How to Use Humor in a Cold Email Follow-Up Without Being Cringe

Ever sent a cold email and heard nothing back? It’s like tossing a paper airplane into the wind, hoping it’ll land on some distant desk. The follow-up email is like your boomerang shot at catching the prospect’s attention again. But gosh, it’s easy to screw this up by coming off as pushy or worse, cringeworthy. The silver lining? A dash of well-placed humor can be your winning formula — if you pull it off right.

In this piece, you’ll see why nailing the follow-up is crucial, how humor can be your secret weapon without getting awkward, and there are some solid tips to keep your follow-ups cool and professional. And yes, we’ve got some email examples that hit the funny bone perfectly — without being a comedy flop.

Introduction to Cold Email Follow-Up

So, what’s the big deal with a cold email follow-up? Well, it’s that trusty sidekick you need after you’ve sent the first email and been met with utter silence. Think of it as your genial nudge to remind them, “Hey, I’m here, and I’ve got something valuable for you!” It’s all about sparking interest or building rapport so you don’t end up in the spam folder.

According to some pretty telling studies, about 80% of deals need a good five nudges before they seal the deal, but most folks give up after just one or two tries. Sending a well-thought-out follow-up can keep the lines open without nudging too hard.

But here’s the catch — you’ve got to do it with some finesse. Go too hard, and you’re that annoying email person. Too bland, and you’ll be as forgettable as plain toast. A sprinkle of humor can make you relatable and memorable — but there’s a thin line between cracking a smile and causing a cringe.

Understanding the Importance of Cold Email Follow-Ups

Your first email? That’s like the opening act. Follow-ups? They’re where you get the conversation rolling. Here’s why you shouldn’t skip them:

• Improve Response Rates: Just one email can get lost or ignored among the inbox tumbleweeds. Sending a follow-up can boost your chances of a reply by a significant margin. Really.
• Show Persistence Without Pressure: A considerate follow-up says, “I’m still interested, but I promise I’m not here to bug you.” It’s about starting a slow build of rapport.
• Allow More Personalization: Miss the goal on your first try? A follow-up gives you a chance to tweak your approach using insights you might have gathered — think of it as your second crack at nailing it.
• Recover Missed Opportunities: Sometimes, your initial email just gets buried. A polite follow-up can resurrect it to the top of their crowded inbox.

Sales pros who’ve mastered cold email magic know follow-ups aren’t a one-size-fits-all deal. Timing and tone? Super important. Your follow-up should feel more like a friendly reminder rather than an overly eager nudge.

How to Use Humor in a Cold Email Follow-Up Effectively

Humor’s a charm — it’s all about connecting and easing barriers. Used wisely in your emails, it can make you stand out among the sea of stiff and formulaic messages.

Know Your Audience

Humor’s a personal thing. What gets a tech startup founder chuckling might just fly over the head of a finance executive. Use what you know about the person’s role, their company’s culture, or the general vibe of the industry.

• Startups? They might dig a laid-back, witty style.
• Corporate folks? A more buttoned-up, subtle approach is safe land.

Start Small and Simple

Kick off with light humor: think small jokes, a pun, or a bit of self-mockery. Save your stand-up routine for comedy night.

Example:

“I swear this is my last email… Unless you fancy a trilogy.”

This playful nod to repetitive follow-ups breaks the ice nicely.

Tie Humor to Your Message

Make sure your joke reinforces your point. If you’re offering a solution, a quip about solving problems might just fit right in.

Example:

“Your inbox is probably as jam-packed as mine, so I’ll keep this brief — promise!”

Avoid Overly Complicated or Risky Humor

Stay clear of touchy topics or anything that might offend. Avoid sarcasm, cultural jokes, and those old, overdone clichés.

Use Humor to Show Personality

Cold emails can be dry as a desert wasteland. A bit of personality makes things more inviting. Humor lets you show some confidence and gain trust.

Best Practices Summary

• Test your jokes on friends (or willing coworkers).
• Keep things brief, light, and context-appropriate.
• Match the humor with the prospect’s personality type.
• Skip slang and lingo that could baffle them.
• Maintain an underlined tone of professionalism beneath the humor.

Tips for Keeping Humor Professional in Cold Emails

Don’t let humor overshadow your main act — professionalism. Here’s how to nail the balance:

1. Focus on Relatability, Not Edginess

Zero in on common workplace quirks, like juggling a mountain of emails or battling everyone’s busy schedules. Keep it lighthearted and relate to their experience.

2. Use Humor as a Hook, Not the Entire Message

Keep your core message — the real reason you’re reaching out — clear and straightforward. Use humor as the opener or closer, not the star of the show.

3. Pair Humor With Clear Calls to Action

Your humor shouldn’t dilute what you want the recipient to do next. After your playful comment, state your call to action loud and clear.

Example:

“Got a few minutes for a chat? Promise I’ll keep the bad jokes at bay — just click here to set it up.”

4. Avoid Forced Humor

If cracking jokes doesn’t feel like your thing, go with something genuine and straightforward. Forced humor just reads awkwardly.

5. Proofread for Tone

Sometimes, those minor wording tweaks shift your email from clever to cringe territory real fast. Read it out loud to catch what might be off, or have someone else give it a once-over.

Examples of Successful Cold Email Follow-Ups with Humor

Seeing is believing, right? Check out these snippets of emails that used humor smartly and professionally:

Example 1: The Friendly Reminder

Subject: The “Last Email” That Isn’t

Hey [Name],

Promise this isn’t one of those “last emails” — although it might become a trilogy if I don’t hear from you 🙂

Just wanted to check back and see if you had a chance to review my note on [solution/offering]. Pretty sure it’d be a good fit for [their business need].

Ready for a quick chat? If not, I’ll zip it and stop cluttering your inbox.

Cheers,
Jay

Why it works: A little humor about repetitive follow-ups keeps it light. The call to action is clear, but not pushy.

Example 2: The Busy Inbox Humor

Subject: Inbox overload? Me too.

Hi [Name],

Bet your inbox is racing like a coffee shop on a Monday morning. Just sliding this note back up top in case it got lost in the shuffle.

Want to show you how we can help tackle [key pain point]. Let me know if you’re up for a short 10-minute chat.

Thanks for your time!
Jay

Why it works: The nod to common experiences adds relatability without sidestepping professionalism.

Example 3: The Self-Deprecating Close

Subject: Still no reply – should I stop?

Hey [Name],

Starting to think my emails aren’t the laughs I imagine. But before I give up on comedy, here’s one last go.

If [solution/product] seems like something you’re interested in, let’s connect. If not, no worries — consider the inbox cleared of my nonsense.

Have a fantastic day!
Jay

Why it works: A little self-deprecation softens the persistent follow-up and respects your prospect’s time.

Conclusion

Cold email follow-ups are crucial to forming relationships and getting responses. Adding humor can make them more engaging and memorable, but carry it with care to avoid sounding cringe or unprofessional. Stay genuine, keep it light, and align your humor with your audience’s vibe. Humor should add to your message, not overshadow it. Pair jokes with clear calls to action and always preview the tone before hitting send.

Having absorbed these email strategies, you’re more than set to boost your cold email game. That tiny, well-timed joke might just be what gets you from unread to conversation. Ready to step up your cold email outreach? Get drafting, throw in a dash of humor, and watch your engagement climb.

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Jay Solanki, with over a decade spent enabling B2B sales, has poured his insights into helping founders and sales leaders refine their outreach strategies. Jay’s advice has guided countless SDRs in fostering authentic relationships and boosting reply rates.

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