• Jon Selig uses principles of comedy to help sales reps engage their prospects more meaningfully and more quickly. He specializes in turning pain points into punch lines, so potential customers stay engaged and sales reps close deals.
  • You have 12 seconds to introduce yourself and establish a connection with your audience before you’ll lose their attention. So engage them right away.
  • Personalize your outreaches by understanding your prospects’ pain, proving you know their world, and showing that you’ve got the solution to their roadblocks.

From starting conversations to closing deals, the sales process is no joke. 

But using principles of humor in sales can help you capture prospects’ attention and create a lasting connection. Establishing rapport and making a memorable impression helps you start more conversations. It also builds trust and keeps you in potential customers’ minds for much longer.

And who knows this better than a standup comedian? 

Jon Selig, who specializes in turning pain into punchlines, helps sales reps close more deals through comedy. 

On a recent episode of INSIDE Inside Sales, Jon and I discuss how using humor in sales helps you stand out from the crowd and how knowing your audience makes way for next-level connection.

Up your personality game

Traditional wisdom dictates that professionalism is primary: focus on polishing your presentation, dress in keeping with business norms, et cetera.

And while appearance is certainly an important element of being taken seriously, it’s also important to bring your personality to work with you.

humor personality

Jon advocates for “being different in a sea of sameness.”

One of the ways I do this is by wearing my signature smoking jacket when I present onstage at conferences. Later, audience members who want to talk to me can easily identify me in the crowd.

And these conversations, in turn, become real deals in the pipeline.

Another way to stand out is by making your audience laugh. Especially if you connect with someone online before you meet them in person, they will decide quite quickly whether they like you, based on the information available to them. 

Your personality comes through in the words you use in an email or your tone in a voicemail. So don’t be shy to make strangers smile—you’ll stick in their minds that much longer.

Establishing rapport with someone right away will work wonders throughout the sales process. 

And Jon knows how to do exactly that.

Applying a comedy formula to capture customers 

One of your fiercest competitors during the sales process is the ongoing shortening of the human attention span.

Comedians know that you have 12 seconds to get your audience’s attention. If you don’t, you can guarantee they’ll turn to their phone screens to quench their boredom. 

If you’ve watched enough stand-up specials, you might have caught onto the formula. When introducing themselves, comedians use the first six seconds to introduce who they are and offer up why you, the audience, can relate to them. They use the next six seconds to deliver a one-liner or something that makes the audience laugh. 

Otherwise, odds are very, very good they’ve lost the audience. 

Selling conversations operate the same way. 

No matter the medium, use the initial characters in your email or lines of a Linkedin message to start a conversation that engages. Use that space to let them know briefly who you are, tell them why they can trust you, and engage them emotionally.

Jon also points out that standup comics often use shorter stories or one-liners at the start of a set to build trust with the audience. They can build up to telling longer anecdotes once the audience has already determined that they’re funny and trustworthy.

You can build trust with your customers in much the same way. First, focus on showing you understand your audience and their pain points, so they know they can trust that you have the answer to their pain points, too.

Know your audience

Jon is the first to admit that this isn’t rocket science.

But the bottom line is that you must know your audience to sell effectively. In order to be relevant to your audience — to engage them and keep them interested in any sales conversation — you have to know who they are and what matters to them. 

This, Jon says, is the intersection between sales and stand-up.

For instance, a comic wouldn’t focus a comedy set around jokes about TikTok if their audience was predominantly Gen X and older. 

The same goes for business conversations.

Ask yourself questions like these about your prospects:

sales humor
  • What are they trying to achieve? What are their objectives?
  • What roadblocks get in the way of achieving their desired end state?
  • What emotions do their roadblocks set off in them?
  • What is the impact of not solving their pain points?
  • Which of their roadblocks can we remove for them?

When you know the answers to these questions, you can show yourself to be a subject matter expert about your prospect’s corner of the world, and they’ll be far more likely to want to keep talking to you.

But don’t forget, Jon says: “It has to be done in a way that obviously gets their attention pretty quickly.”

Here’s how.

Make sure your outreaches are personalized

If you’re using automated email or social touches, but your conversion rates are low, it’s no secret why.

Using a “set it and forget it” template won’t cut it here. Automating your outreach campaigns may seem like time-savers, but in the long run, they will lose you deals, energy, and time. 

You’ve got to personalize your outreaches to prove that you know your audience. Make it clear why your message matters to them individually, so they’re incentivized to keep reading rather than clicking away.

Product knowledge < understanding the customer

A few years ago, we surveyed 2,000 B2B buyers about what they valued most in the sales process. Product knowledge was ranked number two.

The number one most important factor? Knowing the customer

While product knowledge is critical, buyers view it as secondary to their sales rep understanding them, their lives, and their industries.

It takes time, energy, and research to gain this kind of knowledge. You don’t need to be an absolute expert, but you do need to be able to talk about your prospects’ issues.

Know what keeps them up at night

When we try to understand what matters most to our prospects, we often default to big-picture items like hitting sales targets. 

But that’s not actually what keeps your buyers up at night.

The quickest way to find out what does? 

Ask emotion-based questions like, “In the last 72 hours, what bugged you at work the most?” 

This kind of question ties into recency. You’ll get a deeper, truer answer that helps you get straight to the heart of their pain points.

Get specific about your clients’ pain

One of the ways Jon helps his clients use humor in sales is by coaching them to “roast” their customers’ pain.

To do that, you have to have an intimate knowledge of what makes them tick, and what makes them want to tear their hair out.

Get to the actual root cause of what’s causing wasted time or money for your customers. Be as specific as possible.

“The more granular and ‘subject matter expert-y’ you can show your buyer that you are,” says Jon, “the more seriously they’re going to take you.”

When you know your prospects’ pain points well enough to craft a comedy set about them, you know them well enough to sell to them.

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