Bridging the Generational Divide at Work (feat. Chris Tuff)
16 Dec 2025 · 28 min
Chris Tuff explains why generational workplace conflicts happen and how to fix them. He breaks down the 70/30 rule for job satisfaction and suggests concrete moves: lateral job shifts, clear growth paths, personality tools like the Enneagram, and video messages instead of texts to build real connection.
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Foreign Hi, I'm Susan Jerome and welcome to the Enlightened Executive where your personal evolution sparks your leadership evolution. Each episode we feature groundbreaking techniques and strategies to help you get the edge in personal and leadership effectiveness. And this episode is brought to you by Meritage Leadership. At Meritage, we strengthen leaders and empower teams to achieve high performance. Go to meritageleadership.com to learn more. Today we are talking about the power of building connection. And I am thrilled to introduce my guest, Chris Tuff. Chris is the best selling author of the Millennial Whisperer and Save your Asks. His self described obsession with connection began in 2006 as he helped build the early infrastructure and advertising products with Facebook. Chris has worked with some of the most prestigious companies in the world such as Nike, Meta and Amazon. And his first book is a USA Today bestseller that equips leaders with tools to attract and retain young talent through genuine connection. In 2021, Chris shifted his connections outside organizations in writing his latest book, Savior Asks, which provides anyone with tools to become a better networker through authenticity and connection. So welcome, Chris. I'm so glad you're here to talk about connecting at all levels. But particularly my leaders are interested in how do we connect with various generations in a way that moves the business objectives forward.
Awesome. Well, I'm fired up to be here. Thanks for having me, Susan.
Yes, absolutely. So let's start. You have this obsession about connection. Tell me a little bit more about why that's so important to you.
Sure. So I'm an identical twin married to an identical twin. So, you know, you hear this saying that everyone goes into the world alone and they leave it alone. I'm only going to be leaving alone because I actually came in to the world with a wombate. My, my identical twin brother. I am actually hardwired for connection. So much so it's funny. My, my wife is an identical twin too, and I'm massively extroverted. I love being with people. Like that is what gives me so much energy, is getting super deep and real with people. And my wife, who's a huge introvert, I'm now actually in a separate house where I do all of my meetings because she's like, Chris, you just, you're nonstop. Like, you're so passionate. You're always talking to people, you're always bringing people in. Please, just work outside of our house. But, you know, that really got me on this road where I ended up going to Vanderbilt and majoring in Applied Human Psychology. And it wasn't really until my 68th failed job interview that I then fell into this digital ecosystem of digital marketing. And it took me a few lateral moves over five years, getting paid, like $28,000 a year that I finally found myself in 2006, helping to build, really, what's now become the social media, you know, interfaces that we all interact with. And, you know, if anyone remembers when Facebook was first created and they were the main pioneers in this social space, Mark Zuckerberg's whole purpose was to make the world a more connected place. And it was actually through that that I then went on and built a company to 400 people that I walked away from almost a year ago to really just try to change the world. And it took kind of just working on my main business and working with a lot of different executives and companies and doing the keynote speaking that I'm like, all right, this is what I was really born to do. Let's see how much impact we can have.
And what is your mission in terms of changing the world? In what way?
Yeah, so my purpose is to inspire and connect. And my metric of success, I hit rock bottom in 2016, which was actually the. The catalyst of me going and writing the Millennial Whisperer. In a that rock bottom moment, I took a month off, and I looked at myself as somewhat obsessed with connection. And I was living a massively disconnected life. Like, I mean, you know, I was ditching my kids, my daughters, my wife. I was hobnobbing and, you know, the. The yachts in can and playing the status game and my 400 employees, I. I wasn't connected with them. I was too busy trying to win all the big accounts, and. And I was disconnected with myself. My metric of success up until that age of 36 was beating my brothers at the game of life. And so it was in that rock bottom moment that manifested itself as, like, breakdowns and nervous things I'd never experienced before that I was like, okay, I'm going to double down on this thing that I know I hold true in all three realms of my life. I'm going to be there for my daughters and take them to school in the mornings and truly be present with them along with my wife. I'm gonna double down in my 400 employees and try to impact through them versus me just being the one on stage. And then lastly, I changed my metric of success to impact being had in any given day. And when my head hits the pillow, did I have the impact that I intended. And. And that's the metric of success. It's not money. It's not status. It's truly. Did I connect with someone and I hopefully bring them a new perspective or brightness to their life. And so, yeah, it was quite the transition. And it was nine months after that that I was introducing myself to a bunch of executives on a retreat, and I didn't know how to introduce myself. I was like, I'm not really the digital and social guy, but I'm kind of like the millennial whisperer. I got 400 employees, 98% millennials and gen zers. And these guys are like, man, those millennials suck. Right? Another one was like, yeah, half of my staff are VP or above because it's the only way I can keep them. And they all just started complaining. And I took in some of their questions and talked to them through this newer perspective of how did we get here? And, you know, I talked about how there are two main drivers for what's made millennials and gen zers different. One is the adoption of technology and social media, right? Even older millennials, 40 to 37, they didn't have smartphones, right? But 36, 37 and younger, they've. They all had brand, you know, iPhones with Snapchat and Instagram. And so there's that component. And then the component I talked about parenting. I was like, when I was parented, it was very authoritarian, right? And so when I stepped into the workplace, I was expecting that same thing of my boss. My boss would tell me what to do, and I would get in line. And I try to go above and beyond. You juxtapose that to, once again, 36 and younger. They're not even sitting at the dinner table talking about where what their grades look like. They're playing beer pong out back, ripping on a jewel, talking about who they just hooked up with. And so when those young people come into our workplace, they're expecting that same sort of connection and authenticity and almost mentorship from their bosses, and all they're getting is this authoritarian leader. And so there's this massive disconnect that, to me, it's about how can we start meeting in the middle around some of these things and where is it that we can focus to truly create an environment where every generation thrives?
Yeah, I know for sure. As I mentioned, our senior leaders that the Gen Xers and older millennials are. I hear it. You know, they're like, this is not camp. And I'm really struggling. And I try to be empathetic and I try to connect, but at the same time, we have the pressures to get you Know, meat deliverables to serve the client, not ourselves. Right. What are we here to do? And they're frustrated. And so what wisdom do you have to offer those leaders that I'm hearing about all the time, how frustrated they are with not understanding how to lead this generation and just feeling such a sense of entitlement? And it's just, I mean, honestly, I. It's like one said to me, again, again, this is not camp.
Right? Right. No. Okay, so one of my favorite stories is as I lead into what I call my 7030 role, and this is through, once again, that lens of how has social media not just impacted the millennials and gen zers, but all of it? All of us, right? We're all posting, right? And. But what it's done, especially with millennials and gen zers, it's created that the grass is always greener on the other side. And we've seen that reflected in the data as people have been hopping all around and as the data is now coming back and kind of like this post pandemic world, we're seeing 85% of Gen Zers that quit over the last three years regret that decision. And a lot of that is a product of this. And as I lead into my 7030 role, I will tell my team my most embarrassing story ever. And I was out in Sun Valley, Idaho, and I hired a fishing guide in between the wedding festivities. And so I turned this fishing guide and I was like, listen, dude, we were in our galoshes. We had the, you know, he had all the rods. We're, we're walking out the door of this lodge. And I said, all right, so I don't even care about fishing. You can catch the fish, I can catch the fish, but I just want the picture for Instagram of me holding it with the net in the back background. And then I turned to him, I said, and then I want a 15 second video. I go, have you seen a, like, Brad Pitt? And a river runs through it and this guy's just disgusted. And he goes, yeah. I go, okay, I want me Brad Pitting it, going back and forth in the river with the mountains in the background.
Yeah.
So let's go. Yep. And he just is disgusted. And he turns to me, he goes, you're gonna spend 600 on an Instagram post? I said, no, that's two posts, 300 each. Let's go. And that is what we are all doing. We are all posting this. And you especially look at it within these millennial and Gen Z sets. They're talking about their lives in the same realm. Right. Because they want to show this kind of place of a social hierarchy. And that leads me into 30% of your job and life is just going to suck. 70% should fire you up and fuel you up. And on your first week I want you to take your job description and fill out all that job description. What's in your 70% zone of awesomeness and 30% zone of suck. It is my job as your leader that generally speaking it's somewhere in that domain. And it does one of two things. One, when they go through, for me, it's like budgeting and excel and anything orderly. When I go through three days of it, I'm not going to up and quit. Right. But it also lets the leader know where is it that this person is excited and passionate about. And with that is opportunity. And that's actually, it's interesting as I go to some of these, you know, especially like prestigious world renowned companies, I'll do a panel and that's the first question I will ask. And in one case it was a global Fortune 50 brand. And I asked the panel of young rock star, they were all kind of asked to be a part of this thing. I said, what is the 7030 rule in place here? And someone finally was like, yeah, hesitant to kind of share. They're like, yeah, it's 70, 30 the other way. And I go, awesome. Well let's talk about that, right? They go yes, 70 jobs, 70% of our job here sucks. 30% is actually kind of cool. And I said, well that's, that's actually opportunity. And I turned to all these executives that had flown in. I said now it's up to you all to find creative ways to offset that. Right? Yeah, find passion projects, get creative. Like there's so many great examples of that. And so yeah, I like about what.
You'Re doing here is you're really setting the expectation first of all that it's not 90% at times, right. And life is going to throw challenges at us and we have to have the resilience to be able to move through the more difficult times because you're not going to escape them and you will grow from them and they'll actually, you'll look back on them and be like, wow, that was really tough. But that really built a lot of strength in me. And so what I like what you're doing is you're just really setting the framing up front as a leader you need to think about what is that, 70, 30, understanding what it is for the person. Right. So that you can help work and make sure that balance, but just to recognize that it's going to be challenging.
Absolutely. And you know, you look at the characteristics of Gen Z ers and millennials that are different. They are not as resilient, they are not as tenacious and they don't have near as much of an interpersonal muscle. And once again, that is a product of parenting and this move to digital. So it is up to us to reiterate those things at every turn, but to help them build those muscles. And I look at me like as a father of a 13 and 11 year old, two girls, those are the two things that I'm trying to hone in the most, is that this whole idea, when you see the person with the hundred dollar bills on your Instagram account waving it with, sitting on the Lamborghini like that, anything that seems too good to be true is because it is hard. And I also, I'm like, listen, I'm very upfront with how hard the entrepreneurial journey is. I'm like, I don't know if I'm going to be able to pull this off. Girls like, you know, I think there are, there is some realness to the stereotypes that we put in place with the generational differences. But it's up to us as leaders to help arm them with the tools to offset them.
This is great. What other strategies would you suggest leaders do to build greater connection and authenticity with the younger generations?
One of the common themes almost every single time, especially in the mid to larger organizations is allowing people to make lateral moves within that job or within that company. Right. To be able to make lateral moves. Because so many of them make it hard for candidates from the inside to move somewhere that they're passionate about. The other place is setting expectations in their first week around what growth opportunity looks like. So setting a job ladder. Here's what's in your job description. Now you can expect to be promoted into the next one one to two years from now. And it's not until you're doing every single thing in that next column that you're going to be promoted into it. Just those two things statistically will have a massive impact. Then you look through the leadership lens. One of the biggest gaps is the number one leadership trait Gen Zers and Millennials are looking for out of leaders is inspirational leadership. And inspirational leadership is oftentimes misinterpreted. And leaders all think they're inspirational. And it was actually doing work with Tony Robbins's team that Tony was like, you know, the biggest issue with, with inspirational leadership. And we're like, what? He goes, lae. I was like, what's lae? He goes, low ass energy. We have very few opportunities to bring our teams together in today's world. When we're bringing them together, get them fired up. Right. How can we use tactics? And even I've worked with a handful of like super introverted leaders and they're like, chris, I'm not inspirational. In one case, it was a doctor that had a new dental practice out of Charlotte and his name was Dr. Trey. And he was like, chris, can you help me brainstorm some, some ideas? I was like, what about how often you bring your team together? He goes, every Monday morning at 7:30. I said, what about if you use music? He goes, oh my gosh, I've got the best idea. And he hangs up on me. And it was six weeks later he calls me, goes, chris, I've got the best material for your podcasts and speeches. And it's every Monday morning at 7:30. All I do is I play Chaka Khan's tell Me Something Good over the loudspeakers. That's everyone's cue to go to the break room and just tell something good.
It takes the power of music.
You.
You know I wrote a book on the power of music, right?
Well, yeah, I mean, I'm a big fan of that. Exactly. Right. I mean, and it's, it's, it's so profound and, and it literally is just pressing play. I guess my last thing, and I, I know you're going to get fired up about this, is that 11% of people are in the job that actually matches their personality profile. And According to Bloomberg, 25% are in jobs that are deemed acceptable for their personality profile. Companies have got to double down and invest in tools like Enneagram to be a gift to their employees. Because a lot of times you got the wrong people doing the wrong trades for the wrong reasons.
Yeah. They're not. Or even understanding what's driving that person. Why are they motivated to be here? Even if you haven't done the. You have you ever asked that question? That's a very simple question. What motivates you? Right.
Exactly.
You would be surprised how many leaders never ask that question. I'm like, how can you lead if you do not know what motivates this person? But then if you wrap, put it in a wrapper of something as powerful as the Enneagram, where you get a real deep understanding of what their motivation is. But not only Their motivation, what their blind spot is. Right. Because if you're motivated by something, you're looking one direction, but there's something you can't see. So, gosh, as a leader, it's. I don't know, understand how people could even lead without having a tool like the Enneagram. Because with it's. It's like it gives you all the information you need, need to understand what you need to do. How do you inspire? And that's different by type, Right. How do you give feedback? Well, that's different by the person. And it's not just a generational thing. Right. It's. There's flavors within that. So I'm so glad you said it. And obviously. Yeah.
And you look at this neat. Like, the one thing statistically that comes up in every single study, whether it be the Deloitte Millennial study or any of the other ones you want to reference, is continuous learning. And I think a lot of companies or organizations will take their budgets for continuous learning and either give credits for getting some sort of education or sending someone to some convention where nothing really good happens. Yeah, right. Instead, they should be equipping people and investing in Enneagram and. And. And other tools like that to learn about how we're wired. Because there's nothing more beautiful than learning about ourselves and our strengths to then create a path to fulfillment.
That's what builds your other. It's. Because it's not just connection that you talk about it, but it's authenticity. And I think that these types of tools, when they're deep like the Enneagram, are very revealing and allow people to be more authentic. Because you're being authentic, you're taking a risk, they're being more authentic, they're taking a risk. And what often people say is like, wow, I feel. I feel a little bit more exposed. But it felt okay. Because people. This is me now. People know me. And you know what? Now I know them in a deeper way.
Absolutely. And you know what was. What's been interesting in this journey that I've been on? You know, the pandemic hits, and I'm like, okay, I don't know what's going to happen with the Millennial Whisperer and my books and speaking, but what's the book that I was really meant to write? I had done a guest lecture at Vanderbilt for the senior class. How to Network Like a Mofo was the title of it. And there were like a hundred students that came up afterwards. I was like, I think that's it. What if I Made it a call to action that in how we go about our networking and selling, we save our asks. Right. And that's now transitioned me into even you look at like recruitment. Right. You've got to take more of that mentality of creating that connection, saving your asks. Stop, you know, just talking like someone that is trying to check boxes and instead get to know them as a human. The common theme was that creating relationships is actually pretty easy. It happens all day, every day. It's sustaining and deepening them that's so difficult. And so I try to make it a part of my every single day duty to try to go deep and impact someone in an authentic way and inspire them.
Yeah, I love what you're about. You're creative marketing genius with your titles.
Oh yeah. I should be at this point having been in. Yeah, yeah.
So I love that. But also, look, what people don't realize is, you know, you're spending all this effort, you know, trying to get things by asking for this or asking for that. That's actually not where your joy is going to come from. Your true sense of joy is going to come from the deep connections and sustaining relationships, as you just mentioned. So we think getting all these other things, oh, if I could just get the introduction to this person and then jump on this bandwagon. And it just doesn't. It's all a mirage.
It is, it is. I've had so many interactions as I actually practice what I preach that would have never gone anywhere. And an example, I was flying back from a speech in New York. I was exhausted. I was doing a speech and then we ended up pushing two wounded warriors. And it was a 40 mile thing. It was like a late night flight and I was exhausted. I was getting off the plane and there was a gentleman as I was getting my stuff out of the overhead bin as we landed in Atlanta and he and his wife turned to me and they, they were like, dude, I love your Jordan ones. That's. That's all they said. His wife, his wife was like, I love your what? Jordan ones. My Jordan 1 shoes.
Yes.
And I looked down at their shoes and I'm like, I like your Jordan ones. He was like, so what's your story like? Your vibe and energy so good. I'm like, I'm an author and a speaker actually. Just push these wounded warriors who the streets. And it was crazy. I'm exhausted, I'm hurting. He was like, I'm a vet. He lights up, he goes, I'm a veteran. I'm actually an executive at CVS and blah, blah, blah. Like, what's your story? Do you live in Atlanta? Can we hang out that next week? He came over to my house for lunch. We ended up having lunch. We got super deep and authentic. We found out we had common friends, like, so now this is about six weeks later. He comes by every week and we're just hanging out and continuing to deepen that connection. And most people would have just taken that and not done anything with it. Right. But we have these tools like LinkedIn and Instagram and, and other things to. To curate and sustain that relationship and to deepen it to a certain place that it becomes this beautiful thing when it happens, when you least expect it as well. Yeah.
Getting the next person, just like finding the next job or the grass is greener, isn't necessarily going to get you where you want to go. How about deepening the relationships you have right now in your life and those people who stand by you, right, who know you, or if you don't feel like you have that, what can you do to build that and give more than asking exactly, exactly what? What's one thing that a leader could do tomorrow that would help build connection or authenticity with other generations? We've talked about some, but I want to kind of boil it down to, like, if you're not doing this tomorrow, what are you doing?
Okay. I'm going to make people feel really uncomfortable. And it is the art of the video text message. And bear with me, all right? Your team wants to hear and see from you as well as someone that you may have just met on a plane. Your fastest way to do that is not a text message. It's not an email they want to be able to. It's nor is it a audio text message, although that I think is a little bit more profound. When you send a video text message that's 20 seconds long and you just say, susan, that time we had on that podcast, freaking rock. Thank you for taking that time with me. When I send that to you. You were able to actually share, shorten the time or the amount of interactions it takes to ultimately get to that place where we feel at ease. Coupled with the fact, especially from like a rewards and recognition. You've got to understand your younger employees at every single turn. They did get a participation trophy. They did get, you know, they did get this constant reassurance by posting to Instagram anytime they felt a deficit in their self esteem. And when you come through and you send a video text message to them saying, thank you for going above and beyond or for whatever it is. Or maybe it's just that I'm thinking about you right now. You will make a massive difference. And you put that same thing in place with the networking side and people are like, chris, you know, I'm a boomer or I'm an extra. It's incredible to me as my most of the people I video text message, their average age is like 55 or 60. And now they're text. These executives of these companies are video text messaging me back. And they're like, Chris, this is kind of fun. Right? So everyone listening, Try a video text message and see what it does. And even though it feels awkward at first, I promise you it will be impactful.
And for those who don't know how to video text, what are you suggesting? Recording a video from your. The way you would take a picture, record a video and that's it.
That's it. So in everyone's like when you're texting back and forth, all you have to do is in that you have the camera and you just hold down that camera. That's it. And send it. And as long as it's under 30 seconds, it'll, it'll, it'll come still super high quality through. Don't use any outside. You know, I know there's a lot of like different email technologies. Don't worry about that. Just send a video text message. It's all right there on your phone.
Yes. And if, if as a leader, if you don't have phone numbers of people and don't want to go that direction, start using something like Lo Loom. It's made the biggest difference in our team where somebody has a question, just hop on loom and talk to it. And the tone comes through the. So much gets misconstrued all the time on this type of just written word. And if you can just. It's faster too.
Totally.
We always say leave a loom on it. I'm not sure what you mean. Could you leave a loom on it? Right. And now it's actually becoming my preferred way of communicating. So.
And it's. Yeah, yeah, there are lots of. And yeah, I mean, and even on LinkedIn. Right. Don't send them some long. Like just do the. Use the video component within LinkedIn to reply to stuff like.
Yes.
Watch what happens.
I love it. Well, thank you so much. Where can people learn more and how to connect with you?
Yeah. So my LinkedIn is forward slash Christopher Tough. My Instagram is Tuff Tuff to the number and then my website is Chris tough. C H R I S t u f f.me all right, well, thank you.
So much, and I'm glad you're here. This was so fun as well. That's what I also like about you is, like, there's this fun energy.
So awesome. Awesome. Well, thank you for having me.
If you like this episode, you're not going to want to miss my interview with Tommy Breedlove, who talks about the importance of prioritizing yourself and the essence of legendary leadership. Let's all lead the way. Hope you enjoyed today's episode, and I'd like to point you to the next important step. Hit the subscribe button to get notified when we release new content. I'll see you on the next episode of the Enlightened Executive. Sam.
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