Defeat “Boring Email Syndrome” By Using Humour

Let’s face it: your emails are boring.


If you’re following up as much as you should be, it’s unavoidable. You email the same people again and again. You run out of new and interesting things to say. Sometimes, you sound like a broken record.

Fortunately, there’s a weapon you can use to defeat “Boring Email Syndrome”: humor.

I recently attended a fantastic workshop hosted by Rachman Blake, the genius behind the FunnyBizz Conference. Rachman is all about using humor to win business, and he shared some great ideas that you can use in your everyday follow-up emails.

(And no, you don’t have to be a comedian to pull it off. Anyone can make their follow-up funnier.)

Let’s start with your subject line. It’s the very first thing someone sees when they get your email, and it can be the difference between your email being opened or ignored. Think of your subject line as the ultimate ice-breaker, a tool to make the recipient feel comfortable talking with you.

When Rachman invited presenters to speak at the FunnyBizz conference, he knew he had to grab their attention first. In one email, he used “you’re a badass” as his subject line. It was a little bit funny, a little bit flattering, and the word “badass” was pulled from the presenter’s recent blog post. This subject line put him in exactly the right mood to accept Rachman’s invite.

Next, keep the humor going in the body of your email. Don’t fall back on the same old email copy again and again. After all, how many times can you say “Hey, just following up” or “Let me know if you want to talk more about this”? Try something new.

Look for the humor in the situation, and you’ll find a wealth of different things to say. Imagine you’re talking to someone face-to-face. How would you get them to crack a smile?

If you’ve met before, reference a shared experience or conversation from the last time you met up.

If you’ve never met, do a little Internet research about the person until you find something you can comment about.

For example, let’s say your potential client has a blog about their mountain climbing adventures. Why not ask them to get back to you when they’re finally off the mountain…or ask what the weather is like up there. Not only does it show you’ve done your research, it will make them stop and take notice.

Let’s say you’re sending a cold email to a potential customer. Their Facebook profile picture features a cat. Go ahead and send them a cat photo in your email. Like this!


Or tell them you have a strict “No Dogs” policy. Or simply say that their Facebook profile picture is purr-fect. Whatever you say, make sure it’s in line with your own personality. However you draw a personal connection, you’ll stand out from the crowd.

When you’re finished writing the body of the email, think about your sign-off. Rachman is the king of signing off with a photo, whether it’s bunnies high-fiving or a picture of himself wearing a sombrero. See if there’s a little something extra you can add to the end of your email to make it worth reading all the way to the bottom.

Disclaimer time!

Humor is great in small doses, but don’t overdo it. You need to strike the right balance between professional and funny if you want it to work.

The ultimate goal isn’t just to make someone laugh, it’s to seal the deal. If you’re subtly entertaining and take pride in sending awesome emails, you’ll seal more deals. If you’re beating people over the head with attention-grabbing antics, they won’t take you seriously. So tread lightly.

New clients or cold emails are particularly tricky. If you don’t know someone that well, you don’t know what they’ll find funny. You don’t want to offend or confuse them, so I suggest starting small. Include a universally funny image or a quick one-liner in your first email, and leave it at that. If they respond to it, you know you’re going in the right direction. If they’re put off by it, pull back.

Fortunately, you’ll find that most people are dying for something entertaining in their inbox. Aren’t you? Aren’t we all? Email is so tedious, more like a chore than anything else. When you follow up with something fun, they’ll be thrilled.

Plus, you’ll find that you get more interesting, engaging replies when you’re giving people something cool to react to. Increase the quality of your emails, and you’ll get better quality in return.

When you take the time to craft follow-up emails that are creative, witty, or downright hilarious, you’ll see results. You’ll get more replies. You’ll get faster replies. You’ll get better replies. You’ll build stronger connections. And people will honestly enjoy hearing from you.

No more boring emails! Take a chance on something fun.


Published by

Matt McCormick

Matt is the host of "7 Minute Sales" - a podcast from the perspective of a developer-founder who is learning to sell and market more effectively. Follow my journey and lessons learned at Matt is also the founder of - A Better Follow Up System for Gmail.