Gabby.

Gabby Rosely (46:14)
Yeah, this has been wonderful. I feel so tapped into this moment. Like this is why I do podcasts because we get to chat about things that we're so passionate about and it's so clear and I love that so much. So it's, yeah, I'm really grateful. and for anybody who is looking to connect, I primarily use LinkedIn. I talk mostly about my work stuff there. share personal things on LinkedIn as well, but that would be my main form of social media. I do have videos of me speaking. If you guys have conferences coming up and you're looking for anything that has to do

with multi-generational communication, leadership across the different generations, emotional intelligence and leadership. I have some videos of me speaking on there on my YouTube, which is just my name, Gabby Rosely. And then of course my podcast, the Gabby Rosely Podcast. So yeah, come listen. I'm gonna be releasing some episodes pretty soon here for a new season. And ⁓ then for...

Email wise, Sean, I'll give you my email if you want to put that in the description so that you guys can reach out if you're interested in any type of program, workshop, retreat-based experience for your teams. I'd love to chat, so yeah, reach out.

Sean Patton (47:17)
Awesome, thanks so much guys, been great.

Gabby Rosely (47:18)
Yeah. Thanks, son.