5 Ways to Use Humor in Cold Emails: Boost Responses and Build Connections

Hello, Arun here from The GTM Guild, where we discuss growth and smarter strategies for your cold email and GTM. I welcome this week’s 627 subscribers who have joined our community of over 50,000+ sales professionals spread over 56 countries across the globe.

Cold emailing doesn’t have to be cold. Adding a touch of humor can turn an otherwise ignored message into one that gets a smile—and a reply. But humor, when used strategically, does more than entertain; it builds rapport, showcases personality, and differentiates you from the sea of generic outreach. In this newsletter, we’ll explore the role of humor in cold emails, when to use it, and five effective ways to make your emails memorable.

The Role of Humor in Cold Emails

Humor humanizes your approach, making your email feel less like a sales pitch and more like a conversation. It helps:

• Grab Attention: A funny subject line or opening line piques curiosity.

• Break the Ice: Light humor can ease tension and make your message feel less intrusive.

• Build Connections: Shared laughter fosters relatability and trust.

However, timing and context are crucial. Humor works best when:

1. You’ve researched your audience and know they’ll appreciate it.

2. The tone aligns with your brand and message.

3. It’s used sparingly and complements, rather than overshadows, your value proposition.

5 Ways to Use Humor in Cold Emails

1. Start with a Funny Subject Line

• Why It Works: A clever subject line stands out in a crowded inbox.

• Examples:

  • "Do you believe in love at first sight (or should I email again)?"

  • "Opening this email will bring you joy… or at least a good chuckle."

• Pro Tip: Keep it short and relatable to your audience’s context.

2. Use Self-Deprecating Humor

• Why It Works: It’s disarming and shows humility.

• Example:

  • "I’m just a marketer, standing in front of a decision-maker, asking them to hit reply."

• When to Use: When introducing yourself or acknowledging the challenges of cold outreach.

3. Add a Humorous Anecdote

• Why It Works: Storytelling with humor creates a narrative that’s both engaging and memorable.

• Example:

  • "I once tried to fix my Wi-Fi by rebooting my coffee maker… That’s when I realized I needed a real tech partner like you!"

• When to Use: When relating to your recipient’s industry or challenges.

4. Include a Playful CTA

• Why It Works: A light-hearted call-to-action makes your ask feel less transactional.

• Example:

  • "Let’s connect… unless you’re allergic to good ideas. In that case, I recommend Benadryl and a quick reply."

• Pro Tip: Ensure your humor doesn’t overshadow the clarity of your CTA.

5. Use Pop Culture References

• Why It Works: Familiar references can create an instant connection.

• Example:

  • "If Ross and Rachel can make it work, surely we can find a time to chat about [your value proposition]."

• When to Use: When your audience is likely to recognize and appreciate the reference.

Best Practices for Using Humor

1. Know Your Audience: Research their preferences, tone, and industry norms.

2. Be Respectful: Avoid controversial or sensitive topics.

3. Keep It Subtle: A sprinkle of humor is enough; don’t overdo it.

4. Test and Iterate: Experiment with different styles and measure responses to see what works best.

Final Thoughts

When used thoughtfully, humor can transform your cold emails from forgettable to irresistible. It’s a tool that not only opens doors but also builds lasting impressions. So, the next time you’re crafting an outreach email, ask yourself—can you make them smile?