How To Write A Work Email When You’re Really Pissed Off

Just don’t. But if you absolutely must, do it like this.

How To Write A Work Email When You’re Really Pissed Off
[Illustration: “The British Lion’s Vengeance on the Bengal Tiger.” via Wikimedia Commons]

Let’s get right to it: You are writing bad emails. Usually that shakes out one of two ways. In the first, you agonize over each word, padding your emails 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 spend way 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 else it’s the reverse: You under-think, reacting to each group email 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 inbox in the process.

But there are two general rules that can help save you from both scenarios. The first: Say less. The second: Chill. And as it turns out, both rules are super important when you’re angry.

Breathe And Slow Down

Whenever emotions come into play, take “say less” to its ultimate extreme: Just don’t write an email when you’re feeling angry or anxious or sad or ashamed. Don’t speed-read an email that includes critical feedback, get riled up, perhaps misread the message, puff up your chest, respond with something defensive, and subsequently come across as a demented ass.

Related: Six Ways To Write Emails That Don’t Make People Silently Resent You 

If you’re experiencing an extreme level of emotion, write a draft of the email 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.


Say It Out Loud

Read your most important emails aloud before you hit send. If they sound testy or rude, and you don’t want to sound like that, 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 email chain.

Equally, read your correspondence aloud and listen for overly timid language and excessive apologies—some of us do try to overcompensate when we’re upset or frustrated instead of mouthing off. You’re allowed to be direct and ask for what you want. Just do it with correct grammar and a few niceties, like “Thanks.”

Err On The Side Of Formality

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’ve learned in this world as a civilized human. Be friendly, but polite.

Cut To The Chase

Keep it concise, direct, and to the point. Don’t include feelings or extraneous information. This is a business email, meaning you should become the Raymond Carver of the form, 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.

Consider Whether It’s The Right Medium For The Message

And as a final gut-check: Are you sure you want this message in writing, or 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?


For context, let’s apply these rules to an actual email. Imagine you’re trying to get paid for something you’ve written, your payment is late, and you’re following up. Here is your first draft of the email.

Hi [So-and-so who has not paid me]!

How are you? I hope you are well! I’m so sorry to bother you about this because I know you must be super busy and I hate sounding like a nag. (Please tell me I’m not one of those annoying people who email all the time? This is my worst fear.)

Anyhoo: I’m writing today because I wanted to check in about my payment for that story I wrote way back in April. I know we talked about the payment a few weeks ago, and when last we spoke you said I’d have it by June 15th, but now June 15th has come and gone and I still haven’t received a check.

Maybe it’s lost in the mail? My apartment building is weird right now and it totally could have been lost or taken from the community mail table but I just wanted to see if I should be worried about this or if the check actually hasn’t gone out.

Totally fine either way!

Hope everything is great—I really loved working with you guys and would love to pitch something else and write for you again. Let me know when would be a good time to send pitches or what you guys are looking for.

I mean after this check business is all sorted out. Is there someone else I can call/bother about this?

Just want to get to the bottom of it. Thanks so much for your time.


[Person who has not gotten paid]

Here is what you should say:

You’re annoyed, and you sound it! Here’s how you should revise that draft before sending it:

Hi [So-and-so who has not paid me]!

I wanted to check in about payment for that story I wrote in April. When we last spoke you said I’d have it by June 15th, but I still haven’t received a check.

I know you’re busy—is there someone else I can call/ bother about this?

Thanks so much for your time,

[Person who has not gotten paid]

Mastering the tone of these emails is delicate. You should report the facts while using the least emotional language possible. Start by telling them that you’re recapping your conversation, or clarifying expectations you might have discussed verbally. But use this judiciously–after all, you don’t want to create a hostile environment if you can avoid it. Your temper will dissipate, but that might not.

This article is adapted from Weird In A World That’s Not: A Career Guide For Misfits, F*ckups, And Failures  by Jennifer Romolini. It is reprinted with permission from HarperBusiness, a division of HarperCollins Publishers.