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Dave Stachowiak
It sometimes seems like someone with a good sense of humor does everything just a bit better. Perhaps leadership is no different, but it's not about landing jokes in this conversation. Why? Everyday humor is all about paying attention and generosity. This is Coaching for Leaders, episode 787, produced by Innovate. Learning, maximizing human potential. Greetings to you from Orange County, California. This is Coaching for Leaders and I'm your host, Dave Stahoviak. Leaders aren't born, they're made. And this weekly show helps leaders thrive at key inflection points. You know, one of the things that I think so many of us enjoy is humor. We love to laugh, we love to make others laugh. And yet it's not something we often think about in the context of leadership. But maybe we should. And in fact, today's guest has really inspired me to be thinking about humor in a way that brings joy, purpose, connection into our work and also, by the way, helps us maybe to lead just a bit better too. I'm so pleased today to welcome Chris Duffy to the show. He's an award winning podcaster, comedian and television writer. He hosts the podcast how to be a Better Human and you can find his comedic TED Talk to find laughter anywhere online. He is the author of Humor Me how laughing more can make you present creative, connected and happy. Chris, what's happening? Good to see you.
Chris Duffy
Hey, thanks so much for having me. What a joy it is to be on the show.
Dave Stachowiak
I'm so glad, so glad to get connected with you. I just, What a joy getting into your work. Reading the book, I was thinking about humor and let me be serious for a moment because like so much of leadership is like, okay, like the really important strategy and coaching and listening, like so many things we talk about in the show. And if I were to write down a list of what are like the top 25 competencies that leaders really need to do well. And I, and I thought about humor in the context of that humor would be one of those things that I'd say, hey, you know, it's really nice. Humor is great. But it probably wouldn't be the thing, I think, to put on that list of 25. And I totally, I think that's where you and I might differ a bit because I think it would show up on your list. And when you think about humor and bring it into the workplace, especially what's so essential about it?
Chris Duffy
Well, I think there's, you know, I'm not sure that we do disagree. I, I'm not sure the humor would be in my top 25 list as far as the, the thing that you necessarily want. But the thing that I think is so magical about humor, and the reason, a big reason why I wrote the book, is because I think that humor is a tool and a technique that lets you get to all those other 25 much more easily in a way that is much more fun and that doesn't feel like homework. Right. Like, so often we are told, oh, what you want to do is really connect with people deeply. Oh, what you want to do is show vulnerability. Oh, what you want to do is to be present. Oh, you want to pay close attention. Oh, you want to be regarded as relatable. And those things all feel like challenging and homework and tough to do.
Dave Stachowiak
Yeah.
Chris Duffy
And humor, to me is this magical tool that lets you do all of those without it feeling like work. Right. Like you can make a, a joke, you can laugh with people and they will feel so deeply connected to you. They will feel like they like you more, like they're on your side, they're rooting for you without it kind of taking all of the effort where you think, I gotta call someone up, I gotta send them a text message. Right. Just laughing together connects you so deeply. And so I think it is like a shortcut to get to all of those things. And also, especially as a leader, to make yourself seem more human is to be able to laugh at yourself.
Dave Stachowiak
I love this reframe already because I'm just thinking about this as a competency that by getting a little bit better at humor, it actually helps us to do all the other things easier, with more joy, with less friction.
Chris Duffy
Like, what a nice way to think
Dave Stachowiak
about how to bring humor into the workplace.
Chris Duffy
Yeah, well, you know, I think one of the big things too is we can all imagine, you can all imagine, like the way that this can go wrong. Right. So you're the boss who makes off color jokes or is offending people or just won't take it seriously. It's very easy to picture the guy who thinks he's funny but isn't funny, actually that we've all met that guy. So a big part of why I wanted to talk about this and think about this is that people often think of humor and having a good sense of humor as being the center of attention, being the one telling the story or the one on stage and delivering an anecdote that everyone laughs at. And I'm not saying that's not having a good sense of humor, but that's actually not the important part to me. The important part is Noticing the strange and unusual and the absurd and being willing to laugh about it, even if it is in your. So rather than imagining, like, the boss who tells these weird jokes that no one laughs at, I would say what if you imagine the boss who, when something goes awry, when there's, like a technical difficulty during their keynote, or when something has gone in a way that is unexpected, rather than pretending like it's not happening or getting super flustered, what about the boss who laughs about it, who acknowledges it in a way where we all see that they're human and they acknowledge, hey, the microphone just cut out, right? Like, I'm going to try and talk without the microphone. You're not going to hear me in this big, important meeting. Or, hey, we printed up all these gifts for clients and it turns out that there was a big, obvious typo on them. If you treat that as something that is an opportunity to laugh and bond with the people who you work with and who work for you, rather than something that's like a shameful, embarrassing, giant mistake, you create this real opportunity to build culture. You create this real opportunity to build connection and also for people to, I think, view you in a way where you're a person who imperfections can be addressed rather than have to be hidden. And I think that's a huge reason why you want to bring this to the workplace.
Dave Stachowiak
Boy, and there is so much hilarity in the workplace.
Chris Duffy
Like, oh, I mean, there's a reason why the Office is one of the most popular television shows of all time.
Dave Stachowiak
I know, I know.
Chris Duffy
I mean, think about all the.
Dave Stachowiak
Like, just on any given day, there are two or three things I run into regularly that I think that is just hilarious. Like, when you stop to think about it, either things that have happened to me or things. Stories. I hear the stories that come up in our academy sometimes. Like, we all laugh so hard of just, like, the hilarity and the irony of so many things that happen and really does. Like, I've been thinking about reframing things. One of the things you mentioned in the book is that a good sense of humor is inherently generous. And when I think about that word. Again, thinking about things I don't normally think of with humor, generous isn't the word I often would think of. What is it that's central about generosity when we think about humor?
Chris Duffy
So, Dave, I'll answer your question by turning it around on you a little bit, which is if you think about someone who you know in your real life, who, whenever you're with them, they are laughing all the time. You tell them a story, and they laugh, and they say, dave, that is so funny. Oh, my gosh. Or they notice something on the street, and they start laughing about it, and they point it out to you. They are just kind of full of joy and laughter. Not necessarily that they're, like, telling you the jokes, but that they're appreciating that. Do you have someone who you can think of who kind of embodies that in your life?
Dave Stachowiak
Oh, for sure. For sure.
Chris Duffy
Yeah. And who is the person you're thinking of?
Dave Stachowiak
Okay. The person I'm thinking of is our daughter.
Chris Duffy
Okay. And so when you're with your daughter, obviously, you know, you have parental love for your daughter, but the fact that your daughter has this laughter and joy so immediately accessible. How does it make you feel when you're hanging out with her? Does it make you feel like you're energized and you want to hang out with her more? Does it make you feel like there's kind of, like, pressure and. And there's stress?
Dave Stachowiak
Oh, it's. It's fun. It's joyful. I mean, there's all the normal stuff of, like, parenting and family stress and all that things that do come up occasionally. But she. She is really. I. I'm thinking right now, actually, what's interesting is sometimes what shows up when she's not even there. There is a sign hanging over our sink at the moment because it's her week to do dishes. And the sign has a picture of a cat whose name is Jeff with an arrow pointing toward the dishwasher. And then randomly, there's a potato at the bottom of the sign, and it just says on the bottom of it, potato with a arrow pointing to remind everyone to put dishes in the dishwasher. And I'm just. I was walking through the kitchen yesterday morning after she went to school, and looking at the sign, I'm like, what on earth? Laughing out loud, like, why is the cat named Jeff? And why is the randomly potato? I don't know, but there it is.
Chris Duffy
This is why I think it's generous, right? Is because, like, a person who makes you feel seen, who turns something that is, like, mundane into a delight, and who energizes you. I think there's such a generosity in creating that feeling for other people. So, you know, the potato side isn't about getting applause. It's not saying, I'm a genius and the greatest artist of all time. It's about creating delight for other people, which is to, to me, such an Incredibly generous category. And the other thing that I'll say, which is not exactly in this example, but is often in humor, is we are so often intimidated by other people. We think that people want us to be perfect, and we think that they're judging us and that they are better than us. That's a very common feeling that people have. And if someone is willing to laugh at themselves, to point out their own ridiculousness, that makes us feel so much more comfortable and so much more connected to them. So I think there's a real generosity in bringing yourself down a little bit. And interestingly, one of the psychological studies that I found while I was doing research for this book showed that when people were. They did an experiment where they had people going for a job interview, and they had research subjects would rate the people for the job interview. So no surprise, the people who were qualified were rated more highly than people who were unqualified. But the surprise was that in the qualified people, there were two groups. One that just came in and were like, great, perfect for the job. And another group that came in were just as qualified, just as perfect, but had spilled a cup of coffee on themselves right before they came in for the interview. So they came in and said, oh, my gosh, I'm so sorry. I have coffee on my shirt. And then they nailed the interview. Now, the people who are rated the highest, the people who were suggested to be hired, and the people who the. The raiders liked more were the coffee people. And I love that because. Not because it's some sort of tip that, like, hey, if you're interviewing for a job, you should pour hot coffee on yourself. Don't do that. Right. But I love that because it. It undercuts this idea that, like, the way to be rated the most highly is to be perfect. And I think having that relatability where you're a little bit of a mess, you're trying hard, but you're not the most intimidating, flawless person in the world. That makes other people like you more. It makes them want to be around you more. And there's real generosity to that connection to let go of your shield of I am supposed to look perfect, and instead, BAE, say, you know what? I have a giant coffee stain on my shirt. I'm going to acknowledge it, I'm going to laugh about it, and I'm going to do my best.
Dave Stachowiak
Anyway, you've had a few career shifts yourself, and you used to be a fifth grade teacher, and you talk about that in the book. And you also talk about Gary, who you say is the funniest person you ever met who was a kid in one of your classes. What is it that caught your attention about his humor?
Chris Duffy
Yeah, so I was. I was teaching fifth grade, and it was in kind of a school that had, you know, a lot of kids who were dealing with real serious issues like hunger, poverty, homelessness, all sorts of issues. And so I was trying to take my job really seriously. And the way that I thought I should take my job really seriously is to kind of strip humor out, to not joke around, to just do as much work as I can all time, every day, no silliness, just work. And what I found is that I was kind of just banging my head against the wall. And anyone who has banged their head against the literal wall knows it's a very bad way to get through a wall. It will just cause injury to your head. And I was exper. Experiencing that metaphorically. But then what happened is one of the students in my class, a student who actually I found to be really challenging in a lot of ways because he did not like to do his homework, he did not like to write. He had so much potential. But I couldn't figure out how to connect with him. He ended up one day, as I was trying to figure out how I could possibly get him to practice his writing, he was telling me about how his opinions on school lunch. And I said, this is really actually hilarious, the story you're telling me about school lunch. And I convinced him to write a review. And he ended up becoming the food critic for the school newspaper where he reviewed cafeteria food. And so Gary's food reviews were so funny. Right. He would review, like, school pizza day by starting saying, like, this dish, originally from Italy, which is just a hilarious way to introduce cafeteria pizza. Or he would describe the smell of the pizza as it smells like when you've just come out of the shower and used your sister's shampoo, which is such an incredibly specific way to describe pizza smell and also makes me have a lot of questions about what shampoo his sister was using and also what
Dave Stachowiak
was in the pizza. Right.
Chris Duffy
But Gary just had all these really hilarious, very fifth grade observations that made me laugh, and they opened my eyes to the potential of humor one as a way to get Gary to do something that he needed to do, but didn't feel like a task and felt like instead it felt like joy and fun and play. And also for me, that this was like I was trying so hard to take away humor and joy, thinking that when I was trying to do something serious, When I was trying to accomplish it, they didn't have a role. And I realized that as soon as I let them back in, instead of things being so hard, they got a lot easier and more fun. And ironically, when they were easier and more fun, I was accomplishing the goals that I wanted to accomplish in a much smoother way. So I think that is something that I have taken and is a big inspiration behind my whole career since then.
Dave Stachowiak
You write on him. Gary's reviews made me laugh, first and foremost because they're honest. He's not pulling any punches, but they're not mean or cruel. He wasn't trying to drive cafeteria workers to put down their spatulas. He was simply observing the absurdity of the world within the walls of our shared lunchroom and then bravely asking, everyone else is seeing this, too, right? And I think about that message and where you invite us to start in thinking about getting a little bit better at bringing in humor, genuinely. And as you pointed out earlier, a lot of times we think about, I need to tell jokes. I need to be the center of attention. I don't want to be that person that's trying to be funny. But you say, no, the first pillar of cultivating humor being present. Tell me about that.
Chris Duffy
Well, I think that if you think about, you know, if you think about the last time that you laughed so hard that you cried, right? You and this other person, you're laughing, there's tears rolling down your cheeks, clutching your belly. One of the beautiful things about that, aside from how fun it is to just laugh like that with a friend or family member, is that you are 100% in the moment. You're not, like, half on your phone, half thinking about what's due at the end of the day, or thinking about what emails are coming in. You are just locked in with that other person, and you're having such a pure moment of connection and laughter and joy and release. And that's really rare these days to have a moment of, like, true, complete presence and connection. And the other thing is we can only laugh at the things that we notice, right? So much of humor relies on an expectation that things will be one way, and then we see them, and they're actually not quite the way that we expected. And that gap makes us laugh. So seeing the. Seeing the world in that way is where humor comes from. And that is why you have to be really present to see all the funny things that are around you. Because you might think, like, well, okay, sure. Chris is a professional comedian. He finds funny Stuff everywhere because he's in a uniquely funny space or something like that. But the truth is, there are hilarious things happening everywhere, all the time, and it is just about noticing them and seeing them. Right. If you live in a place where you are in a rural area, I guarantee you there is a bird or an animal or a tree that looks weird. There is something hilarious out there, and it's just waiting to be noticed. And if you're in a city or an urban environment, surely other humans are doing bizarre, totally unexpected and interesting things that will make you laugh. So the first step is to just really see them, to notice where you are and to pay attention.
Dave Stachowiak
There's, of course, so many things that are part of humor, but this strikes me as so foundational and something that I didn't really think about until getting into your work of just how humor, like so many things. Listening, coaching, delegation. So many things we talk about in the show, how being present is, like, such a really critical starting point. And you have some really wonderful invitations for us on just getting started on starting to tune yourself to be a little bit more present and to show up in a way where then you can just naturally bring in humor more. And one of the models I really appreciate is what you call the new bathroom frame of mind.
Chris Duffy
Oh, yeah.
Dave Stachowiak
Can you walk us through, like, what that is and how to use it?
Chris Duffy
Oh, I would love to walk you through this. And also I would like to apologize to you and your listeners for, you know, what a distinguished and accomplished array of. Of guests and episodes you've had. And here I am just bringing you down to the lowest common denominator, walking you straight into the bathroom, literally.
Dave Stachowiak
And, you know, that's why people listen to Coaching for Leaders is.
Chris Duffy
Yeah, the bathroom right there. A lot of the reviews are about how much they love the pot of humor on the show.
Dave Stachowiak
Absolutely. Absolutely.
Chris Duffy
So here's what I'll say is you want to talk about really noticing things. One of the problems, I think, for a lot of us is we get into this mode where we don't actually see the things around us, where everything is kind of in a background blur, where we're so focused on where we're going or what we're doing that we don't notice where we actually are. And a way that I think we can get out of this blur mode kind of like that. I think of it sometimes like the blur background on zoom, where you see just the person, but you don't see all the other things around them. Oh, yeah. The way that you can Switch that filter off in your real life and actually see the things is to practice what I call the new bathroom mindset. So here's how I think about this. If you go to a friend's house for the first time and you walk into their bathroom and you've never been in their bathroom before, you notice so many things about that bathroom, immediately you walk in and you go, okay, they have a hand towel. Oh, it's like a little frilly lace hand towel. That's interesting. Am I supposed to dry my hands on that? Is there. Is that decorative? Am I supposed to dry my hands on something else? Oh, what kind of soap do they have? Oh, it's like an interesting lemon scented soap. I wonder if that is, like, an expensive soap or not. Oh, look at their toilet. Oh, they have a really padded toilet seat on top of it. Huh. That seems like maybe they're sitting there for a long time. That's interesting. Oh, there's a pile of books next to the toilet. Oh, the books actually look like they got wet and then were dried. I don't know about that. How did that happen? Probably don't want to know. Okay, what about the toilet paper? Do they put the toilet paper with the roll with or the roll going under in the back like it's some sort of a mullet for the toilet paper?
Dave Stachowiak
Oh, it's gotta be over. Gotta be over.
Chris Duffy
Oh, the over is clearly right. I mean, if you're putting your toilet paper where it's coming down the back, you are a delinquent. And you need to fix that right now. Yeah, we need to.
Dave Stachowiak
We need to. This is where the bad reviews are gonna come in. Someone's gonna be like, no, I gotta have it the right way. But, you know, you gotta be.
Chris Duffy
You cannot be a leader if you are not leading in the toilet roll placement. I will say that that is one of my roles of leadership.
Dave Stachowiak
I can get behind that.
Chris Duffy
But my point. Hey, pun intended. Now, the thing that I'll say about all this is it's silly. It's. I'm kind of making a joke. But the serious part is that you actually do notice these details the first time you go in. And then if you're. You've gone to the friend's house maybe five or six times, you go in and it's just bathroom. It's not that specific bathroom. It's just all bathroom. You don't notice the details anymore. And so what I would encourage people to do is to think about awareness as a muscle. It's not like we can go through life every single day, every single moment, noticing everything. If we did, we would be completely overwhelmed. We'd never get anything done. We'd never move from point A to point B. But occasionally to switch in and say, hey, I'm on this commute that I do every single day. What is actually happening here? What do the license plates say on the other cars? What is on the side of the road? Hey, I'm walking on the block that I live on. What animals live here? What. What signs are up on other people's houses? What decorations? How is the roof set up? What are the paint on the other. The neighbor's house? These things that kind of we just think of as, it's just a house. It's just my neighbor switching into that new bathroom mindset. And actually noticing, I think creates this real potential for you to build the muscle of noticing and then to see things that would otherwise go overlooked, which for me often leads to delight and absurdity and laughter. But I think also as a leader, right, like, this is where you see the opportunities and the problems before they become problems. These, these are opportunities for connection and insight. And so much of what we laugh about is calling into attention a thing that has previously gone right below our conscious level of understanding. Which is why a lot of times people say, like, I never thought about it like that, or I never saw it that way, or that's so true when they laugh because you are bringing explicitly the thing that had been just below their conscious awareness.
Dave Stachowiak
I think how often of folks I work with who are working on getting to be better listeners in their leadership or getting more coach like. And oftentimes a place we'll start is ask a second question. You know, a lot of times we think to ask a first question and then we sort of jump in a lot of us and. Or give our advice or start talking and we'll often experiment with, hey, just ask a second question. You can still jump in if you want, but ask a second question first. And when people start to do that, it is a amazing what they start to hear that they realize, oh, all this information I wasn't hearing, I didn't know what was going on. Organization, this person's thinking about these things. I didn't. I never really gave any credence to. And I think about how true that can be also for this of like your invitation to start with the times that you're least present and most zoned out, which you talk about. And that's the place to notice the things that are happening on the way to work, at the office, at lunch. The things that you normally just sort of like write off or don't even think about because you've been in the bathroom 8,000 times, right. But if you look at it through that new lens and you look at your life through some different eyes, if you're willing to do that, it is fascinating what you start to see.
Chris Duffy
Well, Dave, can I have two things that I want to say based on that. The first is people often say, oh, you're born with it or you're funny or you're not. And I really disagree with that. I think it is a skill that anyone can cultivate. It's a muscle, right? But also like a muscle, right. I could swim as much as I want. I'm never going to be as good a swimmer as Katie Ledecky. I'm not going to. I'm not going to beat her in a race. That doesn't mean that I can't get better at swimming. And so that's how I think of as, as humor. And one of the reasons I believe that so deeply is having worked in an elementary school and now having two young kids of my own. Kids are so naturally funny and imaginative and random in the best way. And all kids are like that. It's so rare to meet a kid who is just bland and serious. I think it really takes years of intensive corporate training before you can get that bland and that serious. So asking that second question right is like if you're talking to a kid and they say something. If they say, hey, I'm gonna start a restaurant and they're playing make believe, you could assume that you know what they're gonna serve in the restaurant. Cause we've been to restaurants before. But if you ask the follow up and you say, what does your restaurant serve? You might get a really funny and interesting and esoteric answer from that kid where they say, I'm serving chocolate covered cars. And you go, oh my goodness, the car is covered in chocolate. And then you get to eat the metal. And they go, yep, it's a new type of. It's a new type of cake with metal inside. I would never have predicted that that would be what the restaurant would be serving. And it's funny to play that make believe thing well.
Dave Stachowiak
And this fits in right with some of the tactics you suggest in the book, which is seek out some of the weird stuff that's out there, like weird facts, and don't dismiss stuff just because it's dull or uninteresting. Like sometimes the Best gold of like, things you can bring in and find joy in and find humor. That's where it starts. It's that everyday, mundane thing that, like, to your point earlier, everyone sort of notices and we all just sort of accept it. And then when someone just does something different shows up so beautifully. And I saw an example of this this Morning, Chris, on LinkedIn.
Chris Duffy
Please.
Dave Stachowiak
So many people like on LinkedIn posts, like, when they get a new job or new position. I'm proud to accept this role. All those things, it's all good, right? Like, we should do that for our brands and our careers. And one of our academy graduates this morning posted a picture of his two cats who look super grumpy. And he just one line on the post. He said, I'm. I'm pleased to announce that I have accepted the role of CEO of my cats. And the cats look so nonplussed. It's. And the hilarity in the comments and the messaging that happened afterwards was just so funny. And when I think about though, that, though it's. It's exactly what you said. It's like sort of noticing this thing that we're all used to seeing on LinkedIn of like, people humble bragging about, like, the positions they've gotten and all that, and him just like totally turning on its head and putting up some just, just this hilarious post. And the funny thing is the engagement, the connection from that, so much better than the serious thing. And it's the result of just not dismissing the everyday, seeking out the weird stuff. So powerful.
Chris Duffy
Yeah. Well, Dave, I bet you that I have the distinction in 15 years of doing this podcast, I would be very confident in betting that I am the only guest that you've ever had on your podcast who has been permanently banned from LinkedIn. And I was for exactly this reason. I was so fascinated by LinkedIn, how it has all these rules and humble brags and all of that. And so as a comedian, you don't really get jobs by posting on LinkedIn, and as a teacher, you don't really have to network your way into a teaching job. So I never really had a clear professional reason for LinkedIn, but I was always curious about it and hearing my wife talk about it and her friends talk about it. So I started a profile on LinkedIn and I was just curious, what are the rules of this world? And one thing that I noticed right away is that when it asks you what your job is, it doesn't confirm with the company that that's your job. Right? Like, you can say I work at Nike. It doesn't email Nike. And that seemed unbelievable to me. I felt like that can't be right. So I wanted to test and see if that was true. So when I made my LinkedIn profile, I said, as my job, I am the CEO of LinkedIn.
Dave Stachowiak
Nice.
Chris Duffy
And I thought it would. I thought if I click save, it would say, no, you're not allowed to do that. But when I clicked save, not only did it allow me to do it, it sent an email to everyone in my contact list saying, congratulate Chris on his new job. He is now CEO of Link. Sent them that email, which is probably the funniest joke that I've ever had in my entire life. And I didn't even write it myself. And then I was CEO of LinkedIn on LinkedIn for one full year. And at my one year work anniversary, it again emailed everyone saying, like, congratulate Chris on one year as the CEO of LinkedIn. And it started going a little viral. And that's when I got a message from LinkedIn's Trust and Security team. And it was from a woman named Faith. Right? You can't make this up. And Faith said, your account has been locked due to concerns about its accuracy. But because I'm a comedian, I really don't want to let go. It was such a joke that I loved. And so I sent her a photo of my license front and back and said, here, Faith, this is proof that my name is actually Chris Duffy. And she said, the problem is not that we don't think your name is Chris Duffy. The problem is that you are claiming to be the CEO of LinkedIn.
Dave Stachowiak
So funny. You know, it just is a reminder to me of, like, I don't think either of us are suggesting people go and like, do like spoof, humor stuff on LinkedIn. Right? It's not those. That's not. But just thinking about, like, you have to be able to step back and just, yes, play the game. But also at the same time, just notice the hilarity in it all and the irony in so much of it too.
Chris Duffy
Well, and acknowledging the artifice, I think, like when you acknowledge the thing that is unspoken, that is so often what makes people feel like, oh, you are a real person, right? Like, hey, I'm on this network that is constantly prompting me to congratulate people, right? If you acknowledge, like, another day, another congratulation, people connect with you more, but they also feel like, oh, you're not just going through the motions, you're actually there, you're actually Noticing. And that's something people really value in a leader, but also in a friend, in a person.
Dave Stachowiak
Speaking of not going through the motions, one of the other invitations you make to us thinking about humor is to celebrate the bad. And that landed with me one because of its simplicity, but also how much stuff doesn't work every day in organizations and teams. And the hilarity of it all. And our tendency, of course, is to not call attention to it, to sort of sweep it under the rug, whatever. And you say, hey, actually once in a while, celebrating that, bringing it out. Really helpful, isn't it?
Chris Duffy
Yeah. I would even say not once in a while. Like making that a normal thing, where when things go wrong, we can laugh about them and it's a plus rather than a minus. It's not like we're trying to make things go wrong, but acknowledging the bad and celebrating it is the way to get to the good. Right. I think anyone who has tried to do anything creative knows that you get to the good thing by having a lot of bad things first. And if you're trying to come up with a good idea, you need a lot of bad ideas. And one place that I think embodies this, that I love so much is in Boston. There's a museum of bad art, and they have exhibitions that are the worst art that they've found. It's often being thrown out on the side of the street or in thrift stores or donation bins. And it's a museum and they take it very seriously. They put it up on the wall, they have a plaque and an explanation. And it will say something like, this work features a close up drawing of hands. But upon closer examination, you notice that each hand has an extra set of knuckles. And then you look and you go, oh, yeah, those hands have too many bones. That's really weird. Or this portrait of a mother and daughter features the flesh tones reminiscent of a top shelf liqueur at a bordello. And you notice, like, oh, yeah, their flesh looks very sick and not the color that flesh should be. And the thing that's fun about that is it's fun because we laugh about how bad the pictures are. But it also changes your relationship to the idea of a museum, because you go into a regular art museum and if you're anything like me, you think, oh, wow, these people know more than me. They're professional artists. And the people who selected them, everything's worth a lot of money. So you're not really allowed to have an opinion. It's just like, this is Good. And if you have an opinion, it might be like, oh, how did they get to do it?
Dave Stachowiak
I know. And you got to be, like, super quiet and walk around and look like you're all being all cool and stuff and, like, totally staring at the picture thoughtfully, like you know what. What it means.
Chris Duffy
Exactly. But when you go to the Museum of Better, it invites you to say, that is what is so terrible about that. That's what's funny. That's my personal relationship to that. And so the people who run the Museum of Bad Art often suggest that people pair it with a trip to a real museum, I guess, a regular art museum, because it then changes how you go into the regular art museum to say, well, what is it that's so good about that? And do I actually think it's good? And having that celebration of the bad changes our relationship to the good. It makes us feel more empowered. So I think there is a direct line between a corporate setting where you are working as a leader and that museum of bad art. Right. How can you actually look at the mistakes, celebrate them, laugh about them, but understand why they're mistakes or what's not working about them so that then you can see what does work about the things that do work.
Dave Stachowiak
What's so powerful about that is the pairing between the two. It's not just going to the bad art museum.
Chris Duffy
Right. And.
Dave Stachowiak
And having the laughs and all that. It's going there and also going to, like, the traditional art museum and noticing the difference. And because you notice the difference, because you see the difference, how that allows you to experience both better and appreciate what's amazing. Right. Like, so cool. Such a cool thing.
Chris Duffy
Yeah. And I just keep going back to when we try to bury the mistakes, when we try to be perfect and flawless, it pushes other people away from us. It. At best, it makes us intimidating, and at worst, it makes us a person that people hate because they think that we are being fake and phony or we think better than them.
Dave Stachowiak
Y.
Chris Duffy
So the more that you can acknowledge the real reaction that you're having to things, the real things where you're falling short, the more that you can connect with people below you. And. And as a leader, there is a real line. Right. It's not. You don't. My. My wife taught me about a phrase called selective vulnerability, which is, you don't want to be a leader who, when you have a bad quarter, goes in and says, I am really terrified, everyone. I have no idea what to do, and this is not good for our business. And I'm just really scared that it's all going to fall apart. That's not going to make the people who work for you feel good at all. Yeah, but it's also not going to make them feel good. If you don't acknowledge that it was a bad quarter and you go like, you know what? Things are great and they've always been great, and there's no issue at all. People know that that's not real. So you have to be selective. You can say, hey, I just want to acknowledge this was not on my vision board. I did not want to have this particular quarter. I know we all know it could have gone better, but I want to tell you that we are going to figure it out together. We are going to find solutions, and I am confident that we are going to make it happen. Right. That is acknowledging the reality without taking yourself so emotionally vulnerable that people can't trust you or you don't feel safe anymore.
Dave Stachowiak
You've obviously thought about humor a ton. You've studied it. You're doing it professionally. When you look back on putting this book together, of teaching people how to get better at bringing in humor in genuine ways, I'm curious, what, if anything, have you changed your mind on?
Chris Duffy
Well, I think I've changed my mind on a lot of things. One is, I used to be one of those people who thought that humor, having a good sense of humor, was being the center of attention. There's a fun psychological experiment that actually was one of the things that prompted me to write this book in the first place, which was these sociologists looked at people in online dating profiles, and they looked at them across the world, and they found that almost everyone in their online dating profile said that they wanted a partner who had a good sense of humor. But then when they looked at heterosexual couples, they drilled down into this and they said, what does having a good sense of humor mean to you? And when they talk to heterosexual women, heterosexual women seem tended to say, having a good sense of humor means someone who I can laugh with. And then when they asked straight guys, what does having a good sense of humor mean? Guys said, someone who laughs at my jokes. And I think that that's not a good definition of humor. Someone who only thinks you're funny, but you can't laugh with them. But I think I used to be more like that. I think I had that idea that it's like a performance with an audience rather than this generous, participatory way of looking at the world where we are acknowledging absurdity in the world. And in ourselves. And changing my view on that has really changed how I go through my day. It's made it so that it's less pressure for me to be performing and more about how can I spend time with and in ways that make me and the people around me laugh and where I'm delighting in the things that they are pointing out or that we're seeing. Or when something bad happens, right? Like we go to the park for the play date and it rains. How can that be a thing that we laugh about rather than cry about? Or sometimes how can we cry while we're laughing or laugh while we're crying, thinking about it less as like a thing that I have to control and more as a thing that I can appreciate. That's been a really a big difference in the way that I approach the world.
Dave Stachowiak
Chris Duffy is the author of Humor Me How Laughing More can make you present creative, connected and happy. Chris, what a joy. Thanks for being with me.
Chris Duffy
Thank you so much.
Dave Stachowiak
If this conversation was helpful to you, three other episodes I'd recommend one of them is episode 235, how to engage with Humor. David Nihil was my guest on that episode and we talked about some of the wonderful tactics many of us can do in our everyday interactions in person over email in order to find humor in such a genuine way. And his message and the values and the strategy match up so beautifully with Chris's. And also we talked about different strategies and tactics. I think it's a wonderful complement to this conversation, episode 235 for that, as you heard today, so much of being good with humor, at least better, is just noticing and watching what's happening. And I can't think of a better conversation for inspiring us on that than episode 408, get better at deep Listening. Oscar Trimboli was my guest on that episode. Oscar's been on the show several times over the years and really a wonderful, wonderful guide on listening. How we can show up, how we can be present, how we can sometimes set aside our habits that don't work for us. Well, and in that conversation we talked about some of the foundational things we could do to get better at that episode 408. And then finally I'd recommend episode 5 90, how to genuinely show up for others. Marshall Goldsmith was my guest on that conversation and Marshall talked in detail about a reality that many of us have as leaders is that we are going from one conversation to another all throughout the day. Sometimes conversations, multiple ones happening at the same time. How do you show up and actually be present in the midst of all those conversations and everything that's going on in your head. And we talked about some really helpful tactics and how to think about that, but also some behaviors to put into place to show up more genuinely for others. Episode 590 for that, of course. Marshall, one of the top coaches in the world. Excellent at always helping us to get better at leadership. All those episodes, of course, you can find on the coaching4leaders.com website. And I'd invite you today to set up your free membership@coaching4leaders.com because it will give you access to the entire library I've aired since 2011. You can search by topic as well. When you get in there, you'll be able to find exactly what you're looking for. Pause my interview and Book Notes Almost every conversation we have on the show, including this one, I will write down notes in advance of my of the conversation. I'm doing interview prep. Of course, I'm highlighting some of the key things I find in the books. Some of those things make it into the conversation. Many things don't. But there are all available there for you to be able to download. And so setting up your free membership is is the best way to access that. Just go over to coaching4leaders.com and when you set up your free membership, you'll see a place for Dave's book and interview notes. And all of them are there for all the episodes I've aired in recent years. An additional way to hopefully support you in whatever's next and whatever's on your mind today. Coaching for Leaders is edited by Andrew Kroger. Next Monday, we're going to go on the other side of the conversation. This show is all about all aspects of leadership. We talked about humor today. We're going to talk about poisonous people next week. I'm so pleased to welcome Leanne 10 Brink. We are going to be talking about how to work with poisonous people, the most difficult people in the workplace. That conversation next Monday. Join me for that. Have a great week and see you then.
Better Leadership Through Humor, with Chris Duffy
June 15, 2026
Host: Dave Stachowiak
Guest: Chris Duffy
This episode focuses on the transformative role of humor in leadership. Dave Stachowiak welcomes comedian, author, and podcaster Chris Duffy to explore why humor—far from being a frivolous addition—can unlock connection, creativity, and presence in the workplace. The conversation dives deep into how leaders can leverage humor not by telling jokes, but by learning to notice, appreciate, and share the inherent absurdities of everyday work life, thereby nurturing a culture of authenticity and generosity.
Humor as an Enabler: Humor isn't necessarily a top leadership “competency,” but it acts as a tool that makes achieving other core skills—connection, vulnerability, presence—much easier and more joyful.
Authenticity and Relatability: Leaders who can laugh at themselves or at workplace mishaps build trust and approachability, making it safe for others to be imperfect.
Being Present to Notice Humor: Genuine humor arises from being present and aware of what's happening around us, noticing the incongruities and unexpected moments.
The 'New Bathroom Mindset': Practice noticing details as if experiencing them for the first time; this invites delight and cultivates the muscle of awareness.
Application to Leadership: This presence leads to seeing problems and opportunities early, strengthening connection, and allowing humor to become a practical, everyday leadership tool.
Generosity of Spirit: The most likable, connective humor is about making space for others, not controlling the room.
Relatability Over Perfection: Referencing a study about job interviews, Chris shares that candidates who acknowledged small mistakes (spilling coffee) but remained competent were preferred—humor in imperfection fosters liking and trust.
Humor Unlocks Engagement: Chris recounts motivating a challenging student, Gary, through humor—turning his reluctance into creative food reviews for the school newspaper.
Humor as Honest Observation: Gary's reviews stood out by honestly observing oddities without being mean, demonstrating how humor invites others to see the world differently.
Celebrating the Bad: Don't sweep mistakes under the rug; acknowledging and sometimes highlighting them creates space for growth and connection (28:26-31:51).
Selective Vulnerability: Leaders must strike a balance—acknowledge the truth of setbacks without undermining confidence or appearing helpless.
On the Power of Humor:
Chris Duffy: “Laughing together connects you so deeply... you create this real opportunity to build culture.” (03:52)
On Generosity in Humor:
Chris Duffy: “A person who makes you feel seen, who turns something that is like, mundane into a delight… that’s an incredibly generous category." (08:49)
On Noticing the Absurd:
Chris Duffy: “There are hilarious things happening everywhere, all the time, and it is just about noticing them.” (15:19)
On Failure and Growth:
Chris Duffy: “When things go wrong, we can laugh about them, and it’s a plus rather than a minus... acknowledge the bad and celebrating it is the way to get to the good.” (28:55)
On Shifting Perspectives:
Chris Duffy: "Thinking about [humor] less as a thing that I have to control and more as a thing that I can appreciate—that's been a really a big difference in the way that I approach the world." (35:07)
- 235: [How to Engage with Humor] – David Nihil
- 408: [Get Better at Deep Listening] – Oscar Trimboli
- 590: [How to Genuinely Show Up for Others] – Marshall Goldsmith
For more details and full show resources: coachingforleaders.com
Summary prepared to capture the essence, flow, and memorable moments of the episode. All quotes are attributed and timestamps provided for further listening.