Multiple Generations in Workplace, with Lisa Ryan

Listen to this Business Results Radio episode with Lisa Ryan, Certified Speaking Professional & CEO of Grategy.

Everyone, Pete Winiarski here, welcome to Business Results Radio. Today, I am here talking with Lisa Ryan. I am excited, Lisa because you and I — we’ve played together a little bit, we’ve shared stages together, we’ve done podcasts episodes together, and you’re a fun person who happens to know a whole lot of important topics. So, welcome back. 

Well, thank you. 

Today we’re getting into generations and what’s interesting, we were just having a short chat before we turn the button on here to record. This phenomenon where there’s the four generations in the workforce at any one point in time. Now you’ve got — there’s still some baby boomers out there who are working, there’s Gen Xers like me. Then there’s the Millennials, which are the Y’s and then the Z’s, which are the new ones those are what my kids are, and they’re working. So somebody has to manage my 18-year-old and 16 year old, and how do you do that? That’s really the big question. 

In some of the research that we’ve been doing, in terms of the biggest challenges business leaders find today, and that they have to deal with, one of those is the generational dynamics and it’s gotten to a point where it’s risen right up there with machine learning and artificial intelligence. It’s side by side in terms of how I figure this out as a business leader. That’s what today’s conversation is, Lisa is going to crack the code for us.

Or at least give you some ideas as far as things you can do.

That’s exactly what we want. You as a business leader out there, go ahead and take some notes on this one because you definitely have to interact with people in the different generations. You may have figured out that not everybody is the same so let’s start with that premise. That’s actually a good thing. Would you say, Lisa, do we want everyone kind of robots walking around our job places or our communities exactly the same?

Absolutely not, and even though there are four active generations in the workplace and the programs that I do on this, I do like to start with traditionalists. I know there’s very few traditionalists still left in the workforce because they were born before 1945 but when it comes to setting that foundation because this was a generation that they had one job their entire life. They made that commitment. There was this lifetime employment that they just assumed that they would have so they didn’t expect things like being recognized or applauded or appreciated for their efforts because they were going to work to support their family. 

And so, you had a very traditional upbringing as far as that goes, but then when boomers came into the workforce that was 1946 to 1964, this was the generation that kind of looked at what the traditionalists had amassed over their career, which you can have a pretty nice career being at one company for 30, 40, 50 years. But the boomers decided that they wanted that much more quickly than the other generation so that’s when they decided to create the term workaholic. This was the generation that they gave so much time, money, they thought it was all about FaceTime coming into work way before their boss gets there working way after their bosses leaving. Being proud of the fact that they hadn’t taken a vacation in 15 years, destroying their marriage in the process because boomers were so busy focusing on the things that aren’t necessarily important in that career that sometimes they neglected their relationships that were and that’s really when we started seeing divorce rates starting to be 50% of all marriages ending in divorce. 

Then, in their 40’s and 50’s is when Corporate America kind of said, “You know what, we don’t really need you. We’re going to hire people who are younger and cheaper than you.” And the boomers found themselves kicked out. Well, all along Gen X, which is 1965 to 1980 comes into the workplace. I like to say that Gen X is the smallest of the generation, 75 million boomers, 40 million Gen Xers primarily because boomers were way too busy working to actually reproduce. But, as Gen Xers are observing what happened to boomers, number one, they were the latchkey children. They were raised in single-family households, or actually they were raised by Barney but that’s another…

Yeah, that’s right. The purple dinosaur.

Very self-sufficient generation, very cynical generation because they also saw how the boomers gave so much of themselves to Corporate America and how they were basically just eliminated. And so, Gen Xers came and they said, “I think I want this thing called work-life balance.” When they came in they wanted to work until 5:00 and not have that be considered a half-day. I still remember, and you probably remember it too, that TIME magazine article with the big pink. It was a pink cover called Gen X Slackers and all the stuff that we now call Millennials, well Boomers were calling Gen Xers way back in the day because that’s what we did.

I remember at one point early in my career, I asked my boss, “Hey, do you mind if I work a half-day tomorrow.” And he said, “Sure, pick any 12 hours you want.”

And he wasn’t joking.

Well, that’s right.

Gen Xers had the same work ethic of wanting to do a good job, wanting to grow in their career. They also had different priorities that the Boomers had to kind of wrap their head around and they weren’t getting it so hence the slacker term. Millennials came in 1982. Now they’re saying about 1996. Sometimes you’ll see it extended to 2000. It’s a little fuzzy when it comes to Gen Y, also known as Millennials, but this is the generation who remember were raised by Boomers, who told them that they could do anything that they wanted to do and be anyone they wanted to be. With the Boomers, remember how I told you the traditionalist didn’t really care about getting recognized for doing the job?


Boomers are like starved for attention because they’re giving all of this effort to corporate America and the traditionalists are like, “Well, why should I thank you? That’s what you’re getting paid for.”

You got a check, be happy about it.

Yeah. Boomers did not want their Millennial offspring to feel that pain of not being recognized. So now, we have the trophy generation, the participation ribbon, all of that stuff that we complain about, but yet, Boomers are the ones that came up with that. What does that mean in the workplace? This is a generation that has been getting feedback since they were young kids. So, if you’re only doing a once a year personal performance review — not enough. It’s constant check-ins, “How are you doing?” Millennials have also had access to leadership.

In my day, because I’m in the last year of the Boomers, my parents would tell me where we were going on vacation. With Millennials, the Boomers would ask them, “So where would you like to go on vacation this year?” Their opinions matter, their opinions counted for everything. So again, if you have a leadership team where there’s all kinds of levels before those Millennial employees can talk to leadership — not happening, They want access, they want to be listened to, they want to be paid attention to. They also are the most educated of all the generations because remember, Boomers going to college was a gift. It was not expected but because they wanted better things for their children, they took them the four-year college route, instead of going to trade in technical schools, which by the way, we have to change that conversation. Not everybody’s cut out for college, and we need people in the trades. 

We do, yeah.

But changing that conversation so these Millennials are coming into the workforce with tens of thousands of dollars in student loan debt, with no and insight of seeing how they’re going to pay that off. When they come to you, and they’re interviewing and they want $50 an hour to start, it’s not that they think that they actually deserve it. They’re just trying to figure out how am I going to pay off these student loans.

Yeah. It’s about making ends meet.

Yeah, getting my parent’s basement.

What’s interesting — before we get into the sort of the punchline on you, this next one coming up. You described that you’re right at the end of that Boomer range, and I’m right at the beginning of the X because I was born in 1966. And so, you shared because you have the Boomers, then the X, then the Y. For those of you figuring out how old your parents are sort of thing, so you pointed out that the boomers had the offspring of the Millennials. Here I am as an X and my offspring is now the Z, the new one. Pretty interesting dynamic there, you have this leapfrogging over if you will.

Yeah. That’s an important thing because remember, with the Gen Xers being the most cynical of all the generations. Number one, they’re this tiny generation, 75 million Boomers. 73 million Millennials. And even though I can’t find the numbers for Gen Z, the newest generation is the largest generation to date. 

I think I saw 90+ million. 

Yeah, so 24% of the population is this Gen Z but we have an entire generation being raised by a smaller and more cynical generation, but if you think about the Gen Z, they came in when we went through an economic downturn. Millennials were in when the economy was wonderful and everything was fine, and the Gen Z saw their Gen X parents lose everything. They’re extremely frugal. They want stability, they want cash, the whole making a difference having a purpose thing that Millennials are all about. Gen Z — no, give me the career path. Give me the cash.

Yeah. Give me the money. One of the things I want to talk about and we’ll get there in a second is related to, what do you do in your company when you have these different groups to make sure that you’re managing and being effective with your teams and how they play nice together if you will. The other thing though is just to round out some of the attributes. I think what you just shared is an absolute critical baseline foundation. Let’s talk about a few of the things that are dynamics out there, just in the economy. So home buying, who are the ones who want to buy homes and who doesn’t care?

I think that because the economy is changing so much to this gig economy that homeownership isn’t as important as with Boomers, it was just something you know, you made it when you have a home. Gen Xers, it was that settling down and being with family. Millennials and Gen Z, because they’re moving so much more, they’re not staying loyal, they’re not staying with a company as long. They may be moving across the country, all over the place every couple of years so it’s a nice to have. But if you think about the student loan debt variables that they have, as well as the price of housing, in basically a seller’s market, it’s not easy for these newest generations to achieve homeownership.

I see a lot of communities where they could care less about owning a car. They’re just happy to hop in Lyft or Uber.

Absolutely, yeah. Back in the day, I think a lot of managers don’t understand is, the very essence of time has changed in the way that we work. Right now, we’re on 24/7 anyway. Back in the day, if I was going to the airport, I would call this thing called a cab and somebody who hates it what they did for a living would come and pick me up and take me to the airport in a filthy car with no air condition.

Now, I have my Uber or Lyft driver that comes with snacks and cold water and charging stations and they love what they do, and I can actually see the little car on the app and know exactly when that person is going to show up.

Yeah, it’s really fabulous.

It’s a different time we’re in. We’re Boomers, we’ve worked well, I shouldn’t say 9 to 5 because none of us stop at 5, but there were hours and we had an answering machine. If we didn’t get back to somebody for a day or two is no big deal, with this thing right here we are on 24/7. With the smartphones with technology, if somebody sends me a text, “Oh, I gotta answer it.” If my boss sends me an email at 3 o’clock in the morning because they can’t sleep and they had a thought pop in their mind, they thought they just blast off an email. Your Millennial or Gen Z employees going, “Oh, crap, I gotta respond to this or else they’re going to think I’m not paying attention.” So, we’re wired differently in the way that we react to business communications.

Let’s talk a little bit about social media because that certainly has created this fear of missing out (FOMO) and the idea of, “I gotta know right away.” “I have to respond back right away and I’m doing it in short back and forth responses.” You may be with an individual but on this platform Facebook or Instagram or Twitter or whatever. Just talk about how that plays in.

Well, it plays in on every level. Number one, you see people making gazillions of dollars being YouTube stars and things like that. We have a different perception of what a celebrity is these days. We’re also — we have this FOMO because of course, we’re not putting on the social media when life is bad and when we’re having a crappy day. For the most part, we’re sharing life is beautiful and then all of our friends are thinking, “Oh my goodness, her life must be awesome all the time,” and it’s not.

From a business standpoint, you have websites like Glassdoor that if I am a potential employee looking at going to interview for a job at your organization and I go on Glassdoor, and I see tons of disgruntled employers, employees writing crappy reviews, and management is not responding to it. There’s a good chance, I’m never even going to submit my resume so you don’t know that they’re on the market. Now granted — you will always have disgruntled employees who will be more than happy to post negative crap about you on social media. But if you see that, if you’re paying attention, and if I go on that same site on Glassdoor and I see a bad review, but then the HR manager or the owner of the company says, “Well, this has come up. This is what we’re doing to change the culture. We’ve had a conversation,” whatever it is that I know that leadership is paying attention, and maybe that employee was just that bad apple. 

Also, for social media, if I go to your website, if I go to your Facebook page, am I seeing people who look like me? Or is it a bunch of corporate basically, old white guys on your website? We have to look at who are we looking to hire. Do you have young, do you have different ethnic races and genders, and all of these type of people represented on your website because Gen Z is the most culturally diverse generation that has ever come on to the scene. It’s noticeable if you don’t have some diversity represented and what you’re putting out there in social media.

Yeah. So what you’re talking about is really from an attractiveness standpoint. As a leader, you’d be thinking, “Oh, wait a minute, do I care about disease yet?” So here’s some perspective. And Lisa, you mentioned that in some cases, the definition started like in the late 90’s, 96 or something and other just started at 2000 depending on when officially the Millennials ended, and then Gen Z started. That means that someone who’s in that 18 to 24 or so range, who is entering your workforce right now is a Gen Z. You as a business leader, you’re pointing out that you are hiring Gen Z’s right now. They’re the ones going into college right now or coming out of college right now, depending on the definition, but essentially, they’re either part-time workers like my son who was 18, or these are people who come out of college ready for a job. These attributes of Gen Z, they’re critical for you to appreciate because that’s your next group coming in.

Right. And something to keep in mind too that when we have these transitional generations, even though I’m the last year of the Boomers, and you’re early in Gen X, I have a lot of Gen X qualities. You probably have a lot of Boomer qualities. As Millennials go into Gen Z, and now Gen Z is coming in, they probably have some of those traits but Gen Z also wants nothing to do with being called a Millennial because of the lambasting that we have been doing the unjust lambasting that we have been doing about Millennials for the last 10 or 15 years, or however long that we’ve been unjustly putting this group into the lazy and entitled category, which is the furthest thing from the truth that you can imagine.

Right. Let me talk about that a second. It’s interesting — I was at a workshop. in fact, it was one that over the course of a couple of days where you and I were there at the same time. I was sitting in the audience so I’m in the back row and I’m sitting down next to someone who’s the Vice President of HR for whatever company she worked at. The presenter was talking about all those Millennials — it’s exactly what you just said. You know you’re going to have trouble with these people and she leaned over and said to me, “I wish people would just stop.” And really, as you pointed out, the Gen Z’s is the greatest number of people but they’re not all in the workforce yet. The Millennials is the biggest number generation in the workforce. Here’s the Vice President of HR, and the speaker who was blasting Millennials, as you just pointed out, was just repeating what we’ve all said. 

I remember the first time that I had about 15 years ago or so. I had a radio program called The Institute of Success and Goal Achievement and that was the first time that I had someone to talk about generations. Of course, there was no Z then and the Millennials was the new one just coming into the workforce. We had in our conversation, as this person was talking about the attributes of a Millennial, you don’t know what it is yet but here it comes and the problem with that — we don’t know what it is, here it comes. It’s going to be different, it’s going to be difficult. That language never stopped.and that’s what you’re pointing out here, and that’s this woman was so frustrated about. She is a vice president in a company because she’s earned it through her skills and her ability to achieve and now she’s a decision-maker and executive. 

For all of you out there who are listening, you’re probably in that group too because the numbers, the raw numbers suggest the highest probability that you in your company are Millennials so we’re not talking about any of these generations as good or bad, etc. I want to emphasize and stress what Lisa just said because it is so important to appreciate, we as human beings have something to offer. I’m different than Lisa, Lisa and I are different than people in other generations, etc. It’s about appreciating differences and then understanding how can we work within our set of skills and our strengths and our weaknesses and come together in a collaborative team.

Right. I remember I saw a speaker a couple of years ago that was doing a program on Millennials and she had the best sentence. She said that for me to say that all Millennials are lazy entitled would be like me saying all women are lazy and entitled, or all Asians are lazy and entitled. You say a sentence like that and it feels icky to even say it. So what right does anybody have to take an entire generation and lump them into this category just because they are wired differently where the Gen Xers were digital pioneers. Now, you guys were the ones that started sharing, downloading, stealing music and movies…

A master.

So you started it, Millennials and especially now Gen Z, because you do have some Millennials that actually know what dial-up sounds like. Gen Z has never heard it unless they go on YouTube and they think it’s kind of cool. And it’s like, not cool. No, it wasn’t at all. We process things differently so were a Gen Z or Gen Xer who’s been playing with an iPads since they were three has a different understanding of technology than a Boomer than maybe it takes a little bit longer for them to understand the technology, and they’re afraid of it. We have one group of people that this is my life. I’ve never known life with a phone with a cord, and this generation over here, going, “What do you mean we’re going to paperless?” 

Yes, exactly.

A different way of doing business, but like I tell my audiences unless you are willing to look at every single area of your business differently today than you did 10 years ago. You are really setting yourself up for failure. We have to think things that have never been thought before and be okay with the fact. I mean I look at how much technology and same thing with you has changed in our lifetime even in the last, since 1996, when I got my first flip phone.

Back then, a cloud was a white fluffy thing.

It’s just different and if we can understand that from generation to generation, we’re processing our world differently. Even though we’ve been complaining about generations, literally since the beginning of time, today, it really is different. Today, the generations are different than they’ve ever been before and that change is going to keep continuing.

It’s interesting. My dad was a high school teacher and of course, he started teaching — I don’t know exactly what year old he was. He had to be in his 20’s, I’m guessing because you get your Bachelor’s and you get your Masters and then you get your teaching job so he gets to be in his mid-20s, I’m guessing. He started then, and of course, he taught until he was in his 60’s. And again, I’m not exactly sure what year but essentially as 20s, 30s, 40s, 50s, 60s, the biggest complaint from teachers that he shared, he would say, every single year, the teachers would say, “Ah, the kids these days just aren’t blah, blah, blah” the setup is exactly what you just pointed out where the previous generation is always complaining about the next one. The new one is always the problem and it’s not really the case. It’s more about understanding. 

This is where some of the programs that we do in the leadership development and the team effectiveness side have to do with understanding individuals as individuals, and what are their skills for sure, but what are their styles and preferences, and what ways into that. And of course, generation and the differences is one of the huge variables that ends up shaping how somebody thinks. It’s their beliefs, it’s their perspectives, it’s their likes, and then you get into the personality side of things and now you’ve got a super unique individual, and it’s on you as the business leader to appreciate first, who you are. But then who are they, and what slight tweaks can you make in your style of communicating of asking for work to be done of sharing ideas, etc., of engaging them? What tweaks can you make to get the most out of that relationship as opposed to just shoving it on them, and hoping that it works out?

Yeah, and asking them for their ideas and suggestions. Again, we have two generations that are the most educated of any generation before them. They also see the world differently. So when they join your organization, and your whole thought is, “What we’ve always done it this way. We’ve been in business for 50 years and so the way we’ve always done it,” but really listening to what they have to say because they may not be from your industry. They may have no experience in your industry or whatsoever but the knowledge, the experiences, the technical expertise that they are bringing in with them, if you’re open to it can completely transform your business and make it even better and stronger than it was before they got there.

Yes, absolutely. Capital YES for sure. Just rapid round at the end here — what are some tips that come to mind for a business leader or for a team? Someone who now has these generations to work with, you could be on a team and there’s someone who’s older than you, there’s someone who’s younger than you. You’ve got to figure out how we get the job done. How do we make it fulfilling for the individuals? How do we get the business results? So, how do you do all that? What are some ideas that you could share today?

Well, one of the best ways is putting together some kind of mentoring mentee program. Number one, it lets you know that you’re Baby Boomers and your more tenured employees that they still have value. A couple years ago, my husband started reporting to two people who were younger than him and it was pretty devastating. He wasn’t feeling relevant anymore. And so just to take advantage of the knowledge, the skills, the experience that that 10 year old employee has, and put them together with this new employee because also you have that tenured employee say, “Well, why should I make friends with that person?” I mean, they’re just going to be gone in six months anyway. Well, what if you did develop a relationship with that person? What if you did become their friend, and now you’re the reason that they stay?

Looking at ways that you can get people of different generations to work together to be on teams together to really understand to have — there’s so many different types of fun ice-breaking opportunities to get together and just kind of learn and come from a place of understanding. Because when you can be, like I like to say, I’m an equal opportunity offender when it comes to the generations, but when you call out the different generations, we all have good points, we all have bad points and we can all laugh about ourselves and understand a little bit better as far as why that person acts like that.

Yeah. And back to the point of, here’s someone who might only be here six months, why do I bother getting to know them? Well, what if you did get to know them? And as you pointed out, you are the reason they stayed? What if they still left and you kept in touch with them? Now, you’ve just expanded your network so you, Lisa are one of the most masterful networks that networkers that I know. You’re outstanding at that so I see the opportunity for an individual to become the friend to others and allow that to expand and continue.

Also, even when that employee does leave for another opportunity, if you have that good relationship because of that mentor mentee relationship, who’s to say that that employee that left for a better opportunity isn’t now going to recommend one of their friends, isn’t going to talk highly about your place of business on social media, Isn’t going to encourage other people to take the job there. Again, we expand our networks, and thank you for that compliment that was really nice, it’s just that not every person is going to stay in every job forever, but they came in. There’s that reason, season type of thing. They come in for a reason, they come in for a season and we’re okay with that and we continue the relationship.

When I was in the welding industry, I left that business in 2003 and my boss that I reported to is still one of my best friends on the planet. When you have those long-term relationships with people, and I will never work for Dale again, when I left that I went on and I knew that but that doesn’t mean that we couldn’t be friends. 

Excellent conversation today, Lisa. Thank you. As we wrap here, my parting words of encouragement to you listeners as business leaders are, as tough as you think you’re having it with the different individuals on your team. Certainly know that there’s — back to what you pointed out, they’re there for the season and for a reason. There’s reasons that you’re having the experiences that you are. Take the value from that and then see what you can do by you making some tweaks inside of you rather than a complaint about the other person, and what can you do to tweak your style, your approach ever so slightly to make a deeper connection and let’s see if that raises up your experience, their experience, your team’s results, etc. 


Excellent. Thanks everyone for joining Business Results Radio and we’ll catch you soon on another episode.

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