The Bregman Leadership Podcast
Episode 107

Chester Elton

The Best Team Wins

How do you get a diverse, multigenerational team to work well together? According Chester Elton, management expert and author of The Best Team Wins, the answer is kindness. Chester and his co-author Adrian Gostick studied 850,000 employee engagement surveys and found that positive interpersonal relationships were the defining factor of great teams. Discover the Five Disciplines of Team Leaders, how to motivate millennials versus baby boomers, and one little policy you should implement to dramatically improve the relationships on your team.


Book: The Best Team Wins
Bio: One of today’s most influential voices in workplace trends, Chester Elton has spent two decades helping clients engage their employees to execute on strategy, vision, and values. In his provocative, inspiring and always entertaining talks, #1 bestselling leadership author Chester Elton provides real solutions to leaders looking to manage change, drive innovation, and lead a multi-generational workforce. Elton’s work is supported by research with more than 850,000 working adults, revealing the proven secrets behind high-performance cultures and teams.



Peter: Welcome to the Bregman Leadership Podcast. I’m Peter Bregman, your host, and CEO of Bregman Partners. This podcast is part of my mission to help you get massive traction on the things that matter most.

We are lucky enough today to have with us Chester Elton, who is a good friend of mine. I’ve described him as both Mormon and Canadian, which is sort of a double bogey for being the nicest guy that you’ve ever met. His cultural background lends itself to that, and he also is just the nicest guy that you’ve ever met. He is the co-author, with Adrian Gostick, of The Carrot Principle and All In. He’s a popular lecturer, and he’s an influential voice in global workplace trends. He’s the co-founder of Culture Works and advises leadership teams of numerous Fortune 500 companies. He’s a generally very smart, very engaging guy. We’re lucky to have him. Chester, welcome to the Bregman Leadership Podcast.

Chester: Well, thank you for that wonderful introduction. Canadian and Mormon, doesn’t get any better than that.

Peter: It really doesn’t get better than that. This book that we’re talking about … I should’ve actually introduced it, The Best Team Wins: The New Science of High Performance. It’s very much about what it says it’s about, which is how do you create great teamwork? How do you develop teams, especially teams that are multi-generational, that are multi-disciplined? Here’s my first question, which I’ve always, having worked with a lot of teams, been curious about.

As I’ve already said, you’re a super nice guy. How much of being effective on a team is based on general disposition, meaning we could create and look at and study the best teams, but how much of it is someone’s general personality, their willingness to sacrifice the good for the people around you, the general sense of caring for others, the general sense of pulling your own weight and doing hard work? We’ve all known people who are amazing on teams, and is there a science to it that betrays that idea, or is it really very much about you’re a nice guy and you care about people, and so you work hard along with them to achieve stuff that’s important to you?

Chester: Yeah, no, great question, long question, so thanks for that. It’s interesting that we had sort of five aha’s when we wrote the book, and it’s based on a lot of research. We’ve got a database of 850,000 engagement surveys and lots of case studies and so on. One of the things that really popped out to me was, when you’re putting together a team, a lot of times we do it backwards, to your point. We look at the CV. We look at your experience. We look at your education. What we found in the best teams was exactly what you mentioned, is that the best performing teams and the best performing team leaders, not only did they have good technical skill … I mean, that’s a given; you have to know what you’re doing … but they had tremendous soft skills. In other words, they did care about each other. They did take the time to get to know each other.

Especially, you know what? Our first big aha was the multi-generational team. It wasn’t just diversity in gender and race or even generation. It was cultural background. It was linguistic. It was are you a remote employee or are you all in one building? So, that diversity lent itself to leaders and teams that had to take the time to get to know each other and make sure there was the right cultural fit. So, this idea of soft skills was a really big aha for me. The best teams really were the nicest teams.

Peter: That’s great. You’re a very data driven guy. Tell us a little bit … you just mentioned that you did this research. You surveyed 150,000 people. Ground the rest of this conversation in the data.

Chester: Yeah, it was actually 850,000.

Peter: 850,000?

Chester: And the other piece to that was we have developed an online assessment for motivators at work. That what motivates me profile. And we had 50,000 people take that.

Peter: And that is an earlier book that you’ve written, What Motivates Me.

Chester: Right. And I’ll tell you what’s really interesting about that is that we were able to take that data and parse it out, and take a look at motivators at work. Did it differ by generation? And of course, it did. We took a really hard look at millennials in particular because now they’re the biggest part of the workforce. And, you know, I’m a baby boomer. I grew up where you got a job, you worked hard, you went from the mailroom to the boardroom, and you stuck it out. Thirty years was not unusual. Now we’re looking at a very mobile workforce and a very smart workforce. I was all about working hard, make money, get married, support your family. But millennial generation, which was really interesting for us … we looked at the top motivators there and it was impact, learning, and family. And I don’t like the work life balance idea. I like work life harmony. I don’t think with smartphones, we have balance at all.

You were just out skiing. I guarantee you there was a time when you went for a coffee, and you pulled up and you were working for-

Peter: Now, let me ask you a question about that. Do you not like that work life balance idea because in this world it has now become unrealistic, so we’re giving into the work life balance? Or do you feel like work life balance is a misguided drive?

Chester: Yeah, I think it’s a misguided drive because I think most people interpret work life balance as this sort of zen. I have work and I have life, and I keep them in balance. I think work is life, life is work. So, you know, you just find some harmony. I think anyone who’s really exceeded and become exceptional at anything doesn’t have balance. We just went through the Winter Olympics. Do you think those gold medal … do you think they had any kind of balance in their life? No, they were all in, in whatever their discipline was. The luge, the bobsled, whatever. So, I think there are times in our life where we know we’re gonna be out of balance.

Peter: So, let me ask you another question because this is very interesting. It’s sort of a departure from the book a little bit but you’ve thought a lot about this and you’ve thought a lot about what motivates us. I want to ask a question about people who, maybe I would be included in this, you would be included in this, people who really throw themselves into things and work very, very hard at them. So, you achieve things. Like you could be in the Olympics or you could write a bunch of books while you’re doing it, and the question is are we better off for that out of balance, drive, focused achievement orientation? Or, is it some dysfunction that we’re trying to make up for, some insecurity, and which we end up never making up for because you can’t really make up for insecurities. You just have to kind of live with them. And so, is it a misguided attempt at achieving something that will never ultimately be satisfying, or is it a really productive, useful, happy way to live?

Chester: So many interesting questions in there because we say shouldn’t family be our more important priority? And I go, “Yes, it should be.” And part of that is that I’m out of balance so that I can support my family and live in a house that’s got heat, which by the way, I don’t have today. Our pilot light went out. I digress. You’ve gotta focus, and there are times when you are out of balance. You’re out of balance when you’re in university. You’re studying hard, you’re getting grades. And I think this comes back to your core values.

You mentioned I’m a Mormon. I have certain core values that come with that. You’ve got a certain faith, and you’ve got core values. And as long as you’re true to those, where I say, “Look, I’m gonna be driven to achieve because I think it’s important and it’s a noble cause, and I wanna make a difference.” I’m also gonna make sure that I take the time to be present with my family and create those moments with my family so that my kids know that Dad’s there for them. And I’m gonna make the exception where I take time off from that incredibly driven moment to make sure that I’ve got time with my spouse, that I’ve got time with my family, that I’ve got time for my faith, and so on.

And so, it is … work life balance, it’s a balancing act. But for me, it’s about harmony. How do you start your day? How do you end your day? How do you make sure that you’ve taken the time to get all of those things done without sacrificing too much in one end? Now, I will say that I’ve never met a driven person and a high achiever that at some point didn’t step back and say, “I wish I’d spent more time with my family.” We all have that regret. That’s why I’m sure you took the weekend, and you took your kids and you went skiing because there weeks where they just didn’t see Dad.

Peter: Right.

Chester: So, you wanted to make sure that you had the time, and we do that. So, I really do think in this hyper-connected world that there is a total imbalance. Can we find the harmony? I think we can, but you have to be disciplined about it.

Peter: Yeah, and it actually might be the way, we might just take that drivenness. You mentioned skiing. I just went on vacation with my family for a week and we didn’t, this is just my style, we didn’t sit on a beach or sit in the living room and watch movies. We went out to Jackson Hole and skied all the steeps and kind of pushed ourselves and skied. We were up at 6:30, and maybe I feel sorry for you kids, maybe I feel excited about it. I don’t know. It kind of depends on how things play out but it was very energized and maybe it’s just sort of taking that, again, personality type and channeling it in a way that meets the various needs to create harmony.

Chester: Well, and to get back to the book, this idea does play very well into how you built your teams because we talk about managing to the one. That old school was we treat everybody the same because that’s fair and those are the rules. Now with so much diversity, you really need to know each person on your team, what motivates them, how to integrate their talents, and I think it’s the same in our personal lives. For some of our kids, yeah, they wanna be up at the crack of dawn and go hiking and rowing or skiing, and there’s other kids where “I just wanna sit and talk to you, Dad.” And this was another big aha, and we’ve had it now three years by the way, is that the principles that create successful teams, the principles that create great workplaces, are the same principles that create great relationships and great families.

The expression is work is life and life is work. The principles that we use to communicate better at work are the same principles we use to communicate with our spouses and our kids.

Peter: I wholeheartedly agree, and I think it’s really important. So, you were just talking about manage to the one, which is discipline number two. You talk about five disciplines in the book. And, that feels really important. I’ve written an article about why I’m not crazy about personality assessments because I’m much more interested in really understanding, being curious about people and understanding what makes them as individuals tick, which is so many variables that you can’t put them in one of 16 boxes. You talk in the book about aspirational conversations in relation to this. Can you describe them?

Chester: Yeah. I think traditionally it was we’d have a year end review, and nobody liked doing them, and they’re always uncomfortable because the first five minutes I’d tell you how great you were, and the next 55 minutes I tell you were you needed to improve. So, the aspirational conversations, what I love about this is it’s getting to know the one. And where we sit down and it doesn’t take a long time. It’s 15, maybe 20 minutes. And I’m asking you questions like, “Peter, have we kept our promises to you? We recruited the heck out of you, we brought you in, we made some promises. How are we tracking?” I’m asking you questions about, “Hey, what have you seen that works well at other companies you’ve been at or other experiences that we could apply here? Be innovative. Give me your ideas.”

And I create a safe place to do that. And questions like, “Where do you wanna be in three to five years from now?” I love the question, and it’s an interesting one, and you have to have a lot of trust is, “Look, have we done anything that might cause you to leave us? Like are you tracking?” You know, the conversation about where you want to be three to five years from now is your career path. And one of the great studies we looked at was the Google Aristotle study, which you might be familiar with, where they looked at 130 teams over five years. And said, what are the most innovative traits of these teams because Google’s innovative. It was emotional security was the number one thing. And we found that Google engineers and whatnot didn’t want to be micromanaged in their work. But they did want to be micromanaged in their careers.

And I thought that was really interesting. So, give me the assignment, let me do it, let me be creative.

Peter: That’s so interesting.

Chester: Yeah. And you know, the other side is I really do wanna know where this is leading? What’s my career path? What am I gonna learn? How am I gonna grow? How am I gonna develop? Interesting stuff.

Peter: I can hear some leaders say, “They’re asking me to be very paternalistic. They’re asking me to let them do whatever they want to do, but then, really make sure that they continue to develop their careers and get all the rewards. So, I’m feeling a little stuck between a rock and a hard place. I have to just let them do whatever they want to do, and on the other hand, I have to really determine and drive the success of their career.”

Is that a fair ask?

Chester: No. I think it really depends on what kind of industry you’re in and what you’re doing. Do I need people to show up and work from 9-to-5, I’m in retail. Yeah, that’s a little different. Google I think is almost the exception to every rule because they’re just so crazy and innovative.

Peter: Right.

Chester: When you go in there though, you’ll see an incredible discipline. I mean, they didn’t get there because they just let people take off and do whatever they wanted to do.

Peter: Right.

Chester: They have hard deadlines. They’ve got smart people that get it. What I’m saying is the new reality is, is yeah, it is a little bit … I don’t think of it so much as paternalistic. I think it’s more relational. You’ve gotta have more of a relation with your people. You’ve gotta really understand.

Peter: And I’m hearing relational and I’m hearing trust.

Chester: Exactly.

Peter: What I just described to you was a response that lacked trust, right?

Chester: Right.

Peter: And so, it’s kind of relational along with trust. They’re actually going to hold their side of the bargain. They don’t want to be micromanaged but they’re going to work hard, and they’re not going to use the system.

Chester: Exactly. And that’s why these aspirational conversations are so important. And we have them frequently. It’s kind of a monthly thing, or whenever we need it. And you keep checking back and tracking. “Hey, you mentioned that you wanted to get into RND. Well, I’ve got an opportunity for you to partner with some people.” You know what I mean?

So, that’s … and relationships build trust. You know old school was I kept information very proprietary. New school is it’s very transparent. And that’s what these conversations help do. It’s very relationship-based.

Peter: I want to take a quick step back to discipline number one. You talked about it a little bit. Understanding generations. We sort of started out the conversation like that and you talked about the motivation survey. What I found interesting as I was reading the book is when you look at the top three motivators of the millennials, the Gen-X, the boomers, and the traditionalists, and you look at the bottom three motivators, they’re kind of the same. The extent to which everybody changes, you still impact number one, learning number two, and family number three. So, as I read that, I thought, huh, there’s a story that says the more things change the more they stay the same and we have all these different kinds of people but their top motivators and bottom motivators are pretty similar.

And I guess my question is, is the challenge that how these things express themselves are different by generation?

Chester: Exactly. You hit it on exactly right. Yeah, we all kind of … we all wanna have impact. We all wanna continue to learn, we all wanna make a difference. But the way we express it is so different. With baby boomers, we tend to be very structure-based. With millennials, it’s very much social-based, it’s sort of this new power. It’s I crowdsource. It’s I get a lot of people involved. I’m not afraid to ask a bunch of different people their opinions. It’s much more collaborative.

So, you’re right. And see, that’s the key is understanding how it’s expressed. Understanding how we get there.

Peter: It’s a very hopeful message because understanding that oh, we actually do care about the same things but we approach them differently is a bridge that can really be leveraged to create relationships between the generations.

Chester: Exactly. And so well said. I love that idea of the bridges. We, to me, it always comes back to communication. It always comes back. “Do you understand what I said?” And we have these issues with our kids. Again, work to family. My son, Garrett, is so interesting. You’ve had this experience. You call your kids on the phone, and they text you back. And so, we set some ground rules. I said, “Garrett, you’re out west. You’re going to school. When your dad calls, pick up. We can text back and forth, that’s fine. But when I call you, pick up.” And he does. We got that down. There were some threats there about maybe not paying his tuition or his rent that I think incentivized him to pick up.

But, the point is how do we do that? Do you wanna meet one on one? Do you just wanna model? How often, what’s the cadence? Do you wanna check in weekly, or is it monthly, or is it quarterly? It’s establishing how we communicate, and in this diverse workplace, you may have six or seven different ways that you’re gonna communicate with people on your team.

Peter: It really does seem to come down a lot, each of these disciplines, to communication because any time you’re in a relationship with other people, you’re working to create a great team, right? The idea of this book is the best team wins. By the way, if you’re just joining the conversation, I’m talking with Chester Elton about his new book, The Best Team Wins: The New Science of High Performance. And teamwork is all about communication. It’s all about what you’re able to hear, what you’re able to speak. And you talk about this third discipline, speed productivity, being a critical element of an effective team so they can work faster and smarter. It’s the bottom line to what seems the criticality of clarity.

Chester: Exactly. And a lot of this has to do with how you onboard, how you hire. Again, that cultural fit. Old school is you had time to develop people, and you could mentor, and if you weren’t productive right away, we had time to recover. Well now, particularly in this mobile workforce, well you maybe only have people for a year and a half, two and a half years. You don’t have six months to get people up. So, this idea of quickly mentoring. One of the great companies that we studied had this mentoring program that was so interesting. On your first day of work, you’d sit down, and the manager would say, “Look, here are five people in the organization that you need to get to know. Now, they’re not on our team and they’re not even in our department. But these are people that you need to get to know because they’re gonna help you get things done in our organization. There might be somebody in marketing, somebody in sales, somebody in accounting, somebody in collections, whatever.”

And I love that whole idea of immediately breaking down silence and barriers.

Peter: Yes. Chip Heath wrote The Power of Moments most recently with his brother, Dan, andhe and I were talking about it. ne of the key things he talked about is the onboarding process which is so often like, “Here’s the password to your computer. Have a good day.” Right, but it misses such a great opportunity. I loved how much he talked about the onboarding process because it’s really a moment that should create connection and create direction.

Chester: We had this little breakfast thing we did down in Atlanta, and one of the healthcare groups was there and talked about creating your first day at work being a forever moment, that you would never forget it. And it went completely overboard. I could just see everybody else in the room starting to roll their eyes like, “We’re not doing that.” But it was to the point where when you showed up, they literally rolled out a red carpet.

Peter: That’s awesome. That’s how it should be.

Chester: I thought that. Why not? Because so often when we hear the horror story. To your point, I came in to, “Oh yeah, look, you’re desk isn’t ready. Your computer’s not ready. Your security pass isn’t ready, but we’ve got a stack of forms for you to fill out for your healthcare plan.”

Peter: Right. Right. Interesting.

Chester: So, why not? And, they would take them around, and people would cheer and celebrate, and they had their badges and everything was ready to go.

Peter: Right.

Chester: Why not?

Peter: When I think about this, and I think about effective teams, a lot of what we’re talking about is relationship and affiliation and connection.

Chester: Right.

Peter: What surprised me when I looked at this, and maybe we’re going back to your previous book, which is also an excellent book, What Motivates Me, is the research that you’ve done around motivation. That connection and affiliation didn’t come up as a top three motivator. That people maybe have connection with their family, but the idea of really being connected to the people they work with isn’t a top motivator, which sort of surprised me. And you look at the Gallup Research that says, “Do I have a best friend at work that’s a determinant of engagement?” I’m curious about your observations about that.

Chester: It’s really interesting. Earlier, you said you had a problem with personality assessments because you didn’t wanna be stuck in a box, and we were very careful about that when we did this, that you were a blend. And so, when you take your motivators, we put them in these various identities, we called them, we said, “Look, be very careful. You’re not just one thing. You’re a blend of two or three, and one of those is caregiver.” And the caregiver is that relationship connection part. That’s where family shows up. That’s where empathy shows up. And that’s those connections, so it’s very interesting as we started to work with teams and we used sort of the assessment as a baseline to start to communicate better.

Peter: Right.

Chester: To clarify, I understand family’s important to you or social responsibility is important to you, let’s understand what we have in common, what we have that are differences, and what we have that are unique to up that communication. So, it’s there. It’s maybe a little more subtle, not so much in your face. But the idea of empathy and family and being a caregiver is very much what you’re talking about.

Peter: I want to shoot through these next two disciplines, discipline four and five, because we’re running out of time, but I’m curious about this challenge everything, which is discipline four. And any advice you have for people about how to challenge and inspire innovation through healthy discord, which is what you talk about, without alienating. Maintaining this thing that we’re talking about. A relationship and affiliation, and I’m in a number of situations where I’m watching people say, “Oh, I can’t say that to that person because they’ll react really poorly and then I’ll lose my relationship with them.”

What advice do you have around that?

Chester: Yeah, and this came from Google, this came from Bell Helicopters, from a lot of companies that we looked at that were very innovative. And you’ve gotta set the ground rules. And you talk about what the ground rules are. And that we have to be able to share everything. It comes back to a lot of the things we’ve already talked about. Do I have a relationship? Do I trust this person? Is it safe? So, we create this safe space. And we have rules, like Bell Helicopters says, “Look, no laughing or ridicule. We talk about ideas. We debate ideas. We don’t criticize people. We criticize ideas.” And that’s … now, I’ve got a great tactic for you. I’ve got a very dear friend, he’s one of the best leaders I’ve ever met. His name’s Scott O’Neill. He works in sports, so he was at the NBA, he was at Madison Square Garden, and now he’s with the Philadelphia 76ers and the Devils. And he loves … he says, “Look, harmony’s overrated. I want you to challenge ideas.” He also has this rule that says we cheer for each other. Okay? So, as soon as it starts getting heated, as soon as it starts getting personal, he’s got this thing he does that’s, “Hey Peter. I don’t mind a healthy debate, but I don’t get the sense that you’re cheering for me on this one.”

Peter: That’s great. So he calls it out, and he goes, “Remember, it’s about relationship, not task.”

Chester: Exactly.

Peter: Or not just task.

Chester: And what I love about that, just when I said it, your reaction, everybody in the room kinda goes, “Yeah, you are clearly not cheering for him.” And it lightens the moment. You say, “Let’s get back on track. What are we solving for here? How are we gonna get there? Let’s get back to the idea. Let’s not make it personal.”

Now, what I also love about this is, he says, “Look, when you look at your team, who are you cheering for?” And then he says, “Who are you not cheering for?” See that’s the tough part. How do you build a team where you know there’s a misfit. You know there’s not a good sync here. How do you work that because your team gets who’s not pulling their weight long before you do. And they’ll blame the teammate for a certain period of time but then the longer it goes, they blame you because you can fix it, and you didn’t.

Peter: Right.

Chester: So, this idea, who are you cheering for?

Peter: That’s great. And then you’re alluding to something I think which is also important, which is a certain lightness and sense of humor is important because when we start taking ourselves too seriously, then it becomes very difficult to manage the fluidity of relationships that often have ups and downs, and people don’t always act perfectly, and you kind of have to be a little light about it too.

Let’s give me one sentence on this last discipline five, don’t forget your customers.

Chester: Well, we’re doing all this stuff to create a great customer experience, and we’ve got a great saying. We say, “Look, the customer experience never exceeds the employee experience.” So, never forget if we’ve got a great team and great kumbaya but we don’t sell anything, it doesn’t matter. It’s all about getting to the customers. And you know, I know we’re kind of running out of time but, there’s a story that we start the book with that I love to tell.

Peter: I love it. I love the story, so tell it. Chris Hatfield?

Chester: Chris Hatfield, yes. Canadian astronaut. He was basically on the back of the-

Peter: Of course, he’s a Canadian astronaut.

Chester: Of course he is. Any way, what I loved about what Chris Hatfield did is he was commander of the International Space Station. Six big guys in a very small tin can for six months. And they prepared for 12 years. That’s the part that really struck me. And again, multi-generational team. Language difference. He had three cosmonauts, two American astronauts, and himself. And he really made sure that not only did they train together and were they smart, they had a relationship.

Peter: Well, and, where did he move?

Chester: Exactly. He spent two years in Russia to learn fluent Russian. So, again, back to that communication.

Peter: That’s amazing. That’s an amazing part of the story.

Chester: So, he talks about the fact, he says, “Look, we exceeded every goal that we set for six months, and yes, we were disciplined, we were smart, we knew what to do, and we knew how to do it.” He says, ” The success though is that we had one unwritten rule. And it was this: that every astronaut had to perform one random act of kindness for every other astronaut every day. It was every day.” And again, back to the soft skills.

Peter: Sometimes anonymously.

Chester: Well yeah. I’ll clean up. Let me help you with the calculations. I’ll cook dinner, or whatever it was. And he said, “Because of that, we never had a heated argument. We never had hurt feelings. And no one ever raised their voices.” He says, “Because when you look at it every day, what’s the message? What are we communicating? I’m cheering for you. You’re on my team. I care about you. I’m here for you. I love you.” Those are soft skills, even in the Space Station.

Peter: That’s great. Chester, thank you so much for being on the Podcast. Chester Elton. His book is The Best Team Wins: The New Science of High Performance. It’s a fantastic book. I already am thinking of people that I want to give it to so it’s well worth the read. Chester, thank you so much for being on the Bregman Leadership Podcast.

Chester: Absolutely. Call me anytime. This is great fun.

Peter: I hope you enjoyed this episode of the Bregman Leadership Podcast. If you did, it would really help us if you subscribe on iTunes and leave a review. A common problem that I see in companies is a lot of busyness, a lot of hard work that fails to move the organization as a whole forward. That’s the problem that we solve with our big process. For more information about that, or to access all of my articles, videos, and podcasts, visit Thank you Clare Marshall for producing this episode, and thank you for listening.