Generational Dynamics: Seasoned Insights for Young Leaders

0:00My wife is like, I am absolutely dead. So we had John and Maria Asaroff over for dinner the night before you came into town when all that stuff started. So that started then. And then, as you know, we came home from the event after meeting with Damon. And then Kim, two of our friends, Kim and Pat, were here and we had dinner and then they were here the weekend. So we did, you know, all kinds of stuff, including brunch yesterday. And today, I'm just like, man, I feel like there's been no weekend. The weekend is gone for the last two weeks. And then I head out of town tomorrow, and you go into a bunch of stuff too.

0:37So it's like one more week of crazy, and then hopefully some form of a weekend.

0:47Hey, everybody. Welcome to another episode of Business Lunch with your host, Ryan Dice, and me, Roland Frazier. Ryan, crazy week last week. We are back from lots of cuddle time together, but it was busy. It's nice to be back. Did you did you get a day or two to recover over the weekend? Man, barely. Yeah. So we had those of you who missed some of the past episodes. We had two days of our founders board mastermind, two days of another like combo at the same not combo because that would be efficient. But simultaneous, Rise, Mastermind, and then Epic Board. So for people doing the business buying and selling.

1:29So it was four straight days of bananas, hanging out with client insanity. It was great. But man, yeah, I was tough. And then I got back. And of course, my children, who I love very, very much, just wanted all of me and my time and the space, which I missed them a ton. It really was great. But to say, did I get any time to just sit there and do nothing? No, no, it's been nuts. It's been nuts, but I'll take it. My wife is like, I am absolutely dead. So we had John and Maria Assaroff over for dinner the night before you came into town when all that stuff started. So that started then. And then, as you know, we came home from the event after meeting with Damon.

2:12And then Kim, two of our friends, Kim and Pat were here and we had dinner. and then they were here the weekend. So we did, you know, all kinds of stuff, including brunch yesterday. And today I'm just like, man, I feel like there's been no weekend. The weekend is gone for the last two weeks. I woke up this morning and I just told my wife. And you go into a bunch of stuff too. So it's like one more week of crazy and then hopefully some form of a weekend. Yeah, I feel like I lost a fight. You know, I like feel like sore and a little bit defeated, but it was all good stuff. all really really really good things um speaking of wisdom how you like that for transition i actually had i was like speaking of being like old and sore and defeated no i wanted to i i did have a chance to um to kind of catch up on on some reading and stuff like that and i there was a there was an interesting article in the harvard business review um that was entitled why wisdom work is the new knowledge work and it was actually written by um a gentleman named chip conley he who uh ran the, like had a big group of, of, you know, boutique hospitality businesses called Joie de Vie.

3:25I believe he sold out and did a whole bunch of consulting, you know, for Airbnb. But it's this idea. Do you remember that scene from Dumb and Dumber? When Jim Carrey's character is like asking the little lady on the cart to like watch his stuff for him and she agrees. And he's like, you you know what? Apparently, despite what everybody says, like, oh, people can still serve a purpose. That I felt like was basically the subject of this article. It's essentially saying that in a time, in an era where knowledge is infinitely available, right, especially when you think about AI, this concept of being a knowledge worker that was introduced by Peter Drucker is actually getting replaced.

4:07Like now being a knowledge worker, having access to the knowledge and being able to implement the knowledge, everybody has it. It's all readily available. And so everybody can be a knowledge worker, which is access to some basic tools. What's really in demand now is what they're calling wisdom workers. So people who have actual experience. And I just love this quote. I felt like it summed it all up. He said, according to Harris Interactive, 38 % of Americans reported to a younger boss, and the Department of Labor suggests the majority of Americans will have a younger boss in the near future. Physiologically, 60 may be the new 40, but when it comes to power in the modern workplace, 30 is the new 50.

4:51And so they're basically talking about how power has shifted away from tenured legacy employees who maybe they've got some wisdom, but they don't know how to use all the cool tools towards younger employees who knew all the new fancy tools. And now they're kind of suggesting a shift back. So there were some tactical recommendations that I'd love to get your take on, but just initial thoughts, feelings. Hey, Ryan Dice here, co-host of Business Lunch. And before we get to the show, I have an exciting invitation for you. My business partner and Business Lunch co-host, Roland Frazier, and I are hosting a live in-person event and if you're a bootstrap business owner who wants to build a 10 million and even 100 million dollar business in the next three years you need to be there this event is called get scalable live and over the last four years it has transformed from a small gathering of entrepreneurs into the largest bootstrapped entrepreneurship conference in north america now i know what you might be thinking you're probably thinking ryan really another business event?

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7:41That's all I got. I'll see you in Austin. All right, back to your regularly scheduled programming. So the reason that they're saying that, is it just, it's because of the tech, basically, just because of things that are coming along that maybe folks who are older aren't aware of? So the shift towards tech and all these tools are what were, what rendered a lot of, you know, older, more experienced workers at a disadvantage. But what they're realizing now is that all of this tech, while valuable, absent actual wisdom and experience, isn't always deployed properly. And so organizations are starting to realize that, hey, maybe we do need some of those old people back.

8:23Maybe we can't just knowledge work our way through this. We need actual wisdom around. So the pendulum in some organizations is shifting back to where some companies wait for it or even hiring people over 50. Gross, right? Can you imagine? Goodness. You know, so I had, I have the benefit of, uh, and I think you, you probably experienced this too. I had the benefit of growing up, um, always being the youngest guy, uh, in a bunch of older people. Cause I was always, you know, when I was selling real estate and securities and all of those things. And when I opened the law firm, you know, it's like, we ended up partnering with, we would look for what you call gray hairs, which I still, I saw that term used a couple of times and some recent content that I was consuming, that it's good to bring those in.

9:12Usually that's done in reference to so you can have credibility because you're too young to be taken seriously. I think that depending on the market, like I think it's industry specific because if you're in AI and SaaS, then the oldest I've ever felt in my life was sitting on the top of Facebook headquarters in the nine acre park with the grilled cheese stands on top of a building. where they planted an entire park with the 23 year old who had sold his third company to Facebook and was bored because he had been there for 16 months and wanted to get away. I mean, that I was like, I'm a loser, you know?

9:48So, so I think, but you know, he had started when he was pre, pre-born. But the, the thing is, is I think that now it's, you want the gray hairs, not just for the appeal to other people, but you actually value them in your business. And I think even before, like when we ended up partnering with a person that was maybe 20 years older than me and my business partner in the law firm, we were just straight out of law school. So I think that puts us about 26 years old. And we're going for big accounts and things like that. Now, that person did bring a lot of experience that was helpful too. And so I think it's just the same old thing, that it makes sense.

10:31The studies have shown that having a diverse age spread and a diverse group of ethnicities and gender identities in your business is pretty much always going to result in a better company. and so that these people who are significantly younger realize that, hey, we don't have all the experience that we need and the business maturity and maybe the networks that have been developed. So let's bring that in and get and take advantage of it. The difference, I guess, would be saying that it's going to be more that that those people are in charge. But I mean, we were in charge when we were doing it back then.

11:07So I think it's interesting and I think it's true in terms of it's valuable, but do I think it's like a revolutionary shift, like, you know, like the great resignation was or something like that? Probably not. What do you think? It seems to be a somewhat revolutionary shift, at least this article would suggest it, at a lot of, call it Silicon Valley type companies, like a lot of companies that really value tech and they really value, you know, that level of understanding. It's a bit of a rediscovery. And that's why I say, I think it's a pendulum shift back because same, like when I grew up, I mean, and granted, I only had a real job for, you know, about six to eight months, but I almost instantly sought out mentorship of people who had been there longer.

11:49And not only did I seek it out, but it was readily offered, sort of baked into the culture at the company. And I don't think you see that anymore. I think what you have seen is it's this notion of like the okay boomer concept, like, okay, boomer, I don't need to listen to you. Okay. What do you know. You don't even know absolutely. It's a re-respect for the knowledge and experience is what you're saying. It's a re-respect for the knowledge. Yeah. Because again, now what they're realizing is, oh my God. And I think where it's happening is it's happening with the 30-year-olds because the 30-year-olds are realizing, holy crap, these 20-somethings are just as smart as I am because they got access to the same tools, but I don't have that much more experience.

12:26And so if you're sub 30, some of these recommendations, I think, can provide a really good path for you to get the experience that you need and maybe to seek out. If you're operating within a company as an entry-level team member, if you're over 50, I think that this is going to provide a possible path, a second mountain for you to climb within your same organization or even others. And if you're in that middle, certainly if you're in some type of leadership capacity, certainly if it's your company, looking to implement some of these might make a lot of sense. So there were a number of recommendations.

12:57There's three that I kind of plucked out and highlighted that I'd love to get your take on. The first was encouraging legacy leaders to act as internal coaches. So essentially getting your legacy leaders to take off some of the day-to-day work and beginning to have them go through a coach training program. And you know, there's a billion of these that are out there, But it's, hey, we would love for you to expand your role to include coaching up and even mentoring some of our up and comers and creating an expanded role, if you will, on that and getting them some of the additional training. I know that's nothing that we've ever really done, not in a formalized way.

13:40Have you ever seen that done where when you reach a certain point, you actually got cross-trained in coaching, consulting type deal? Have you seen or heard of that? I haven't, but I'm in a weird spot. I mean, like I'm not in that world much. So I don't know. And in our world, I feel like we already cross every, you know, like we don't, we're all interested in improving ourselves. So we're all in programs like that and teaching programs like that. And that's our entire business. So, so I think it makes sense. So I have to, it's hard for me to get out of that. Also, it's, it's like, if you keep up with things, then you still, you know, you're still plugged into everything.

14:27And I feel like we're all very much on the front edge of keeping up with things. So, well, I think if this is less about maybe the owner, like think about some of our other holding groups, you know, you think about like prime or something like that. I mean, they've got, they've got younger leaders, then they've got, you know, more experience and they've got some older ones. Right. So is there that formal coaching? So I thought that was interesting. And the, the idea of the way we do it, like, like I am, uh, you know, I am no longer the youngest person in all the companies I'm in. Uh, so in that one, in particular, uh, since you mentioned it, like I, I have a regular meeting that's scheduled with several different different executives that's just one-on-one basically for coaching, you know?

15:06So it's basically, let me add what value I can tell me what you're working on. How can I help? So, and that's a, that is a formal scheduled meeting, even though it's not a formal program. So, so yeah, I guess we do have that. Yeah. So there you go. That was kind of the first suggestion. The second one, which is, it seems obvious in retrospect, but, but when it comes to process documentation, so obviously something that we're pretty big on at the scalable company, Typically, the way that process documentation happens is the person who's uniquely accountable, responsible to it, they build the process.

15:38This recommendation was when you're doing process documentation, make it intergenerational. So get somebody who is like the youngest person on the team and get the maybe the most tenured person on the team, let's say, to also be involved in the process documentation because younger people are going to suggest ways to optimize it using tools that maybe older folks might not. And older folks are going to suggest certain recommendations that others aren't. So I know a lot of times documentation just is who does it? Cool. You document it. this idea of who does it cool when you do like a field test on this, when you're looking to optimize it, ask a younger person, Hey, what tools do you know about that could make this even better?

16:22And ask somebody who's more senior, what did I miss? Like, what, what are some pieces? So I thought, again, just being intentional about putting that in the process documentation phase. Any thoughts there? Yeah, I like it. No, I mean, that sounds, that sounds great. I like it. But I think the hardest part about that would be, hey, you're old, so we want you to do this thing. I think figuring out how to message that in a way where somebody isn't necessarily, you know, maybe you're the most tenured person on this team with the most experience. We'd love to have you involved in this project. I feel like it's easy if you just say, look, hey, we're looking for some extra perspectives on this.

16:58And I think you would be I think you'd be able to add a lot. Would you mind helping us out by taking a look and seeing how you might improve it or if you think there's anything missing or lacking? I think it's like if you're just asking for help generally instead of saying, because you are old, female, a minority, those are less good frames to put that in than we think that we value your opinion and would love for you to have a look at it and see what you think. But I do think that that's an interesting one. Because I think that when we're doing processes, you do have the person who's doing it, document it.

17:40And then you have the managers who are usually older than the person who's doing it to review that. Although if the managers were younger, they would be younger people reviewing it. So how would they get an older perspective? And would that perspective add anything to it? you know, would it be, you know, back in my day, we used to, or would it be, you know, and there's going to be a ton of that, right? That you move to paper and pen accounting systems, you know, a less good, a less good thing. It's interesting, but I guess it's, it's just different. I agree. I mean, so even on the other thing I was saying, I didn't mean to be critical of it.

18:21I just, I feel like in our companies, and we are certainly far from perfect, that the age thing is much less of an issue because we work with people from certainly 20s to 60s, if not more. And certainly then when you add in the clients that we work with in portfolio companies, because there are a lot of people who are at exit stage, they might be older as well. So we're getting a pretty broad swath of those things all mixed together. But that said, I think that makes us way better. I think that's one of the reasons we are able to be successful and happy and have good cultures and all of that stuff.

19:03And if that is not the case in a company, then it could definitely benefit from it. Yeah. I mean, I know for me, when I started my first business in my early 20s, I benefited mightily from seeking the advice of people who had been there, done that. I'm not always sure. But I guess that's the point. Like, it sounds so obvious to us. But let's be honest, dude, like I'm now, you know, I'm a lot closer to 60 than I am to 20. Right. And, you know, you may or may not be on the other side of 60. I'll let 40, you know. Yeah. So I think it's one of those things that's more obvious for us than it might be for some of our younger listeners, if you will.

19:44The third suggestion. This one is is really interesting. And again, I think a lot of these if your company is really, really, you know, if you're less than 10 people, this probably doesn't apply to you. This is as you're beginning to scale up and you're bringing on more folks in your organization. he recommended developing a mentorship program. And a mentorship, it's a combination of internship. Working with other men? I don't think that's it. No, it's mentor and intern. But it's a mentorship program because essentially what you would do is you would put together intergenerational team members.

20:22So you'd put together somebody in their 50s, somebody in their 20s, and they would essentially flip off who's the mentor and who's the intern. so like this week i want to learn everything from you and and and i put on my my mentor hat and next week we're gonna we're gonna flip roles and we're gonna do this for you know for a season you know switching off who's the intern and and who's the mentor kind of giving permission for you know for the old guys to you know like dispense wisdom to the young guys without sounding like some dude telling kids to get off their lawn. Back in my day, we'd walk uphill both ways in the snow to get to school and eat our shoes for lunch kind of thing.

21:03It's like, no, no, this is my job. But also, because I know that, wow, I know, right? I mean, I did until I ate them. I got it for one day and then lunch happened. It's like, well, damn it. I think it's almost more important to give the frame for the younger people to give advice and suggestions to more tenured senior people. Because what's unique about you? You said you're like, I never stop learning. I'm always trying to figure new stuff out. When the AI stuff happened, you were the first in it. You were in it earlier and deeper than anybody else on our team earlier than me and certainly earlier than any of our team members who are much, much, much younger.

21:47You were driving that initiative. I don't know that that's typical of everybody who's been in business for, you know, multiple decades, right? I think that you're a bit rarer in that, especially when you get into organizations and people are more, a bit more corporate. I learn regularly from people who are 30 years younger than me because that's on my team. I have my son, one of his friends, and other folks like that. And so I am learning from them. And they bring stuff. And the environment that we've got is really, it's basically, we're not equals. We're equals in learning and we're equals in getting things done, but I'm going to prioritize because I am the, you know, the manager, basically.

22:40So I think we kind of have that, like that, you know, the formalization of something like that sounds, you know, I have to get past my initial bias of, you know, that sounds like a writer trying to coin a phrase and get to like, what would a formal program look like? And I think about, you know, with me, I could formalize that and say, you know, hey, teach me, you know, in our weekly stand up or something like that, you know, teach me something this week that that I don't know about AI or about, you know, about anything or whatever, you know. And then I go back and say, here's some cool stuff that I've learned this week as well.

23:24So I think that formalizing that exchange of information is definitely healthy. How would you go about that? Let's say that your task today was create a mentorship program in Scalable. What would you do? I think it's got to be opt-in. Well, and Scalable specifically, I think Scalable may be too, you know, Scalable as a company, you know this, but for context for our listeners, it's only about three years old. Like, so Scalable is a baby. Yeah. So at DM, because I do think there needs to be some time there and also some size, right, for there to be enough people. the way that I would roll this out is I would I would I would share this concept and I'd say I think that that there's a lot of knowledge to be gained cross-generationally I think the younger folks have a lot to learn from the more senior members of the team and and vice versa and and sometimes that communication doesn't flow at all and sometimes it only flows one direction which is the, the, cause the classic mentor mentee relationship is, you know, old guy, young guy, you know, or gender, you know, non-specific, you get what I'm saying?

24:41Saying we want really the learning to go across the board. And so we're going to have this, we're going to be doing a program. It's fully opt-in. You don't have to participate in it, but here's how it's going to work. We're going to pair up two folks who want to participate and you just switch off. And basically it's like meet, grab coffee, grab lunch. And it's just share the issues and challenges that you're dealing with and seek out advice from the person who's acting as the mentor that week. And you're going to, you're going to rotate. You're going to flip it off. I think it's got to be opt-in.

25:09I think you try to force it. It's not going to do well. And I would look to pilot it with people who I knew were interested about doing this kind of thing, who I knew were open-minded before I rolled it out to the company as a whole. So I'd try to find two people, older person, younger person. And again, could be male, female. I don't think it matters. But try to find two people, run it as a little pilot, see what they liked. And if it works, say, we're not going to roll this out across the company. And if you want to participate in this, you can throw your name in the hat and we'll look to pair people up based on that.

25:42That's probably how I would look to do it. Okay. I like it. I like it. Very cool. And so did they have any other pointers or thoughts or comments or anything? I think the big thing is we're about to see there's been a lot of laughs. You know, the government can say all day long that the economy is, you know, is super strong and that, you know, the unemployment rate is high. I don't know if you've seen, they keep downgrading it. Every time they do a look back, they're like, oh, we added all these jobs. And then they do a look back 30 days later and like, just screw him with you. We didn't. They just had to do a 30 % downgrade of the new, of the jobs report.

26:18Like, so like we had all these jobs. No, we didn't. So there's a lot of people who are sitting on the sidelines and a lot of people have got my, my neighbor just took, he's in his late fifties, maybe early sixties, just was one of the 18 ,000 people who took an early retirement package from Intel, you know, and you're talking about somebody who has tremendous amounts of wisdom and he doesn't need to work. Like he's good. Like he's, he's saved well and has done well in his career. He doesn't need to work, but he wants to work. And I think that there's a lot of companies right now. We talk about picking up talent on the sidelines.

26:57I think there's a tremendous amount of talent to be had in people who are more tenured, who are over 50, who while hiring managers can say all day long that they don't discriminate based on age, race, things like that. I do think that ageism, more than anything, more than even race and sexual orientation and gender, I think that ageism is one that still more times than not feels like it's almost accepted. It's just, oh, we need to get some youth in here. It's almost accepted that you're not going to hire the more tenured person. My hope is that this article and this discussion makes people look a little bit more at some of those folks who do have a bit more wisdom in adding them to the organization.

27:38Yeah, I mean, it's in other cultures, they respect it a lot more. I don't know if that's, you know, changed in Japan, for example, or China, but, you know, it's there's something to learn from everybody and certainly experiences. the experience, the version of me, and I bet the version of you that there are right now versus the version of us 20 years ago, you just know so much more. Hopefully you're always improving and learning and you're not just frozen in time. But if you are, then bringing those people in and just even the networks they've got, if they've been around for longer, they're going to know people you don't know.