The Funny Business: Why Professionals with a Good Sense of Humor Often Get Ahead

Let's be honest: There is almost nothing worse than an office or work environment completely devoid of humor. Whether you are running a large consulting team on a tight deadline or driving the fork-lift in warehouse at the height of the Christmas shopping season, a well-placed joke or clever witticism that provokes amusement not only provides a moment of levity but can lift everyone's spirits and endear you to your fellow workers.

Sure, some environments are more conducive to laughter and joking around than others, and there is always a time and a place, but I have yet to run across someone I have met in life who really excels at what they do and gets fulfillment out of their job without having not only an appreciation for good humor but who also oftentimes sports a very highly developed sense of wit themselves.

Now I know some of you may be shaking your head, thinking, "Not in 2023. Not in this era where everyone seems to take offense at everything."

Not so fast.

Here's what I think most people don't realize about humor in the workplace and why its such an effective tool in an organization's culture and, most importantly for the purposes of today's chapter of Leveraged Storytelling, why it tends to be one of the hallmark characteristics of those who excel within their professions:

When you interrupt an otherwise serious conversation or task with a clever remark, or you take a group down a tiny tangent with a funny payoff, what you are very subtly communicating to everyone is that "Yes, what we are doing here is important work, but we are also humans, and I am willing to take time out of my day to put you at ease, entertain you, and bring you joy. You matter to me. I want to connect with you. I value the camaraderie we share. And by sharing laughter in this tiny moment, I am communicating my desire to further our bond."

That's it.

Humor, in a nutshell, is about connection.

Its about bonding.

Its about camaraderie.

Humor is, in my experience, the absolute most effective way one human being can connect with another on an emotional level in a professional setting.

Now, of course, humor is a risky business.

Not everyone shares the same cultural mores. Not everyone has the same religious, political, or philosophical grounding, so to effectively wield a sense of humor requires a high level of emotional intelligence. You need to be able to read a room. You need to be able to quickly assess your audience. It requires quick thinking. And since some of the best workplace humor is self-deprecating, it oftentimes requires a strong sense of self.

As such, the intangibles which are key to someone's ability to create humor in a professional setting -- quick thinking, emotional IQ, self-confidence -- represent many of the same characteristics that will elevate certain individuals over others in a competitive work environment.

Said another way, humor serves as a proxy for the key human intangibles that form the blueprint for personal success in the workplace.

Have you ever heard someone say, "So and so takes themselves too seriously."? What they are really saying is that this person, who may have a considerable intellect and may have deep expertise in their field, is failing miserably at creating that human connection with peers whether within an organization's four walls or vis-à-vis vendors, clients or peers.

Now, let me tell you a quick story.

There is a guy that I grew up with (I shall keep his name out of it because it doesn't matter for the purposes of this story) who was extremely smart. He ended up graduating as the Salutatorian of our class in high school class of 450 in Minnesota. He went to Harvard for undergrad and then stayed there to do a dual MBA and JD. (OK, I realize that, for those of you who know me from high school, I am doing a pretty shitty job of protecting this person's identity. Oh well.)

Anyway, growing up, throughout junior high and high school, we were in all the same "accelerated classes" for Math, English, Physics, and other core courses. (This is way before there was AP this and IB that, etc.) and I never, ever, recall him cracking a joke.

He was serious about everything. Ruthlessly competitive. (Fun fact, I once ran into him about two years after high school at a local gym during summer break and, instead of him telling me about his time at Harvard or asking me what I had been up to, he launched into the great indignation that he had endured because, due to some technicality, his final high school GPA was a 4.27 and not a 4.26!! And that .01 difference had cost him the Valedictorian honors to another classmate of ours! And this is two years after graduation and he is already ensconced at Harvard. The Horror!)

Anyway, this guy, Mr. Triple Harvard, has gone on, as far as I can tell, to have a fairly successful career in finance living in the New York area. But not the crazy success that many of us that knew him in our teens had assumed was awaiting him.

Yes, I am sure he is doing quite well financially but he didn't build a name brand hedge fund, or create some super disruptive company. Hell, he didn't even become a senior officer a bulge bracket investment bank. He wasn't appointed to some high ranking role in government. The fact is that, I think, relative to the intellectual horsepower he was born with and his stellar academic credentials, he underperformed.

And I think I know why.

He has no sense of humor. He didn't as a kid. And I also know he didn't as an adult either.

Over a decade after graduating from high school, while I was living in New York City and working for Mayor Bloomberg, I had invited a number of fellow high school classmates that were also living in the city over to my apartment in Lower Manhattan. We were all part of that same "accelerated program" in high school and we had spent hundreds if not thousands of hours together as kids.

There were about 5 of us and several brought their spouses. Now all of these people had left Minnesota, gone to top schools, and were doing interesting things in New York City. And while it was good to see everyone, I distinctly recall this guy, Mr. Triple Harvard, acting quite oddly. He only talked about himself and what he was doing, never showing the slighted interest in anyone else. I remember it vividly because it struck me as such weird behavior. He was humorless. Even when we were recounting funny stories that we all recalled from high school -- ones that we were all part of -- he seemed to even struggle to smile. (Almost as if he was still smarting from being passed over for Valedictorian.)

And I am absolutely certain that a big part of what held back his career was his personality -- specifically that he didn't wield humor as a tool in the workplace. There was no proxy measure for his emotional IQ or level of self-confidence. Actually, his lack of humor signaled that he wasn't self-confident at all. He couldn't be self-deprecating. It almost came across as Narcissistic. And I am sure this is what held him back from reaching his true potential.

This, of course, is just one proof point, but I have seen versions of this behavior over and over in my life and in many different types of industries, situations, and cultures.

People with a good sense of humor almost always over perform and go on to have fulfilling and successful professional lives because they have used their humor to bring people along with them and created allies who, in turn, buoy their success.

I hope you are enjoying Leveraged Storytelling. If you like what you read, please share.

Until next time,