3 min read

Email FAIL — 11 tips to improve your emails

You suck at email. All of you. If you talked to people the way you emailed them, you would be pepper sprayed. The good news is: I’m here to help.
Email FAIL — 11 tips to improve your emails
Photo by Brett Jordan / Unsplash

You suck at email.  All of you.

If you talked to people the way you emailed them, you would be pepper sprayed.  A mental patient would look at you warily, thinking, “At least I don’t talk like that guy.”  Honestly, do you ever re-read what you wrote before hitting ‘Send’?  Or do you just write stream-of-consciousness like a damn lunatic?

As much as I’d like to blame you, I can’t.  Email is a skill you develop (no one is really taught how to get good at it), and the only way to get better is to cold email a lot of people.

The good news is: I’m here to help.  Here are some suggestions you can use so you won’t sound like a moron when emailing someone you’ve never met for the first time:

  1. Keep it short and sweet. A lot of people are busy, and they will scan your email.  Strangers don’t need to hear your life story, so don’t give it to them right away (after a few positive exchanges, you’re welcome to delve deeper into your history).
  2. Be interesting. Have something cool to share with them, or even help them out in some way (it could be as simple as a suggestion for their website).  They want to know why you’re emailing them, and why they should care.  If you have nothing interesting to say, you will not be memorable.
  3. Reference their work. This is hugely important, and is an extension of the previous tip.  You want to be interesting?  Tell the person how their work has affected you — be excruciatingly specific.  They’ll love it because it’s genuinely flattering, which leads to…
  4. Give GENUINE praise. If your compliment is insincere or half-hearted, the reader will see through it.  You have to take into account that you’re emailing a complete stranger, and they have their guard up.  Reel them in not by being a brown-noser, but by being someone who has an honest appreciation for their work.
  5. Get to the point. If you have a question, get to it within 3-5 sentences.  And be sure to use a question mark (more important than you’d think).  A good rule of thumb is to picture yourself running into this person on the street, then reciting the email to them.  Are you talking way too much?  The answer is probably yes.  Tighten things up a bit.
  6. Have a point to begin with. Why are you emailing this person in the first place?  Is it just to make friends?  That’s retarded and ironically anti-social.  You need to have a specific question/proposal/comment.  Don’t email them until you know what that is.
  7. Read out loud before hitting ‘Send.’ Typos and grammatical errors make you look lazy and/or stupid.  Avoid this by running through the email a few times.  Whenever I write an email to someone busy who I’ve never met, I re-read it around five times before I hit ‘Send.’  This OCD-like behavior has saved me more than once.
  8. Avoid sarcasm and ambiguous humor. A lot of people think they can make a joke or be sarcastic in their first email to a stranger, but they can’t.  First of all, you’re not as funny as you think.  Second, it’s impossible to tell if you’re joking.  You can’t tell how someone intended a sentence to be delivered in an email, so the reader will assume you’re being serious.  Don’t make jokes until you’ve actually talked to the person.
  9. Acronyms are for little girls. I’m absolutely floored when grown men use “LOL.”  You can only use acronyms if you are trying to be sarcastic (see previous tip).
  10. Diffuse loaded sentences. I used to be wildly opposed to using smiley faces and exclamation points, but they’re actually very useful when emailing strangers.  If you place a smiley face after a potentially loaded sentence, you will come across as friendly and not creepy.  It’s an easy way to do damage control.  But DO NOT use multiple exclamation points, winky faces or any other weird emoticons (again, this behavior is reserved for little girls).  Every time I see the tongue-sticking-out face, I want to put my fist through the monitor.  And now, for the most important rule…
  11. NO SPAM. If you are promoting any product of yours on the very first email exchange you have with a total stranger, you are a worthless human being with no regard for other people.  Consider the fact that there’s an actual person on the other end of that email, and they aren’t going to whore themselves out so easily.


I cast these stones because I too have committed these sins.  It’s taken me hundreds of individual emails to total strangers before I finally realized the error of my ways.  I pass my wisdom onto you.  Enjoy, LOL!!!!  :-P

Any additional tips?  Leave them in the comments.

[Note: Take this post with a grain of salt, knowing that I genuinely enjoy receiving emails from strangers (even when they are poorly written).  Also, this post was not instigated by any recent emails I’ve received.  I’ve been wanting to write about this for a long time.]