Humor in Sales Emails

Email is the immortal grandfather of communication who refuses to retire. Despite the market being flooded with instant messaging apps, the respect an email commands hasn’t waned one bit. By extension, emails are considered serious, important, and not fun. They aren’t a source of entertainment, unless it’s a newsletter. Now, that’s a subtle plug.

So, where does humor fit into an email? Can Grandpa still be funny without provoking sighs and cringes?

Before we get into it, here’s a quick summary of the glib side and the flip side of infusing humor into emails.

Quip Pro Con


  • There are lots of references available online to find inspiration. Find what you like, and add a personal touch.
  • There’s no need to rehearse or improvise, because this is not an audio/visual medium. Edit ad nauseam.
  • The possibility of getting feedback from peers before sending the email is a real advantage. Create a support group and rely on them whenever in doubt.
  • Low-to-no fear of rejection – remember, this isn’t a live medium. You’re not being put on the spot, because it’s not a call or a meeting.


  • Depending on the reader’s mood, your tone can be misconstrued. Everyone has a “reading voice” inside their head that takes over whenever words appear in front of them. It takes experience and patience to craft a message with little to no margin for misinterpretation. Remember, Misinterpretation is Humor’s evil twin.
  • Lack of personality, voice, face, or tone attached to the content is a real consequence of the con above. Your email should still engage the prospect, which means you can’t sound like a textbook.
  • The low possibility of immediate feedback is an unfortunate reality. Until your receiver actually responds to your email, you will never know if you were successful in getting a reaction.

The Anatomy of an Email

There are 5 parts to every email. Everyone knows three of them – the subject, the body, and the sign-off. The two parts that are always taken for granted are the sender (you), and the receiver (them).

The responsibility of making an email memorable falls solely on the sender. So, when it comes to adding humor to your email, instead of worrying about the subject line, the body, or the sign-off, focus on the receiver first.

The Sender-Receiver Paradox

Start with finding quick answers to the top 3 W questions – What, When, and Why?

  • What is the prospect’s pain point?
  • When will they receive your email?
  • Why should they choose you?

While this is research every salesperson does, you can choose one of the questions to leverage your humor. That question will help you empathize with your prospect, and relate to them. Humor works best when paired with reliability.

The Rule of 3: The Subject, The Body, and The Sign-off

It’s a tough choice. But, you must decide which of the three parts of the email will contain humor. It might seem natural to put a twist on the subject, the body, and the sign-off as an insurance policy – if the subject and/or body copy isn’t funny, you could always win them back with the sign-off.

You shouldn’t lose focus on what the email is supposed to convey. You’re not writing a satire piece, where you can use humor limitlessly. Trying too hard and too often within the same conversation will make you look unsure and under-confident.

While applying humor in sales emails, it would serve you well to choose one area and hone your skill over time.

Subject Line

The subject line is a good place to start. Brevity is key, and being able to create a hook in 10 words or less is a good target to start with. Avoid question tags, “guess what?”, and “did you know” prefixes. These sound like second-hand advertisement copy and do not motivate the receiver to open the email. Instead, your email will directly greet the spam folder. And, that’s an awkward blind date nobody should endure. If all else fails, think of the most important part of your offering, and lead with it. Even if it’s not funny, it will serve as context and make your prospect take notice. Where humor fails, honesty saves face.


Context: You’re selling soap made from 100% natural ingredients.

Route 1: Humor

Subject Line: Here’s one soap you definitely don’t want to drop!

Route 2: Leveraging the most important part of what you’re offering

Enjoy 100% natural showers! And, we’re not talking about rain.


As a reward for opening your email, it’s wise to cut to the chase here. You have a 5-second window before the shot clock buzzes on your prospect’s attention span.

  • Open with a quick line. You can choose to start with a witty introduction, or begin with the pain point and add a humorous twist.
  • Addressing the obvious is the quickest way to humor, because it’s counter-intuitive to call attention to something uncomfortable. Eg: “Yes, this is the fourth email I’m sending you. And, there’s a lot more where this came from. But, we can save your inbox some space by starting a conversation.”
  • Using images and videos to personalize isn’t just a great way to engage your prospect. It can also serve as an opportunity to infuse humor.


The sign-off is often ignored as a device, because most of us don’t expect the receiver to read the entire email. But, it’s important to consider the sign-off as a quick going-away present. If you can sneak a reward in the sign-off, it will serve as a humorous takeaway, and help you cement an impression. The next time your email lands in their inbox, the curiosity of “what’s it going to be this time?” will replace the need for a hooky subject line.

One of the simplest hacks is to reimagine your job title. Come up with a funny abbreviation for SDR or BDR. If you have a nickname at work, slip that into the sign-off.

Example: John AKA J-Dawg.

Up Next

In the next edition, we’ll focus on Humor in Sales Calls. This will not include voice exercises.

<insert personalized sign-off here>

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