005: Jabez LeBret - 4 Keys to Working with Millennials
28 Jan 2026 · 25 min
Podcast episode (Beer 30) in which host Bill Gallagher interviews Jabez LeBret about managing and engaging millennial employees. After brief sponsor/promotional segments, they review generational context (differences between baby boomers, Gen X, and millennials) and present four core tactics for working with millennials: bake purpose into work (organization + individual role), emphasize team dynamics and clarify each person’s impact on the team, provide structured mechanisms for opinions/voice (teams, suggestion systems), and give frequent, regular reinforcement/feedback. The conversation includes practical examples (agency marketing for law firms, team exercises, suggestion/ENPS tools), references to related resources (Good to Great, Jabez’s LinkedIn), and closing sponsor promotion for Align/Scoreboard and Doxatalent.
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All right, welcome, welcome. Jabez Lebret. We're talking today to Jabez labrett. He's entrepreneur, speaker, all around groovy guy. We're going to talk today about working with millennials. All the secrets he's going to share. Four core ideas about doing a better job working with millennials. I think you'll be surprised. They actually make a difference for working with everyone, but they really make a difference in those of us. I don't know how many of you struggle with this, but I hear this a lot from many clients about the challenges of working with Millennial millennials and their team.
So.
Hi, Jabez, welcome.
Hi, Bill. Thanks for having me. Yeah, you know, I'm excited. What I love about this topic is there really are like a couple of core fundamentals that when you get those down, it just fundamentally changes the whole environment, the effectiveness of your millennial employees. I think you're right. I think a lot of these things are good for any employee. But oh, my goodness, you know, some of the tactics that we're going to talk about today are so impactful for just helping that millennial employee really just be more effective, go to the next level and actually produce, be more loyal. I mean, you name it, everything.
So you're a millennial?
I am.
And I'm a baby boomer. And we managed to be able to share a beer.
I think we literally just gave away that we actually are drinking a beer right now.
We are having a beer today.
It's the end of the day. Here we go.
We've done a couple podcasts today, so this is one of a series. It's beer 30 here. So how'd you get into this? Why is this a focus area for you? I mean, as a millennial, how did you get called on to share about this.
It really was on accident. I've done a lot of presentations at corporations and I own a company. All of my employees are Millennials. I was doing a lot of management and presentation training and leadership work at companies, as well as kind of on the side. And I kept getting asked, like, how do I manage you? Like, people wanted to know, like, how do I, how do I help manage your generation? And so I kept getting asked and asked and I was like, finally I was like, you know what?
That's it.
I'm just going to create an entire program around a presentation around how to manage Millennials and take some of the lessons we learned from our own agency and experience and really break it down into, you know, what are some actual fundamental steps and foundational pieces that you need to put into place to take advantage of the Millennial that you have on staff. And it always started with education. What are the other generations? I think that sometimes people forget that you have to know where all the other generations fit into the whole puzzle before you can really, I think, tackle this new generation.
You know, a generation is a funny thing. So I'm a baby boomer. A lot's been written and said about baby boomers over the age, but baby boomer span, each generation typically is articulated as expressed as a 20 year period. Right. So 46 to 64 is the, is the boomer span. So I'm 64 baby. Right. My wife says 63, but we're barely there. And yet I certainly identify more as a boomer than a Gen Xer.
Yeah. So you're kind of a cusper. I would say I'm a cusper as well. I'm on the older end of the millennial spectrum, but I associate with millennials. A lot of my cousins were a few years younger. A lot of my friends growing up were a few years younger. So I really, really connect with that side of my half. I guess it's kind of one of those things where you can straddle and obviously not everybody's going to fit the entire generational stereotypes, but that doesn't mean there's not some useful information there. You know, I look at, I look at baby boomers. You know, baby boomers really came about when post World War II, the, you know, everybody came back, the economy was starting to do well, things were picking back up and they started making a lot of babies. Literally making babies, a ton of them. Huge generation. And, you know, your generation grew up with Vietnam War. Your parents grew up during World War I and World War II and the.
Pressure tested the war. I saw the moon landing. Yeah, those were my grandparents went through the Depression.
Yeah, you had the Cold War, you know, was a big part of your generation. And technology advances were a major part. The computer, you know, those things becoming, you know, a television in everybody's home, you know, wasn't necessarily what was going on in the 40s and 30s. And baby boomers really grew up with a different kind of technology around than their parents, the silent generation, you know, and they had baby boomers, had Gen Xers. They were the parents of Gen X, right. And the baby boomers went into workplace hard. A lot of females started entering the workplace. And we ended up with the latchkey generation, which is Gen X, you know, and the Gen X, they saw the fall of the Berlin Wall, you know, they were also. I mean, that was a big part of the Cold War. Kind of ending, if you will, was a big piece, you know, and they saw the Internet become prolific in people's lives, and that had a role in just the way that they perceived availability. Excuse me, the information. And so the Gen Xers were the discovery generation, right? They're the searchers. They were all about the journey. And you would hear, like, the Gen Xer talk about, like, it's not getting to the top of the mountain, it's the climb, you know, and those were the kind of the inspirational posters that.
Were coming out at the time, you.
Know, were all about the journey and discovering yourself and being at peace with yourself. And they fit in very comfortably with the baby boomer work environment. So the baby boomer manager had no problem managing the Gen Xer, because the Gen Xer was about, what do I need to do to make this a part of the journey? But then the Millennial came around. So for the listener that doesn't know, Gen Y and the Millennial is the same thing. It's just two different words for the same generation. And the Millennial generation saw the advent of search on the Internet. Didn't exist before the millennial was a kid. And so they grew up with Google. They learned to type on a computer at school, not a typewriter. Cell phones were prevalent everywhere. Social media. Millennials literally created social media. They actually invented it as a way to further connect with each other and strengthen that tribe or that team to become a collective whole. And that plays a role. Here's the deal.
So my first experience were with two kinds of computers. There are these very homebrew kinds of hobby computers that I played with and built digital circuits and did Things and then there were mainframes that I had periodic access to. And then if I had a terminal later on, I had acoustic couplers and things like that and early dial. We talked about 300 baud and stuff. And I remember distinctly as things started to increase and then I had an ISDN line at home in my home office. And I just thought that was.
I don't even know what that is. Right? So like you had floppy floppies, like.
For real eight inch and five and a quarter. I didn't even know they came in eight inch.
Right.
So it's like a whole other joke right there. We should have another beer. So each of those things and then if my kids and I have a 19 year old, 16 year old right now, start complaining about the bandwidth at home, right? Just I'm like, are you kidding me?
It's like this page is taking longer than 2 milliseconds.
You're whining about how your wireless connection can't stop stream high res video. You're out of your mind.
That's ridiculous. It should be able to, but that's the whole point. And so the technological advances play a role in the millennial in the workplace. Also the fact that we had helicopter parents. So where the latchkey generation, both parents were at work, the kids came home by themselves, they were really taking care of themselves. Millennials had parents that were hyper involved, taking them to all the sports, involving them in all the organizations, making sure that they were participating in all of the team environments that they could possibly participate in, and letting them share their opinion constantly. And I think those were educational moments. I think back, like when I was a kid, I was eight, nine years old, and my parents were looking to move to a new house and they asked my opinion about where we should move. Now, they weren't really going to decide where we should or shouldn't move based off of a nine year old's opinion. Like, I want this house.
Are you sure?
Well, God, I hope not. But I think that was like a learning moment, right? They were there trying to teach me and saying, here's things you have to think about. How good are the schools? How good is the neighborhood? And so in that process, I grew up thinking my opinion mattered. It doesn't mean that it had to be followed, but it means that I have to be able to share it. And so you start to like move forward. The trophy generation, you know, people refer to millennials a lot as the trophy generation. We got a trophy for everything, just for showing up.
Well, you maybe have heard you mentioned helicopter parents. You probably also heard the term teacup kids who are over sensitized to interference, criticism, feedback and that kind of thing. That's the more extreme example of that.
Yeah. And, you know, it kind of stems from the, you know, all that matters is participation. And if all that matters is participation and you get an award for participating, then criticism isn't as welcome because it's not about winning. And you know, I think that, that it's not that millennials don't want to win, it's that their perspective of training as they grew up. I mean, I always like to point out, I was like, you know, we weren't the one buying the trophies, right? Like, we just showed up to play little league baseball. The parents were the ones that actually bought the trophies.
Everybody just needs to see that old movie, the Legend of Ricky Bobby. Right?
Exactly, exactly.
Winning is everything.
If you're not first, you're last. And so you start now, you know, you fast forward. So then let's start to talk about, like actual, you know, you're in the workplace. You got these millennials that are in the workplace, and we are a little bit of a different generation. And you and I were talking about this earlier and you brought up a really good point. I think that something that is crucial to note is that we're a purpose driven generation. We actually really, really care. And purpose is a very key component to how we just want to function and live our lives and the decisions that we make.
Nice. All right, so you've got four main ideas. Nice.
Purpose.
Get it out of here. All right, let's get, let's get to this. That's very Boomer of you.
Purpose.
Yeah, yeah, yeah, that's nice. I donate to charity. Let's get this.
I, I think, let's get this moving.
Purpose. We were saying that these things apply to everyone. And I think a lot of times as, as coaches, Gazelle's coaches, applying the principles, the Rockefeller habits and scaling up with people, we go right away, purpose is core to strategy. People are like, oh, just tell me what to do. No, if you don't know your purpose and your values, you can't go from there. And you're saying actually purpose matters to engaging the millennial in the work they do.
I think you need to bake it into the process. So step number one, if we were going to go through just some steps you should be doing as a leader and a manager, step number one is to bake into the process, the purpose of everything. So it's Two sides. It's the purpose of the overall organization or department as a whole. And. And it's also the individual's purpose with their contribution. And so, you know. So our company does marketing for law firms. Not the sexiest marketing agency job.
No, no.
Law firms aren't exactly cutting edge on their marketing, believe it or not. That could be a shocker.
Computer games, more.
Yep. Virtual reality's next.
Alcohol.
They do like the alcohol. Unfortunately, they. When it comes to the marketing side of the fence, we have to help our employees understand that helping a law firm. So if we have a client that we believe in, that's a good client, they could be working with businesses, they could be working with individuals that have been hurt in a car crash. They could be working with real estate transactions, whatever kind of law they practice, that person. When they need a lawyer, they need a lawyer for a very important reason, because that lawyer helps them accomplish or bridge a gap that they can't do on their own. And that if we don't help our clients get discovered, then we're missing an opportunity to help this individual that genuinely needs help. And so the purpose isn't to get. Have a successful campaign for our clients. The purpose is to help our clients. Clients. Yeah. And that's building more. A deeper level of purpose into what we do. And it matters. It makes a huge difference to millennials. And I think you're right. It does to any generation. We all like to feel like we have purpose.
I was talking to a lawyer earlier today, and a lawyer converted to a coach now who mixes his lawyering with his coaching. And he's known as a shark. He's got shark motifs all over his office. And I think it started with his dad or someone who blessed him with this thing. And a lot of people think of lawyers, sharks, and far less flattering things. And yet when you're in a bind, you want your own shark. Oh, yeah, right.
Oh, lawyers are easy to make fun of until you need one.
You've got an HR issue, I need an HR shark. You've got a liability issue, I need an hr. You got somebody defending something. You got somebody ripping you off. Oh, I need a shark for that. So we all need our own thing in that. And yet we do like to. My train's coming.
All right, we're out of here, folks. Train's here. We're off to Hogwarts.
I think you're right. Discovery of something and then identifying with that, like. No, we all play a role.
Yeah, absolutely. And then breaking it down into the individual Level. So what is the purpose of their, like, what they do to the overall team and to the success of the team. And I think that leads into really, the second component of leading Millennials and making them more effective is to understand their interaction with team versus individual. And so, you know, millennials grew up being on teams, regularly on teams, participating in teams, team school projects, team sports, team everything. And it is crucially important. Loyalty is something that people often say that millennials are not loyal. And the deal isn't that millennials aren't loyal. The issue is that management and leadership hasn't given them all of the reasons to be loyal. I mean, our parents got laid off. Baby boomers kind of grew up in an environment, especially the baby boomers parents, where when you got a job at a company, that company was loyal to you and you were loyal to that company. Well, guess what's not happening anymore. Our parents, the companies were not loyal to them.
Yeah.
And so when layoffs were happening and people were losing their jobs in employment at will, it became apparent that if a company is not going to be loyal to us, why should we be overly loyal to the company? And so that's just kind of a reality of the world that we live in today. So how do we, how do we circumvent that? As managers, One of the ways to do it is to help them understand the impact they have on the team as a whole. So what's their contribution to the team? What is their. When they do something, if they do something wrong, how does that impact the team? When they do something right, how does that impact the team? And bringing it to the team, to the team, to the team, to the team come out like a broken record. You know, when I played baseball growing up, I remember in high school the coach that we were not allowed to hit pop flies. And at first that sounds kind of crazy, but the like mechanics of it is, in baseball, the only way to hit a pop fly is to drop your back shoulder. So, like, there's a mechanical reason that you end up hitting a pop fly. And in practice, we just weren't allowed to do it. Well, if you did hit a pop fly, what do you think happened? You didn't run. The entire team ran. So you would stand on home plate and coach would make the whole entire rest of the team run a lap.
So they reinforce your relationship to the team. You're playing by the rules of the team. And if there is a victory to be felt, it was given to the team, not to you personally.
Correct. Which is incredibly Important to start to build that dynamic into the, into the environment, into the work environment. You know, I think another thing that often gets missed is the concept of, you know, the fact that millennials feel like they've got answers. So we kind of grew up with the idea that experience isn't really what drives things that we can get. We have Google, it can give me an answer in milliseconds. And so I think that what's important to understand as a leader and a manager is that we have to build mechanisms in place that allow millennials the freedom to share their opinions and to feel like they're contributing to a greater good. Because, you know, if they don't feel like they're contributing to the overall process, they're going to be a little bit disenfranchised.
Yeah, yeah, yeah, get it.
So you build that into the process. Ask them their opinion again, you don't have to do it. So asking them to share their opinion and a process, sometimes we'll put them on teams to go discover their ide of how to solve a problem to come back to you with some solutions. And you may or may not use those solutions, but you're involving them in that process and that's building their team dynamic, but it's also letting them share their opinion.
Yeah, we have a kind of a electronic version of the old fashioned suggestion box on our Align software now. And we also have an implementation of the E or the employee Net Promoter system, the enps. We have both those things baked into our management software now, which is crucial.
And that's fantastic because that's really the component to help them reinforce that team mentality in the workplace. And then lastly, it's about the phrase, did you ever hear no news is good news?
Oh, yeah, all the time. And keep your head down and avoid the scrutiny, especially if you're not the leader of something. Right. Don't look at me. Oh, shit, he's angry today. I'm going to just go over here.
Yeah. Which is for a baby boomer or even a Gen Xer, no news is good news. Meant if I get assigned a project and I'm working well and I'm moving forward, if I don't hear anything, then that means that I'm doing well and I'm almost there. You're cool and I'm good. I'm good. And then I get to the end and I get the praise. Congratulations, you've completed this project. To a Millennial, no news is the worst news. And this is a forgotten thing because we're used to as managers and leaders, applying the methodologies that worked for us to the generations below us. And it's kind of our job as leaders and managers to pivot and grow and to learn and adapt and be nimble in how we communicate, how we lead, how we manage, because they don't have the experience. The millennial doesn't have the experience that we do. And so we have to be able to harness our experience and. And be willing to change. And one of those mechanisms is to build in more constant reinforcement. I mean, regular constant. I see you going in the right direction. I give you a task, you've got a goal to complete, and then I say along the way, good job. I see you're working hard. Good job. I see you're heading the right direction. Hey, I appreciated you finished. That little tiny step in the long journey of where you're going. And that constant reinforcement there goes so far with your Millennial employee as far as getting them engaged and making them feel wanted.
I got it. So where you might think you could just let that go in other cases. So let's recap the four concepts. Right. So the first one is purpose. Purpose.
Got a bacon. Purpose.
Bacon.
Purpose.
Purpose to the organization, purpose of the team, Purpose to the role.
Correct.
I know my purpose. I know your purpose. I know how they connect.
Yep. So next, get to the why. I mean, those sorts of things. Start with why. You got to really get into that.
And that's at the core of our work in Gazelles and was helping companies to scale up.
Yeah. Second is team understanding the crucial importance of team dynamic to a millennial recognizing.
Their role, their relationship to the team.
They thrive on teams. And if they disappoint the team, that's a bigger issue than them disappointing themselves.
Yeah. Or maybe the boss.
Correct. Absolutely.
To each other versus the team.
Yep. And so sometimes, you know, as a boss, you want to be like, you let me down. That's not the right response for a millennial, actually.
You know, when you talk to Navy seals and we've interviewed them and spent time working with them as entrepreneurs, you see that they'll get people to do more for the team than they even care about. You know, the politics or the policies involved.
Great.
They'll fight for each other.
Perfect example. Perfect example. And then the third one that really kind of starts to tie it all together is building in a mechanism for opinion and helping them express that they.
Are giving them a voice. Giving them a voice, not having them feel junior.
And if you don't want to hear it if you're too busy, put them on a team and have that team hash it out. Have that team work the solutions, have the team boil down a couple of talking points to bring back to you.
Right.
I think that's fundamental.
Right.
There's a lot of times that you're like, oh, that's a really good idea, but I just can't deal with anything more. And with the feedback loop, as with other things, you don't have to do it all. You can bake it into the structure of the organization, the way you operate your culture like that.
Absolutely. And then last but not least, constant regular reinforcement that they're heading in the right direction. That doesn't mean you can't. Course correct. You can. It just means you have to also regularly acknowledge that they're moving in the right direction. And I hate it when people are like, well, shouldn't they be going in the right direction? Yes, they should be. Of course they should be. And that's what you want them to do. And they are doing it. All I'm saying is acknowledge. It doesn't cost you anything. It is free, it's great.
And it goes right along with both the classic management lessons of Ken Blanchard and the One Minute Manager. To praise publicly and give them feedback, but also to everything that we teach when we're developing people in their coaching skills, that people need acknowledgement, especially when they're dealing with something new, something challenging. Acknowledge everything all the time. Acknowledge every step, acknowledge all the progress. If you just keep people in the game by acknowledging them along the way, give them some positive strokes instead of keeping it silent or being worried about over inflating them. You keep people in the game and they will eventually find a way to win at things.
And if you want rockstars, that's how you're going to create them.
Yeah, it's really powerful. Well, this is really great. Four core ideas to work with Millennials and to boost your thing. Easy to pull away anything you want to point to as resources or like that going forward.
I mean, I write and talk about this stuff a lot, so, you know, connect with me on LinkedIn is usually the best place for me. I mean, I'm on all of the socials, but it's just Jabez Labret, J A B E Z L E B R E T and we'll get that in the show. Not the most common name on the block, so I find it gets misspelled a fair amount of times. And then it's really just kind of, I think, finding some of the people out there that are good to follow. I mean one that really jumps out to me right off the top is Chelsea Krost. K R O S T. She's amazing. She's a little younger than I am. Brings a really good perspective on millennials and managing millennials in the workplace and then certainly getting back to some of those fundamental Good to Great. I mean those books are still relevant, especially for this younger generation.
Had a challenging client recently and I reread Good to Great just because we had some deep work to do with the whole thing always fundamental there. And it's amazing. I mean that doesn't just apply to millennials, but it underscores certain things are maybe really critical in engaging that, especially if you've got across. Every generation has complained about the generation that came after it, and this one is no different. And there are some things that matter more than others. So thinking about those things, being thoughtful and engaging those folks is a great opportunity.
Fantastic.
Thanks so much for spending some time. Thanks for having me coming into our office, visiting with us.
Beer 30 I will come in and.
Sharing a beer in the process. It's been great. Hope you all like it. We'll throw the links and information in the show notes and as always and we'll share it back with you.
Sounds great. Thanks for having me.
Thanks.
Foreign.
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