The following is a conversation between Tim Elmore, Founder & CEO of Growing Leaders, and author of A New Kind of Diversity: Making the Different Generations on Your Team a Competitive Advantage, and Denver Frederick, the Host of The Business of Giving.

Denver: One of the biggest and most disruptive shifts that the American workforce has seen is the vast diversity of several generations working together, and this generational gap has become an undeniable source of tension in the global workplace, which includes nonprofit organizations.

Yet only 8% of US companies even recognize the impact of diverse generations on teams. Here to sort this all out for us is Tim Elmore, the founder and CEO of Growing Leaders and the author of A New Kind of Diversity: Making the Different Generations on Your Team a Competitive Advantage.

Welcome to The Business of Giving, Tim.

Tim Elmore, founder & CEO of Growing Leaders, and author of A New Kind of Diversity: Making the Different Generations on Your Team a Competitive Advantage

Tim: Denver, it’s great to be with you. Thanks!

Denver: You know, you write the generational gap, which I can recall really became talked about back in the 1960s, has widened today, making collaboration even more difficult on teams than ever before. Describe for us what is going on.

Tim: That’s a loaded question.

Well, you’re absolutely right. I think it was Look Magazine editor John Poppy, way back in the ‘60s that came up with this term “generation gap.” And by the way, ironically, the Baby Boomers were the young whippersnappers back then. And now, we’re the older folk going: “These young kids today…” you know?

Denver: Get off my lawn.

Tim: That’s right.

It’s so true. So, here’s my theory, and I’ve proven it in this book; I think my hypothesis has been proven several times. Back in those days when the term generation gap first came up, there was a gap between older and younger, for sure, but we had one screen in our house.

It was a black and white television. And most of the time, families got together to watch I Love Lucy or Dick Van Dyke or Andy Griffith. We laughed together. We talked about it together, but we were together. Fast forward to today, we all have now our own individual screen in our hands, and we’re in echo chambers.

So, the young are with other young, and we’re with our echo chamber– People that talk like us, vote like us, speak like us, live like us. So, I feel like the gap is wider in the workplace and in nonprofits because we’ve been in these lanes that are just so different. So, my fear is we just feel like the goal is to tolerate each other. Got to put up with those Gen Z-ers or Millennials when I think we need to be leveraging the strength of each generation that comes in.

Denver: Yeah, that makes an awful lot of sense. You know, going back to TV for a second, it was even a point where we always had appointment TV. So, the whole nation would come around and watch television.

Now, if there’s a great show on, and you start to talk about it, and somebody hasn’t seen it yet because they’re going to binge it, you don’t even have a common conversation about what was on television last night because you’re going to ruin the plot. So, other than maybe the Super Bowl and sporting events, there’s really nothing, you know?

And not even the news because we’re on two different stations, you know.

Tim: Yes.

Denver: Diametrically opposed, and stuff like that. So, what are some of the common things that create discord between generations in the workplace?

Tim: Great question. Well, first and foremost, I think, modes of communication. So, a Generation Z team member that comes in at 22-years- old, right out of college, is smart as a whip, but maybe in very different categories, and might want to communicate in very different ways than the X-er or the Boomer who’s in charge.

So, one example might be I just talked to an HR executive who said she had an employee just quit through a text message. I’ll just send you a text. And some just ghost you. I mean, they’ll just not show up the next day, and you find out later: I guess, they’re done here. Not all for sure, but too many of us don’t settle those communication norms in the beginning, or expectations.

That’s another one, Denver. Expectations are very different. We live in a day of audacity. In the interview process, a Gen Z member, they may blow you away with what they’re asking for, what they’re demanding. And so, I recommend in the book, we need to find out early on their preferences, expectations, and demands.

And then, of course, we have our own, and see if it is worth it to go on with the interview.  Or do we need to show them the door and say, “I think you’ll fit somewhere else.” Those are the kinds of things we’re having to talk about today that maybe we didn’t have to  40 years ago.

Denver: Yeah. You know, I have found that to be the case too, and I think it’s a great point, Tim, that I think when these Z-ers come in, they think that their voice is of equal value to everyone else’s, but if you tell them that it isn’t, they’re actually reasonably receptive to it.

We assume that they know that this is not a democracy. If you let them know how it all works a little bit, they may push a little bit, but they’re much more, you know, agreeable than when they don’t really know. And we don’t really understand that because we don’t take the time.

You know, I mentioned in the opening that I think 8% of companies recognize this to be an issue. 

Now, there is no shortage of conversation about the workplace these days.

Tim: Yeah.

Denver: We’ve got leading remotely. We have diversity, equity, inclusion, and belonging. I mean, “psychological safety” was a term that I  hardly ever heard of 10 years ago, and now it’s sort of a condition for employment. I have to have psychological safety. But we do not, to any great degree, talk about this generational diversity. Why do you think that’s the case?

Tim: You know, I think it became an elephant in the room. So, we do have language to talk about ethnic diversity, gender diversity, income diversity. You know, the elephant in the room is that we all know what’s there, but we don’t know how to talk about it.

I think it’s primarily because it hasn’t been a topic of conversation through the years as much as race, for instance. And, I think, we find ourselves at the water cooler talking to our own kind about the other, rather than talking to the other. So, one of the rules in our workplace is: when there’s a bit of a conflict, talk to the person, not about the person.

And, that’s just good ethics. Now, we can solve a problem rather than just talk about it. But I think this elephant in the room just started looming. But, Denver, I’ll tell you what we found as I researched for the book. Age discrimination lawsuits are popping up everywhere, including Fortune 500 companies.

Denver: Yeah.

Tim: IBM and Marriott and others. So, the young are suing their workplace because they felt like they didn’t get the promotion because they were too young. And then, the older people will do the same thing. I didn’t get promoted because I’m 60, and you want to get rid of this dinosaur. So, I feel like what we need to do is: Let’s bring it out in the open; let’s talk about it.

And what I love is when companies figure out: our workplace has both modern elders and young geniuses.

Denver: Yeah.

Tim: Both.

Denver: That’s a nice term. Yeah.

Tim: Yes.

Denver: Language is everything. Yeah.

Tim: Absolutely.

Denver: Next conversation we’ll have, we’ll talk about the generational diversity at law firms who are getting all this work.

Tim: I love it.

Denver: You know, you did an incredibly comprehensive and thorough and very entertaining job with this book, and one of the things that you helped, I think, articulate with people– when we all think about it– is the different generations and their characteristics. So, why don’t you run through them?

And we don’t want to  generalize, but there are certain characteristics of each of the cohorts. Why don’t you start with Baby Boomers.

Tim: Okay, sure. So, Baby Boomers would obviously be at retirement age. I think about 10,000 Baby Boomers retire on average every day. But, I’m one of them, and we’re still in the workplace. I lead and own my company.

So, I would say, the value that Boomers bring are stories from our 40 years of experience, life coaching, understanding of the pitfalls to avoid because we went through some back in 1985 or whatever. I think what we bring is, first of all, years of experience, for sure. But our contribution, because we grew up in post- World War II America, is a large-and-in-charge mindset.

We can do this, let’s go. Our parents grew up during The Great Depression. So, theirs was a generation of caution. Ours was one of confidence.

Denver: Yeah.

Tim: So, that would be my Baby Boomer summary, without stereotyping, of course.

Denver: Yeah. Yeah. I think what Baby Boomers need to do, and you probably make this point, is that they just need to learn how to communicate better with younger generations.

Because, you know what, I have been told? I’m in that cohort, needless to say myself, is that it’s not relevant to today. That was so yesterday, and you want to be able to say there are not many, maybe, but certainly important, timeless lessons that don’t change, you know. But younger people sometimes look at that and say that that doesn’t apply to what’s going on today.

Tim: Denver, you just said a mouthful, and I love the word “timeless” you just used. I feel like, today, there are two categories of knowledge or insight that a workplace needs— timeless wisdom and timely intuition. And the young often bring the timely, they know where culture’s going. They can see what we need to do to market to Millennials and Gen Z.

But, you’re right, there are some timeless values and virtues we dare not leave behind. The stuff our grandparents taught us about honesty and work ethic and so forth. So, if we can blend the two, we’ve really got something. It’s not either/or, it’s both.

Denver: Absolutely. Gen X. Tell us about that.

Tim: All right. So, Gen X would be in the throes of their career. They’re now the heart and soul of the workforce. They’re in management positions often. They’ve been through midlife and now beyond. Gen X would bring a very pragmatic wisdom with them. They grew up in a little bit more difficult times, late ‘60s, all the way through the ‘70s.

Often, they were latchkey kids growing up. So, what shaped them was: I had to be self-sufficient. I let myself in the door. Mom’s working; dad’s gone perhaps… divorce rates were higher. So, there’s a self-sufficiency; there’s a pragmatism. I’ll tell you what, Denver. There’s a contrarian insight they often bring with them. And very often, without stereotyping, they’re the ones that would say, ” Let’s watch out for this. This might happen.” And even though nobody likes that downer, “we need to watch out for that over there.”

So, I feel like our Gen X team members bring that contrarian insight that we need where we’re not just hopeful and optimistic without careful thought. Yeah.

Denver: Yeah. They’re a little cynical.

Tim: That’s right.

Denver: At this point of cynicism, it can be pumping the brakes a little bit and being cautious because everything may not be as it appears. And that is really good to have in a workforce; there’s no question about that.

Tim: Yeah.

Denver: Onto the Millennials.

Tim: Okay. We’ve been talking about the Millennials now for 15 years.

Denver: Yeah.

Tim: And we’ve been throwing shade at them all the way through. To all Millennials listening, please forgive us. Please forgive us. So, this might be helpful to note. There are more Millennials now in the workforce than any other generation.

Denver: Yep.

Tim: They are the largest generation in American history, even larger than the Baby Boomers. So, they were their own boom of population. So, 80 million strong. Millennials, because they grew up in the time that they grew up, they bring hope and optimism. I referred to that earlier. Remember they were the generation we gave trophies to just for showing up on the soccer team. And we’ve been joking about that ever since.

Denver: Absolutely. I remember one that I saw was the last winner, and that was for the person who came in last place.

Tim: Yes, but they’re still winning. Yeah.

Denver: Still winning. Yeah. They got the trophy.

Tim: It’s crazy. I was at an awards ceremony once, this would’ve been a decade ago, where 9th place ribbons were given out.

Denver: Wow.

Tim: I’m going, What the heck? This is not a picture of life. This is not what they’re going to be entering into in adulthood.

Denver: But see, I’m an optimist, Tim. So, I would say, at least I haven’t gone to double digits yet.

Tim: That’s true, that is a plus. So, I do love the Millennials. I have always been working with the next generation since 1979 when I was the next generation. So, here’s what I believe, by and large, with some exceptions Millennials bring to the workplace: They bring an idealism, which we do need. We need to not give up on our ideals.

These non-profit listeners right now: you’ve got ideals you want to reach for feeding the hungry or housing for the poor or whatever it is. So, the Millennials will often come in a bit confident, like the Boomers– idealistic, hopeful. And I’m telling you, our Millennials in our office are the ones that bring the energy.

Denver: Yeah.

Tim: And I don’t mean to stereotype. By the way, this might be important for listeners to know. We’re not talking about Psychology, we’re talking about Sociology. So, everybody’s got a different personality. They’re optimists and pessimists in every generation. But there is a demographic tone to each as they grow up.

Just like all Democrats don’t think alike, and all Republicans don’t think alike, but you can learn a lot about a person by how they vote. You can learn about their values. I think that’s what we’re talking about here.

“Our goal is not to stereotype, but to understand.”

Denver: Yeah. Really, one of the things we need to do to be able to make sense of the world. Otherwise, it would just be the Tower of Babel. So, you have to do a little; you don’t want to stereotype. But you have to put things in categories so you can make some sense of things, and then be more effective in addressing them.

Tim: No, that was very well put. In the book, I even used the phrase, “Our goal is not to stereotype, but to understand.”

Denver: Right. Perfect.

Tim: That’s what we got to do. Yeah.

Denver: And one other thing about the Millennials too, you say, life is a cafeteria.

Tim: Yes. Okay, let me explain that. So, Millennials, by the way, my two kids, Bethany is 34. Jonathan is 30. They’re Millennials. So, they grew up in a time of digital customization. So, in the same way that you go to a cafeteria and you grab your tray and your plate, and you make up your own meal tailored for your taste buds….Little bit of roast beef, little bit of mashed potatoes, little bit of jello. 

These young professionals are making almost every major decision of their life as if it were one large buffet. So, here’s some examples. My two kids stopped buying compact discs to get their music years ago. Why would they buy CDs?There might be six songs they don’t even like on that CD. They get one song at a time from their own playlist on Spotify, Apple Music; it’s a cafeteria. 

School, they’ll make educational decisions this way, Denver. They’ll graduate high school and go to two or three different colleges for one degree. One of them is overseas, you know?

Denver: Yeah, yeah, yeah. Absolutely.

Tim: Then, also spiritually, they’ll make faith decisions this way. A little bit of Jesus, a little bit of Buddha, a little bit of Oprah, shake it together, I’ve got my faith, you know, there’s no one true source. Now, I’m not cutting it down or insulting. I’m just saying it’s like a free agent mindset.

Denver: Yeah.

Tim: And, as donors, they are feeling this way. And as workers, they’re feeling this way. So, it’s just good to be in the know. Yeah.

Denver: Yeah. You know, I was always really resentful of when free agency came into sports because I had tremendous loyalty to the players on the team, and I had a difficult time, Tim, caring more about the team than the players on it.

And I just said, What is going on here? But then, I looked at the workforce and realized what was happening in sports was just merely a reflection of what was happening in society. You know, I started at The United Way back in the late 1970s, and everybody would give their payroll deduction and stuff like that.

But then, I also realized that was a time that a guy would work at Union Carbide for 40 years and get a gold watch.

Tim: That’s right.

Denver: And then, you begin to see the way society is, and it’s reflected in everything around you, but you sometimes don’t make those connections. You tend to look at those things and make judgements in isolation where it really is just all part of the same pond.

Tim: It’s so true. It’s a reflection. That’s a great statement. It’s all a reflection. So, let me volley back. The Builders and the Boomers; the older generations, as donors they’ll give to programs… loyal to programs that I believed in for decades. 

Boomers often give to productivity. They want to see results. Say, I always give data when I have Boomer donors in the audience. It’s data, the data, but with productivity. Millennials give to passion… what’s their passion, so you need to find out what they’re passionate about. I think Gen Z, they’re young. They’ll often give their parents money, which  actually is what they’re doing.

But, Gen Z, I think, they’ll often give to causes that they feel like serve the marginalized who need equity. I think there’s such a sense of: I want to bring that. And that’s a good thing. But it’s a really different mindset than the Builder or the Boomer who may be more loyal to a person or a program.

Denver: Yeah, no, that’s a good insight. And the other thing I would add about Gen Z, because we’re going to get into that next, I think they’re probably going to be the ones who are going to be most interested in giving to systems change because they don’t see that the organizations or the causes can make a difference. 

They think the system is set up. It’s rigged; it’s wrong, and either needs to be overhauled or maybe more than overhauled to be able to create a new system where the equity will come from the system and not people trying to, you know, swim against the tide with a particular program or a particular organization.

Tim: It’s well-put. Totally well-put. In fact, that really explains a little bit: Defund the Police or some other.  You go, What in the world would you want to do that for? Well, they’re saying, right or wrong: I think the whole system’s broken.

Denver: Yeah.

Tim: Education, government, organized religion. So many are walking away from traditional institutions because they just go: It’s not working.

Denver: That’s right. Start again.

Tim: Yeah.

“So, the two things that I think your listeners need to know most, the two biggest realities are high sense of agency, high sense of anxiety.”

Denver: Well, talk  to us a little bit more about Gen Z because I tell you, probably of all the four we’re going to talk about, this is the one that people are sitting at the edge of their seat, perking up, because so many do not understand, you know, the dynamic there. Give us a little insight.

Tim: Yeah. So, we’re doing lots and lots of studying on Gen Z and, by the way, I should start by saying I absolutely love these kids. I’ll say kids… young professionals, young adults, college students, high school students. So, you had me walk through the generations. I see a pendulum swinging back and forth over the last 90 to 100 years.

The Builder generation was a generation of caution, growing up in The Great Depression, World War II; Boomers, generation of confidence, Gen X– back to caution, little jaded, little cynical.

Denver: Yeah.

Tim: Millennials, back to confidence. Gen Z, back to caution. So, mental health issues are a huge issue for Gen Z. You know this.

Denver: Yeah.

Tim: Anxiety, panic attacks, depression. I would say, anxiety has been normalized for their generation. I don’t think we realized what this smartphone would do to our brains, especially to our kids’ brains. So, the two things that I think your listeners need to know most, the two biggest realities are high sense of agency, high sense of anxiety.

Denver: Yeah.

Tim: The agency is: I don’t need your help. I’m good. I got my smartphone. I’m asking Google questions I used to ask Dad.

Denver: Yeah.

Tim: But high sense of anxiety is that same smartphone has overwhelmed me with information, and I just feel anxious. And so, in one moment, they may be saying, Don’t need your help. In the other moment, they might be saying, I desperately need your help on any given day.

So, I think it’s good for employers and officers in nonprofits to realize there’s just going to be this paradoxical “don’t need you/ need you” experience with Gen Z. Yeah.

Denver: That’s really interesting. You know, I would always remember how I dreaded my performance review.

Tim: Yeah.

Denver: I think we’ve all dreaded our performance review. I sometimes… picking up on your point, think with Gen Zs, when they pick up their phone, it’s a performance review.

Tim: Yes.

Denver: They’re always comparing themselves to what somebody else is doing; and how am I stacking up?

Tim: Yeah.

Denver: And, unfortunately, they come to the conclusion, “Maybe I’m not stacking up as well as I would hope.” And that creates a real sense of angst.

Tim: No doubt about it. In fact, part of the reason is what’s being posted on that social media feed is the best vacation ever, you know?

Denver: Oh yeah.

Tim: The best moments of people, not their everyday moments. Nobody posts “Did the laundry today.” So, let me press in on that.

So, we all know that Generation Z, as a generational cohort, struggles with FOMO, fear of missing out. I’m also beginning to hear the term FOMU, fear of messing up. So, there’s inordinate anxiety about making a mistake or failing or falling, and part of the reason for that is there’s this perfectionistic standard that oftentimes is held over them.

Sometimes, they hold it over themselves, and they also know if I make a mistake, somebody’s going to capture it on the smartphone, post it on YouTube, and that will be my reputation for the next several years. So, you can see, “Oh my gosh, I’m going to be more private. I’m going to hide some things. I’m going to have different personas on social media.”

So, mom and dad know their daughter in high school has an Instagram account. They have no idea she has five Finsta accounts, fake Instagram, where she’s developing personas and identities and talking to God knows who. So, it’s a very, very complex time that we’re living in. Yeah.

Denver: Yeah. When I was a kid and I went to school, you know, the teacher was always telling me when I did a bad thing that was going to go on my permanent record. And then, you know, after a number of years, I realized that was a lot of loaded crap, you know, because there was no permanent record. Now, there’s a permanent record.

Tim: Yes.

Denver: You know what I mean?

Tim: Yeah.

Denver: Now, they’re right. It’s a permanent record, and it can haunt you. I mean, we look at even some of our politicians, you know?

Tim: Yup.

Denver: Something they did at 16, you know? A picture they were in, or something along those lines, it just follows you around.

Tim: Yeah,

Denver: That’s a lot of pressure, you know?

It doesn’t disappear.

Tim: Yep.

“He put the older with the younger, the veteran with the rookie, and they both swapped stories. You can always find something in common when you swap stories.”

Denver: Well, how do we take these diametrically different cohorts– there’s four of them that you just went through– and turn what seems to be a challenging situation into a real significant advantage in the workplace?

Tim: Great question. Let me give you a couple of thoughts that come to my mind immediately, and I do talk about these in the book, so they’re kind of documented and detailed. One is a little exercise I call “Ditch the Niche.” So, we all find ourselves in niches of people that are like us, age-wise and voting, record-wise, and everything else. So, I think it’s really good to be intentional in our workplace to put a younger with an older– on purpose.

In fact, you’ll appreciate this, Denver. When we began to market this new book, I sat down with Gen Zers, Millennials, Gen Xers, and Boomers, and said, “If we were to try to reach your generational cohort, what should we say? How should we profile this encyclopedia on the generations?”And they gave a different answer.

 Another fun, fun, fun activity that I think workplaces can do is reverse mentoring. So, Jack Welch came up with this way back in the ‘90s. You remember the  ‘90s; computers were kind of new in the workplace. And Jack Welch had some 59-, 60-year-old executives that were not feeling at home with that PC.

And he had some young MIT grads coming on the team that were very at home with them, but they were the young rookies, but here’s what he did. He put the older with the younger, the veteran with the rookie, and they both swapped stories. You can always find something in common when you swap stories. And then the older would be a mentor to the younger on: Here’s how to succeed in this workplace.

But then I love this, they’d switch hats, figuratively speaking, and the younger would then mentor the older in technology, or today, it might be how we can use the latest app we just got to market our company or whatever. But I love it. Both became ” menterns.”

Denver: Yeah.

Tim: I’m a mentor and an intern, both at the same time.

Denver: Yeah.

Tim: That’s what I think you need to do because there is stuff to learn from both sides. Yeah.

Denver: Yeah. And, you get more, I think, even out of being a mentor than you do when you’re being mentored. It is unbelievable. You know, I read this study the other day. They had a guy on the show, and they were with patients of MS, and they had two groups, Tim. One received a phone call every week for an entire year about how they were doing, checked in, et cetera, et cetera.

And the other group who had MS made a call to another MS patient and mentored that patient. They made the call. And at the end of the year, the group that had made the calls– as opposed to who received them– were eight times better in terms of optimism, in terms of their feeling of  belief in the future.

And every indicator you can look at. It was just such a powerful study that I saw. I said, “Wow, that makes so much sense, but we don’t think about that.” How do you get that started? Because I’m always curious about ignition because… Look, reverse mentoring, as you just mentioned, has been around since the 1990s.

Tim: Yeah, yeah.

“Start with humility. Meaning, even if you’re the old guy, you know, on the team, just set your ego aside and enter humbly, which I think screams, “I know I’ve got more to learn myself.”

 If I start with respect, it tends to be reciprocated, but I lead the way as the leader.

It’s EQ, not IQ. We don’t have to be any smarter, but we need to read others before we lead others. Self-awareness is huge. Social awareness is huge.”

Denver: Not enough people do it. You know that, you know. What do we do? How do we get them started?

Tim: Well, here’s something from our findings that might be a good starting point. I ask each generational cohort, “What do you want from other generations as you interact?”

Denver: Oh, I like that.

Tim: There was a truckload of answers, but three came up in every generation. The oldest to the youngest all wanted three qualities. Number one was humility. Start with humility. Meaning, even if you’re the old guy, you know, on the team, just set your ego aside and enter humbly, which I think screams, “I know I’ve got more to learn myself.”

Number two was respect. That’s an old-fashioned word. Thank you, Aretha Franklin. But, I think, as older guys, Denver, we’ve often said, “Well, you’ve got to earn my respect.” What if we led with it?

Denver: Sure.

Tim: What if we started with that 22-year-old right out of the University of Michigan, Cam, on our team? If I start with respect, it tends to be reciprocated, but I lead the way as the leader.

And then, the third one I thought was interesting was curiosity. What if every one of us entered a conversation curious about what we might pick up? So, humility, respect, and curiosity. That’s number one. And, by the way, can I point out? All of these are emotional intelligence-related qualities.

Denver: Absolutely. Yeah.

Tim: It’s EQ, not IQ. We don’t have to be any smarter, but we need to read others before we lead others. Self-awareness is huge. Social awareness is huge. Again, I talk about another book: How do we build our EQ, which can be built by the way, so that we can better pull the best out of each generation.

Denver: Yeah. You know, I got a little worried about the EQ with the latest generation because they just are not getting…, “Look, I know how much I picked up when I was a young person going into the workplace every day.”

Tim: Yeah.

Denver: Being with my elders, and they didn’t teach me anything per se. I just went to meetings and I was lost. I saw how they dealt with situations. It was osmosis, you know? Often, when you’re at home in a remote world, I don’t know if that emotional intelligence, it’s going to be just a harder climb in order to be able to get it than when you sort of had it around you all the time, and you could get it by observation, like a baby almost. You know?

Tim: You’re exactly right. And that’s what the data shows. Now, here’s something interesting. The data that we’ve gathered also says Gen Z was among the first of  the generations to want to get back to the office because they hadn’t built any social capital yet.

They knew they needed it. And you’re right. When you’re around other people, real people, right in front of them, you just pick up all kinds of insights by just watching. So, we’ve got to somehow make sure we’re face-to-face, not just on a screen.

Denver: Absolutely. No, I remember watching these conflicts and saying, “What is she going to do here?” And then I say, “Ooh, that was pretty darn good.” You know?

Tim: Yeah. Absolutely.

“I think mediocre leaders play checkers with their people. They treat them all alike and get average performance. Great leaders have learned to play chess in the relationships of their life, and those people flourish under the leadership because the leader connects with them based on their personality, their strength, and their generation.”

Denver: She resolved that. Hey, let me run through a couple of other things you had in the book, “Chess versus Checkers.”  Tell us about that.

Tim: So, we teach timeless leadership principles with the power of an image. We call them “habitudes.”  Habitudes are images that form leadership habits and attitudes.

So, “Chess and Checkers” is a great management or leadership principle I wish I would’ve learned 40 years ago. Both of those games have the same game board, but you play them very differently. When I play the Game of Checkers, all my pieces look alike… they all move alike, so I treat them alike.

In chess, I have to know what each piece can do if I’m going to win the game. I think mediocre leaders play checkers with their people. They treat them all alike and get average performance. Great leaders have learned to play chess in the relationships of their life, and those people flourish under the leadership because the leader connects with them based on their personality, their strength, and their generation.

So, I really encourage: do the work of playing chess. Read your people before you lead your people.

Denver: I love that. Let me ask you something which came up fairly recently, and it kind of is in the category of diversity, equity, inclusion, and belonging… and we obviously have different expectations based on the generations. But I have a few organizations that I know really ran into a lot of trouble on how to deal with the Dobbs decision on abortion. Okay?

Tim: Yeah.

Denver: Now, what you had is that you had a lot of the Millennials and Z-ers insisting that the organization make a statement about this. And you had the X-ers and, to a limited degree, the Boomers, saying, ” Well, look, this is not our area or domain. We’re not in this area. And we need to get things done with the government, and we have a lot of donors, and I understand your passion. But if we’re going to come out on every issue like this and make a statement, it’s really going to have a limiting effect in terms of our effectiveness going forward.”

Well, you know, it blew up. Give us a little sense of what’s going on there and how an organization can address that generational divide.

Tim: It’s a huge question and one that deserves hours of conversation, I’m sure, and probably people with a higher IQ than I’ve got. But, in the book, I actually get into some of the ways that generations view these kinds of social and political issues. First of all, every one of your listeners knows it seems like almost every issue has been politicized now. So, we just divide up so quickly.

So, we polarize instead of unionize ourselves. Here’s the advice I give to a leader that’s got this issue in front of him. It’s a little acronym. I call this “A leg we have to stand on.”  The letter A reminds me “I need to start with asking, not telling.

So, ask questions about “How did you come to that viewpoint?  I’m sure there’s some great reasons on both sides of this terribly divided issue.” And then the letter L is listen. When I truly, genuinely listen, they feel heard. Even if I don’t agree, I’m listening. They feel heard. The letter E is empathize. When I empathize, they feel understood.

So, ask, listen, they feel heard. E, empathize, they feel understood. And then G is guide. Now, I’ve earned my right to offer any input or guidance. Even if my bad says, “They owe it to me to follow me.” Now, I’ve earned my right to say, “Let me offer a couple of thoughts that might be helpful for you to put on that back burner, or at least put in the filing cabinet up there. That has helped us even at Growing Leaders with four generations on our team.

Denver: Yeah. Yeah. No, that’s really good. And sometimes you need a rubric like that that you can call on, because otherwise you get too caught up in “he said, she said, and what’s going on.”  So, you just have to have some touchstones, points that you can begin to start to carry on a conversation like that. Well, speaking with leaders, what are some of the key questions leaders can ask to better close the generational gap in their organization?

Tim: Well, I mentioned a little bit ago: share your story; we all have something in common. So, I do think even in interviews and early onboarding, make sure and ask them to tell their story. As silly as that sounds, you’re going to pick up common ground, and you’re also going to learn a lot by what they say and what they leave out. So, have them share their story.

I think we enjoy asking “Tell me about past experiences you’ve had with authority figures.” Because that’s going to let me know what I’m about to experience as the founder and CEO of our organization. And that’s not a loaded question. Just tell me about past experiences. I want to ask who are the mentors in your life. That really tells me a lot about that 22- or 25-year-old, what kind of mentors, or they may say: I got nobody.

Denver: Yeah.

Tim: That tells me a lot about that. And, by the way, you can see already by those questions, those are questions of the heart as much as anything. And I’m really getting at some of the root issues, not just: “Tell me about your work ethic.”  Or “When do you want to arrive at work each day?” Those are helpful, you know?

Denver: Yeah. Yeah. And then, they also seem to at least tack a little bit towards behaviors.

Tim: Yes.

Denver: Because you really can’t tell anything about someone’s opinion as we’ve learned from past presidential campaigns… and the pollsters are way off. You almost have to look at their behaviors in terms of giving a case, in terms of authority, and how you acted or what you did in a situation like that, which really tells you a lot more.

Do you have any favorite team activities that can help bridge this generational divide that you’re particularly fond of?

Tim: Well, I mentioned reverse mentoring. So, we’ve got several reverse mentoring relationships going on. I have two. Andrew, on our team, is one of our vice presidents. He is 30 years younger than me, and I teach and learn every time I’m with him.

Now, I will say this, Denver. He approaches every relationship or every interaction with me with humility, respect, and curiosity. I try to do the same. And then I meet with Cam, who’s 40 years younger than me. I just make sure I’ve got those meetings on the calendar; that just keeps me honest and real.

And I’m going to tell one of the big takeaways, early in the book: I tell a story that happens at our office all the time. Tony… Tony Piloseno, was working a part-time job when he was in college, and it was at a major retail brand paint store. Everybody listening would recognize the brand.

While he was there, he started a TikTok account. Of course, he did. And he started posting videos of himself mixing the paints and creating vivid colors. Well, when he posted them, Tony went viral. He had 1.4 million followers on TikTok.

Denver: Wow.

Tim: 37 million views. And it was at that point, he thought, “I could probably help our company monetize this. I mean, this could be used for marketing. There’s another million people that probably don’t even follow the company  in general.”  So, Tony put a slide deck together to take to the executives there. When he approached them, Tony did not get one manager interested in talking to him, didn’t get one set of eyeballs looking at the slide deck.

Tony did get something he didn’t expect. Tony got fired. He got let go because they were just sure he was stealing the paint, or it was on company time, or disrupting the customers. And, of course, they had drawn the worst opinions or assumptions on that young whippersnapper.

Well, get this, Tony’s fired. Tony moves from Ohio to Florida, now has over 2 million followers and has started his own paint store.

Denver: Yeah. That’s great. I love that story.

Tim: Yeah. There’s probably a bunch of stuff we don’t know about the story, but here’s what we do know. They missed an opportunity. They could have kept that young man. He probably should have been promoted, not deleted, and who knows what they might have been able to leverage.

Those are things we’re going to see more and more as time marches on, and we’ve got to leverage what those young people bring.

Denver: Yeah, that’s a great story. And it kind of reminds me a little bit of what you were just saying about respect, about having to earn respect, and essentially in both stories, it’s essentially assumed best intentions.

Tim: Yes.

“That gives me hope. If we’ll just stop and listen as well as tell, we may have something really great coming in the future.”

Denver: So, when somebody comes in, don’t earn the respect. Give them the respect. Have them lose it if they’re going to lose it, but start from that point of view. And when Tony comes in, assume best intentions as opposed to what they’ve done here, the worst intention, that he’s stealing from us… and he’s going to do something along those lines.

Finally, let me ask you this. Let’s take a look at the future a little bit. What makes you optimistic in terms of bringing these four generations together, or at least three? And we got the Alphas replacing the Boomers, so you’ll have another book coming out pretty soon. And, what makes you optimistic, and what are some of the things that you would caution us that we really need to be wary about, or we’re not going to get the high level of productivity and opportunity that is in front of us?

Tim: You just asked a fantastic question. Let me try to do it justice. One of the qualities of Generation Z that makes me optimistic is this: 72% of public high school students in America today want to be an entrepreneur. So, seven out of 10. Now, are they all going to succeed at that? Probably not.

But that predisposition to want to start something, not just join something, to launch a new idea. Boy, that’s what America was built on! Entrepreneurship! We were an experiment in 1776. So, we need to cultivate that, maybe by creating gig economies within our organizations where they can launch things and start things, and so forth. But that’s a cool thing.

I actually love their sense of agency if we can channel it in the right direction. So, here’s some interesting data. Generation Z is slightly lower than Millennials in their sense of entitlement. In other words, Millennials were feeling more entitled, which we hate, but here’s what’s happened.

Entitlement has morphed into empowerment. So, it’s a cousin, but it’s a better cousin. I feel empowered to try things. I grew up with a smartphone, not just a cell phone. I can learn, dig, search, research. So, I think we need to put that to work, and I think they have an intuition on where society is going that we need to be listening to, just as much as talking to them.

That gives me hope. If we’ll just stop and listen as well as tell, we may have something really great coming in the future.

Denver: That is great advice. And, you know, it’s almost as if with that generation, try to make your workplace the same as the way they will live the rest of their lives. Sometimes I get this sense that when we cross the proverbial threshold into the office, we’re going into a wayback machine.

Tim: Yes.

Denver: And if that can mirror more the way they’re living their lives and you tap into that, you’re really going with the current of the river as opposed to having them come into work and say, “Well, let’s swim against the current,”  which we’re sort of asking them to do. And that doesn’t work.

Tim: So true. That was very well-put. That’s exactly what I see, and I’m hoping that we can get with the flow and take it forward.

Denver: Sounds great. Well, the book, again, is A New Kind of Diversity: Making the Different Generations on Your Team a Competitive Advantage. It is so difficult to get a competitive advantage these days. This is something which is right in front of you, right under your roof, and you’ll never find a better guide than the book that Tim has put together on the subject. I want to thank you so much for being here today, Tim. It was a real delight to have you on the show.

Tim: It was my pleasure to be with you, Denver. Thank you.

Denver Frederick, Host of The Business of Giving serves as a Trusted Advisor and Executive Coach to Nonprofit Leaders. His Book, The Business of Giving: New Best Practices for Nonprofit and Philanthropic Leaders in an Uncertain World, is available now on Amazon and Barnes & Noble.

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