Cold Email Introduction

A cold email introduction is one of the first pieces of text your prospect will see. As a result, a high-quality cold email introduction is critical to getting replies as it creates a white-hot first impression.

To improve your cold email introduction use:

  1. Humor
  2. Stand-Out Content
  3. Personalization

Once you’ve covered this section, head over to our guide on how to write a cold email.

Cold Email Humor

Dry, efficient cold emails are everywhere. Just google “best cold email templates”. These are the ones most sales reps are using. The formulas are easy for salespeople to copy and just as easy for prospects to ignore.

Not impressive.

Humor is a fun, positive way to grab your prospect’s attention. Most sales reps aren’t up to this challenge so an email with a touch of humor has a white-hot chance of standing out from the crowd and keeping your reader actively engaged. As a result, it makes for a great cold email introduction.


A simile describes something by comparing it to another thing, using like or as. It is the simplest and fastest way to inject humor into your cold email introduction.

Simile examples:

“That’s as useful as rearranging deck chairs on the Titanic.” 

Rearranging the deck chairs might look useful but ultimately it makes no real difference to the outcome. The Titanic will sink no matter what position the deck chairs are in.

How To Use Similes In Your Cold Email Introduction?

Find a snippet of information about your prospect. This can be personal or work-related information. Then think of how it is similar or dissimilar to the solution you are selling. Connect the information about your prospect to your solution.

Simile examples for cold email introductions:

Jessica is doing a wine tasting course.

“Hey Jessica, unlike the fiery tannins from a tart Barbera, it can be difficult for smaller companies to stand out in the job market. Similar Company is using ACME’s interactive job postings to attract 77% more candidates. Open to learning more?”

Julius works for a company that manufactures televisions.

“Hi Julius, like a crisp 4K OLED TV, our CRM helps you see the bigger picture. Since Similar Company started using ACME’s CRM their sales team has closed 23% more deals. Open to learning more?”

It can help to look up idioms (like see the bigger picture) relevant to your solution or the information you are using about your prospect.

The Rule Of Three

The rule of three (also known as the “triple” or “triad”) is a cornerstone of wickedly effective copywriting. Why? A group of three is punchier, more memorable, and more enticing. This technique is used in stand-up comedy, films, advertising, and many other storytelling mediums.

Comedians use the rule of three to establish a pattern with the first two items before introducing an unexpected third item that subverts the audience’s expectations. The final item becomes the punch line.

I got my first bikini. It’s a three piece: It’s a top, a bottom, and a blindfold for you.

Wendy Liebman

The rule of three in comedy relies on building tension to a comedic release. Tension is built with the first two items in the pattern and then released with the final item, which should be the funniest of the three. When using the rule of three in your cold email introduction, keep it short and punchy for best results.

Why Does The Rule Of Three Have Such Power?

  1. Audiences expect to receive a beginning, middle, and end
  2. Three is the minimum number required to create a pattern
  3. Three offers a clear “middle” choice
  4. Three has a naturally satisfying cadence

How To Use The Rule Of Three In Your Cold Email Introduction

The List

Formula: Item 1, item 2, unexpected/absurd item 3

Example: Developing software is like running a marathon, cycling up the Alps, or juggling chainsaws while dodging bullets.

Example: To get the most out of your sales team you need excellent leadership, high-quality software, and a bottomless coffee machine.


Formula: X is like Y, only I’m both the expected element and the unexpected element.

Example: Keeping out hackers is like having your teeth pulled, only you’re the dentist and the patient.

For comparisons, think of two elements that go together such as a doctor + patient or bartender + patron,


Formula:Formula: Item 1, item 2, item 3, a twist on item three that reveals further information

Example: Writing cold emails is like digging ditches, mining coal, or chopping firewood with a pair of scissors.

Example: Improving your ad setup is like unblocking a sink, shoveling snow, or raking leaves with a kitchen fork.

Humor You Should NOT Use In Your Cold Email Introduction:

  • Anyhing to do with politics, war, religion, sex, race, political correctness, or other controversial topics
  • Long form jokes – keep it short and simple, ideally one line
  • Humor that relies on jargon or inside knowlege – unless you are ansolutely sure your prospect will understand
  • Jokes that are creepy of too personal – you don’t want to seem like a stalker

Cold Email Empathy

Empathy is the shortcut to opening your prospect’s mind and getting them to actively engage with your pitch. FBI negotiator Chris Voss explains when you use empathy correctly you trigger a rush of endorphins. This makes your counterpart feel good. When people feel good they are more open to suggestions and persuasion. We all know that feeling. It’s the one you get when someone thanks you for your hard work. It’s the one you get when your friend really understands the problem you’re dealing with.

Empathy is a way to create a disarming first impression that sticks with your prospect.

Cold Email Empathy Research

The first step is to research your prospect. Social media and a Google search are two good places to start. Look for their passions and interests. These can be personal or professional. For example:

  • Leadership styles
  • Sales strategies
  • Kayaking
  • Scuba diving
  • Learning Spannish
  • Improv classes

Thereafter, use this information to show your prospect that you understand their challenges, interests, and situation.

Here’s how I got a reply yesterday:

“Hi Trevor,

The diagnostic section on your website is super detailed and useful. It looks like you’ve put a lot of time into developing useful tools for motorcyclists. As a developer, father, and dog owner, no doubt your time is a scarce resource!

It seems you’re using Competitor for hosting. Sites like Similar Company have switched to us because we deliver faster response times, less downtime, and we’re 17% cheaper. Open to learning more?”

Here are some key formulas you can use to acknowledge your prospect’s situation:

  • It looks like…
  • It sems like…
  • It sounds like…

For the knockout punch, establish similarities between you and your prospect based on your research. This is where Cialdini’s liking principal comes in.

Cialdini’s Liking Principal

According to Cialdini’s research, people are more likely to say yes when there is an exchange of personal information with the aim of establishing how similar both parties are. People naturally like others who are similar to them. It’s a tribal reflex that is hard to ignore. Similar things are easy to understand, safe, good.

Cialdini’s liking principle is most effective when you can use genuine similar interests or compliments. Don’t get caught saying you love the NFL, then get on a call with your prospect and find yourself unable to name the starting QB for the LA Rams.

Similar to the empathy approach, you need to research your prospect to figure out where you are similar.

Here’s how I got a reply from a prospect who’d just done an interview on the benefits of remote working. She loves remote working and believes that forward-thinking companies should embrace the movement.

“Hi Taylor, great interview with I’ve also been remote (based outside of Austin) for the last 4 years now and loving it. It’s allowed me to find a better work-life balance and spend more time with our son (now 6 months). It sounds like COMPANY is doing a big overhaul. As part of that, are you looking at a new hosting provider?”

Here’s how I got a reply from the CEO of one of the world’s largest websites:

“Hi Chris, caught your podcast interview on Podcast Name. It sounds like your approach to has been to build useful tools and let the growth follow. Like, our company has not had to take outside investment. This has enabled us to focus on building useful solutions and create a good (100% remote) company culture.”

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