The Strategic Use of Humor in Business: How To Laugh Your Way to Better Sales

If your sales team is missing something, it might just be a good punchline.

Humor is for everyone. Sure, comedians and class clowns may think they own the space, but it’s a powerful and underutilized sales tool, too!

In this episode of Strategy Talks, I sat down with humor-driven sales trainer Chris Castanes to explore how laughter can disarm objections, build relationships, and make your pitch memorable.

Chris, who got his start selling insurance door to door in rural North Carolina, now teaches professionals how to use humor strategically, not just for laughs but for results.

Chris brings the kind of wisdom you don’t expect, and that’s exactly the point.

He’s the founder of Stand-Up Sales and author of You're Going To Be Great At This!, and he’s trained countless professionals to sell smarter (and funnier) without crossing the line.

Why Humor Belongs in the Business World

Most people shy away from humor at work. It feels risky, unprofessional, or hard to get right. But Chris has a different take.

“You’re not gonna go into a funeral home business and dress like a circus clown... read the room a little bit,” Chris explained. “But a little levity in the right moment can lower defenses and open people up.”

The key is understanding when and how to use humor. It’s not about telling jokes—it’s about lightening the mood, building trust, and showing your human side.

Real-Life HUMOR Tip

Chris likes to keep a few safe, silly one-liners in his back pocket.

For example, when checking someone’s policy info, he might ask the wife, “Is Bob behaving this week?” Most of the time, it gets a chuckle.

But even when it doesn’t land, like when Bob is actually getting divorced or just passed away, Chris reads the room, recovers with grace, and uses it as a way to connect more deeply.

Sales Success Starts With Reading the Room

Chris’s early days of knocking on doors taught him to read people fast. The porch light, the body language, the energy all told him whether the person inside was going to buy or not.

“It's not a science,” Chris says, “but you get a vibe. Sometimes it's welcoming. Sometimes it's scary.”

And that gut feeling doesn’t disappear in the digital world.

While Zoom can make it harder to gauge reactions, Chris recommends using memes, light-hearted content, and even just a self-deprecating opener to warm people up.

“I'll say something like, ‘You can trust me, I’m in sales.’ That always gets a laugh. And when people laugh, they relax.”

Use Humor to Drop the Sales Tension

Let’s face it, sales conversations can feel stiff and awkward, especially when you’re talking about serious stuff like life insurance or disability coverage.

Chris finds that inserting just a little humor makes the conversation smoother and more human.

Here’s how humor helps:

• Builds rapport quickly with strangers

• Breaks tension in emotionally loaded topics

• Makes you memorable long after the pitch

• Diffuses objections before they fully form

“People like to be picked on just a little bit sometimes,” Chris shared. “But more than anything, they like to laugh.”

The Humor Toolkit Every Seller Needs

According to Chris, your humor doesn't need to be groundbreaking, just genuine and well-timed.

Here’s what he suggests for anyone wanting to sell with a smile:

• Create a “patter”: A handful of go-to comments or jokes that fit your personality and work situation.

• Practice on the fly: Test what gets a laugh and keep what works.

• Use AI (yes, really): Tools like ChatGPT or Perplexity can help you find appropriate jokes based on your industry.

• Make yourself the punchline: If you're not sure who to joke about, make it you.

“If something falls flat, it falls flat. But when it lands, you can feel the tension go out of the room. That’s where the magic happens.”

Virtual Selling? Humor Still Works—Just Use It Differently

During the pandemic, Chris shifted his work online and quickly realized something was missing: feedback. “You don’t get the laugh on Zoom,” he admitted.

His solution? Embrace other forms of humor, like:

• Memes and GIFs in follow-up emails

• Canva-created visuals that lighten the message

• Funny (but appropriate) social media posts to stay top-of-mind

You may not hear the laugh, but the smile is still there.

Can Humor Be Taught?

You don’t have to be born funny to use humor strategically in business.

If you are interested in using humor strategically, Chris recommends:

• Toastmasters for public speaking and confidence

• Reading widely to expand vocabulary and storytelling skills

• Trying improv or stand-up classes to get comfortable in the moment

And if that still sounds intimidating, start small.

• Give a compliment.

• Tell a cheesy pun.

• Make a joke about yourself.

  
  

And see what happens.

Final Thoughts: Humor Is a Sales Superpower

Whether you’re selling insurance, software, or anything in between, a little levity goes a long way. It’s about being real, relatable, and memorable.

As Chris put it:

“You're always selling, whether it's a product, an idea, or yourself. Why not have some fun doing it?”

And I’ll leave you with my favorite reminder from this episode:

“Wives hate life insurance. But widows love it.”

Now that’s a line that sells, and sticks.

10 Smart Prompts You Can Ask ChatGPT about Strategic use of humor in business:

• How can I use humor in my sales pitch without offending anyone?

• Give me 5 appropriate jokes for selling life insurance.

• What are some light-hearted ways to start a Zoom meeting with a new client?

• Help me create a “patter” of humorous lines for sales conversations.

• Write a follow-up email with a touch of humor for a potential client.

• Give me examples of brands that use humor successfully in marketing.

• What’s the psychology behind using humor to build trust in sales?

• Draft a short elevator pitch that uses humor effectively.

• How can I inject humor into my personal brand on LinkedIn?

• Suggest safe, professional jokes to break the ice in a meeting.