The Hidden ROI of Humor (and why funny people lead stronger teams)

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Dear Legend,

I don’t know about you, but I’ve stopped reading the news. Mostly because I’m trying to protect my sanity. These doom scrolling nights filled with never ending clickbait headlines, I’ve had enough (what about you?)

So it’s been excitingly refreshing to chat with a comedian a couple of weeks ago. Why did I seek out a comedian? (No, I didn’t have a private show to keep my spirits up😅.)

I wanted to learn about humor. About its power and about why don’t we have more of it in our lives, especially in our professional lives.

Do leaders fear humor? Is it too risky to tell a joke?

It turns out, after speaking with Kate Davis, that humor is not risky at all, it’s actually ROI-positive.

Kate’s a 15-time veteran of the comedy stage, a Canadian Comedy Award nominee, and a sought-after keynote speaker for organizations like Coca-Cola, Microsoft, and the Canadian Armed Forces. She’s been a finalist for the Stephen Leacock Award for Humour, has appeared on major networks like CBC and CTV, and trains leaders across industries to wield humor like a leadership superpower (so yes, we did have quite a few laughs, but I learned a ton as well.)

The lessons she shared stuck with me… how come?

“People don’t learn from stats. They learn from stories. And when you can make those stories funny, you create connection and belonging.” – Kate Davis

She shared so many stories! Here is how you can listen in too: Apple, Spotify, or on the web (the tampon applicator story takes the cake 🤣)

So the main lesson I took away is this:

Playfulness isn’t unprofessional – it’s strategic.

Humor at work isn’t about cracking jokes. It’s about cracking open connection.

It’s about bonding your team before the storm, so you perform in the storm.

Like Kate says: “If we bond during the good times — through jokes, memes, playfulness — then when things get hard, we work better together.”

The fact is that from the earliest ages, we crave connection and there is nothing like laughing and smiling that connects us (if you are a parent, think about the smiles and giggles from your baby you crave so much.)

Humor is fundamental to our survival, so we connect and we care for each other.

Similarly at work, bringing a sense of humor, getting the team to laugh, builds trust, psychological safety, and makes you magnetic as a leader ❤️.

All those quarterly reports, and business updates, nobody remembers them. But if you got them to laugh, now that feeling sticks. “People will forget what you said, people will forget what you did, but people will never forget how you made them feel” - Maya Angelou

If you want to bring more of that to work, you need to let go of the lie that “important things can’t be funny.”

This isn’t about making light of serious moments, 🧠 it’s about making serious moments lighter, so people can move forward. Kate said it beautifully, “Take your work seriously. But don’t take yourself too seriously. The first is imperative. The second? Disastrous.”

🧰 Here is the Humor-In-Leadership Playbook (5 practical ways to bring humor into your leadership)

1/ De-risk humor with memes and shared moments

Humor doesn’t have to be risky. Drop a Ted Lasso meme in the Slack channel. Share a “fail” gif to open the next meeting. It sends a message: You’re human.

“Even naming boardrooms with funny names changes the culture,” Kate said. Google does this. Why not you?

2/ Use humor to bond before the breakdown

Plan team-building games or fundraisers with a twist. Kate shared a story where a machinery company (yes, serious business) had their VPs play games against middle managers. The result? Communication skyrocketed.

That’s legendary ROI, my friend.

3/ Know your humor style

Not everyone needs to be the clown. You can be dry. You can be quirky. You can be self-deprecating (Kate teaches this as the safest form of humor). What’s your natural style?

Just don’t punch down. If someone’s always the butt of your joke, you’re not leading — you’re mocking (and remember the key learning from Will Storr? Always elevate their status.)

4/ Create rituals of levity

You don’t have to “be funny” — just create space for humor to exist.

• Have a “Weekly WTF” roundtable

• Run a “Rant Rap” challenge where people rhyme their biggest stress

• End meetings with “what made you laugh this week?”

Make it repeatable. Make it expected. That’s how culture is formed.

5/ Tell funny failure stories

One of Kate’s coaching clients — a former tennis pro — told a story of being on center court and worrying what the crowd thought of him. “They think you scream like Serena,” Kate quipped. Boom — relatable.

Failure stories that are told with humor make you human, and they bond people faster than polished highlight reels.

Want more? I shared 10 Hidden Rules of Humor on LinkedIn last week (with 33,041 impressions so far!) and be sure to check out Kate’s podcast Humor in the C-Suite as well. And here is a short 30 sec clip of Kate on the comedy stage (warning: explicit language.)

We can all use more laughter in our lives don’t you think?

I would love to hear how you’ve brought humor into your workplace. Shoot me a note and let me know!

This week, for our influence psychology lesson:

The Halo Effect

Ever met someone smart and instantly assumed they were also kind, trustworthy, and competent?

That’s the Halo Effect in action.

It’s a cognitive bias where one positive trait creates a “halo” that makes us assume other positive traits—even without evidence.

In one of the earliest studies by Edward Thorndike (1920), military commanders were asked to rate soldiers on traits like intelligence, physical appearance, and leadership.

The findings?
If a soldier was rated high in one area (like appearance), they were consistently rated higher across the board—even if there was no real proof.

💥 One positive impression distorted the rest. (A study in 2024 in the use of AI beauty filters found the same thing.)

One positive trait translates to others without evidence.

This is why attractive, confident, or well-spoken people are often perceived as smarter, more capable, or even more moral—whether they are or not.

How can you use the Halo Effect to influence?

Here are five ways:

1. Lead with your strongest trait or result. “Our team grew this brand from zero to 10k customers in 9 months.” That one stat builds instant credibility for everything that follows.

2. Polish your visuals. Design, presentation, and packaging matter more than most think. Clean = capable. Sloppy = suspect. First impressions spill over.

3. Show up with energy and confidence. “Trusted by 300+ clients across healthcare, tech, and finance.” That credibility casts a halo over your pitch, your offer, and you.

4. Highlight social proof early. “Would you mind grabbing my package if it gets delivered while I’m out?” Small neighborhood favors build real-world rapport.

5. Pair yourself with powerful associations. “Our advisory board includes former execs from Google and Mayo Clinic.” The halo rubs off on you—and your product.

Remember Legends, when people like one thing about you,
they’re more likely to like everything about you.

So shine bright in the right places.
Let that halo do the work. 😉

See you next Sunday.

Make your mark, live your legend 🤘🏽,

Howie Chan

Creator of Legend Letters

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