EntreLeadership - Why Humor Is a Secret Weapon at Work with Naomi Bagdonas

Episode Date: September 26, 2022

Join us as our host, George Kamel, talks with Naomi Bagdonas. She’s a lecturer at the Stanford Graduate School of Business and an executive coach. Naomi is also a coauthor of the bestselling book, Humor, Seriously. In this episode, she shares the benefits of humor at work, the different humor styles we use, and what to do when a joke doesn’t land. Later, George chats with Kacy Maxwell—the executive director of marketing for EntreLeadership. He shares when not to use humor at work (from personal experience). When figuring out what type of humor is appropriate for the workplace, it’s important to be aware of the fine line between stuff we should and shouldn’t say. You’ll learn: •      Why you should laugh more at work •      The four styles of humor at work •      How to recover from a bad joke at work •      How humor can go completely wrong at work Sign up for The EntreLeadership Podcast takeaways—a weekly email where you’ll get three tangible takeaways and a tactical action step related to each episode: https://bit.ly/podcast-takeaways Support our sponsors: •      Hite Digital: https://bit.ly/HiteDigital •      Kyro Digital: https://bit.ly/KyroDigital •      NetSuite: https://bit.ly/NetSuiteEntre •      Trainual: https://bit.ly/TrainualEntre Links mentioned in this episode: •      The EntreLeadership Podcast: https://bit.ly/TheEntreLeadershipPodcast •      Humor, Seriously by Jennifer Aaker and Naomi Bagdonas: https://amzn.to/3BML5lV •      Take The Humor Typology Quiz to find out your humor style: https://bit.ly/3Ljr1Ld •      Naomi Bagdonas and Jennifer Aaker’s TED Talk: https://bit.ly/3RPr9Et •      Sign up for your 30-day free trial of EntreLeadership Elite: https://bit.ly/3x40ASS Learn more about EntreLeadership Events: •      EntreLeadership Master Series: https://bit.ly/EntreLeadershipMasterSeries •      EntreLeadership Summit: https://bit.ly/EntreLeadershipSummit   Learn more about EntreLeadership Coaching: •      Elite: https://bit.ly/3tI2fN8 •      Advisory Groups: https://bit.ly/EntreLeadershipAdvisoryGroups •      Executive Coaching: https://bit.ly/EntreLeadershipExecutiveCoaching •      Workshops: https://bit.ly/EntreLeadershipWorkshops Listen to all the Ramsey Network podcasts anytime, anywhere in our app. Download the Ramsey Network app: https://apple.co/3eN8jNq Learn more about your ad choices. Visit megaphone.fm/adchoices

On today's episode, we're going to have a lot of fun. Literally, we're talking about the power of humor in the workplace and how to do it the right way. And then some stories of how to not use humor at work. Welcome to the Entree Leadership Podcast from the Ramsey Network, where we help you learn the proven principles for winning as a business leader. I'm your host, George Camel, and each week here on the podcast, I sit down with some of the best leadership minds out there to help you grow yourself, your team, and your profits.

Our guest today is Naomi Bagdonus. a lecturer at the Stanford Graduate School of Business, an executive coach, and best-selling author of Humor Seriously, Why Humor is a secret weapon in business and life, which she co-authored with Jennifer Aker. One of the most interesting parts about Naomi is that one of her passions is teaching improv comedy to inmates at the county jail. That's pretty cool. Now, here at Entree leadership, we believe humor is a part of effective communication and building trust with your team. So we're excited to have Naomi on to help us grow in this area to have more impact. Let's jump right in. Here's our conversation.

Naomi, welcome to the Entree Leadership Podcast. How are you? Thank you. I'm great, and I'm super happy to be here with you. Well, our team, we're big fans of yours because of your book that you co-authored with Jennifer Humor Seriously. It has made the rounds at Ramsey. Every writer has read it, and we are becoming funnier by the day. Can You Tell? Whoa, yeah, I am holding back a lot of laughter right now. Thank you. A lot. Just for professionalism.

No, that's super sweet. Yeah, for, yeah, exactly. I will not laugh on this podcast. Very serious. Yeah, just for the sake of professionalism. No, I'm super happy to be here. Thank you for saying that. I really, I really appreciate that.

Absolutely. Well, we're here to help the business owners, the leaders listening become funnier. And as you know, humor is not always natural at the workplace. Sometimes it's a point of contention and awkwardness, and we don't know how to do it well. So is there still benefit to humor at work? work? Yes. So I first, I want to demystify the belief that this is about being funny. I know that

that's sort of a nice that happens and it is nice, but a lot of people get caught up on this idea that this is about being funny. And most of the leaders, senior leaders that I work with don't consider themselves to be funny, don't want to be funny. It doesn't seem like a business imperative. It seems like something that you do at home, not at work. And so I want to demystify both this belief that this is about being funny. It's really about accessing joy more easily and showing that you have a sense of humor. And absolutely, there's incredible ROI to, especially as a leader, showing that you have a sense of humor. So the course that we teach in the business school at Stanford, we often start with a couple of quick stats. So leaders with a sense of humor,

and this is any sense of humor, George, not even a good sense of humor, just you have a sense of humor, are seen, just attempting, even smiling, how. are seen as 27% more motivating. Their teams report being about 15% more engaged, and they're about twice as likely to solve a creativity challenge. And there's also a wealth of benefits when it comes to feeling more connected to colleagues. So yes, there is a wealth of benefit for humor today.

Well, at Entree leadership, we always talk about how business moves at the speed of trust. And when you have that approach of you're smiling, you're excited to be there, you're making an attempt, you're trying to work together. It really does build trust. How have you seen that happen with the executives you worked with, with working at inmates at the county jail,

all of the incredible work you've done? What's the relationship between trust and humor? Yeah, so I'll tell a quick story from early in the pandemic. So this is a CEO that we work with, who we actually teach with at the business school at Stanford. He's the co-CEO of Merit America. And it was in his first couple of months of being, co-CEo. And it was early 2020. So just the start of many people in the U.S. going into quarantine

during the pandemic, it was a super scary time. It was a tense time. And the entire organization is looking at this brand new leader, you know, saying, okay, what do I think of you? Do I trust you? And there's no interpersonal connection, right? It's everyone's on Zoom. So Connor joins his first ever all-hands call with his organization. And on Zoom, right? So normally all 150 people are in a room together is on Zoom. He says his remarks, and he has that moment that we all have experienced where he's like, he's talking and he realizes, oh, my gosh, my remarks are totally falling flat. This is not working. How do I actually build trust in this moment? And so he passed it off to his co-CEO to speak. But when he did, he intentionally left his screen share on.

And so the entire organization was watching terrified as Connor closed his PowerPoint slide, opened up a Google search and typed in things inspirational CEOs say during hard times. And everyone lost it. Everyone started laughing. But it was really interesting, right, it's this beautiful moment of genuine vulnerability. Right. He's saying, I actually genuinely don't quite know what to say right now. And he's sort of putting that on display. But he got so many emails from employees afterwards.

words saying things like that was the first time I saw a screen full of smiles. And then I feel safer to bring my own vulnerability to work. Like, thank you so much for modeling that. And he felt like it sparked this shift in the organization of feeling more connected to him and feeling like they could bring more vulnerable, hard things to him. I remember Dick Costello, former CEO of Twitter, visited our class at Stanford. And he said, the most important thing I do as a leader is break down the status barrier because there's an incredible trust barrier that comes with status, which means that my employees aren't going to come tell me the bad news. They're not going to be transparent with me about the things I need to know. And for him, humor was one of the

most effective ways to break down that status barrier and foster trust. That's a powerful reminder. And I can think of all the leaders at Ramsey here. And the ones I have the best connection to are the ones that have that sense of humor, that have that vulnerability that I could feel like I can come with them with anything and trust them. And so there's a magical symbiotic relationship there when we can build that. And everyone's got a different style of humor. We know that. Some people are a little more dry. Some people are sarcastic. And you cover four different types in the book, stand-up, sweetheart, magnet, and sniper. Can you walk us through those quickly so people can self-identify? Okay, great. And then I'm going to ask you to identify what

style you are as well. So get ready. There will be a pop quiz. Okay, so first is the stand-up Stand-ups are bold, natural entertainers, not afraid to ruffle a few feathers for a laugh. Love the spotlight. They are, yeah, really bold and brash humorists. Opposite the stand-up is the sweetheart. Sweethearts are honest, earnest, understated. They tend to lean on self-deprecation because they're super aware of how their humor lands on other people, and they always want to uplift others.

Next is the, we'll go to the sniper. So snipers are dry, sarcastic, edgy, witty. They are masters of the unexpected dig, that one-liner that just crushes you. They're also the hardest to make laugh. So when you make a sniper laugh, you feel really good about it. And then lastly, is the magnet. So magnets are charismatic, outgoing, uplifting. They tend to be a bit more risk-taking with their humor.

So they'll jump into characters and voices, and they'll be very emotionally effusive with their humor. Wow. So those are the four styles. What do you think you are? Oh, gosh. I mean, my heart leans towards stand-up because I'm literally in front of bright lights, and my job is to be, you know, brash and bold in front of people.

But I do, I think my favorite approach is a sniper. I love when you least expect it, you just snipe a joke in there and it catches everyone off guard. So I'd say that's my favorite type. But I think naturally, if you just met me, you'd probably just say stand-up. Sweetheart feels like the sweet. Like, I think everyone would be like, I'm a sweetheart. Yeah. You think people want to be sweethearts?

I don't know. What have you found? Is there a majority of people you say fall into one category? No, we actually find a pretty even distribution, pretty even population distribution. Also, one thing I love about the humor styles assessment, so you can go to Humor Seriously.com and take a quiz that tells you what your style is. One thing I love about this is, once you start to know the styles, you can guess pretty quickly what someone's style is. is. So, for example, listeners may not have heard this, but we had to pause the audio real quick because I was making too much noise with my hands, ruining everything. And George says something like, let the record show that my audio was perfect and Naomi messed up everything. This was like a quintessential sniper line. And I loved it so much. And it's such a reveal, right? So now I know, one thing that we know about snipers and standups is that they build intimacy through teasing.

And so if you're a sniper, George, I know that I can, sort of dig at you, make fun at you of you, and that'll be a way for us to build rapport with each other. If you're a sweetheart or a magnet, I might want to lean on sort of a little bit lighter, sillier humor that we can both sort of laugh about a third thing, and that'll be more connecting for us. And so this humor styles assessment is super powerful once we know our own style, once we know the styles of our teams, and ideally of our families too. Can I guess what you are? Yeah. Would you fall into the magnet? Yes. I nailed it.

And why did you think that? I think you've got to, it just feels like a magnet is a balanced approach to humor. While you're not afraid to take some risks, but you're also not there to tear down. Right. And so I think there's a mix there. Yeah. Well, one thing I want to say for folks who are listening and who are self-assessing right now and thinking, okay, I'm a sweetheart or I'm a stand-up or sniper or magnet, we are not stuck in these cubby holes of our style. And in fact, it's really powerful, especially as leaders, to be able to shift our style. So as one example, when I was relatively, so first of all, I'll say humor and status are inextricably tied.

So if you use self-deprecation as a high status individual, others will view that as status enhancing. Because you can take a, you know, you can take a joke, you don't take yourself too seriously, you're sort of showing your vulnerability. If you're lower status or you're not quite sure the hierarchy and you over-index on self-deprecation, that can actually decrease your status. Simple example from my own career is when I was in my like mid-20s and I was designing and facilitating these off-sites for groups of executives, I was often at the front of the room as the youngest person in the room by 15 years. And I sort of had to show a certain degree of status in order to be able to hang. I really quickly found that magnet-style humor was not going to work in that context. So if I was silly, if I was jumping into characters, that was going to crash my status in the room.

And so instead, I leaned really heavily into sniper-style humor, where I was really choicful with what I said, and I would, you know, take people down in sort of a light-hearted way, but it was super status-enhancing for me. Fast forward 10 years, I'm teaching in the classroom at Stanford. and I remember making a sniper-style joke at one of my students pretty early in the quarter, and you could feel the air leave the room. I mean, it was so uncomfortable because in that context, I was the highest status person in the room. And here I was doing what comedians call punching down. So making fun of someone of, quote, lower status in the room. And so as a leader, it's super important for us to keep a pulse on.

What are our natural tendencies? what are the risks of those natural tendencies and how do we shift our style based on the context? That's a great point. You've got to change. It's like being a chameleon. You've got to know the right times, the right environments, the right rooms to use right types of humor. So how do you have that kind of self-awareness? Obviously, we don't want to offend people in the workplace and it can be very touchy and tears can be shed and humor might not be taken the right way if I don't have a great relationship with you. So how do you figure all that out? Because some people just go, this is all just too much work, Naomi. I'm not even going to delve into these waters.

Yeah. And let the record show that George is crying while asking this question. So many tears. Yeah, humor is so context dependent. The one tip that has been most universally helpful for the execs that we work with is never ask, will this make me sound funny? Will this make me look funny? Instead, ask, how will this make other people feel? So recognize that the goal isn't to get a laugh. The goal is to warm up the room to make people feel more comfortable. My dog is sleeping next to me, and he is growling in his sleep. Can you hear that?

Is it being picked up on the microphone? I heard a little bit of noise. Now, I did see that you have a revolving door of rescue dogs. Is this one of them? Yes. This was a foster fail. So I've, yeah, I fostered like 20 dogs. and then this guy came along and I accidentally kept him forever.

So he is indeed a foster fail. Sorry, I didn't mean to cut us off. I just Max was snorting in the corner. This is authentic. You're being vulnerable. This is authentic. Yeah, I lost my trip. Oh, yeah.

Don't ask, will this make me sound funny instead ask how will this make other people feel? And recognizing that, yeah, the goal is not to look funny. The goal is to shift the environment in a way that fosters trust, vulnerability, makes everyone and feel safer bringing their full selves to work. And then, of course, there are a couple other techniques that are super practical, like never punch down. So making fun of someone of lower status, check your distance.

How close are you personally to the thing that you're making light of? Do you have permission to make light of this thing? If not, let's not go there. Those types of things. That's some good guard rails there. And another thing to ask is, is this helpful? Is this about me and making me look cool or funny? Or is this creating an environment

where it's conducive to sharing ideas and for us to have a good time and to get the business results that we want? Because that feels like the right way to do humor in the workplace. Yeah, totally. And for a lot of people, joking can come from a place of genuine insecurity or discomfort. And so it's really important to check ourselves. Where is this coming from and is this in service of our goals? Because the stats that I shared earlier,

I mean, humor is so wildly powerful for teams and for leaders. but we also have to check ourselves and make sure that it's in service of our goals. So I work with one CEO who had this realization in sort of an uncomfortable moment that he was trying to diffuse tension for himself. He was trying to make himself feel better. But the impact was that he alienated the room. So he had to step it back, apologize, and say, listen, where this is really coming from is my own genuine discomfort with having let go this senior member of the team.

So I want to open up the floor and let's have a real problem. conversation about that decision that I just made. Well, that's a good point. What do you do when the humor doesn't land? Is there a, here's the four steps to take when a joke bombs or the room just you suck all the air out? Yeah, so there are, we get failure wrong when it comes to humor. We think that failure means no one laughs. And the research is actually pretty helpful and optimistic here that if we make a joke and it doesn't get a laugh, there's actually a body of work done by researchers, done by Allison Woodbrooks, Maurice Schweitzer, and a couple others at Harvard and Wharton that shows,

if you use humor, as long as it's appropriate, if it fails to get a laugh, it still increases people's perceptions of your confidence and competence and has no meaningful impact on perceptions of status. And so as long as you're not doing this like every five minutes, it's actually not so bad to fail in that way. Now, the really bad failure is where you make a joke that's inappropriate, that crosses a line that hurts someone's feelings. And when we do this, that it's so easy to write it off and say, well, that person just didn't get it. They didn't get the joke. They're being too sensitive. And a humor fail is an empathy fail before anything else, because humor is this super unique context-dependent art form. And so when you do fail,

get really curious. What are you missing? What's the context that you're missing? What is the empathy fail that you've made because especially as leaders, we lose our barometer for what is appropriate with humor because we know from the research that when you rise in status, people laugh because you're the boss, not necessarily because you're funny. So we always have our leaders create a set of trusted testers. So people in the organization, maybe it's your COO or whoever it is that you know that you can trust. And before going into a big presentation or a pitch or an all-hands meeting, ask the question, hey, how could this land poorly? Help me understand how this could go poorly,

which is a very different question to ask than, hey, is this funny? Because people will be like, yeah, cool, that sounds good, it's funny. But how can this land poorly? That'll help illuminate some sort of blind spots that you might have going into it. Yeah, that's great to have someone else who can look at all the angles and go, well, I think you're not thinking about how it could affect this person and how it could be taken in that context. Right. Naomi might be so self-conscious about her audio. And so you calling your audio perfect and hers awful could break her.

You're clearly still bitter about that. Wow. I will hold this. Unbelievable. Well, one of the goals of this podcast is to help leaders grow themselves, their teams, and their profits. And it's pretty clear to me how humor can help you do that. But for those who still might not be clear, we talked about the benefits, but what do the results look like when you do this well, when you start to integrate this intentionally? Yeah.

So the research is super. compelling around sales as well. So one of our favorite studies researchers had individuals come into the lab and negotiate over the purchase price of a piece of art. So you, George, are walking to the lab. You're negotiating with the person across from you. You're trying to buy this art piece. And in half of these conditions, the negotiating partner offered you a final offer that was significantly above your final bid. And they simply said, my final offer is X. So that was half of the of the participants. For the other half, exact same experiment, exact same script, same percentage above your final bid, but they said my final offer is X and I'll throw in my pet frog. Now, this is an objectively awful joke showing that

the bar is incredibly low in business, but the impact was significant. So those in the pet frog condition reported, or they were willing to pay on average an 18% higher price for that item. And what's even more profound is they walked away from the experiment saying that they enjoyed the experience more, saying that they felt less tension with the seller, and saying that they liked the person across the table more. So this is borne out in a number of different experiments around sales. I think probably for this moment in time more than anything, it's humor's impact on retention and humor's impact on our ability to attract and retain top talent. And this is, so Jennifer Ocker and I teach a course at the business school at Stanford called a new type of leader. And the premise is that it used to be that leaders needed to be revered. Now they need to be understood and they need to connect.

People no longer want to work in places where they can't bring their full selves to work. And so the majority of the leaders that we're working with right now are undertaking enormous cultural shifts to try and make it safe for people to bring their full selves to work and to create an environmental. where people feel like valued members of a winning team on an inspired mission. We talk a lot about bosses versus leaders around here. And one of the keys is bosses don't lead with humility and humor, but it is one of the hallmarks of a great leader. And I look at Dave Ramsey, our CEO, and he embodies this. And so that's a huge way to go, how do I make that shift?

Oh, I'm just going to lean into humility and humor and connect with my team instead of just pushing them telling them what to do. That's huge. Yeah, and a little more humanity. I mean, I think that's the first step here is just bringing more of our humanity to work, telling stories from the weekend, being more candid and transparent about our follies, about the mistakes that we've made. And when we do that, when we bring more of our humanity, our sense of humor really naturally follows. So as we wrap, what are some of your best tips for leaders out there who are going, all right, I love this conversation. How do I practically add more humanity, more humanity, more human. humor to my life, to the workplace, to those I lead. Yeah. I think one thing is telling more personal stories from our lives. So recognizing that creating humor doesn't have to come from the leader, all you have to do is set the tone,

that people's humanity is welcome here, that people's sense of humor is welcome here. And so it can often be as simple as instead of opening an all-hands meeting with the results from the quarter or whatever KPIs you want to share with the org, open with a personal story. And the impact of that is wildly profound. We teach another course around storytelling. So yes, so more personal stories. The second thing is just look for more moments or reasons to smile. So the signals to the organization that this is an important thing.

And again, makes other people feel safer to bring their sense of humor to work. And then the third thing I'll say is make time in the agenda for it. So one of our favorite guests in class was Gene O'Lwing and Richard Branson. So Gene runs Virgin Unite and, of course, Richard Virgin. And they shared about the founding of the elders. So the elders, this group of global leaders, independent global leaders, whose mission is to solve some of the world's most intractable issues. So founding members included people like Nelson Mandela, Kofi Annan, Archbishop Desmond Tutu, President Jimmy Carter.

And in this first meeting of the elders, the sort of let's convene and figure out what this thing is even going to be, it was on Richard Branson's private island, on Necker Island. And so Richard's team had spent months preparing the agenda for this multi-day offsite where they were going to define what the elders was going to be. So a couple days before the offsite starts, Gene arrives with her team with this like stacks upon stacks of PowerPoint decks and agendas and the plan for the intents. entire time. Richard walks in, Richard and Peter Gabriel walk in. They look at the agenda, and Richard flips through. He says, this is really great. I'm going to need you to cut it in half. And Jean says, well, what do you mean cut it in half? Are we shortening it? Or the elders leaving early? He said, no, but I need this to be half work and half play. So literally, they threw out half of the agenda and the entire rest of the time was, quote, playtime. So it was things like

unstructured time on the beach or swimming lessons or walks or different activities where people could just connect outside of this really incredibly important and heavy work that they were there to do. And I remember Gene telling us afterwards that it was during this playtime that some of the most important work happened. And in particular, she recalled a moment where Archbishop Desmond Tutu and President Jimmy Carter were sitting on the speech together during playtime, their toes dug into the sand. When they came up, they were laughing, when they came up with the founding principles of the elders that Nelson Mandela would later report out to the world.

I share this story to say, we are all doing really important work. We're all, we believe in the mission of what we're doing, of what we're building, of the teams that we're convening. and in that context where there is such gravity, that is where levity can be so powerful to help us towards our goals. And so make time for it, build it into the agenda, and recognize how important it is.

So good. I felt like I just witnessed a TED Talk for free. So thank you for that. So good. Naomi, I love how you embody the principles that you teach. You live them out. You're telling stories.

You have that humor. Trust is built instantly. And that's where results happen. That's where impact happens. So thank you for what you do. Again, our team, huge fans of you and your book humor seriously. Every leader needs to pick it up. Thanks for being on with us today.

Thank you. And I am a huge fan of your work in this podcast as well. So it's a super honor to be on. Thank you for having me. I told you guys, we're going to have some fun today. And I feel like I delivered on that promise. Big thanks to Naomi for joining us today. We've got links in the show notes for you all, her book, humor seriously, and her TED Talk,

why great leaders take humor seriously. Be sure to check both of those out. All right. Up next, we've got a brand new. segment on worst leadership mistakes. And today's, of course, is about humor at work. We'll have a conversation about that right after this. All right, we're back with our brand new segment, worst leadership mistakes, and I'm joined by Casey Maxwell, or executive director of marketing for entree leadership. And we all know there's a fine line between appropriate humor and stuff

we shouldn't have said. And occasionally, we crossed the line. This is going to be a lot of fun. Here's our conversation. Casey, welcome back to the podcast. Thanks, George. I'm tentatively excited about today's topic. Tentatively. That's promising. Yeah. Well, I mean, depending on how it goes, it's going to be really good or really something else. Yes. Well, this one's a little different. I thought we'd actually have some fun today for once. Are you okay with that? You want to have fun on the podcast? On the podcast. Let's give a shot.

You're known around here as one of the funny guys, if you will. Oh, that's nice to hear. Yeah. I've never said that. Of course. But I've heard other people mention that. But I thought we'd talk about humor today and its role in the workplace. Okay. This is a hard thing for a lot of leaders to grapple with because personally, when we're off the clock, we're always making jokes.

We're telling stories. We're having fun. But sometimes at work, the vibe can be a little different. Yeah, definitely. Have you experienced workplaces like that? Oh, yeah. Well, I mean, growing up, I don't know what you were like in school, but I like to be the class come home. Right. And so I would have fun all the time. I would always be joking in class. I had one teacher. I made some sort of joke. And she was like, Casey, do you know why you're sitting in that chair in the back? And I said, no, why? And she goes, because it's one step closer to the door. And I was like, oh, I completely misjudged this relationship.

Wow. So, like, I kind of learned from an early age that joking and humor was not appropriate. It was something that you would get in trouble for. And so, like, when I got into business, I kind of translated that there. So I never, I never really brought humor there, especially to presentations or in any sort of meetings. And so, like, something that was a huge part of me, I just kind of shelved when I would enter the door. Yeah. Well, in the stuffy corporate world, there is a lot of times where humor is looked down upon. It's not appropriate. It's not professional. But, you know, here in the Entree leadership world, we deal with a lot of small businesses, and it's a different vibe. They're not

dealing with stuffy corporate environments, but there is a fine line between appropriate humor and things that you probably shouldn't have said. How do we find that line? Yeah. Well, the way that I've found that line is I've crossed it and messed up a bunch of times, and then I realize, oh, that's not appropriate. Like, to me, when I've found that humor is good, it calms people down, it can break tension, it can make you seem more approachable, like people won't want to talk to you and you're more engaging. And when it does when it's wrong, it belittles people. It makes people lose parts of their dignity. And so again, sometimes it's been trial and error. Yeah, I've noticed that sometimes people make jokes at other people's expense and it's

attacking character and it's not well timed and there's not a deep enough relationship or that person doesn't understand the context. And so there's a lot of factors where a lot of people just go, I don't think I'll even want to try because I'm not here to, I'm not wanting to get sent to HR because I said something cringy. And we've all seen the office and we've all seen Michael Scott and those first few seasons where he's trying to be funny or whatever. And it's just not coming across the right way. Yes. No one wants to be that guy.

Yes. That is honestly one of my biggest fears as a leader is that I'm going to find out one day that my team members are laughing at me because I'm the boss and not because I'm funny. Like that keeps me up at night. So there's two things. They're laughing not with you, but at you. And number two, they're only laughing because you are their leader and they're like, well, this is what I need to do as the team member. Yes, exactly. I need to stroke his ego. Has anyone ever admitted that to you? That like Casey, honestly, that wasn't funny, but I laughed because you're my leader. Never in that direct way. But I've learned over time, like, oh, that laugh is not authentic. Oh, you can sniff it out. I know. I mean, you know your A material and your B material. And when you put out the B material and you get like a standing of.

ovation, you're like, some of that, you're dialing some of that in, people. Yeah. How do you tell? Is it a, just a gut feeling? Mostly a gut feeling, yeah. And again, you do it enough times and you gauge the feedback, especially if they've heard it multiple times, you're like, you've heard this before. You knew that punchline before I said it, and you were still laughing like you heard it the first time. Yeah.

Well, and humor on some level is universal. It's like music. We all love people with a sense of humor. We all, hopefully, like to laugh and have a good time. And it's important to bring that into the workplace and in meetings in an appropriate way. Obviously, this is largely dependent on your team and your culture. And there's probably inside jokes about the company and about specific people. And it's hard because some people don't have the sense of humor that you might have. Is that one of backfires? Of course.

Yeah. I mean, I like sarcasm. Sarcasm for me just helps me kind of sometimes if something is frustrated, I can talk about. it in a sarcastic way. And for me, that's a bit of a release. For some people, it's a defense mechanism. And for some people, they don't know how to read sarcasm. So it comes across as like, oh, he's really angry about something in a very passive-aggressive way. And so it just creates this weird, like, I don't understand how my leader is actually approaching this situation. So motive matters. Correct. When you're using humor in a passive-aggressive way,

not the right way to go about that. Exactly. But if you're using it, it to just diffuse the tension. Maybe you just want the right tone in the meeting. You have an icebreaker or a great well-time joke and the room breaks and when it was really tense. There's some great ways to use humor to actually increase productivity and increase trust. Yeah, we have, so we have a weekly stakeholders meeting in Entree leadership. And one of the three rules of that meeting is well-time jokes. We want it not to be a stuffy meeting where we're constantly coming in here and getting updates, there are times that we're wrestling through stuff and it can get pretty intense. And so we want people to be like, hey, just be yourself. We want to have fun.

We want people to laugh. And we know that if people, if we set that expectation up front, we'll have more of that in the meeting and people can be themselves. Do you have any examples of this that maybe you've seen or heard have been a part of recently? In terms of jokes that maybe have gone wrong? Maybe both. I mean, I think we're all here for the ones that went wrong, for sure. Well, I could get out my journal and just leaf through the many pages of the times that my jokes have gone wrong. One in particular is, so we do a thing around here called $100 handshakes. Sometimes they're $100, sometimes they're more.

But it's basically a way for us to just give a out-of-cycle reward to someone for just doing really well. So it's like, hey, here's just a nice little bonus for you. How am I doing? So. Curious. Well, we can see if you can get a maybe handshake in a couple months or something. We'll figure it. We'll circle back on that. But so we were going to give it to one of our best employees. Like she was amazing. She actually still works here. And so we planned it, got it ready, set up the meeting. And she didn't have any context for that meeting. So it just says, hey, like a checkup or something. So she comes in the meeting and she sees her two leaders, the business leader and kind of like the discipline leader was going to be in that meeting. And so right before we go in, the discipline leader leans over to me and goes, hey, let's pretend. like she's in trouble.

And I was like, what do you mean? He's like, let's pretend like we're kind of like reprimanding her for doing something wrong. And then we'll give her the bonus and she'll be super excited. Just like a slingshot, rubber band. Yeah, like it'll make the rewards so much better. And so I instantly thought, that's a terrible idea. Let's not do that. That's not what I thought.

I wish that's what I would have thought. My instant response was, oh, that's awesome. And the thing that I needed to dig in later is I was like, he said, oh, I could never do this, but you're really good at lying. And I was like, what do you mean? I'm really good at lying. He's like not, sorry, not lying. He's like, but just kind of like joking, but being serious. And I was like, okay, I've got to work on that piece of my personal brand as well.

But we go in a good bluff. Yeah, yeah. So we go into the meeting and we sit down and in my mind, I'm like, she's going to love this. This story, she's going to laugh about it, tell her friends. So I start going and I've fabricated this story that she was listening to something on her headphones and like some sort of work, like it bothered somebody and so we just had to talk to her about it. And as the words are coming out of my mouth and I'm seeing her face, her face starts getting beat red. And her eyes start getting really big.

And in my mind, I'm like, oh no, what have I done? And so as I'm saying these words, and I know that she is just, her heart is racing and freaking out, I just kind of stopped in the middle. I was like, no, no, no, that was a joke. That was a bad joke. Hey, we're giving you money. You can, here's some money. And I gave her this, and it just, it ruined everything about that event that was supposed to be a really nice thing.

But because I didn't understand, like, there was a leader, there was a power dynamic in that room that if I was doing that sort of joke to appear, right, probably would have landed differently versus someone that I was a leader that I was, that I was responsible. responsible for. Yes. Yeah. And in comedy, they call that punching down. It's not as funny. When you punch up, it's a little bit funny, which is hard to do in an organization. You know, and I make fun of Dave on air in a lighthearted way. Clearly, I respect Dave. But we're on the Ramsey show. Sometimes a well-time joke just snuck in there makes for some great radius. Yes. But the same principles can apply in the meetings. And it all, it comes down to, do I have a mutual respect? Do I have a relationship with this person? Do they have the context. Is this the right time? Is it actually a serious time and not the right time to crack a joke? Or is there tension that could be diffused? So there is a lot of benefits to humor in the workplace.

Of course we got to do it right. We don't want to violate HR policy. We're not here to upset people and hurt feelings. But that's a good filter of why am I making this joke? Am I doing it to hurt someone, to harm someone to be passive aggressive? Or am I doing it to light the mood, diffuse some tension, you know, build morale. It's a very different world. Yeah, yeah, and people like to laugh. People like to have fun. And so if you have a work environment that has none of that, people are not going to want to come to work. They're not going to enjoy their work. All of those jokes and fun is going to happen at lunch or at a water cooler, you know, or some other place like happy hour. And then it's going to be this boring dredge of a day at work. So you got to, you know, as a business leader, as a leader, you got to figure out a way to like, how do I bring this in, make it approachable, make it. make it fun because if people enjoy their work, they're going to work harder, they're going to stay longer. It's going to drive that loyalty and unity that we know is essential to drive business forward. Yeah, and whether it's a one-on-one or it's a company staff meeting and Casey's up there

and he's doing an announcement, everyone loves when there's a joke up there because we have great staff meetings. But there's still times when you just love a joke when we all can just take a breath, laugh, especially if it's a heavier update and we're talking about budgets or whatever. it is, any kind of communication. So if you're a leader out there, make this a part of your growth to get better at this. You don't have to be a funny, you don't have to be a stand-up comedian, but you can bring a tone, a sense of humor, to situations. Yes. I love that. Any other benefits you want to talk about here? I would just say mostly if you're not good at humor, I would say if you want to start telling jokes, don't lean into like dad jokes, right? And don't

make fun of anybody else. Like, make fun of yourself. Like, if you want to add some of that, just like, self-deprecation. Yeah, it'll show you're not taking yourself so seriously. It makes you more approachable. People want to be around people that don't, like, aren't so prideful that they can't even laugh at themselves.

Yeah, it shows humility, and it shows some vulnerability, which then creates trust, which then creates results. Yep. And Dave Ramsey, you know, it trickles down. And Dave Ramsey's really good at this. He's the first one to say, I got a Ph.D. and D-U-M-B and he owns those things and he's got humility and calls himself a hillbilly redneck and all these things that make us laugh. But it creates a culture over time when you do that.

And so I want to encourage all of the leaders listening to make that a part of their business because it's going to keep your team engaged and it's going to drive results and it's going to create an amazing culture. 100%. Well, thanks, Casey, for having some fun with me today. It's always fun with you, George. I'll laugh at your jokes soon. I promise. It means a lot. Thank you, Casey, for being brave and modeling what great leadership looks like. Well, we talk to thousands of business owners every year, and one of their biggest challenges is leading people. As we always say, business is easy until people get involved. So you need to stay connected with your team consistently. And that's why we created Entree

Leadership Elite Weekly Reports. This is our system to help you track your team's morale, workload, and stress every week at a glance. Our team uses it here at Ramsey, and it's an incredible tool. And right now, you can try it for free for 30 days. You can start your free trial today, at Entreeleadership.com slash Elite or click the link in the show notes to learn more. If you enjoyed today's episode of the show, follow or subscribe and leave us a review. Even better, share this episode with your team, with your friends, or on social media. Speaking of which, you can follow us on social media at Entree Leadership. This episode is produced by Tim Hull, edited by Jacob Harrison and mixed and mastered by Will Rudder.

I'm your host, George Camel, and on behalf of the entire Entree leadership team, thank you for listening. Until next time, keep learning. and keep leading.