How NOT To Use Humor In Sales

Humor is a secret weapon in sales. When used well, it builds rapport, lightens tense moments, and makes you—and your pitch—memorable. But when it’s misused, humor can backfire, alienating prospects or derailing conversations. For sales managers and teams, understanding how to wield humor effectively isn’t just a nice-to-have skill—it’s a game-changer.

Here’s what to avoid when using humor in your sales process—and why it’s worth mastering the art of selling with a smile.

The Hidden Risks of Humor in Sales

A good joke can connect you to your audience, but a bad one? It can cost you the deal. Humor, like any tool, requires precision. It’s not about being the funniest person in the room but about using humor intentionally to foster trust and build relationships. Missteps can harm your credibility or even damage the trust you’ve worked so hard to establish.

Here’s how sales teams can avoid common humor pitfalls:

1. Don’t Punch Down

In comedy, the golden rule is never to punch down—don’t make jokes at the expense of those with less power. In sales, this means steering clear of jokes that mock competitors, customers, or anyone in the room.

Mocking competitors might feel clever in the moment, but it risks making you look unprofessional. And joking about your prospects’ challenges—even in jest—can come across as dismissive, not empathetic.

Instead: Use humor to elevate, not denigrate. Focus on shared experiences or self-deprecating anecdotes that show your human side without diminishing others.

2. Keep It Relevant

Humor should support your message, not sideline it. Off-topic jokes might get a laugh, but they can derail your sales flow and make it harder to steer the conversation back to your key points.

For example, a quick quip about industry trends or a lighthearted observation about the challenges of virtual meetings can help you connect without losing focus.

Pro Tip: Plan your humor strategically. Think of it as a tool to enhance your pitch, not as the star of the show.

3. Read the Room

One of the biggest mistakes salespeople make with humor is failing to gauge their audience. Humor is contextual—what works with one prospect might flop with another.

Take a moment to assess your audience. Are they engaged? Open to humor? Or are they distracted and pressed for time? Humor can deepen rapport, but only if your audience is receptive.

Checklist for Success:

Are they engaged? If they’re responsive, a light joke might enhance the connection.
Are they preoccupied? Focus on delivering clear, concise value first.
Are cultural sensitivities in play? Avoid humor that might misfire due to cultural or personal differences.

Why Mastering Humor Matters

Using humor effectively is more than a “soft skill” for sales professionals—it’s a strategic advantage. It can humanize your team, differentiate your pitch, and build trust in ways that traditional techniques can’t. But like any tool, it needs to be used wisely.

That’s why sales managers should consider humor training as a way to sharpen their team’s edge. By learning how to incorporate humor intentionally and appropriately, your team can build better relationships, close more deals, and leave lasting impressions on prospects.

Bring Humor Into Your Sales Strategy

If your team struggles with how (or when) to use humor, I can help. Drawing on years of experience in corporate sales, stand-up comedy, and keynote speaking, my workshops teach sales teams how to use humor strategically to build rapport, break tension, and drive results.

Whether you’re looking to improve team morale, boost conversion rates, or simply stand out in a crowded market, a humor-driven approach to sales is practical, effective, and proven to work.

Ready to transform your team’s sales strategy with the power of humor? Let’s get started.meaningful connect

Stuart Preston is a seasoned professional with over 20 years of experience in sales and 10 years performing stand-up comedy. Blending his expertise in corporate strategy with the sharp wit of a comedian, Stuart empowers teams to communicate authentically, foster meaningful connections, and thrive in dynamic environments.ions, and thrive in dynamic environments.