Leading with humor: The AI comedy playbook

The AI debate is like your favorite sci-fi movie: some envision a utopia where AI revolutionizes work, transforms lives, and boosts health, while others predict a dystopia where robots swipe our jobs, dull our brains, and maybe even spell doom for humanity. Spoiler alert: the truth is somewhere in between.

The future of AI? It’s all on us and the choices we make today. As business leaders, it's our gig to tap into AI’s superpowers while setting up ethical guardrails to maximize the good stuff and minimize the risks. With a dash of smart leadership and a sprinkle of strategic implementation, we can use AI to conjure up some serious positive change and innovation.

Today, let's take a detour from the usual AI deep dive. Instead, let's explore another side of AI… Can it crack a good joke? Humor is the ultimate stress-buster, so I challenged ChatGPT to finish some joke prompts. Russell Peters and Jim Gaffigan don’t have anything to worry about. LLM AI is about as funny as a comparison of the merits between qualitative vs. quantitative data analysis.

Me: Complete this joke - How many engineers does it take to replace a light bulb?

ChatGPT: None. That's a hardware problem.

Hmmm… not very original. That joke has been around for a while – often at the expense of software programmers.

Me: Write a Knock, Knock joke involving AI.

ChatGPT: Knock, knock.

Who's there?

AI.

AI who?

AI'm here to make your life easier!

Better….

Me: Complete this joke. A CEO, a manager, and a chatbot walk into a bar.

ChatGPT: A CEO, a manager, and a chatbot walked into a bar.

The bartender looks up and says, "Is this a setup for an automated happy hour?"

You get the idea. While AI’s ability to make jokes is improving along with all its other large language model (LLM) based output, it’s not quite ready to replace Jim Gaffigan or Michael Che. The reason? Humor is highly contextual and situational, requiring an understanding of cultural references and linguistic nuances. Large language models can generate canned material because hack jokes (like the ones I tried above) rely on systematic pattern recognition, which is essentially what LLM is.

The truth is, experts believe that original, groundbreaking comedy will likely remain beyond the reach of such technology, at least for now, due to its uniquely complex nature. You see, AI is good for low brain power, high accuracy tasks like writing basic procedures, stock answers to basic questions, and even some decent talking points. What AI isn’t good at is reading an audience, understanding modern life, or producing something from nothing.

AI synthesizes data sets, drawing from thousands or even millions of examples to craft something that mirrors past work. This is fantastic for quick results that don’t demand originality. But, like all creative endeavors, AI falls short in generating truly novel ideas. Producing edgy, boundary-pushing content—like groundbreaking insights and countercultural concepts—requires the knack for spotting hidden parallels and understanding cultural norms. If AI can’t grasp taboos, how can it ever hope to break them?

So, we get why AI isn't great at cracking good jokes, but why does humor matter at all? I mean, shouldn't leaders be focusing on improving processes and boosting productivity? Leadership is undoubtedly a weighty responsibility, but I can't help thinking that many of us take it too seriously and forget to have fun along the way. Numerous studies highlight that humor is a powerful leadership tool. It fosters a positive and open environment where employees feel comfortable and engaged. Research indicates that leaders with a sense of humor are viewed as 27% more motivating. Their employees are 15% more engaged, and their teams are more than twice as likely to solve challenges creatively. This isn't surprising, considering that laughter triggers a release of hormones in our brains that make us feel happier, less stressed, and more trusting.

For leaders, incorporating humor provides numerous benefits, such as signaling confidence, humanizing interactions, and capturing their teammates' attention. For employees, humor enhances well-being, creativity, job satisfaction, and work performance. For teams, it improves communication and cohesion, while fostering creativity and innovation.

So now you may be asking, how can we as leaders find our funny bone? It's true that humor is subjective, and some of us are naturally funnier than others, but don't worry, much like other areas of leadership, the rest of us can still develop this skill with some practice. Here are a few simple tips to try:

• Notice Incongruities: Humor often comes from noticing the oddities in life. Start to pay attention to these incongruities and call them out.
• Read the Room: A misplaced wisecrack or bad joke can do more harm than good. Learn to read the room and don't force the funny.
• Keep it Positive: Focus on positive, uplifting humor. Be careful not to cross any lines.
• Be a Good Sport: If you want to make jokes, be ready to take jokes. Laughing at your own mistakes puts everyone else at ease.

According to two Stanford experts, Jennifer Aker and Naomi Bagdonas, who teach a course on the power of humor in leadership, our lives are brimming with humor if we know where to look. Sharing personal anecdotes is far more effective than stressing over a witty one-liner. For example, poking fun at things that aren't working, and everyone is worried about, or using witty puns and retorts, are great opportunities to use humor to our advantage.

So going back to our ChatGPT prompts above, a more fitting response to the third one might have been:

A CEO, a manager, and a chatbot walked into a bar.

The bartender looks up and says, “What can I do for you?”

The CEO says, “I’m trying to learn how to be funny. Can you help?”

The bartender says, “Well you should start by ditching these two. They’re both programmed to parrot back whatever you say!”

Bottom line: Leaders who sprinkle in humor don't just come across as likable—they're also seen as smart and trustworthy. Whether you're naturally funny or using tools like GenAI, embracing laughter can seriously boost your leadership game. So, why not lighten up and lead with a smile

So, how do you use humor at work? I’d love to hear from you.