How To Get Your Cold Emails Read Without Getting Shamed

In 1995, email was a novelty. Whenever I got an e-mail it was a big deal. Whenever anyone I was reaching out to got an email, it was a big deal.

It was cool it.

It was new.

60% of the time it worked every time.

Way back when, and certainly prior to then, if you wanted to connect with someone in business, you picked up the phone and called them directly. In many cases they had gatekeepers or secretaries or admin assistants that would screen your calls so you couldn’t get through to them. It was a pain in the heinie (did he just say heinie in a business blog post?).

Email, however was a way into the fortress that very few people were using – especially as a cold pitching technique.

Yo, Back in the Day

Back in the day, I could email 100 companies directly, gathering emails from actual web pages that listed titles and contact information. I’d get 10 responses, or even 20 sometimes, from people that were open to my pitch and ready to purchase my services (copywriting).

That all went away very quickly because people started getting inundated with emails. Then came spam filters and the Gmail spam button. Remember SpamAssassin and Razor?

Aside: Please don’t go nuts about sales spam here. I’m talking about targeting business people that depend on vendors and solutions to help them do a better job. This isn’t about Nairobi financial scheme emails. Think about it. You’re not going to increase sales if you don’t try to get new people (who you have a reasonable suspicion can benefit from your product/solution/service) to listen to your cold pitch. Put in other terms: You’ll never get a date if you don’t approach girls you don’t know.

The evolution of social media allowed us to target specific types of people (even by their job title and company) and customize pitches. But the digital inbox gatekeepers got better and better, reducing the chances that we’d get through.

Poorly written emails or boring emails were the casualties.

How to Get Noticed Without Getting Shamed?

Ok, so how do you deal with this inbox craziness? First you need to find email addresses that are actually reachable. How to do this is another blog post. Let’s say, however, you have a mechanism for finding people’s email addresses. I don’t need to tell you that targeting is key. Find the right companies for your goals, the right titles of people, and the right people.

Once you have the right email addresses, you have an opportunity to pitch and make an impression.

You must break through the inbox noise and capture people’s attention much in the same way advertisers capture the attention of TV viewers that have no interest in seeing their ads (great model, huh?). Seriously though, we’ve all been conditioned by ads to buy things like beer, insurance and Sham-WOW.

“This Is Professional Show Business”

One way to learn this skill is to pay attention to comedians. (In any given year, 53 to 81% of the super bowl ads are humorous).

The key is to study mechanisms that work. I like to revisit old goofballs like Steve Martin and his “reversals” on songs like “Grandmother’s Song.”

“Be courteous, kind and forgiving. . .”

“Be obsequious, purple and clairvoyant.”

“Be gentle and peaceful each day, and have a good thing to say. ..”

“Be pompous, obese and eat cactus..”

“Be dull and boring and omnipresent..”

“Criticize things you don’t know about. Be oblong and have your knees removed.”

“Put a live chicken in your underwear. Go into a closet and suck eggs.”


I could go on.

The point is – you can DO THIS in your emails. Of course, you can’t be as off-the-wall as Martin, but you can try to get close. It has to fit your personality. But you can be funny. You’re allowed to, just like you are at trade shows and in the office. Being in an inbox doesn’t mean you have to act like you’re wearing a three-piece suit!

So, you need a hook. A way to capture attention. Be careful, though. Humor can easily cross into shock, disgust, potty talk, and other socially unacceptable blunders. Interestingly, the same kinds of trouble humor gets you into . . humor can get you out of.

Humor can cover over shock, disgust and many other things by being itself. Humor is the babysitter that lets you get away with murder while the parents are gone. You can cover your tracks and be excused for all kinds of things. Humor lets you say and do stuff that’s not otherwise socially accepted – everything from the innocuous and subtle to the politically poisonous and downright horrific.

But for Business Communications?

Subtlety is best for communications with business people that you’ve never met. Here’s one of my openers from a cold email: “Your name came up when I ran a Salesforce script against a LinkedIn Sales Navigator search. . . then filtered by most captivating head shot.”

Here’s how I dissect it in terms of audience and approach: 1) The targets for this email are marketing directors and the like who know all about Salesforce and LinkedIn Navigator. 2) They’re also usually technology companies. 3) The gag is a vanity hook, but the fear that drives it is this notion that we’re all trackable and traceable. Everyone’s discoverable and “data mineable.” And, that’s a little unsettling. The vanity provides a little humorous relief.

The following is a little chart I crafted to show you the difference between formal stodginess and humorous accessibility: