Starting with this one may not be putting my best foot forward. Intelligence and creativity would be far better and easier to work with. But if I led with only the easy ones, where’s the fun and challenge in that? The main idea with responsiveness and leadership must involve the leader figuring out what response is appropriate and then the best way to implement those responses. If you think about the importance that incongruity plays in humor, then the relation between humor and responsiveness is clear.

We are living in the Renaissance of Work. Just like great artists know that an empty canvas can become anything, great leaders know that an entire organization — and the people inside it — can become anything, too. Master Artists and Mastering the Art of Leadership draw from the same source: creation. In this series, we’ll meet masters who are creating the future of work and painting a portrait of lasting leadership. As part of this series, we had the pleasure of interviewing Mike Cundall.

Mike Cundall is an author, public speaker and philosophy professor with published research on the positive impact of humor in our lives. He has given talks on improving resilience, defeating procrastination, and how to become more effective and engaged. He has also delivered keynote speeches for the US Army on leadership and the power of memes in our work and personal lives.

Thank you for joining us. Our readers would enjoy discovering something interesting about you. What are you in the middle of right now that you’re excited about personally or professionally?

My name is Mike Cundall and I am a university professor, researcher, author, and speaker. As a researcher I study humor. That’s right, I study funny things. One of the great things about my work is how important humor is to having a well-balanced and happy life. My recent book “The Humor Hack” is about finding ways to use more humor in your life. It’s not a bad gig at all.

I’ve given keynotes on humor and leadership to the US Army. I’ve published and presented on humor in the classroom. I’ve presented to medical professionals on the importance of humor in medical care. For me, humor is an often untapped part of our lives and I want to help people find ways to bring it more into their lives. I am so sure about this that I started a company dedicated to it, Mirth Management. You can find out more about me and the company at

I am married to a loving spouse, I have three boys, two dogs, and cat. I received my Ph.D. in Philosophy and the Sciences from the University of Cincinnati and an undergraduate degree from the University of Kentucky. When I am not working I spend time carving bowls and spoons. I am well-known for using humor in the classroom and my talks are educational, enjoyable, and funny.

Who is the leader that has influenced you the most, and how?

A leader that has been influential is Freeman Hrabowski who was the former chancellor of University Maryland Baltimore County. His way of connecting with an audience, his ability to help grow and university, and his commitment to his university over the long haul, has been and continues to be a model I use in my work.

Sometimes our biggest mistakes lead to our biggest discoveries. What’s the biggest mistake you’ve made as a leader, and what did you discover as a result?

The biggest mistake that I made as a leader, as someone in a new job, was forcing myself to try and find success when the situations simply wouldn’t allow for it. It’s important to me to be steadfast, to rise to challenges, to push myself. But sometimes there is nothing one can do to meet those internal demands and to try leads one to more failure. I wish I had learned to relax my own internal demands. My life would have been overall better.

How has your definition of leadership changed or evolved over time? What does it mean to be a leader now?

I have a ambivalent relationship with the idea of leadership. As someone in higher education, I have seen the demand for “leadership” become one of the most important things that students hear. As faculty, teachers, staff, we are told to increase leadership development. It has set up unhealthy and unhelpful expectations on what we expect of young folks. It’s also created expectations that cannot be met in the rank and file. We expect too much of a leader, more than should be from any individual. Me sense of leadership now is that leaders should build structures that promote collaboration, communication, and excellence. They should be willing to step up when needed, but should be all too ready to step aside and let the people they work with succeed.

Success is as often as much about what we stop as what we start. What is one legacy leadership behavior you stopped because you discovered it was no longer valuable or relevant?

The biggest thing for me that helped me, that I learned to stop, that I learned was ultimately a maladapted strategy, was trying to find ways to succeed in places where the “defined” success was simply not possible. I saw the toxic effects that such misaligned expectations had on my coworkers, my direct reports, as well as myself. It was here that I saw disengagement really rear its head for the first time. It wasn’t an immediate thing either. It was insidious and debilitating. What I did is a worked with my people and started to develop ways we could work and fulfil our mission that were attainable. As a result, while we couldn’t do all we wanted or was expected, we knew that what we were doing was important, valuable, and positive outcomes, in spite of the negative situations that we found ourselves in.

What is one lasting leadership behavior you started or are cultivating because you believe it is valuable or relevant?

The main thing that I’ve come to learn through my work is that leaders need to be approachable, have good listening skills, see people for more than what they do for the organization, and have a sense of humor. Humor does so much work in making the other three happen. Someone who laughs, makes jokes, shares smiles and mirth with those they work, is someone that those people will identify with, will feel comfortable approaching. It’s not that hard, you just have to be willing to interact in those ways, and we’re too often told that work isn’t a place for humor. And that’s just plain wrong.

What advice would you offer to other leaders who are stuck in past playbooks and patterns and may be having a hard time letting go of what made them successful in the past?

The biggest thing I can say is that when you keep running into the same obstacles, when you keep running into the same problems, perhaps it’s not you or your various strategies that are the problem. Maybe it’s something else. There may be a fundamental factor that won’t change regardless of who or what approaches it. Don’t think of it as a failure on your part. Don’t tie your own self-worth to that issue. Realize that you’re only human and then reach out for help. We all want to see those we care about succeed. Build partnerships, relationships that can help you weather those difficult times. It’s those things that will be the springboard for later success.

Many of our readers can relate to the challenge of leading people for the first time. What advice would you offer to new and emerging leaders?

The best piece of advice I was ever given was to be yourself. If you go trying to be something you’re not, just to please this person or that, if you’re constantly trying to change to meet the various challenges, authenticity will no longer be there. You will be better served starting with the things that got you there, that made you successful rather than trying to change. Work slow, steady, and smart.

Based on your experience or research, what are the top five traits effective leaders exemplify now? Please share a story or an example for each.

The answer I give here is an excerpt from chapter 7 of my book, “The Humor Hack.”


Starting with this one may not be putting my best foot forward. Intelligence and creativity would be far better and easier to work with. But if I led with only the easy ones, where’s the fun and challenge in that? The main idea with responsiveness and leadership must involve the leader figuring out what response is appropriate and then the best way to implement those responses. If you think about the importance that incongruity plays in humor, then the relation between humor and responsiveness is clear.

People who can see incongruities who seek them out, who are attuned to and paying attention for them are going to notice more than others. They’re working and looking for things in the world. They’re paying attention. That’s crucial. When you’re not attentively engaged, important things pass you by. Opening mind to the variety of ways that things can relate to one another, some obviously and others less so, helps you as a leader be more aware. The first step on being responsive is noticing that there is something that requires your attention. You have to recognize. You can’t respond to something you don’t notice. If using humor makes us cognitively more flexible and aware, then we can respond more quickly and thereby be overall more responsive.

This flexibility has other benefits as well. If you’re used to solving problems and addressing issues in typical patterns, you may be unable to appreciate a novel way to respond to an issue. With responsiveness, it’s not just that you see a problem and respond to it. Part of responsiveness is crafting the correct response. Often there are a number of possible and effective solutions to any issue that arises. Humor, and the cognitive flexibility it creates, is going to help you see more and more creative ways to respond the issues that arise. The essence of most humor lies in the fact that some new way of seeing the world — a way that was unexpected or different. When you use humor you’re finding new ways to respond to things, and this will provide a richer mental space from which you can respond to the variety of situations you will encounter.


The relationship of intelligence to humor is much easier to describe. One of the hallmarks of intelligence, of being smart, is to be able to recognize patterns. Some of those MENSA tests that used to make their rounds on the Internet rely on the recognition of patterns. Some of those patterns are numerical, spatial, verbal, etc. Incongruity recognition is directly related to pattern recognition. To recognize something as incongruous, you have to know a pattern, have an expectation that’s violated. For something not to fit, it has to not fit in somewhere. If pattern recognition is important to intelligence, so is the recognition of violations of those patterns. That’s exactly what incongruity is — a violation and in the case of humor, often a benign violation. Interestingly, comedy writers know this too. They often use the rule of three to help move their jokes along. The first and second instances help set the pattern, while the third instance allows the incongruity to blossom. When I was teaching dance (yes I, as a philosopher, know how to dance — there’s always more to folks) I was told that when you do a dance move in a show, you need to do it three times, but that four times and the audience gets bored. It seemed to work.

There’s something else less obvious that shows how humor and intelligence are related and it’s related to, (surprise!) play. One of the ways humans, and many other mammals learn is through play. Think about how much more effective things have been when you had fun while learning. I may have mentioned that I dreaded chemistry in high school. I barely passed. But if I had found a way to make the learning of the concepts and such fun, I would have done so much better. Play makes all the work that goes into learning seem a lot less arduous (we’ll talk about this more later). When our work has elements of fun, we accomplish the tasks more efficiently and effectively.

The playful intellect enjoys finding patterns and the incongruities within those patterns. Intelligence isn’t just about having the knowledge; it’s about enjoying the process of getting the knowledge. The playful intellect delights in its learning, but also finds ways to make the learning, when it can be arduous, playful. Someone who enjoys learning and someone who knows the value of play and humor to learning is not only a good model for those they lead, but they also help those they lead learn more and themselves become more engaged learners.

One final thing. Years ago when I was in one of my first philosophy classes, my advisor said to me that “Philosophy is the playground of the mind.” I can’t say that all the time I’ve spent in my studies in undergrad and grad school was like being on the playground. Well, it kind of was if you think of Heidegger as big philosophical bully. But I can always reflect that it is fun to do the work that I do and even when it’s tough, it’s still rewarding.


Humble leaders are good to be around. They are approachable, they listen, and they engage. I can’t tell you how off putting it is to know that the person in charge of your area is unapproachable. Leaders who occupy mythical places “at the top” who are less approachable can do a disservice to their organizations and the people with whom they interact. They may try to have lunch and listen sessions, but the more they create these events to relate, the more it reinforces how they are, in fact, unapproachable.

One of the ways that humor makes us approachable is that, when we share something that tickles us, that hits our funny bone, we are opening up ourselves to those we share it with. One of the examples I often use is that if we were at a party, and I was a friend of a friend of a friend, and we just happened to be in the same groups chatting away and you found me funny, would you be more or less likely to go have a cup of coffee, or hang out again in the future? Most people find that one a no brainer. When we share a sense of humor, or even when we see someone enjoying something funny, it humanizes them and makes them more approachable. That a leader can laugh shows that they are like us in important respects. I don’t always find the same things funny that other people do, but I appreciate that they find things funny. Imagine appreciating your boss as something beyond their signature on a paycheck.

Another way that humor can help us to be humble is in being able to laugh at ourselves. We all make mistakes, we all have goof ups. The ability to laugh at our foibles, the ability to see the humor in some of the odd things that we do, humanizes us. Having the ability to laugh at oneself, to not be so worried that everything has to be perfect makes those around us relax and work at their projects without the specter of a bosses’ glare looming in the background. If you are able to poke fun at yourself, this not only shows that you too are human, but also that you are self-aware.

Quote break: “a man must not be too thin-skinned or a self-important prig.” Judge Learned Hand — on a case related to libel by humor.

More importantly, often having a sense of humor, shows that you can take a joke and, that you understand that a lighthearted approach is helpful. One of the worst things you can be seen as is lacking a sense of humor as the above quote so nicely lays out. If you make fun of others but cannot tolerate being the object of some good-natured ribbing (taking the piss, giving the business), then this shows us a character flaw. It’s sometimes hard for me when my kids make fun of me or beat me to a quip, but when they have, when they’ve been quick to the quip, I am quite proud of them. Of course my sense of super-dadness wears off a bit, but so much the worse for being super-dad. I’d much rather them feel comfortable enough to approach me and make jokes. I get to enjoy their growth.


To be seen as funny, as being capable of using humor well, is generally a good thing. We tend to like and regard well people who use humor. On the face of it, being funny doesn’t seem to relate to self-confidence does it? If you list the adjectives to describe a confident person would humor be in the top five? Try it. Think of a few words you use to describe a confident person. But hear me out. Confident people are often good storytellers, and jokes are little stories in a way. Maybe you feel as if you’re humor doesn’t connect or work with others. Try not to let that impede you too much. Even the best comedians have to stubbornly believe in themselves sometimes: believe their material is good. You may, at first, have to do that. But if you believe your stuff is funny, then you’ve made the first step towards self-confidence — belief.

Humor, the effective use of it, and the ability to share it with others is important for confidence. When you use humor as a leader you’re sharing a lot about who you are. You’re giving people a snapshot of a part of who you are that is not something we are typically exposed to in more professional environments. Sharing a joke is inviting someone to be closer to you, to get to know you in ways that are different and more intimate that we typically see in our day-to-day organizational lives. Anyone willing to take that risk has a certain level of confidence in themselves or else they wouldn’t do it. They’re willing to take that risk. They’re also confident enough to invite you to be closer to them. These are subtle but important ways good leaders can connect with those around them.

Sharing humor with others also shows that you’re willing to relate to people in this different way. You feel strong enough and have the desire to reach out to people and share with them. Not only is it an emotional connection, but it’s a cognitive one as well. When I experience really creative humor it makes me happy, but it also challenges me to see things in these new and different ways. These interactions help us build the connections we have to one another — to strengthen our social cohesion. This increases trust and camaraderie. Someone with whom we have these experiences seems more confident to us and, reciprocally, us to them. Reach out, take the risk, and share things you find funny. The more you do it, the better you’ll get and the more confident you’ll feel and the more confident you’ll seem to others.


The notion of authenticity is quite the thing right now. It’s such a cool-sounding word. Who wouldn’t want to be around someone who’s authentic? We love authentic styles of food, and castigate the non-authentic. Say it out loud. Au-then-tic-ity. So important. I don’t want to work with someone who’s inauthentic. So it’s quite reasonable that we would want to work with an authentic leader. But a warning first. If authenticity is being talked about everywhere, that’s your first indication, just like leadership, that it’s become jargon and is losing or already lost its real meaning. Regardless, there is something to authenticity or it wouldn’t have grabbed our attention. So how does humor relate to authenticity?

Effective and engaging leaders are authentic, they don’t try and hide things. They’re open and inviting. Humor is one of those important ways to invite people to become closer to one another. When a leader shares their sense of humor you get an insight into something beyond their organizational persona. If you happen to find that same sort of humor, it’s like bonding over liking the same sort of drink. Leaders who honestly share humor with those around them, that take the risk of inviting people to see some of what they find funny risk some, but the reward is great. You will have a lot of folks identify more with you and in more important ways than just being the boss.

It’s hard to hide what you find funny. When I share a joke with you, or a meme I find funny, it’s quite revealing. It’s like revealing to the person you just started dating that hobby you keep hidden for fear of judgment. Take puns. Some people love them, and others hate them. There’s very little in-between on the issue. I happen to love good ones, clever ones, spontaneous ones, and tolerate the bad ones.

American Basketball Coach John Wooden said, “Make each day your masterpiece.” How do you embody that quote? We welcome a story or example.

The pursuit of excellence is important and should be a guiding factor in our lives. I work to make sure that the writing I do, my teaching, and the rest aims for excellence. I don’t always hit the mark, and I don’t have to be excellent at everything. But I try to and that’s the important part.

What is the legacy you aspire to leave as a leader?

The thing I would most like to leave as a leader is the sense that when we think about leadership, when we think about what we do as leaders, as coworkers, as friends, that we see people as more than what they do for us or for our organizations. We’ve developed a bad habit in reducing people to their work, students to their graduation rates, leaders into what they can do for us. We need to remember and focus on each of us as individuals. When we start to see people as more than their particular role relative to us, our world will drastically improve.

How can our readers connect with you to continue the conversation?

They can find me through my website, find me on LinkedIn visit my YouTube channel The Humor Hack or find my substack where I write about humor, work, and other topics. They can also look for my new book, “The Humor Hack” available on Amazon or through the publisher’s website.

Thank you for giving us the opportunity to experience a leadership master at work. We wish you continued success and good health!