Ep 063

It Pays to PLAY & Building a Winning Workplace Culture


Kristi Herold

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Inside This Episode

Today, I’m chatting with Kristi Herold, a workplace culture expert who has built a multi-million-dollar global organization called JAM.

Kristi founded JAM in 1996 and grew it into one of the largest adult recreational sports league providers in the world. When the 2020 pandemic forced sports to pause, Kristi and her team pivoted to helping corporate teams around the world improve their culture by connecting people through PLAY.

She’s also the author of It Pays to PLAY – How Play Improves Business Culture, which is her guide to helping organizations playfully connect with their teams in order to improve retention, engagement, and innovation while also benefiting employees’ physical and mental health, and the company’s bottom line.

3 of the biggest insights from Kristi Herold

#1 Why 64% of people are not engaged at work – and how investing in your culture can lead to less sick days, less turnover, and increased productivity and profitability.

#2 Why you don’t have to burn the bridge when someone quits – and a smarter alternative that will lower recruitment & onboarding costs and strengthen your team.

#3 The ROI of workplace culture, and fun ways to infuse playfulness into your company to boost team spirit and drive way more engagement.


  • Kristi’s entrepreneurial journey
  • The crisis that sparked a culture shift
  • Benefits to Rehiring Ex Team Members
  • Vibrant culture leads to meaningful ROI
  • More money, more problems?
  • Innovative ways to celebrate employee milestones
  • Dollars and cents of team trips and events
  • Rapid fire team building ideas
  • Plato on the importance of play




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  • I don’t believe in burning bridges. You can’t retain everybody all the time but if you can win some of them back down the road, that’s pretty great.” – Kristi Herold

  • Spell workplays with a Y. So, get the PLAY inside your workplace culture.” – Kristi Herold

  • You can discover more about a person in an hour of play than in a year of conversation.” – Plato

Brad Johnson: Welcome back to another episode of Do Business Do Life. Excited to have Kristi Herold here with us today. Welcome to the show, Kristi.

Kristi Herold: Hey, Brad. Thanks so much for having me. I’m super excited to be here.

Brad Johnson: It’s been a long time coming. We’ve crossed paths. And I think the first time we’re actually officially in the same room, although I don’t think we officially met, was Mastermind Talks with Jayson Gaignard, who I know you’re a big fan of, I’m a big fan of. And I actually sat in on this session where it was 100% dedicated to workplace culture. And how do you get great talent on the team? How do you keep great talent? How do you keep them happy? Which is all it can be a challenge some days. And I just remember you had a lot of wisdom bombs you were dropping on and had a chance to have your brother, Cameron, on my prior podcast. Obviously, he does some really cool things out there too.

And so, when we finally connected, it was awesome, just the energy you bring to every conversation. That was my first impression. That’s like I know you like to have fun with it. Like, the first two minutes of talking to you you’re always laughing, having a good time. So, yeah, let’s just talk about your journey, started, running a painting company, I think, when you were still in college, learned some things along the way, and then it transitioned into you’re just helping companies have fun and build amazing cultures. So, give us Kristi’s version of that journey.

Kristi Herold: Yeah, sure. Yeah. I do love to have fun and I do love to laugh. Life is too short not to be having some laughs, right? So, I grew up in a small city north of Toronto, very entrepreneurial family. I have two older brothers, Cameron you know, and all of us are entrepreneurs. And my dad was an entrepreneur. And our family dinner tables revolved around running business conversations. And so, there was never any doubt in my mind that I wanted to run my own business. And I think at the age of 15, I started a lawn-cutting business. I pushed my lawn mower around and walked to people’s yards and cut the grass. So, that was like the first business I had. And then, yeah, I did a painting business, and I ran a custom clothing business during university.

After university, I moved to Toronto, and I was now like a small-town girl living in this big city and I wanted to try and meet people. I didn’t know how I was going to meet people and I looked into playing. I had been an athlete growing up. I’d been an alpine ski racer, and I looked into playing some soccer and thinking maybe I’d meet people. And the only soccer leagues I could find were super competitive leagues, which I just was like, they’re out of my league like I was not that good of an athlete. And so, I had heard about these adult recreational sport leagues in Chicago, and I’d heard about one in San Francisco and I was like, “Hey, maybe I should try starting that. Like, that would be a fun business to run. I love organizing people, I love sports, I love being social.”

So, in 1996, I started the Toronto Sport and Social Club, and we had about 52 teams the very first season that I started things up. It was hard work. I spent about five months getting it off the ground. And I think that first year I had about 250 teams total in the first year playing beach volleyball, soccer, flag football, basketball, and ultimate Frisbee. And then over the next sort of ten years, like ‘96 to 2006, I’ve built a great team of people to help me run the operations. I was all in working really hard. I also had three kids during that time. And so, by 2006, I was like I think I always just wanted a lifestyle business, by the way. Like, that was my intention from the start was just something that would allow me to be home for dinners. My dad was always around for meals with us. He was always at our extracurricular events.

That’s the kind of parent I wanted to be. I wanted to be really hands-on and involved in my kids’ lives but have a nice lifestyle business that I was in control of my own time. So, that was sort of what I built. And then in 2006, I really sort of stepped back, started doing some passion projects. I started a community musical theater group for charity. I’d always wanted to be an actress. So, it’s like this fun way to connect adults through play a little differently. I was connecting adults through play with our sports leagues, and now I was producing musical theater and having fun on stage and have raised over half a million dollars for charity doing that. So, I did that for like ten years, and I was still pretty involved in the business, but on a more of a part-time basis. And I was really involved with my kids’ lives. So, that’s sort of the next ten years.

Now, I’m at 2016, and I’m bored out of my mind with my business, and I think I need a change. And I think I should sell this business and do something else but then when I thought, “What’s the legacy I really want to leave here behind me? What do I want people to say and think about or say about me when I’m gone?” And I realize what brings me the most joy is when I’m driving down the street and I see people playing a game of soccer or kickball or softball or beach volleyball, and I know they’re doing that because of the work me and my team are doing, that’s what brings me so much joy. So, I thought, well, instead of selling this, I should grow this. My kids don’t need me around as much anymore. It was 2016. They were all much older. Now, I should start to grow this.

And so, I started doing acquisitions. So, from 2017 to 2019, I did I think nine acquisitions, grew from being in three or four cities to, I don’t know, about 15 at the time. Pandemic hits and everything gets turned completely upside down. We lost 18 months of revenue in the pandemic because the mandates in most of our Canadian markets were really harsh. We were completely shut down. And so, then I’m like, “Now what?” Like, I should be celebrating 25 years of this great business of changing people’s lives through play and instead, I’m depressed and I’m scared and I don’t know what’s going to happen to my business. And that’s when I thought, “Well, what’s our core purpose?” Our core purpose is connecting people through play. So, how can we do this differently during a pandemic?

And that’s when we came up with the idea to start corporate team-building events online. And we started doing Bingo and Trivia and escape rooms. We created 12 different escape rooms and scavenger hunts and game shows, and we ended up producing over 1,500 events in that first year between 2020-2021 for companies all around the world and did over a million in revenue, which didn’t… We still were losing money. I had at that point 40 full-time employees and a lot of overhead but it helped a lot. It helped to sort of give us some focus. It helped to we were making a positive impact in people’s lives because all these companies now are working from home and not connecting and not having fun with their employees. It was a stressful time for everybody, so that made a huge, huge difference and it helped cover some of our costs.

So, fast forward a few years and now here we are in 2024, I’ve done three more acquisitions post-pandemic. We’re in 25 different cities now in Canada and US with our adult rec sports leagues. And the adult sports leagues are bigger than they’ve ever been. So, that’s super exciting. And then that’s sort of I tell people, we had this 28-year-old business, the B2C sports leagues that were on two and a half years of life support and now back and fully healthy. And then we have this sort of three-year-old toddler of a business, this new corporate events team building business, which started off virtual, but like any toddler, just sort of keeps changing its mind about what it wants to do. And so, now it was virtual but now we’re also doing a lot of in-person events, amazing races, and scavenger hunts.

And now I’m doing a lot of keynote speaking as well because I wrote my book, It Pays to PLAY: How Play Improves Business Culture. I wrote that during the pandemic, having seen how much play was helping companies around the world. It’s inspired me to interview a bunch of our customers and write the book. So, anyway, it’s sort of turned into, I realized in hindsight now, looking back, my whole life has been around connecting people through play and in so many different ways, the adult sports leagues, the community musical theater for charity, and now the corporate team building events. It’s what I love to do. And I’m so excited and grateful to have been able to make a career helping people play and have fun with their lives and make an impact.

Brad Johnson: Yeah. It’s pretty awesome when you can just step back, which it sounds like you’ve done a couple of times through your journey and just kind of observe like, “Wait, why am I doing this? Do I want to do this?” But when you really reinforce that and you’re like, “I get paid to help people play,” I mean, that’s a pretty awesome job. So, one of the things I read in your book, and this started in your journey, you ran that painting company, which I think you and Cameron both had that in common in college. But was it College Pro Painters or something like that? Am I butchering the name?

Kristi Herold: Yeah. No, that’s what it was called. Yeah. College Pro Painters. And both my older brothers did that. Cameron did it for three years. My middle brother, Todd, did it for one year, and then I did it for three years as well. Yeah. We all learned a lot.

Brad Johnson: Was this like the Cutco of Canada? The Cutco sales?

Kristi Herold: Yeah. Well, it was a little different. It was a franchise. It’s a student franchise. But they teach you like so much. They taught us about what it means to run your own business. They taught us hiring skills and interviewing skills. They taught us sales skills. They taught us marketing skills and production skills. I did a commerce degree in university like I have a business degree, but I learned way more about how to run my own business from those years of College Pro Painters than I did doing a degree at university, for sure.

Brad Johnson: Yeah. Well, one of the things I picked up in your book is you’re very almost like a little bit cerebral with because I think a lot of business owners they just get down in the trenches running, and they don’t ever step back and think like, “Wait, why am I actually doing this? Like, does this even make sense?” And you had an early story where you lost like half your workforce when you were running the painting company.

Kristi Herold: Yeah.

Brad Johnson: But you actually thought about I think a lot of entrepreneurs fall into the mistake of pointing fingers externally, like, “Oh, well, they suck or they didn’t follow through.” And you kind of looked internally and said, “Wait, maybe my culture sucks and maybe this isn’t that fun to work here.” And you had a little breakthrough there but I see that like in your journey like, “Oh, COVID hit. Oh, curveball thrown. Time to adapt.” Maybe we start with the Pro Painter lesson because I thought that was a really cool one out of the book but maybe we follow that journey through your career. I’d love to hear a few ahas along the way.

Kristi Herold: Yeah. That’s a good one because it actually changed the way very early on in my business career. It totally changed my outlook on workplace culture. And I will say that wasn’t me coming to that conclusion by myself. My dad helped me come to that conclusion. So, what happened was I’m halfway through my first summer of running this painting business. I have ten painters working for me. It’s my summer. I’ve got a four-month window to produce about 100,000 in sales of that. This was 30 years ago.

Brad Johnson: As a college kid, that’s insane, by the way.

Kristi Herold: Yeah. No, it was like serious business. And so, I’m halfway through the summer, and half of my painters, five of my painters quit, and I was like, “Oh, what? Like, now what?” Like, I have to now stop marketing, stop selling, stop producing because I need to go recruit, interview, hire, and train a whole new crew painter. So, everything stopped. And so, like, I’m now behind the eight ball and I remember being really frustrated and why are they quitting and angry almost. And I sort of sat down with my dad and was talking and ranting about it, and he was like, “Why do you think they quit?” I was like, “Well, I don’t know like they say they’re not having fun or whatever.” I can’t remember all the details.

But effectively, he kind of called me on my BS a little bit and he was like, “Do you think it’s maybe because you’re a bit of a dictator and you’re sort of bossy and you’re…?” And I was like, “Huh. Wow. Yeah. Actually, I think that’s exactly probably why.” And so, I realized I have to change. I had my goals, which I was just driving them to hit my goals for me, and they had no buy-in. I didn’t share my goals with them. I didn’t tell them why those were my goals. I was just like, “You got to do this. You got to do this. Come on.” And so, I changed. I was like, I made contests for them to try and help me. So, they were now incentivized to help me hit my targets. And I planned social events. And so, every Friday we would like go play laser tag or paintball or we’d go like out for drinks and I do host barbecues at my house and have them come over.

And if they were working late on job sites, I remember, like I literally in my book, there’s a photo of this, like I literally took a barbecue and drove it over to a job site where they had to work all weekend and I barbecued. I’m grilling hot dogs and hamburgers for them all weekend so that they’ll keep feeling like I’m caring about them. I’m there with them and I’m fueling them. And on hot days, I would bring them popsicles and ice cream cones and like just trying to keep their spirits up and keep them motivated. And what a game-changer that was, Brad. That group of painters for that second half of that summer stayed with me for the next two and a half years. There was only one painter that didn’t come back and that’s because he got signed to be a hockey player at the Montreal Canadiens, Brian Savage. So, he didn’t need the money as a student painter.

Brad Johnson: Your culture wasn’t that good that you could keep him from that opportunity. Yeah. Oh, well, You win some, you lose some.

Kristi Herold: Exactly. And I will say I ended up being the rookie manager of the year for Canada first year. And the next two years I was the Canadian manager of the year like produced the most sales of any manager in Canada for my franchise. And my painters all did very well because I incentivized them to help me. And so, that was a game changer for me. And so, since then, in other businesses that, I mean, the main one was I did start my sport social club now called JAM. I started JAM in 1996 and very early on realized as I hired people that I wanted them to feel incentivized. So, profit sharing plans, we have taken their staff on many, many trips over the years to Jamaica and Mexico and Disney World and like, I don’t know, probably 15, 20 trips over the years, incentive trips.

We have so many fun things that we do that have just been layered on over and over through the years now. I mean, I could go on for days about the ways that we have fun with the work we do. And I’m not talking about necessarily stopping everything to play all day, like, we get a lot of work done. I mean, get sh*t done is one of our core values but we have a lot of fun.

Brad Johnson: My business partner, Shawn, will love that one. He’s got a GSD text group, so he’ll love that one.

Kristi Herold: Nice. That’s the name of my holding company is Get Sh*t Done as well. I get sh*t done everywhere I go. It’s like that’s my favorite core value, GSD. Anyways, but yeah so while we’re getting sh*t done, we have a lot of fun with the way we do it. And I talk in my book, I share two stories about two employees that left JAM to go have different career opportunities and earn more money. And they came back because of culture. They came back because they wanted to work with people who cared about them as friends. And that’s actually in the last three years now, there have been three employees. There’s one I haven’t even written about in the book, three different employees full time that left for other careers and came back because they want to work in a place where they work with friends and can have fun with the work they’re doing. There’s more to life than just a salary.

I mean, ideally, if you can have great compensation for your team and they’re engaged with the work and they care about the people they work with, like if you can provide that full package, it’s really, really valuable. And having core values, having vision, having purpose to your company, all supercritical pillars but if you don’t have your team of people connected, cohesively working together to bring all of those pillars to life, who cares that you’ve got your core values written on the wall? Like, you got to have your team of people having fun together, bringing all those things to life, right?

Brad Johnson: Couldn’t agree more. I want to hit that story on that employee. I don’t remember his name, but I do remember the story from the book.

Kristi Herold: Sandeep.

Brad Johnson: Sandeep. Yes. Thank you. And this actually ties into, I actually pulled up my notes from Mastermind Talks. So, 2018, Deer Valley Montage. Beautiful property. I sat in on a break out with you, Nathan from ConvertKit, Bob Glazer, who I’ve had on the show, Tony, Tracy. And it was about employee culture. And one of the things that I remember hearing there for the first time is this concept about not firing employees, which, by the way, we have some bad words at Triad. Employee is a bad word. We have team members. Firing is a bad word. We have transitions out. We don’t have firing. But if you’re going to run a business, guess what? That is going to happen. Everybody you have on the team today is not going to be on the team five years from now.

And so, let’s talk about Sandeep because what I remember the story is everybody at the company loved him. Incredible culture fit, incredible skill set where he was a high contributor and got this insane offer for a large amount of money that just mathematically didn’t make sense to match at the company. So, let’s talk about that, where you have somebody you don’t want to lose that leaves and how you handle that the right way, or maybe the wrong way, and what you can learn from that because I think there are so many companies out there that do that so poorly, where that great contributor would never come back based on the way they exited.

Kristi Herold: Yeah, 100%. So, there’s a lot. I think it’s a very easy thing to do. And some people struggle with this because I think there’s a little bit of pride. I’m going to put my pride aside for this, for someone who I think is an amazing teammate. If they’re leaving, which, as was the case of Sandy, I was so sad when he told me he was leaving, but I was like, “Okay, dude, I’m really sad you’re leaving.” He’s been working at this for six and a half years. But I understand, I get it, and I wish you only the best because I genuinely care about you as a friend. So, I wish you only the best. I hope you have an amazing new chapter and that you learn a ton. And I do want to let you know if you ever find yourself wanting to come back to JAM, please let me know. Please know that I would love to get you back on our team one day.”

I say that. I use those words with many of our teammates. There are certain teammates who they leave and I’m like, “Okay. See you later.” Like, good luck in your next chapter. And I care about them but I maybe wouldn’t welcome them back because you’re kind of like, “Whew, like that was a good transition.” They did great work for a little while, but for whatever reason, it’s better that they move on. But there have been a number of teammates over the years who I’ve said, “If you ever wanted to come back, please don’t hesitate to reach out.” And the reason I think it’s important we say this as leaders to certain teammates is because if we don’t say this, there can be a lot of, I mean, natural human emotions, right? They can feel kind of guilty that they’re leaving you high and dry. They feel kind of badly about it, and they think that maybe in some ways they might think they’re burning a bridge.

I like to let them know, “You’re not burning a bridge. I get it like you’ve got this new opportunity. Go for it. Go have a great good new adventure. We may never see you back here again and that’s okay. But know that if you ever want to, we can’t guarantee you that we can have a role for you but I hope you would call me and let me know.” Anyway, so I think it’s important to say that. So, what happened in Sandeep’s case, he’s gone for four months. I sent him a text, which because he was a friend like I really cared about him. I wasn’t having him over for Saturday night dinners or anything but I just thought he was a great guy.

Brad Johnson: But he also wasn’t dead to you because I’ve seen a lot of companies like the moment they’re not on their team it’s kind of like, “Oh, you’re dead to me,” you know? And literally, all contact is cut off at that point.

Kristi Herold: Absolutely not. I mean, I keep in touch with, gosh, there’s probably, I mean, I had a lot of employees over the last 28 years of running this business, right, and there’s probably 15 different teammates, maybe 20 that I keep in semi-regular touch with. Every few months I’ll be like I think of Kyle for some reason, or I’ll think of JK for some reason, or I’ll think of Michelle for some reason, or Blythe then I’ll shoot them a text and say, “Hey, I was just thinking about you. I hope you’re well.” And we had a little banter going. Anyway, so I sent Sandeep this message and I say, “Hey, just want to check in. I hope things are going great at your new job. I miss you. How are you doing?” And he writes me back and he said, “I’m miserable. I’ve got my letter of resignation that I’m submitting this week, and I don’t have another job to go on to.”

And I was like, “Wait, what?” And this is a guy who doesn’t complain. He’s so happy. He’s so upbeat. And I’m like, “Can we talk? Like, what’s going on?” So, we jump on the phone and he explains that he’s earning a lot more money, but he’s absolutely miserable. He said the place that he works has no culture whatsoever. Like, no one cares about each other as friends at all. They don’t care about each other’s mental health or wellness. They’re just there grinding it out. And he didn’t even really care about the work he was doing. So, he was miserable. And I said, “Well, like, would you ever want to come back to JAM?” And he said, “Nothing would make me happier.” And I said, “Okay. Well, okay, like this is all it’s hitting me pretty like holy crap. I didn’t expect this. I don’t know how quickly we can get you back, but let’s talk more about this.”

So, we started the conversation, and six months later he was back on our team and he’s now, so this was, I don’t know, two and a half to three years ago now. And he’s now probably three years ago now. So, he’s now on track to be our future CFO and we have a roadmap in place. And within probably the next 18 months, he will probably be the CFO of our company. And I’m just so thrilled. We refer to that time as his sabbatical. And then, you know.

Brad Johnson: He was finding himself. He was finding himself.

Kristi Herold: Yeah. Exactly. But then, funnily enough, like four months later or six months later, Taylor who sort of followed him out the door but she was sort of six months behind him. She had left. And then six months after, he came back. Taylor sees a job posting at JAM for her old job. And she reached out and she said, “Hey, I really want to apply for that job again. I miss working at JAM. Can I come back? Would that be okay?” And we were like, “Are you kidding? Of course, we love you. Like, come on back. Interview for the job,” and she got the job because a lot easier to bring back a teammate you know. I mean think about onboarding someone who’s already worked at your company for a few years. It’s so much easier. You know what you’re getting into. And so, they can get up to speed that much more quickly.

So, I don’t believe in burning bridges. And then Tony, Tony who I didn’t write about in my book, Tony left during the pandemic. He wanted to go back to Brazil, where he hadn’t seen his family for a long time during the pandemic. It was a tough time. So, he left. He was gone for probably a year and a half, and then he was ready to get back to Canada, and he reached out and said, “Hey, I would love to come back.” And he had been working, doing some other things in the meantime, and he was just not enjoying them as much as he had enjoyed JAM. So, Tony’s back on the team and I just love that. Like, as we’re growing, we’re going to need more great teammates. And if we can bring back some people that we know are absolute all-stars, fantastic. You can’t retain everybody all the time but if you can win some of them back down the road, pretty great. So, I think it’s really important to transition people that way.

Brad Johnson: Yeah. Well, Kristi, what I think about I think that is a better litmus test under your culture. I heard one entrepreneur that I know, he calls him Boomerang team members because they left and came back.

Kristi Herold: Yeah. Yeah. Exactly. Yeah.

Brad Johnson: But I think that is a better litmus test on your culture at the company than a new hire because, obviously, a great culture, what you put out on the website, all of the stuff can attract great talent. But then they know the internal ingredients. You know, they know what you’re cooking internally. And if they leave and come back, that is a much greater test your company has passed. You’re out of the newlywed phase at that point, you know.

Kristi Herold: Yeah. And also, you think about the message that’s sending the people on your team as well, like when they see people that they really liked have left and then they see them six months a year later coming back or asking to come back. Like, that’s a pretty powerful message that they’re like, “Huh, those guys left and they came back. This is probably a pretty good place to work.”

Brad Johnson: Maybe the grass isn’t greener on the other side.

Kristi Herold: Exactly. So, that’s why I really think it’s shortsighted for anyone who sort of is like too much pride on, “Oh, don’t let the door hit you on the way out.” If you’re going to have that kind of pride, I think you’re only hurting yourself, honestly. Like, I think we need to recognize we’re not going to be able to hold on to everybody, nor should we want to. I also kind of think it’s great that people go get other experiences. And one of the guys, Barry Glassman, do you know Barry from MMT?

Brad Johnson: I do, I do.

Kristi Herold: Yeah, I talk about Barry in my book, and he and I share, we have a similar strategy in that, Glassman Wealth, and they’ve been awarded best places to work culture for like culture awards many, many, many times in the Washington, D.C. area. But their strategy is they don’t like to hire people fresh out of college or university. They like to hire people who have already experienced other workplace cultures. So, then when they come to Glassman, they’re like, “Well, this is a great place to work,” and they’re less likely to… And so, we do the same thing like I’ve asked my head of people in culture really unless it’s a very junior role. Like, let’s try not to hire fresh at the university because we want people to have a taste of other workplaces so that when they come, they really know JAM is an amazing culture. It’s a great place to work.

Brad Johnson: I’ve never thought about it that way because I’ve actually seen that where before Triad, I was fortunate to work at a place that was pretty intentional about culture. They didn’t get everything right, but they did make an attempt to make it a great place to work. And I saw that exact because I worked three years in corporate. And then I went there and I’m like, “Oh, this is night and day difference,” but you would have the college kids come in and they just think this is what the real world is. You’re like, “No, you need to experience a bad culture and then you’ll appreciate this.” So, I like that. That’s an interesting thing to incorporate into your hiring process. I want to go back to one other thing that I thought as you were talking about, Sandeep.

I think unfortunately in business sometimes culture is like this woo-woo word kind of like vision, and those that actually have done the work and you talk to them and they’re like, “No, this matters more than strategy, more than our marketing plan, more than our sales process.” But I think those that haven’t actually taken an intentional it’s like, “Oh yeah, culture. Yeah, I get it. Everybody says that.” But monetarily, here’s what I heard out of that is that culture is not only attracting great talent in but it’s attracting great talent back. And so, what are your thoughts on ROI when it comes to culture? What are the ROIs you’ve seen internally when it comes to culture?

Kristi Herold: Well, I mean, there are so many ways that you get return on investment and that’s why the book, my book is called It Pays to Play because if you think of culture as an investment, the return is massive when it comes to, I mean, turnover is so expensive, right? Like, they say it’s sort of 50% to 150% of someone’s salary is what it costs every time you lose someone. So, if you’re losing 15%, 20% of your team every year, that’s costing in a 100-person company, I mean, that’s in the millions of dollars that it’s costing you. If you invested a couple hundred thousand in your workplace culture, having some fun and making it a great place to work, and if you can see that your turnover all of a sudden drops from 20% to 15% to 12%, all of a sudden, that investment starts to make a lot of sense. Not to mention people who like working there become your recruiters for you so it makes recruiting less expensive that way, right?

Because they become, you think Sandeep tells people that JAM’s a great place to work? Yeah, he does. And so, he’s doing our recruiting for us, right? Many of our team, if they enjoy working with us, they’re going to spread the good word about that. So, there’s that engagement.

Brad Johnson: On that note, before you move off of that, do you have an intentional program in place around rewarding your team members for recruiting or referring per person?

Kristi Herold: We do for part-time because it’s such a constant flow for our part, like we have, I don’t know, 400 or 500 part-time employees. So, we do have that. And anyone, our full-time or our part-time, we have dabbled with it. Barry, actually, Barry Glassman has a big one. I can’t remember the details of it but he gives huge amount over like three years or something. And it’s something we’ve talked about. We haven’t implemented it yet but the idea that best that I’ve heard that I most like is you make it a significant amount of money. And so, let’s say, I don’t know, maybe it’s like $15,000. I’m just going to pull a number out there. It depends on the role you’re hiring for but let’s say the $100,000 salary.

And so, you’re going to say the $15,000 recruiting bonus. And you get that if you and that person are still here, you get it $5,000 a year the next three years if you and that other person are both still working with, you know? So, it’s sort of this retention. I mean, it’s something like that that I’ve heard. Yeah. We’ve played with it. We haven’t implemented it yet but I suspect as we continue to grow, we may be looking more at that for sure. So, back to your other question about…

Brad Johnson: Yes, thanks. I’ll let you keep rolling. I was just curious there.

Kristi Herold: No problem. The return on investment, so you’ve got retention and turnover savings that way and the recruiting. Then if you look at, think of engagement and productivity, I mean, the studies have shown that when you have someone who reports that they have a close friend in the workplace, and that’s really what I’m talking about here, is I’m talking about getting people sort of upping the level of the relationships with the people they work with. And so, if you can foster friendships by having some fun, those friendships that get fostered, when people say someone important that they have, a close friend at work, studies have shown they’re far more likely to recommend your organization as a great place to work. They’re far less likely to be looking to find another job elsewhere. And when 60% of your employees, 60% or more of your employees say they have a close friend at work, profitability is up by 12%.

So, like this stuff really works. That’s a whole productivity angle. Then there’s mental health, physical health. When people are happier at work, they’re far less likely to take sick days, right? I don’t know. I’m just going to mail it in today. I’m going to call it a sick day because I just… If you have friends at work, you actually look forward to going to work. You’re excited with the work you’re doing. So, you’re that much more engaged. The engagement studies have shown I think it was a 2022 or was it 20? No, it was a 2023 study. And it was 64% of our workplaces are not engaged with the work they’re doing.

So, imagine you got a boat, a boat with 100 people in your boat, rowing a boat, and you’ve got 24 people at the front of your boat pulling hard towards your vision, and then you’ve got 51% are in the middle of the boat there. So, there’s disengaged and actively disengaged. Okay. So, you’ve got 24% engaged, and then you’ve got 51% who are disengaged. So, they’re basically sitting in the boat. They got their hands behind their head. They’re just sort of along for the ride. They don’t really give a sh*t. They’re just coasting. And then you’ve got 13% who are actively disengaged. Those are the people in the back of the boat, and they’re actually rowing the opposite direction. They’re fighting against you. They are the bad apples that are poisoning your culture.

And so, if you think about that, it’s like, if you look at that at your payroll and you think 64% of my payroll is either working against me or not working for me, they’re just coasting, that’s a huge expense. If you can change that engagement level so that you flip that around and you get people more engaged, and how do you get people who are engaged? You make sure they’re having fun and feeling like that they have friends in the workplace and that they care about the work they’re doing. And you think about someone who is working at their job. They’re not really engaged with what they’re doing. They see that their coworker, okay, their co-employee using words that we would never use. They don’t really care about that person.

And they see that they’re stressed but they’re like, “Not my job. Like, sucks to be him,” kind of thing versus you or me with teammates who we really care about because we’re teammates, we’re on the same team or we’re driving towards the same goal together and we care about each other because we have a friendly relationship with each other. If I see my teammate is stressed out, I’m going to be, “Hey, are you okay? Like, can I help you with that?” So, your productivity, like you have people caring about each other and actually trying to help each other so productivity improves and engagement improves because that person then who is stressed out feels cared about by their teammate, their friend. So, that’s where fostering friendships really can help across so many different levels.

And then when people are more engaged and having more fun with the work they’re doing, they’re happier as an employee. Their mental health is better. They are also then creating happy customers, right? If you have ever been on the end of a phone with a customer service person who is miserable in their job, we’ve all experienced this, right? You’re like, “Wow. Who woke up and who got on the wrong side of the bed this morning?” You’re clearly grumpy and you’re not making me want to use your service or buy from this company again because you are a nightmare. But on the flip side, you deal with those people who you’re on the other end of the phone and you’re like, “Wow, this is a ray of sunshine. Holy. This person’s engaged and energized and like, I can hear them smiling through the phone.” Then you’re more apt as a customer.

I tell people about those experiences like, “I just used this company and they did this service for me, and wow, were they ever great. Their team was amazing.” So, happier employees make for happier customers. So, there’s just so many ways to get return on investment from having some fun in the workplace.

Brad Johnson: Yeah. There was one other that you shared in the book. Share what you can publicly but Sandeep left for more pay. And when he came back, I’m going to assume you didn’t match the high pay. I’m going to assume he came back somewhere around where he left. And we just had a team member join the other day. Once again, incredible talent. He was getting paid incredibly well. She’s a rock star or like, sorry, that’s like it was way above the budget for the role. But she was miserable in her job. She’s like, “Just like kind of corporate America.” And she was like, “Man, I just love how you guys are doing business, doing life. I love what you’re about. We try to live the culture. Everything that you just said, it’s not just words on a wall.” And she took a step back for a happier life and actually contributing to a cause that she was passionate about. And so, I think there’s an ROI sometimes on the actual salaries because people would rather make less and be happier. Have you found that to be true?

Kristi Herold: Yeah. I mean, honestly, I sort of wish we could pay more, like, the business can only afford so much, right? Because players, people playing sports leagues can only afford so much. And that’s where if you have to increase salaries, it’s going to impact prices. So, I guess so. I just don’t, I’ve never really sort of thought about it like that because my preference would be how can we pay even more?

Brad Johnson: I want to frame that. And I’m glad you called that out. Same. I think the worst businesses in the world are like, what’s the least we can pay our team and get away with it?

Kristi Herold: Yeah, yeah, yeah.

Brad Johnson: So, I definitely do not look through that lens. However, I would say it’s almost like probably a better way to say it is almost like a gravitational force that pulls people in, where if I’ve got two options and this one pays here, but this one pays here, but I’m passionate and this one speaks to me, I’m going to choose that one.

Kristi Herold: Well, yeah. And let’s be honest, like there are jobs that you can have. I know some young people in my life who have jobs in, whatever, investment banking, finance, consulting. They’re high-paid jobs, they’re high-stress, and they’re highly overworked. Like, they’re taking these kids out of university college and they’re giving them these JP Morgan, I don’t know, I shouldn’t name companies, but like big investment banking salaries. And these kids are grinding it out with no life whatsoever. Like, they’re working until 2 in the morning. They’re sleeping under their desk so that they can be back at their desk at 7. And they’re grinding it and they’re pale as can be because they never see the light of day. They can’t sign up to play on a corporate sports team because there’s no time to have fun. And so, they’re grinding it out just for the dollar.

Well, like is how much is that really? Is it worth it? So, I think that’s where, like you said, you’re trying to live the culture and have balance. And that’s where we are as well. I mean, we have Go Play Fridays from May long weekend until the Labor Day long weekend, every Friday afternoon. Any of our teammates can take Friday afternoons off. All we ask is that they make up the time. If you’re going to take the afternoon off on Friday, make sure you put in a little extra time during the week to just sort of get the work done that you normally would have done on a Friday afternoon, get that work done, and go take off early. Get to the cottage early on a Friday. Go have some fun. Get to a patio early with your friends. Have some fun.

And that’s the kind of thing that like we can do that. We give big vacation time. Your first year with us, you get four weeks of vacation. Second year you’re at five weeks of vacation. Like, we do that but we don’t necessarily have the best salaries. I can’t give you investment banker salaries, but can I ever give you a great balance and culture and a fun place to work where you care about the impact we’re making on people’s lives. The stories we get to hear and share about our customers, people who’ve gotten our logo tattooed on their body because of how life-changing the leagues have been for their lives. When you get the email from someone who says, “Your league saved my life because I was suicidal and I didn’t know anyone and I was depressed. And then I joined your soccer league. And now I have all these friends and it’s changed my life.”

Or people who email me and say, “Here’s a picture of me and my family. These kids who are now 15 and 18 years old wouldn’t have existed had I not met my wife playing in your Football League 20 years ago.” Those are the kinds of stories that we get to experience. And so, the work we’re doing really is making such a positive impact. So, I think that’s where I knew that’s where you were coming from about the bull. We can’t pay those investment banker salaries but frankly, like you’re kind of not getting the great life if you’ve taken that salary, like there are certain industries that are way overpaying.

Brad Johnson: Welcome to finance. Yeah. So, finance is known for what we have labeled redline behavior, which is grind your life away. The hedonistic treadmill that it actually doesn’t ever slow down. It just speeds up as you get more successful because you have more demands. And that’s one of the reasons that Triad exists. Like, Do Business Do Life, we don’t say it, we try to live it because it’s born out of a bit of a selfish pursuit because I lived a lot of that. I missed family dinners. I was on an airplane a lot as I was “being successful.” And so, yeah, that’s why this podcast exists. That’s the reason. We call it work-life integration. So, on that front, I want to go to you talked about the investment banker like sleeping under the desk, which, by the way, is real. Like, that actually does happen.

As we go towards how you all actually do have fun in the workplace, there’s a really cool concept you shared with me. It’s how you celebrate the first day of employment at JAM. And, obviously, it has to include hockey jerseys because you’re in Canada, right, or aesthetic Canada. But please share that. That is one of the coolest first-day experiences. And I saw a video somewhere on the internet. So, we need to put that in the show notes so people can experience it but, please, like describe what that looks like or how that feels.

Kristi Herold: Yeah. For sure. Joey Coleman uses the video from this in all his talks about how to keep an employee. So, at JAM, when you hit your one-year mark with us, you get official. And we’ve been doing this for probably 20 years now. When you hit your one year, you become a veteran on the team and you get officially drafted at that point. And when you get drafted, that’s when you get your jersey, your hockey jersey. And so, your hockey jersey has a JAM logo on the front, your name on the back, and your number is the year that you started working with us. And so, actually today, we do a daily huddle, and after huddle today or at the start of huddle today, one of my teammates she’s getting her veteran’s jersey today. It’s her one-year mark today. So, we’ll be rewarding her. We’re going to be officially drafting her. So, she’ll get her jersey and it’ll have her name on the back.

And everyone keeps those typically at their desks or hanging up in their offices. Or if they work at home, you can always see their jerseys hanging up on the wall behind their desk. People wear them proudly. So, when we onboard a new employee, we do a high-five welcome. And so, if it’s in the office, it’s super fun. Anyone who can be there in the office. And our people and culture team always like to send out invitations so you know if someone’s being onboarded and any veteran is wearing their veteran’s jersey, and if you’re a rookie or you have a hoodie, you have a JAM rookie hoodie, so you’re wearing your hoodie. So, we’re all sort of in our uniform. They get the walk-up song. When you get onboarded, when you join our team, part of your onboarding is you tell us your walk-up song. What would be the song that I’m walking?

Brad Johnson: You secretly ask it to them, right? Like, hey, if you’re on a sports team, what would you look like? It’s kind of a playful interview question.

Kristi Herold: Yeah. It’s part of the application process, I think, honestly, so they don’t even really even know it. And so, when they show up, their team leader meets them in the lobby. If they’re coming into the head office that day, the team leader will meet them in the lobby. And it’s always at 10:00. We don’t have them start at 9:00. So, everyone else can already have gotten there first. And then when they get to the office door, their walk-up song is blaring. They open the door and they see this tunnel of people ready to high-five them, and they walk through and they’re getting these high fives. And then they end up in the boardroom and everyone gathers in the boardroom. And they look up on the boardroom screen. And anyone who doesn’t work in the head office in Toronto is up on the boardroom screen wearing their jersey or their hoodie, ready to welcome them to the team.

Usually, I will do a quick welcome speech and then their team leader will sort of say something about them to welcome them. And then we always do. We have this little tradition where we do three questions and we jokingly say, “As is tradition, we’re going to go to Simon for the first question.” Well, Simon doesn’t know what’s coming to him. We sort of jokingly say, “Like, we always go to Simon.” So, no one knows who’s going to have to ask the first question. So, everyone’s sort of on their toes, ready. And they ask a playful question like, what’s your favorite chocolate bar? Tell us who your favorite sports team is. What was your favorite Halloween costume growing up? Like, silly questions, little get-to-know-you type questions.

So, one person asks the question, and then they pass the baton to someone else to ask a question. And they’re officially welcomed to the team. And then the last thing we do, which is something we just started this past year, we now have houses at JAM, sort of like Harry Potter style houses. So, we have four houses and you’re assigned to your house and we now have house challenges and this is just stuff that runs throughout the year. And once a year we’ll have a big house award. They win the House Cup. So, you’re told what house you’re on and the houses help with any of the social events that we do. You get points. We have a lunch ‘n laugh once a week. If you go to lunch ‘n laugh, it’s a virtual. You just sit and have lunch with people and you could be in the Toronto office or you could be on your Zoom. Everyone, there’s always a Zoom available.

So, everyone sits and has lunch together for half an hour on a Wednesday. If you show up, you get a point for your house. So, there’s like all these different ways to get how to get points. If you come to book club, which we do every two months, you get a point for your house. If you win a core value award once a month, you get a point for your house. So, we have these houses now. Because as we’re growing, we want people to still feel part of sort of a smaller team almost. So, having house challenges is really a fun way of doing that as well. So, the houses are all named after the original streets our offices were on. So, Cottingham was my first office and then Huron was the second street, Avenue and Bridgeland. Those are all different streets that the offices have been on over the last 28 years. So, those are the names of our houses.

Brad Johnson: That is such a fun idea. That’s what I love. Like, how fun is it to be an entrepreneur? And you’re like, “This was kind of cool on Harry Potter. What if we did that in our company?” But think about the engagement that has to drive. So, I’m curious, so you’ve made it team games based on the houses. You’ve created I’m sure like probably there’s these teams have created like probably swag for their houses I’m assuming like now they’ve…

Kristi Herold: Like, at huddle. When you come to huddle now, like every house now has their own backdrop and they’re all colored, right? So, Cottingham, I’m the captain of Cottingham House and so we’re yellow. And so, we have these yellow submarine backgrounds that are someone on our team made, someone in our house. And Huron is red and Bridgeland is green and Avenue is blue. And so, they all have these backdrops for Zooms. So, every day at huddle we see, I don’t know, it’s filtering in all different ways. And we just started this like literally in October I launched it. It was an idea that I had that I thought would be really fun. And part of it is as we’re running all these corporate team-building events for different companies, we’re doing some consulting now and helping companies integrate playfulness into their workplace. And we’re not just doing teambuilding events.

So, these are ways we can teach them. You know, there’s lots of things, there’s a huge buffet of options. You don’t want to do it all at once but start picking a few things, maybe onboarding, start doing a fun onboarding. Make it special because our employees will never forget the first day they joined the JAM team. They’ll never have that experience at most other organizations, right? It’s a really special thing. The way we do our core value award, the way we do our veterans jerseys, the way we do the houses. We have all these things that we can teach now other companies that they can sort of take what works for them, book clubs and music, have a rock band, have a corporate sports team. There’s tons of different ways to have fun at work that can be fully inclusive so that whether you’re a remote team, you’re a hybrid team, you’re all in the office team like you can make it work. There are lots and lots of ways.

Brad Johnson: Well, how fun is that to be the idea lab and the experimentation? Like, oh, this was really cool. Now, you just get to share it with people.

Kristi Herold: Exactly.

Brad Johnson: So, on the teams, because obviously, you’re making it a team-based game for collaboration. Do you also have an individual scoreboard in the houses like this team member has generated the most points, or did you not do that? So, you didn’t have like any I players on the team?

Kristi Herold: We haven’t yet. I guess we must have that tracked, but we’re not planning to focus on that. We want to make it because sometimes people are really busy and can’t come to. But like on a Wednesday when lunch like our Cottingham house, we have a little chat amongst just the Cottingham house and people will be like, “Hey, like it’s house chat, we’re behind in the standings. Like, we’re in third right now, which is not great. We want to move our way up.” So, everyone will be like, “Come to the lunch ‘n laugh, like let’s get points for our house.” So, it’s just a fun way to encourage people to be partaking in some of the social things and engaging with each other. And by the way, when we set up the initial houses, we made sure that they were very evenly balanced.

So, like, we have a four-person people and culture team. Every one of them is part of a different house. A four-person marketing team, they’re all in a different house. The finance team all in different houses. So, that you’re not stuck with your same department again like you’re interacting with different people. I don’t know where the house system is going to go. We just started it. It’s like seven months ago. It’s been really fun so far. Like, the whole idea is this goes on forever. Once you join the team, you’ll be put on your house and you never leave that house. You’re on that house for as long as you’re with JAM. And the other part of the reason I wanted to do this was as part of our onboarding, when someone joins our team, if they’re in my house, it’s our house’s responsibility.

We have inside our house sort of it’s our responsibility to be the welcoming committee for that. So, there’s like a bit of a buddy system, and the buddy is assigned through the houses. And so, the first week we make sure they don’t eat lunch alone and they always have somebody to go to. And it’s all done within the house system. So, it sounds maybe more complicated than it is. It’s actually not very complicated. It’s really fun. And there are just so many ways to have fun that it doesn’t cost a lot of money to do this stuff. It’s just implementing slowly but surely one step at a time, implementing a few things. You need to have leaders that are bought into having fun. And if you have that, it’s not that complicated. It can be pretty easily done.

Brad Johnson: A couple of benefits, I’m just thinking. Number one, you hit it. One of the things that there’s always a challenge as you grow an organization is the natural siloing that occurs where it’s like, “Oh, finance is over here. Oh, sales teams over here.” And if you’re not careful, “Oh, finance just doesn’t get it, right?” or whatever. Some of that thought process can start to leak in. You’re naturally breaking down those walls by cross-pollinating teams within these houses. You’re already breaking those barriers down. The other thing that really comes to mind as far as the houses is like just this super intentional, like back to the playfulness. Like, I’m just picturing, I can already see it like three, four years down the road because you’re part of this now.

I played football in college. You have like a locker room, like where you’ve got teammates and you’re all on the same mission and you’ve got seniors. They’re like the big brothers to the freshmen that come in and you kind of take them under your wing, so you’re creating that. But also, every team starts to develop their own language, their own little inside jokes, their own culture, and you’re creating little mini versions of that that aren’t like a negative to the culture, but actually in addition.

Kristi Herold: Yeah. Exactly.

Brad Johnson: So, I’m assuming this is already playing out a lot of these little things.

Kristi Herold: Totally. And we do Jamboree once a year. That’s why because our team, similarly to yours, we have people that the core group are in Toronto, but then we have people that live in Calgary, in Michigan, in the Atlanta, and Barry, and Kitchener Waterloo. And so, once a year, we all get together for what we call Jamboree, and it’s a three-day event. And at Jamboree, there’s a lot of house space. That’s where we launch the houses this past year was at our Jamboree and so we do these fun teambuilding events, field days, and like scavenger hunts and stuff at Jamboree and everything that we’ll have you’ll be getting house points. But then we’re also doing virtual events like once a month when we do our JAM escape room, we’re breaking the escape room teams into house teams so that you can get points for houses, but then not everything will be house-based.

So, we’re trying to make it, it’s just a different have a bit of both, a different flavor to sort of keep things fun and it’s really all about encouraging engagement and encouraging people to join in to have some laughs because you don’t want to force people to come to a social event. right?

Brad Johnson: So, that’s the other thing. I heard this story years back and it was a Dwight D. Eisenhower story, and he was talking about leadership. And I believe it’s a true story around D-Day. And he had these generals that had these troops, and they were planning, obviously, this big invasion. And he listens to the plan. And then he says, “There’s only one problem,” to the generals, and he just pulls a piece of string out of his pocket. Excuse me. He pulls a piece of string out of his pocket. He sets it on a table and he tries. He says, “You’re trying to go here, right?” And he points the spot in the table and he starts pushing it, and the string folds up. Have you heard this story? It folds up upon itself.

Kristi Herold: No. I’m just picturing. Yeah, yeah.

Brad Johnson: And he said, “You can’t lead like that. You have to lead like this.” And he takes the string from the front and he pulls it. And the problem was the generals were trying to tell everybody what to do, but they were like sitting back and watching. He’s like, “No, you have to be in the trenches with them.” And what it made me think of when you shared the houses is, as a leader, you would love it if 100% of your team showed up at book club because they’re learning, they’re growing, they’re getting better. You would love it if 100% shows up at lunch ‘n laughs.

And I see a lot of organizations forcefully like, “Everybody report to lunch ‘n laugh,” like, okay, that sounds fun, you know? But now you have a team competition that’s pulling them into the stuff you want to be and actually having fun with it. And it’s just like a complete opposite of what most businesses and corporations do. So, I just think that’s a brilliant idea. I love that. We’ll probably be borrowing it at Triad. This is going directly to Kenzie, our Director of Culture, once we’re done recording here.

Kristi Herold: Well, tell her to reach out. If she needs some help, let her know to reach out. We’d be happy to help.

Brad Johnson: Would love that. Okay. I know we’re close to time here. I would love to. There’s two thoughts here and then I’d love to get just one last question answered. First one, you mentioned earlier that you do fun trips to incentivize the team. How do you mathematically get there? Is it related to, hey, a stretch goal? And so, now the goal pays for the trip. Or like if you’re a financial advisor out. So, what’s your math or whatever you feel like sharing? Like, how far out do you plan the trip? How much is the team involved? What’s the runway to earn the trip? How does that work?

Kristi Herold: So, I’m actually kind of foggy on this because we haven’t done it since before the pandemic. The pandemic really rocked our world a little bit, as you can imagine. So, in the past, it was definitely stretch goal related so the stretch goal paid for it effectively. And it was all… I can’t remember the details but, I mean, you look at the gross margin and you make sure that the gross margin from the stretch is going to cover the cost. If you hit that number, you plan this trip. Now, it was also getting more and more complicated because as we are getting bigger, it became hard to leave a bit like to have the business shut down for three days is a hard thing to do.

So, it’s something I do want to get back on our radar. How can we look at this and maybe it’s houses that go on trips together or I don’t know. Like, maybe they’re different times or maybe it’s two different houses go at once and two different houses go to a different time. I don’t know. I’m not sure. But this is partly why we’ve started doing Jamboree because Jamboree is we’re not all getting on a plane and going to Mexico for four days, where we’re going somewhere closer. It’s easier. We fly those that aren’t close to Toronto. We’re going to typically it’s been Niagara the last few years, which is about an hour outside of Toronto. But it’s still hard to like because it’s usually that we go up on Thursday morning and we’re there until Saturday. And we still have Thursday and Friday that you need to sort of cover. There are certain work things that have to get done.

So, it is a bit tricky, but it’s not impossible. And I think having incentives is great. Now, we also have bonus plans in place. So, if we hit numbers, people are earning, they have opportunity to earn more money based on the growth of the company. So, whether it’s through a trip or whether it’s through bonus plans because not everyone necessarily is inspired by the trip. So, it’s not perfect but it was good. We did it for a long time. That was really fun.

Brad Johnson: Very cool.

Kristi Herold: Yeah. Also, we had a very young team who didn’t have young families. That’s changing. Like, our team are staying around longer now or getting a little older. We still have a lot of young people but people have other responsibilities. Like, I think for some people they’d be like, “I can’t go to Jamaica. I’m a mom or I’m a dad.” So, it’s not quite as easy but it was fun the years that we did it.

Brad Johnson: Yeah. Oh, cool. Time for two quick questions.

Kristi Herold: Absolutely.

Brad Johnson: All right. So, the first one, so you’ve got a lot of founders, a lot of financial advisors that have kind of the young probably somewhere between a team of five to maybe 50. And say they want to incorporate some play into their culture, what are two or three quick ideas they could implement, wouldn’t take a ton of work, wouldn’t be crazy expensive, that would have the maximum impact for just having fun with their team?

Kristi Herold: For a five-person team or a 50-person team there are tons of ways. I mean, my book has an appendix which is filled with tons of ideas. And by the way, for your listeners, Brad, I’ve got a landing page if they want to get the ten ways to integrate play into the workplace. It’s a PDF that’s ten quick and easy tactical ideas. I gave you a link for that. It’s KristiHerold.com/DoLife25. So, in there, there are lots of ideas but some quick and easy ones off the top of my head. First of all, I would say if you don’t have a shout-out channel on your Slack or Microsoft Teams chat, I would highly encourage you to set one up in the next five minutes.

And so, this is something that everyone in the company is invited to the shout-out channel, and start by getting a few leaders in the team who populate with shout-outs over the next few days and encourage everyone in your team to share shout-outs. And so, what this is, it costs nothing and it takes 30 seconds to send a shout-out to say, “Hey, I just want to shout out Sue for our core value of treating everyone like her best friend. She did X, Y, and Z for me this week, which just really made me feel super cared about. And I so appreciate Sue. What an all-star.” Boom. Send. Everyone in the company sees this shout-out and it’s always tied to core values, which is a great way to sort of live and breathe your core values, not just have them written on a wall and then never thought about it again. And it’s celebratory and playful. So, that’s super easy thing I would encourage everyone should consider doing.

Having a huddle, a daily huddle, incredibly powerful. Our huddles are every day at 1:00 Eastern. So, whether you’re in Europe or you’re on the West Coast, it’s very doable to make it to huddle. And the way our huddles work, it’s seven minutes. Exact same agenda every single day. But it’s a different leader every single day. So, everyone in the company, from C-suite to student interns, take a turn hosting huddle. They have the agenda. And so, they start with good news and good news. As the huddle leader, they’ll start off and they’ll say, “Hey, this is Kristi coming to you from Costa Rica. I’m the CEO.” And we’re trying to get people to share now that we have new teammates joining us all the time, and we’re not all in the same office.

You say who you are, you say where you work, you say what your role is. It’ll get new people to start to understand who everybody is. And then you say, “I’m going to start us off with good news. My good news is…” and it can be a personal or a work win like, “My brother just had a baby,” or whatever, like whatever the news is. Anyone else have good news? And then they move to department updates. Every day of the week is a different department, and they do a quick highlight from their department of what’s going on, maybe a quick metric, a number that we want to be on top of. And then there would be a call out for, are there any other cascading messages, important updates that we need to hear about? Then you got a helping hand. Does anyone need a hand with anything? Any help needed out there? Call it out right now. And closing off, I’m going to close off with leader’s choice.

Leader’s choice is always something playful. And I’m going to share a riddle with you for my leader’s choice or I’m going to ask everyone to upload into the banter channel. We have a banter channel, which is where silly banter happens all day long. In the Banter channel, post a picture of the very first sports team you ever played on. Post a picture of yourself as a child playing sports. And so, you see these hilarious photos of… Or I’m going to encourage everyone for my leader’s choice today to get outside and just take a ten-minute walk without any devices. Get rid of your AirPods. Just go, be, and enjoy fresh air. Leader’s choice is different every single day. You never know what it’s going to be because it depends on the leader and they have free reign to make it whatever they want.

And so, that’s just a fun, playful thing that it can happen. Every meeting we run at our company, as long as there are three or more people, starts with, “Press play to start,” and you take three minutes and you have some kind of playful banter. Whoever is the leader of the meeting, it’s on them to get the meeting started with a joke or a question or whatever, something playful, just to sort of have everyone connect as friends for a minute, and then you get into the work. And these are all simple little things that don’t cost the company any money. It’s just a mindset. When we have meetings, they are in-person.

We have a dodgeball that sits on our boardroom table. If you’re holding the ball, you have the microphone. You get to speak. If you’re not holding the ball, don’t interrupt. Let that person finish. Make a note of what you want to say. Put your hand up. They’ll throw you the ball. Then it’s your turn to speak. Gives everyone it’s a visual, playful aid that helps everyone to sort of respect each other’s time. And so. And then when you are holding the ball, you’re also a little more conscious of being aware to not go on tangents like I got to get my point across because I’m holding the ball. Super easy things like this is not complicated stuff that we do, but it makes for a really playful, fun organization to get sh*t done at.

Brad Johnson: Love those ideas. That was rapid fire. We’re going to have to clip that and be like, “Everybody do this.” Once again, we’ll be borrowing many of those. Okay. Well, as we close here, this is the Do Business Do Life podcast. That is why I Triad exists both for our members as well as our team. And so, I think this will be a fun one for you. What is Kristi Herold’s definition of doing business and doing life?

Kristi Herold: My definition of doing business and doing life, oh my goodness. I would say spell workplays with a Y. So, work, play, get the play inside your workplace culture. Does that make sense?

Brad Johnson: It makes a lot of sense. Yeah.

Kristi Herold: Yeah, a little bit of work, a little bit of play can go a long way to improving your workplace culture. So, that’s sort of, I guess, my definition is make sure that your workplace culture has a Y in there. A little bit of work, a little bit of play integrated into your workplace culture.

Brad Johnson: So good. Well, Kristi, thank you so much. Thanks for carving out some time while you’re in Costa Rica. Probably doing a little work and a little play, I’m guessing.

Kristi Herold: Hey, you know what? I just thought of one other thing I should share with you before we wrap up. A quote that I just recently heard, which this speaks volumes and I’m going to be starting to use this in most of my keynotes. Plato, pretty smart guy, right? Plato said you can discover more about a person in an hour of play than in a year of conversation. So, play with your colleagues. Play with your teammates. Integrating a little bit of play, you’ll learn a lot more about them as human beings by playing together. And that’s why this is so powerful and so important.

Brad Johnson: Couldn’t agree more. And it’s a lot more fun when you do. Well, Kristi, thank you so much. This has been a very fun, very playful conversation as I knew it would be. And I can’t wait to get this out to the world. It’s going to impact a lot of financial services firms, not just in the US, but actually we’ve got a lot of listeners up in Canada too. So, they’ll probably be hitting you up.

Kristi Herold: Awesome. Well, thanks so much for having me, Brad. It’s been really fun and I appreciate your time.

Brad Johnson: All right, Kristi. Until next time. We’ll see you.

Kristi Herold: See you later.


These conversations are intended to provide financial advisors with ideas, strategies, concepts and tools that could be incorporated into the advisory practice, advisors are responsible for ensuring implementation of anything discussed is in accordance with any and all regulatory and compliance responsibilities and obligations.


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