4 Ways to Completely Transform a Boring Email

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Aja Frost
Aja Frost




You’re probably not the only salesperson in your industry contacting your prospect -- and you’re definitely not the only salesperson contacting them in general.

Unsurprisingly, it'll be tough to get a response if your emails sound just like the other ones your prospect is getting.

But with a little creativity, you can win their attention and motivate them to respond. Read on to discover how to write a sales email that stands out.

1) Insert a GIF

A funny or relatable GIF won’t just make the prospect smile -- it’ll also make your email one of the most memorable they’ve received all day (or even week).

Take this sample breakup email:


Hi Luke,

It’s been a couple months since we last talked, and usually that means one of two things:

1) You’re all set with file storage, and I shouldn’t bother you.

2) You’re still interested, but you haven’t had the chance to get back to me yet.

If I don’t hear back from you, I’ll assume it’s time to say goodbye.





GIFs also remind your prospects there’s a real person on the other side of the email.

However, use them with caution. You'll seem out of touch with industry norms if you send a dancing cat GIF to a prospect in a conservative industry. Better safe than sorry: If you’ve got a hunch a GIF will fall flat, look for a different way to make your message stand out.

2) Add a Personalized Postscript

Writing a personalized “P.S.” is a great way to surprise and engage your recipient, especially if the main body is all business.

Here are a couple ideas for your postscript:

  1. Pay them a (genuine) compliment
  2. Wish them luck on an upcoming event
  3. Allude to a hobby or interest you both share

Check out this sample email to see the technique in action:


Hi Jane,

Congratulations on the Candle acquisition. Helping your employees adjust is probably a huge focus for you right now -- you might’ve come across this stat before, but 30% of M&As fail within three years because of cultural changes.

I’ve helped several SaaS companies handle their acquisitions without any road-bumps. Would you be interested in scheduling a quick call to learn some strategies your HR team could implement?

Have a fantastic Thursday,


P.S. Saw on LinkedIn that you’re speaking on a Women in Tech panel tonight. I’m a member of the Boston chapter! Hope the talk goes well.


3) Add Some Humor

Humor can help build rapport, put your prospect at ease, and make your email feel less “salesy.”

But before you start cracking jokes, use social media to gauge the prospect’s personality. Are her posts pretty light-hearted, or are they strictly professional? What type of content does she interact with? You can usually get a good sense of how open to humor someone will be.

Plus, going through her social profiles helps you find things to riff on. Maybe you see the prospect retweeted something about Doctor Who, so you crack a joke about Doctor Who in your email. Or you notice she self-describes as a cupcake addict, so you bring up your own baked goods addiction. Even small touches like these have a big impact.

4) Reference an Uncommon Commonality

When establishing common ground with your prospect, don’t be afraid to get a little creative.

“Similarities matter most when they’re rare,” explains Adam Grant, a New York Times bestselling author and professor at the Wharton School of the University of Pennsylvania. “We bond when we share uncommon commonalities, which allow us to feel that we fit in and stand out at the same time.”

Grant describes the time he emailed Tony Hsieh, the CEO of Zappos.

“My first instinct was to mention that we attended the same college,” he says. “But after realizing that thousands of people share that connection with him, I ended up writing that I first learned about him when my college roommate followed in his footsteps to run the Quincy Grille.”

With that in mind, take a look at three possible rapport-building lines:

Good: “I also went to school in California.”

Better: “I’m also a huge Ultimate Frisbee fan.”

Best: “I’m also a major frozen custard fan. I’ve been known to eat it every day -- even in the dead of winter.”

When it comes to email, cutting through the noise feels harder every day. Use these four strategies to make your messages feel fresh and different.

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