The Beautiful Art of Sending a Well-Crafted Email — When so Many Others Are Sending Trash

This is how to write a knockout email that gets a response.

Tim Denning
Jun 17 · 7 min read
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Writing an email that gets someone’s attention and achieves your goal is not easy. We all have email on our phone or computer, yet many of us treat email with a form of domestic violence. We take something that is beautiful and spit all over it with our poor choice of words and selfish sentences.

I love writing emails. The look of that beautiful blank email with its empty subject line and loads of empty white space makes me all warm and fuzzy inside.

Why? Because I’ve used email to contact some of the hardest to reach people.

Email created the opportunity I was given to be a blogger; email got me the career I have; email got me a romantic partner; email changed my life and it can change yours too once you know how to use it.

Here’s how to send a well-crafted email:

Think about the other person

O-M-G! This is the most important step that everyone misses: it’s not about you. The subtle art of writing an email that is worthy of the worlds greatest art prize is to think about the other person first.

How might that person you’re writing to be feeling?
What is important to them?
What is their ‘why’ that drives everything they do? (Hint: Google It)

There is nothing worse than being spat on with an email that has nothing to do with you and is all about someone else’s goals or desires. When we open an email, we are secretly saying to ourselves, “What has this got to do with me?”

Sit in the office chair of the person you are writing to and spend a day in their life. Think about their circumstances. Do this for an entire day and then come home and write your email.

Now you’ll be full of empathy and compassion which is the single most important ingredient for a knockout email that gets the same applause the winner of Best Actor gets at the Oscars.

Write an email worthy of a standing ovation.

Don’t be wanky

Ask yourself, “Are you kissing too much ass in your email?”

Wanky emails that are full of sucky one-liners, do not work. It’s okay to compliment someone’s work but don’t go overboard. Your intended audience knows when you are full of shit and kissing ass, so don’t give them an easy reason to delete your email and never open it.

A way I’ve found not to be wanky is to pretend I’m writing the email to my boss or best friend. Thinking about one of these two people stops me becoming a total suck and ruining my chances of ever getting a reply.

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Making them laugh is like smiling in real life

This tip is one I came up with in the shower this morning while thinking about emails. When you write an email, if you can make someone laugh, it’s the equivalent of talking to someone in-person and smiling at them.

If you ever do public speaking, at some point, people will tell you to smile more. Smiling makes us feel good and it builds rapport. The problem is that in an email, the other person can’t see you unless you attach a photo which I don’t recommend you do.

The way you make someone smile in an email is to use a little bit of humor. Notice I said, “A little bit?” Don’t overdo it. The best emails encompass many of these tips but in a subtle way — that’s what makes for a beautiful email.

In one example, I sent an email to a fella named Justin Dry. Having done my research and read many of his articles, I knew that he liked a bit of humor. So, when I dropped him a note, I added some humor around why I wasn’t trying to pitch him or suck up his ass. Guess what? He appreciated it and showed it by replying. That’s the power of humor in an email when used in small doses.

Succinct and simple (no acronyms)

What does succinctly mean? Make it nine sentences, split into three lines per paragraph. From years of A/B testing, any more than nine sentences, and the goldfish attention span we have in 2019 kicks in and tells us to move on.

Also, write using simple words. The best messages are simple. If English is not the first language of the person you are writing to, it’s even more important. One other tip is to remove acronyms or industry talk.

Using either is like walking up to a Japanese man talking on the phone in his native tongue and speaking Swedish to him. He has no fucking idea what you are talking about.

‘Simple’ wins every time when it comes to deliciously written emails that make strangers go “Wow man, that person knows how to write. Hell Yes!”

Make us say Hell yes! (Sorry Derek Sivers, I couldn’t help myself my New Zealand Amigo.)

Killer subject line

If your subject line is not well-thought out, no one will reply. When you think about writing a killer subject line, ask yourself two questions:

  1. “How do I make my email not look like spam?”

2. “How do I ensure there’s no ask attached in the subject line?”

These two steps typically help with having a subject line that will lead to your email being at least opened rather than farted out the backend of cyberspace and ending up in a sewerage bunker of an asteroid that is still yet to be discovered by scientists.

One other quick tip: put your name in the subject line. Real people have names and your goal is to come across as a human rather than some fake-ass brand, influencer, or legal entity known as a company — we open emails from humans, most of the time.

They may not read their own emails

This is one that is lost on so many people. With the power of virtual assistants that cost less than a meat pie, many people have opted out of opening their own emails because of the common disease of badly written emails.

So, when you are writing your email, remember someone else could be opening it so address that in your email. If your email is rubbish, the virtual assistant will not pass it on the correct recipient.

Get out clause

If you followed step one, then you will have realized a few life truths:

  • People are freaking busy
  • You may be pitching something irrelevant to the person
  • They could be taking a holiday from emails
  • You may have the wrong email address
  • They might be tied up with a huge project that gives them a sense of fulfillment and helps them create a legacy far bigger than any email proposal or ‘ask’ that you may put in an email

Read the last point again. Many people are off in the fantasy land of a huge goal and if they are good at making progress, then they probably have an unwavering sense of focus that simultaneously means they will not check emails — which are for many, a full-time job just to keep up to date with.

Coincidentally, many of my own emails go unread. Not sorry.

So, back to the point, you need a high-quality get out clause. Saying something like “Thanks for reading and if what I’m saying is not interesting, feel free to reply with a two-word reply such as no thanks.”

Sign off with your contact details

This does not mean sign off with a “follow me on every single social media platform known to humankind.”

No one wants to follow you from an email.

Sign off your email with your full name (so people can Google your name), phone number, and website address. This tells the reader you are a real human being. The reason you want to add a few different ways to contact you is that not everyone works well on email.

For example, someone like me hates going back and forth on email and would rather pick up the phone and talk to someone instead of sending 64 emails back and forth that still doesn’t answer a question such as “What do you need help with?”

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Do not tell your life story

No one, these days, reading email has time to hear your life story.

Save your storytelling for when or if you get a reply that allows you to have a further conversation.

Follow up

This tip might seem like it doesn’t fit but stay with me. The art of sending a well-crafted email is knowing that sometimes you have to follow up politely. The first message doesn’t always get the reaction.

Crazy people like me sit at home reading our emails and then wait for the second or third message before we respond.

You know why? We’re seeing if your email is just a brain fart or something real.

Subtle follow up is required if you ever want to get a response — typically after about one week is a good idea. The follow up should take into account the other person’s circumstances and also feature another get out clause.

Check your junk email

This has happened to me many times. My email client has put an important email in the junk email which I never check. Check it in case your reply is sitting there with a delightfully, addictive, bold subject line and a reply from that person you’ve been trying to reach and thought would never respond.


Emails can be fun when you put some thought into them. Don’t send lots of emails; send a select few that are well-crafted instead.

Go out into the world and make good email art.

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Tim Denning

Written by

Viral Blogger - Inspiring the world through Personal Development and Entrepreneurship.

The Startup

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