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.
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.
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.”
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.
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.
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?
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.
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.