March 1, 2020

JF2007: Understanding The New WorkForce With Chris Tuff #SkillsetSunday

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Chris Tuff is an expert in working with millennials and getting high levels of production from them. His new book “The Millennial Whisperer,” explains that there are two different types of millennials; the “Snap-Chat” and “Oregon Trail”. In this episode, you will learn about each of these two different types so you will be better prepared when you are looking to build your own business and hiring help for the first time. He also shares some great stories to put you in the seat of each generation so you can have a better understanding of why they think the way they do so you will be better prepared.

Chris Tuff Real Estate Background:

  • Expert in working with millennials and getting high levels of production from them
  • Youngest partner in the 100-year history of Atlanta-based advertising agency, 22squared, where he turned a team of Millennials from an “investment” to a major profit center
  • Based in Atlanta, GA
  • Say hi to him at 

Best Ever Tweet:

“They want to hear from you where it is you’re making mistakes, where it is that you’re gaining ground and why you’re making the decisions that you’re making. They want context, they want to see the full picture.” – Chris Tuff


Theo Hicks: Hello, Best Ever listeners, and welcome to the best real estate investing advice ever show. I’m your host, Theo Hicks, and today we will be speaking with Chris Tuff. Chris, how are you doing today?

Chris Tuff: Awesome! Good to catch up.

Theo Hicks: Absolutely, Chris. I appreciate you coming on the show. Chris is actually a repeat guest, so make sure you check out his first episode, which we will have a link in the show notes. Since he’s  a repeat guest, we’re going to do a Skillset Sunday, because today is Sunday; we’re gonna talk about a specific skill that Chris has, and how that could apply to you as real estate investors.

Before we get into that, a little bit about Chris’ background as a refresher. He is an expert in working with millennials and getting high levels of production from them. He is the youngest partner in the 100-year history of Atlanta-based advertising firm 22squared, where he turned a team of millennials from an investment to a major profit center. He is based in Atlanta, Georgia, and you can say hi to him at, which we will also link to in the show notes.

Chris, before we hop into the skill that we’re gonna talk about today, which is going to be the six ways the business landscape will change as baby boomers retire and millennials take over… Do you mind telling us a little bit more about your background and what you’re focused on today?

Chris Tuff: My background – I grew up in the tech space; I was one of the first advertisers to work directly with Mark Zuckerberg right when he was graduating out of the colleges into the real world. People ask me what he was like back then, and I will attest to how far he’s come with his interpersonal communication, because I sat at a dinner with him and he didn’t say one thing the whole dinner; it was like a group of us…

So I kind of fell into this niche spot within the digital social media/emerging media world, and grew within that niche to one of the leading experts and go-to people, which brought me to my agency where I’m a partner (22squared) ten years ago… And it was during that ten years I’ve always been surrounded by millennials. And I was so sick and tired of everyone taking them down that on an executive retreat I felt inspired to introduce myself instead of as the digital and social media expert, which I had for so many years, I was like “I don’t really know what I do anymore, but we’ve got 390 employees at our firm and I’m kind of like the millennial whisperer.”

And it was from that point forward that Tommy Breedlove, who I didn’t know at the time, who has turned into one of my best friends – he challenged me to [unintelligible [00:03:36].29] he goes “You’d better write that book.” And I wrote the book. Here we are, nine months later we’ve sold over 50,000 copies of it, and we are now trying to really bring it into the world, and we’re gonna be releasing an online work series, training series, we’re doing a bunch of consulting gigs at Fortune 50 companies around the U.S, and I’m finally starting to feel like I have the impact that I intended this book to have.

Theo Hicks: What’s the title of the book?

Chris Tuff: It’s called The Millennial Whisperer. For those that have not spelled “millennial” recently, it’s a difficult word to spell.

Theo Hicks: It really is.

Chris Tuff: Two l’s and two n’s. Some people do two l’s and one n, so yeah… is where you can find a lot of this stuff, and you can find my book on Amazon and your local book retailer.

Theo Hicks: Perfect, perfect. So the skill we’re gonna be talking about today is basically how the business landscape is going to change as the baby boomers exit the workforce, and the millennials make up the main part of the workforce… But one thing I wanted to ask you – because I see a million different definitions, quite literally, of what a millennial is… So from your perspective, what is a millennial?

Chris Tuff: 1981 to 1996. And I set out in my book, The Millennial Whisperer, that it’s really two different generations, and it’s what I call the younger millennials or the older millennials. What makes them different are two main factors, which is when they adopted technology in their lives, and then when the recession of 2008 either hit them or their parents.

So instead of trying to cast a wide net, like a lot of us do – instead of doing that, I actually treat them as two very different generations within that. So 1981 to 1996. In the application that’s 23 year olds to 37 year olds.

The ones that are graduating right now  – that is actually gen Z. So what I tell everyone is if you can get the younger millennials  – and I’ll talk about some of these, obviously, coming up – you can also get gen Z. But don’t even try with the younger millennials until you get the older millennials. We’ll talk about that.

Theo Hicks: So 1981 to 1996.

Chris Tuff: Correct.

Theo Hicks: So you say there’s two different generations… So 1981 to what would be older?

Chris Tuff: I would say late ’80s to 1990, and then younger millennials – really, I call them Organ Trail millennials, because older millennials, they played Organ Trail as their computer indoctrination in high school… And younger millennials were given a brand new iPhone with a Snapchat account on it, and that’s why I call them Snapchat millennials.

So I think that if you can ask “Oh, did you play Organ Trail, or were you on Snapchat?” and people will either be like “What’s Organ  Trail?” or they’re gonna say “Yeah, I’m all over Snapchat.” But there’s a nondistinct line with any of this stuff. The important piece is to at least look at it differently.

Theo Hicks: Okay. So let’s go into the skill… You can take this any direction you want. Or we have six particular ways, so if you wanna just go down the list of six, and then I can ask follow-up questions after that…

Chris Tuff: I can do that, yeah. Absolutely. Okay, so I’m gonna bang these out… And this is in no particular order. I would say one of the big things that people can start seeing in what millennials are gonna be changing their (especially) work environments around is work flexibility. If you look at what millennials are looking for according to the Deloitte Millennial Survey of 2018, you will find that work flexibility is one of those main pieces that they are demanding of their organizations. So one, work flexibility.

The second piece is that they’re looking for different things in their leadership… And the two pieces that are super-important are 1) inspiration, and 2) autonomy. And I can talk more about what those look like.

The third piece that you’re gonna start seeing in terms of this shift is boomers retire and millennials take over is millennials are demanding purpose out of their companies that they work for, but also they are demanding that they give back to the world around us and our environment. So if you don’t stand for something and if you are not looking into LEED certification for your buildings etc. you will be losing clients. So it’s super-important, this over-arching purpose piece… And that only gets more important as you look towards younger millennials and gen Z.

The next piece I would say is that our conditioning to brand loyalty, as well as employee loyalty has gone out the window, and that will continue. So the idea that someone might stay for 5-10 years to get the watch or the reward that your company might look for, that will continue to take the trend that no one’s gonna be staying in places for as long as they were conditioned to, or at least the boomers were conditioned to. So be ready for that brand loyalty flip in terms of employees, but also in terms of businesses.

People are willing to ditch businesses overnight if they find a better product or one that stands for something that’s more important than the other ones. That’s why these big CPGs and massive companies have been struggling so much in this new world, where trends move faster than ever before.

And then the last two things that I would add to that is reward and recognition for your employees – if it’s not at the core of what you’re doing, then you’ve gotta start bringing it to the core of what you’re doing.

One of the big pieces of what makes this next generation and the one following it so different is there’s a lot of truth to the fact that they are products of helicopter parents, as well as anytime they wanted any sort of recognition or boost, they would post to social media and get it; when they post a picture, they get their 120 likes, and if they don’t get their 120 likes, they take it down… So making sure that you have a program and pieces and tactics in place to reward and recognize your people.

And then the last piece that I’ll add to it – and this is more tactical for the listeners, but with work flexibility, as well as the trend that we’ve been seeing in terms of open work environments – I think we’re gonna see massive transitions there. And I’m not gonna tell you exactly what those transitions will look like or what the workplace of the future should be, but I can tell you, incorporate your people or the employees of the companies that you’re working with, to help dictate what those spaces should look like. Make them a part of the process. I think that’s my probably juiciest for this discussion, of things that people that are listening can do differently. I can rant about any single one of those.

Theo Hicks: Okay, before you rant about any one of those, something you said multiple times when you were going through that is the conditioning; the reason why the business landscape is gonna change is because millennials were conditioned different than baby boomers. You gave a few examples of that, but what are some of the main differences in conditioning that millennials went through compared to previous generations?

Chris Tuff: Well, the two main pieces are the recession and technology. If you look at just technology — one of the things I emphasize to everyone is that what I’m saying is not that millennials are the best generation ever; what I’m saying is that this next generation and the one following it, gen Z, have a lot of good and important points that we need to start incorporating into our businesses and our decision-making, and use them as the catalyst towards change.

At the same time, there’s a lot of things these next generations can learn from us. They can learn from boomers before they’re gone out of our corporations and retired, because along with gen X’ers — so if you look at that whole picture, technology is massively important, but the other side of it is true as well, where we’ve gotta help our people build that muscle with interpersonal communication.

And if you look at even the simplest of things, the conditioning is just that older millennials and gen X and boomers in order to just flirt with someone they had to pick up a phone, they had to call a house, they had to talk to a parent, before they even got to this person on the other side. And then they would have to set up with that person (whoever it is that they wanted to flirt with) a time to actually meet up in person to get the permissions etc. So all of that built interpersonal muscle, it builds this EQ, that you  compare that to a first flirtation of a younger millennial and gen Z’er is actually all happening on their back, in one moment, via Snapchat or an Instagram story.

So it’s up to us to help build that in, and it’s why I talk about rules that I have in place for the younger millennials and gen Z’ers that are entering our workforce. If you’re in the same building, as people, you’ve gotta walk your butt over to their seat, and not IM, and not text, and  not do a lot of these things that they are conditioned to and comfortable with. So two main places is that conditioning piece…

I talked a lot about the technology influence, and then also the helicopter parenting that a lot of that millennial generation was a product of… But then you look at the recession of 2008. And what’s scary is that any older millennial that went through the recession of 2008 – they built a resilience into their lives, because they had to experience what it was like to go through a massive recession while having a job or losing their job. So there’s more of that entrepreneurial spirit and ability to move around, from shop to shop.

The younger millennials saw their parents lose their jobs while they were in school, and then they inherited a bunch of student debt as a product of that, and are actually looking for a place where they can hang their hat for a little bit longer. And then you go into gen Z, and gen Z – they hardly even remember what it was like to go through a recession. So their conditioning is very different as they enter the workforce, whereas everyone else is like “Uh-oh, when is this all gonna end? When is it gonna come tumbling down?” These guys are just whistling as they rock and roll… And a lot of their priorities and what they’re looking for are different because of that, which is this move to purpose and impact on a worldwide scale etc. So that’s my quick rant there.

Theo Hicks: Okay, we’ve got a little bit more time left, so… Of those six, the one I wanna focus on is number two, so different things in leadership. I think that’s something that as real estate investors – if you wanna grow your business, you’re gonna need to create your team, and you’re gonna have to work with millennials. So me as an investor – how should I be a leader if I want to attract millennials, if I wanna keep millennials and I want to get a lot of productivity out of my millennial employees.

Chris Tuff: Sure. So the biggest thing is what millennials are looking for more than anything else is inspirational leadership. And the unfortunate side of what comes along with inspirational leadership is most leaders think they’re inspirational, whereas in fact they’re not. It’s why I created the millennial leadership assessment, which can be found on my website… But the millennial leadership assessment actually asks your people whether or not that leader is inspirational, among 7 other points.

So the first piece is you’ve gotta be an inspirational leader. If you’re not an inspirational leader, maybe you’re more of the order person, and maybe you’re more of the operations side… So pair yourself up with someone that is inspirational. We’ve gotta look at pairing up teams and leading teams, versus asking someone to be all things to all people.

The second piece of leadership is autonomy… And the best example of autonomy when writing this book that I got was Ben Kirshner, who Forbes called out as the number one boss for millennials. He and I had a discussion about what autonomy meant, and he reminded me of this thing that he tells his team every time they meet; he goes “It’s up to YOU to protect this house.” I said “Well, tell me more.” He was like “Well, it comes from an UnderArmour campaign”, and anytime I get together with my team I tell them – whether it be a culture thing, whether it be unlimited paid vacation, whatever it is, I tell them “It’s up to you all to protect this house.” So I push down that control, but I also emphasize the fact that we’ve got something worth fighting for. I thought that was a great explanation of how you can take autonomy and bring it into your workplace.

Then the third piece of leadership that I’ll just quickly touch upon is transparency. A lot of times when people hear about transparency, they think that it either needs to be monetary transparency, or on the other side vulnerability, where they have to cry in front of their people… And it’s neither one of those things out of the gates. They want to hear from you where it is that you’re making you’re making your mistakes, where it is that you’re gaining ground, and why you’re making the decisions that you’re making. They want context. They wanna see the full picture. And what they’re looking for in transparency is for you to help build that for them. Interpret it that way, versus a lot of the other ways.

If you do just those three things you’ll see a massive improvement in both morale, retention rates, as well as ability to attract the right talent.

Theo Hicks: Alright, Chris, is there anything else that we haven’t talked about as it relates to the change in the business landscape as boomers retire and millennials take over that we have not talked about already?

Chris Tuff: No, but the one thing I’ll end with is a lot of the times, especially when talking about this move to work flexibility, where you ask any business leader if they are willing to provide the infrastructure for their people to not be stuck in traffic on Fridays for four hours, and to give them four hours back to their bottom line or their billable rates or whatever it is, “Are you willing to make the changes to let that happen?” and a lot of the times their main obstruction/barrier to doing that is “I had to do it this way. Why don’t they?”

So I encourage everyone, especially in regards to work flexibility, is find a way to at least move in that direction, because it’s such a simple fix that will alleviate so many of the issues, as well as probably have the most immediate impact on morale, as well as ROI and bottom line.

Theo Hicks: Perfect. Alright, Chris, I really appreciate you coming on the show and sharing your wisdom on millennials. I definitely learned a lot, and I think the Best Ever listeners will as well. Again, Best Ever listeners, try to think about this advice and process it and figure out how you’re gonna apply it to your business.

Just to quickly summarize what Chris went over – we’ve defined what a millennial is, 1981 to 1996, and this is my first time hearing about breaking it into the younger and the older… The Organ Trail millennials and the Snapchat millennials. I really like those names. Basically, the difference is when they adopted the technology, and then whether the recession hit them or their parents.

Then we went over the six ways that the business landscape will change as baby boomers retire and millennials will take over. I’m just gonna quickly run through those, but if you relisten to the episode, we went into details on at least two of those.

  1. Work flexibility
  2. Different things in leadership
  3. Demanding a purpose out of their company
  4. Brand loyalty and employer loyalty is no longer really a thing
  5. Reward and recognition of millennial employees
  6. Open work environments, and making them a part of the process of creating their work environment.

We also talked about the differences in conditioning between the boomers and the millennials. If you want more details on these six different ways, as well as more details on just the millennials in general, make sure you check out Chris’ book, The Millennial Whisperer, which we will link to in the show notes.

We also mentioned a survey that you can download, the Millennial Leadership Assessment that will let you know if you’re a good leader or not by interviewing your millennial employees.

Chris, thanks again for joining us today. Best Ever listeners, thanks for tuning in. Have a best ever day, and we’ll talk to you tomorrow.

Chris Tuff: Thanks!

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