Boost Sales with these 3 Humor Tips

How to Close More Deals with Laughter

“Why did the salesperson cross the road?”

That was the subject line of a recent cold email I received. I knew it was a cold email, I knew that the subject line was only used to get my attention, and I knew that I still needed to know the answer. So I clicked.

The actual punchline wasn’t all that great but the use of humor to capture my attention was. Because, like you, I get dozens of pitches in my inbox everyday, even more if you count the number of people “who stumbled on my profile and were impressed” on LinkedIn. And yet this one made me open it.

Why? Because of curiosity and the implied promise of a bit of joy once I read the punchline. This type of humor can be a powerful technique in sales (or any other type of influence) and is one we’re teaching to a number of sales organizations early next year as part of their SKOs (for the non-sales people, that’s “Sales Kick Offs” not “Strategic Karaoke Outings”). 

That’s because humor isn’t just a nice-to-have in sales; it’s a powerful tool for building rapport, easing tension, and making a lasting impression. Ever notice how the best conversations leave you laughing? Imagine if your sales calls felt like that—easy, fun, and memorable.

So if you want to bring a smile to your sales process like the 20+ sales organizations we’ve already worked with, here are three simple but effective humor hacks that will help you connect, engage, and, yes, close more deals with laughter.

1. Comic Triple: Surprise with the Unexpected

The "Comic Triple" is a classic humor technique where you set up two expected items, then throw in an unexpected third. It’s a quick and easy way to get a smile, even over email.

How to Use It: Think of a list relevant to your product, service, or the buyer’s needs. Mention two standard items, then add a quirky, funny third option that catches them off guard. 

Example:

“Our platform will boost your revenue, streamline your workflow, and give you more time to pretend you like golf.”

This technique works because it’s short and plays with expectations, making it ideal for both conversation and written communication. Plus it’s easy to see where you can use it: anytime you have a list, see if you can add something unexpected at that end.

2. Planned Ad-Lib: Be Ready for Reactions

Ever had a potential client respond in a way that caught you off guard? Instead of fumbling, try a “planned ad-lib,” where you have a few ready responses to common scenarios (note: this technique also works well for my fellow introverts in small talk scenarios). This strategy keeps you quick on your feet while sounding natural and personable.

How to Use It: Write down a list of common objections or questions you get during sales calls, then brainstorm a few humorous responses for each. 

Example:

If someone says, “I don’t know if I’m ready to switch to a new provider,” you could respond with, “I totally get it! Switching feels like deciding to break up with your hairstylist—terrifying but worth it.” 

Just a little light humor can ease the tension and open up the conversation.

3. “Yes, And…”: Build on Their Ideas

“Yes, And” is a fundamental technique in improv and is one of the best tools for any type of collaboration, which is what sales should be. It’s about listening, affirming, and building on what the other person has said. By using “Yes, And,” you show clients that you’re not only listening but also looking for ways to help.

How to Use It: When a client or prospect shares a concern, start with “Yes, I see why that’s important…” and then add an “And” to build on it with a humorous but relevant solution. This response validates their thoughts while letting you keep the tone light and constructive.

Example:

Client: “I’m worried about implementation time.”

You: “Yes, that’s definitely a fair concern, and the good news is we’ve actually helped clients get up and running so fast, one client called them caffeinated tech wizards.”

This approach not only keeps the mood light but shows that you’re attentive and responsive, which will boost the client’s confidence that you can deliver on what you’re selling.

Why Humor Works in Sales

Using humor isn’t about becoming a comedian—it’s about being human. By incorporating these lighthearted strategies, you’ll stand out, build rapport, and maybe even enjoy the process a bit more yourself.

Whether you’re just trying to drive one smile per hour or looking to make a lasting impression, humor can be a surprisingly effective sales tool. So, go ahead and add a bit of comic relief to the sales process. You might find that, along with making the day a bit brighter, it’s also making a difference in your results.

So why did the salesperson cross the road? To help their client get around a roadblock. See, I told you it wasn’t the best punchline, but it was effective.

Got a better sales joke? Let me know in the comments.

(an)drew

PS. Work on a sales team? Let’s connect to see how we can bring humor to your sales process.

PPS. Here’s a slightly better sales joke:

A salesman approached a potential client and asked: “Would you like to buy a pocket calculator?”
“No thanks,” the man replied. “I know how many pockets I have.”