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How to Write a Work E-Mail and Not Seem Unhinged
Collage by Maria Jia Ling Pitt

Let’s get right to it: you are writing bad e-mails. You overthink them or underthink them. You agonize over each word, padding your e-mails with too much information, a sundae of cover-all-bases requests and hedge-your-bets recaps with an overwrought cherry of pleasantries on top. You take too much time crafting the perfect message when the recipient is only going to skim your soliloquy for action verbs, sort out whether they need to respond and discard it like a flyer for Live Comedy in Times Square. Or you underthink, reacting to each group e-mail upon arrival, rapidly crafting a response, your finger hovering over the reply-all button so you can join the group conversation and get your name on the board, clogging everyone’s in-box in the process. First rule of thumb with e-mails: Say less. Second rule of thumb: Chill. Here are the other rules on the other thumbs.

1. Don’t write an e-mail when you are feeling angry or anxious or sad or ashamed.

Don’t speed-read an e-mail that includes critical feedback, get riled up, perhaps misread the message, puff up your chest, write something defensive and subsequently come across as a demented ass. If you are experiencing an extreme level of emotion, write a draft of the e-mail you want to send and wait at least two hours to send it, after reading it over first. Don’t pop off and send something you may later regret. It’s in writing forever.

2. Read your most important e-mails aloud before you hit send.

If they sound testy or rude, and you do not want to sound testy or rude, soften the language. Kindness is a choice, and it’s an easy one, once you let down your guard and realize that no one can actually hurt you over this e-mail chain. Equally, read your correspondence aloud and listen for overly timid language and excessive apologies. You are allowed to be direct and ask for what you want. Just do it with correct grammar and a few niceties, like “Thanks.”

3. When in doubt, go slightly more formal.

(Unless you’re writing to someone you know well, and a formal tone would seem spiteful or passive-aggressive). Use all of the manners you have learned in this world as a civilized human. Be friendly, but polite.

4. Keep in mind that the person you’re writing to is probably receiving dozens of e-mails a day.

Be considerate of their time; ask them to do the fewest things possible, and identify the point of your e-mail or what you want help with in the first few sentences.

5. Consider whether you want this message in writing.

Would you rather not have a permanent record of this conversation? Can you achieve what you desire by picking up the phone or walking a few steps to an adjacent cubicle? Would this actually make things less complicated?

6. Have a goal.

Whenever possible, an e-mail should be about one topic and about how the other person can take action on this topic.

7. Keep it concise, direct and to the point.

Don’t include feelings or extraneous information. This is a business e-mail, not a love sonnet or a Dear John letter. You should become the Raymond Carver of e-mail, conveying your message in the most specific and sparest of prose. Before you send, see if there are words, thoughts, or paragraphs you can completely delete and still effectively make yourself heard.

There is one occasion when you should abandon all of the above e-mail rules. This is when you are intentionally sending a passive-aggressive fuck-you e-mail, a covering-my-ass e-mail or an I’m-documenting-this-for-posterity e-mail, the contents of which you want a permanent record of with a date and time, basically when you are formally, covertly being a dick for a greater cause. These e-mails are annoying and should not be used frequently, but they’re often necessary for recapping live conversations and protecting yourself or your job down the road, or when you are trying to fire someone and are creating a paper trail of how much they suck.

You should use these e-mails when an unreliable boss makes you a promise you’re afraid she won’t keep, a client agrees to something verbally and you want him to acknowledge the terms in a more official way or you are reporting on problematic events in the office that need to be documented and addressed. Mastering the tone of these e-mails is delicate. You should report the facts while using the least emotional language possible.

If you have a delusional employee who is spiraling into ruin but thinks she’s the best, you should leave your in-person feedback conversations and write down what you discussed. “Hi employee X, I wanted to recap what we talked about today. . . .”

E-mail can be a smart tool to gain control over an out-of-control situation, to check someone who is behaving childishly or inappropriately or dishonestly, but you must use it judiciously. You don’t want to create a hostile work environment if you can avoid it, and you want plausible deniability that you are playing passive-aggressive games, even though of course you are.

Jennifer Romolini is the chief content officer of at Shondaland.com, a website founded by Shonda Rhimes. She was previously the editor in chief of HelloGiggles and Yahoo Shine, and the deputy editor of Lucky magazine. The above is adapted from her new book, Weird in a World That’s Not: A Career Guide for Misfits, F*ckups, and Failures.

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  • tmm16

    #1 is incredibly important, especially when you are managing clients. Always remember: The client is always right! Even if they are wrong. It’s important to always stay professional and not showcase aggression, frustration, or negative communication. It may seem a bit much, but I almost always include “thank you” in any email I send as well.

  • #3 is excellent advice. Beginning an email with pleasantry also helps instead of plunging right in with the business at hand. Yes, you should keep it concise and to the point, but adding a “good morning or afternoon” goes a long way.

  • Great advice! I usually believe my emails are quite tempered – not too much, not too little. Super concise, super polite. But sometimes I see my coworker taking like 20 minutes to write one email, and I’m like… “Okay, what are you waiting for? You’ve read this like 52 times!” Of course, it’s super important to respect all the correctness rules, so thanks for reminding us of these basic rules and tips! 🙂

    Meg @ its.meg-ramsay.com

  • Kay Nguyen

    Great tips! I’m in college so professional emails are required but I still don’t get it when people don’t know who to write a professional properly. I’m not sure if that’s something people get taught in school but then again I went to a private school so I wouldn’t know.

    https://www.myblackcloset.com/

    • I definitely didn’t get taught how to send good emails at school and struggled with it when I landed my first fashion job! Although, it should be mandatory learning for everyone, at least at degree level!

  • BabyGotYak

    I have a colleague that writes these long tomes pontificating on the nuances of this or that. Dude, NO ONE WILL READ THAT. You’re asking people to do something and burying the lede!

    If it takes more than a couple of paragraphs to write, a meeting is probably a better way to get shit done.

    And remember, when people open an email and see a wall of text, they are never ever ever going to read that email.

    • Meg S

      Tell your colleague that all the important information goes in the first 3-4 sentences. After that is when people start to check out on emails. That said, I’d never want to go to a meeting with that person, much less run by that person. At least I can close the email.

  • Beasliee

    This is so useful. It’s something you don’t really get taught (well I didn’t) but hen you realise how many mistakes there are to make!
    I would add:
    # Do not use smiley faces in professional emails, or sign off with an ‘x’;
    # If you need someone else to read it for clarity or tone, do not send in its current format;
    # Do not copy people in unnecessarily;
    # Don’t crash people’s inboxes with giant attachments – compress or pdf;
    # Bullet points, lists and bolding are your friends;
    # Do not get offended by other people’s very brief, informal emails as this is really how the format was supposed to be used;
    # Consider reflecting the email style of your line manager;
    # Include your phone number on your autograph;
    #Use clear and relevant subject lines and keep replies relevant to that subject;
    # If in doubt, do not ‘reply all’;
    # Give people longer than 30 minutes to read and reply, even if you did mark it as urgent!

  • Meg S

    #7 is the best advice I’ve ever received. I took a seminar, and part of it covered writing emails to work with different personality types. I once worked for someone who wanted everything important in the first paragraph, and would never read it if it was more than 3-4 sentences. It may have been harsh, but he received dozens of emails every day and would never get anything done if he read the full email. I learned to put the important things in the first 3-4 sentences because I knew anything past that would never be read by the department head. I stick to that email writing format today. It works for everyone. All the important details are first, and are read before the recipients can check out (probably about 30 seconds-1 minute).