The Updated Guide to Writing Unforgettable and Unignorable Emails
“Invented” in 1971, then wide spread by 1993, email is still the primary way to communicate in 2021.
When I’m in Washington DC, I always like to visit the bar, Off the Record, known as the, “place to be seen and not heard.” The bar has a reputation for getting visits from political powerhouses and celebrities. Who knows who you’ll run into!
Although the thought of happenstance sitting next to a power broker that then opens up magical doors sounds enticing, it doesn’t happen anymore. Instead, opportunities are now borne out of virtual interactions. Emails to people we’ve never met. Likes and comments on profiles of people we’ll never meet.
In this new world, our success depends on great digital communication.
And since email is king, let’s make our emails unforgettable and unignorable.
Email is still king.
Below, I cover what I call the “New Basics” of email etiquette. If you’re not doing them, you better have a great reason why.
Put you “ask” or “action” in the first sentence of your email. Think of it like a Call-To-Action (CTA). Everybody is busy, so state your bottom line point immediately. Hook them, and then they’ll read on if they need to.
Rethink FYI emails. Most likely we forward emails as FYI because the information is beneficial to the recipient. You’re being inclusive, which should be applauded. Good intention, but total misfire. What you’re actually doing is giving someone else work, that may or may not be useful. Congrats, you’re now a prick. I advise, go further — do the work and break down exactly what their takeaway should be. If they want to know more, then they’ll read on.
DO NOT reply to every email. First, ditch the zero-inbox goal, because not every email is important, whereas your time is important. Secondly, don’t let other people’s email dictate how you spend your time. It’s your time, so you get to prioritize what you should be doing with it. Just because you got FYI’d on an email, doesn’t give them the right to suck up the next 15 minutes of your life. And thirdly, if it’s important enough, trust me, they’ll find a way to contact you.
Write your email subject line like click bait. Ok, I’ll probably regret this piece of advice. One day you’ll get an email from your boss saying, “You Won’t Believe Your Performance Evaluation Results!” or “10 Incredible Tips On How To Use The Group Fridge.” Yet, I do believe we can do better with our use of the email subject line. I find most of them too boring and non-descriptive. A good step forward is to write in the subject line what type it is, such as “Action:” or “FYI:.”
DIG DEEPER — From a humorous GQ article: Tip #1 Never, ever match the tone of the person who emailed you. They go polite and formal? You respond with “k.” They go light-hearted and casual with something that even resembles an emoji? You gearshift your tone straight to academic. 
My relationship with emails.
“We are living in a world where business is being transacted across borders, often times without even physically meeting. An email then becomes the ‘1st impression’ of an individual, a professional, or of a company. It must have the desired, impressive effect.” 
Even pre-pandemic, we’ve been relying on emails more often to make first contact and then sustain them. Emails can be cold, transactional, and just plain boring.
But let me ask you, how do you come across when you’re at your best? For me, that’s when I’m completely comfortable with close friends, no judgement, and can be funny or intellectual, or both! The best version of me is when I feel great in my own skin.
Here we discuss how we can bring our “whole self” more so into our email conversations. On our journey towards greater success, it’s critical to form deep relationships and here’s how we can with emails.
Here’s 5 things I actively do to help foster deeper relationships via email.
1. Be Funny — I suggest inserting minimal humor into your business emails. Don’t open the email with a joke, but rather slip in some casual humor in the body of the email. Two rules when using humor in email:
- 1. Use affiliative humor that does not make fun of anyone. Making fun of yourself is ok.
- 2. “Something perceived as funny when spoken may come across very differently when written. When in doubt, leave it out.” — Pachter
2. Be a Mirror — In real-life interactions, we are taught to “mirror” the energy level of the person we are talking to. For example, if the person is energetic and loud, we should try to match it. Research shows that people are perceived as more likeable when this occurs. Same applies to email.
“If the sender is brief in their emails, be brief and to the point in yours. If they keep it direct and focused on business, keep it direct and business focused. If they ask about your family, ask about theirs too.” — Maria Neve, Founder & Transformation Coach at Fearlesshe 
3. Be Careful With Vocabulary — Sounds stupid, but I try extremely hard not to use negating words, like “but, don’t, can’t.” Just like in-person conversations, I avoid using those words because they’re too emotionally charged. The word ‘but’ makes people defensive. Instead use only neutral to positive words in email. If you need to deliver bad news, then do it over the phone or face-to-face.
4. Be Trendy — In my research, I love this tip:
“Leave ‘Best’, ‘Take Care’ and ‘Kind Regards’ in 2020. While these all have good intentions, they’re bland and overdone words that can come off as impersonal. If you’re not sure, I always say end everything with gratitude. A simple thank you neurologically creates a more positive reaction in the brain of the sender and the receiver of the email.”
5. Be Relatable… While Out of the Office — Most out-of-office responses are boring and is therefore a wasted opportunity. You’re taking time off for a reason, whether it be for vacation or sick leave. So why not include a bit more personal detail and also include advice #1 be funny. For example, one of my past OOO was:
“I’m taking some time off to go hiking in the mountains and will be back on Month Day. If you don’t hear back from me, then something went terribly wrong.
If you need anything, you’re in great hands with John Doe at email@example.com. In fact, I’m slightly afraid I won’t have a job to come back to. It’s a risk I’m willing to take.”
DIG DEEPER — From a humorous GQ article: Tip #4 Mark every e-mail “Urgent.” Especially if it’s not urgent.
Brandify Your Emails
I was mentoring someone the other day and I asked him, “what’s your reputation?”
Everybody responds with the positive adjectives, such as they’re reliable and have integrity. Guess what, that’s a bare minimum compliment! Dig deeper and really be honest with yourself. What do people say behind your back?
For me, part of my reputation, unfortunately, is that I’m perceived as seeking attention, vain, and selfish.
Knowing this, I actively (a) try not to do them!, and (b) take control of the narrative about me.
Next we discuss using email as a powerful weapon in our arsenal to promote the reputation we want. Emails are usually our first impressions on others and also a history of who we are. Here’s how we can use email to leave a legacy.
Two basic things to understand about using email.
First, the emails you send are a part of your brand. If you don’t know what your brand is or what you want it to achieve, then spend some time figuring that out. Here’s my articles on how to Control Your Personal Brand to help and how Joanne and Chip Gaines utilizes it.
Secondly, don’t you ever send an angry email. Sending an angry email is like writing your own obituary in the history books. “Here lies my reputation, unable to handle stress and died from a stroke (of the keyboard).” Instead, wait until tomorrow to react when you’ve had a chance to sit on it. Or if it’s an urgent matter, get on a face-to-face call.
Ok, now that we have emails basics out of the way, here are some next-level ideas to control your narrative.
Use email to amplify or counteract your reputation. In other words, if you want to be perceived as an expert in your field, then write in a more academic style. Use facts, figures, citations, etc. Still keep it to the point, and write in a logical fashion. Or, if you need to counteract your reputation of being too serious, then write your emails with softer language. Open and close the emails with some personal touches, such as asking about something personal about the recipient, to demonstrate you do care.
Use humor in your email. In my research, there are several articles that advise against using humor — I disagree. You should be cautious, be mindful of “lost in translation,” and if you’re second-guessing the joke, then leave it out. Yet, humor can do something that is almost impossible, which is make you feel like a real human being and not some robot. And when you come across as human and relatable, the recipient will want to converse with you and be more apt to reply positively.
DIG DEEPER — From a humorous GQ article: Tip #7 Sprinkle in ASAP 2–3 times per e-mail. Plant the seeds of anxiety and watch them blossom into fully fledged panic attacks. 
Your emails are a work of art.
Now we cover the last topic on my series about the uncommon rules of email etiquette. For this last topic, we need to get a bit more meditative about emails.
Consider the Netflix documentary Jiro Dreams of Sushi, which profiles sushi chef Jiro Ono, an 85-year-old master whose 10-seat, $300-a-plate restaurant is legendary among Tokyo foodies. Or consider Esquire’s 2017 profile on baseball player Ichiro Suzuki, “at an age when star athletes embarrass themselves trying to stay at the center of the game, the Japanese MVP has done something extraordinary.”
The common thread between those two is that they take EXTREME pride in their craft. They practice it to the point it becomes zen-like.
When I approach writing emails, I approach it as if I’m writing the next chapter of a soon-to-be New York Times bestseller. I’m not telling a long-form story, but I am taking pride in what I’m creating.
Next time you begin crafting an email, whether it’s a normal one or one of importance, see if you can keep these in mind:
Each email is a work of art. Show your value and make it worth the read. In my research for this article, there are conflicting advice on how long you should spent writing each email.
Fast Company advises, “never spend more than five minutes writing a work email. And when I manage other people, it’s a rule I ask them to follow, too. Ideally, each email will take 30 seconds to write — then, even if you write 100 emails a day, it’s still only an hour of your day, but five minutes is the max.” What are you, a robot in an automobile factory?!
Consider Erin Greenawald’s An Editor’s Guide to Writing Ridiculously Good Emails, where he states, “effective communication (and good writing) takes time. It takes time to formulate your thoughts, to figure out what you’re actually trying to say, and to write your message out in a clear way. And ultimately, that’s what email is — a form of communication. Not a task.”
What if your email went viral? Ideally, your email is going to communicate something of importance and is crafted in such a way that others will need to share it. Therefore even though you are writing the email to a specific audience, keep in mind that “emails are dangerously easy to forward” and may end up getting unintended eyeballs on it.
Besides checking for basic spelling and grammar mistakes, also fact check name spellings, events you refer to, and dates. Don’t include anything confidential. Imagine your email being printed in a newspaper — make sure you’re proud of it.
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- Finally! The 23 Unwritten Rules of Email by Alex Cavoulacos
- How to Assert Your Dominance Over E-mail Like a BOSS by Andrew Goble
- How to send an email: a guide for powerful people
- The five-minute email rule completely transformed the way I work by Deborah Tennen
- “Correct, Convincing Email Communication is Key to Millennial Business Success” by Kartik Bajoria
- 15 Email Etiquette Rules Every Professional Should Follow by Jacqueline Smith
- Email Etiquette to Boost Your Career This Year: Practical tips from a Global Human Resource Executive by James Barrett
- An Editor’s Guide to Writing Ridiculously Good Emails by Erin Greenawald