We don’t do email well—that is, if we even do it at all. Maybe it’s just that email feels like a prehistoric practice to us, some hilarious relic of the past. While our parents were still getting motion sickness from the speed of email, we had already moved on to IMing. Then to texting. Then Facebook, Instagram, Twitter, Snapchat, Tinder, Bumble . . . you get the point. Sure, we might be rich in likes and followers, but it’s starting to feel like the digital world has robbed us of the patience, skill, and social deftness to craft a simple piece of writing. Excuse me while I get all Carrie Bradshaw for a moment, but when did our baseline level of decorum completely flatline?
In my wildest millennial-turned-professional fantasy, I am waxing poetic from my Eames chair, eating an acai bowl, and fielding TED Talk invitations while firing off flawless emails with executive ease. In reality, however, when it comes to navigating the professional world, I’d much rather run naked into a cactus than compose an email. I’m serious. There is truly no greater act of torture than sitting in front of an empty email window. Maybe it’s the la-di-da unconcerned nature of the millennial generation, but honestly, the whole formality of it seems perverted. I end up feeling defeated, and who am I kidding? The inability to rise to a simple occasion is damaging to my inflated sense of millennial self-worth. If I were a magician, my residency in Vegas would be billed as The Illusion of Competency. I’m literally Holden Caulfield with an Internet connection—except in this scenario I’m also the phony.
My email anxiety rears its ugly head when initiating a correspondence with someone higher on the professional food chain, which is pretty much everyone. I’ve been known to spend an hour deliberating between greetings. Is “Hi” too casual? Is “Hello” too curt? Does “Dear” make me seem like I’m a goody-two-shoes? Don’t even get me started on the name. First name? Too forward. Full name? Stilted. Mr.? Ms.? Mrs.? Does Googling someone’s marital status come off as creepy? What if they’re one of those Ph.D.s who insist on being called doctor? I have thwarted myself before even beginning and, before I know it, I’m a one-woman disaster area. So I called Patricia Napier-Fitzpatrick—founder of The Etiquette School of New York, hero of this story—and asked her to break down the do’s and don’ts of email etiquette.
Do err on the side of formality.
Millennials are used to very short messages and even shorter turnaround time. Needless to say, good form has a tendency to get lost. But “if you’re junior level,” cautions Napier-Fitzpatrick, “a good rule of thumb is to always start with the most respectful means of addressing someone. Greet them with ‘Dear Mr./Ms.,’ and then depending on how they refer to themselves in their response, you can follow their lead.” And never forgo the greeting altogether. “It seems a little abrupt and a little bit rude,” she says sternly. As for the rest of the email, it should be “clear, concise, and polite—and, of course, if you’re asking for something, always end it with ‘thank you.’”
Do be meticulous.
Check your grammar, check your spelling, check everything. “This is your first impression—you want it to be a positive reflection of your personal brand,” says Napier-Fitzpatrick. And don’t send it the minute you finish. Do something else for five minutes, then come back and make sure it’s what you want to send—because remember: You’re leaving behind a paper trail. You should always send something you’d want read in front of your friends and family.
Don’t spell names wrong.
“It’s nearly impossible to rectify spelling someone’s name incorrectly,” warns Napier-Fitzpatrick. It’s true. A couple of years ago my friend (who will remain nameless to protect her identity) misspelled a potential employer’s name when emailing a job application. This is, word for word, the response she got back:
Thanks so much for your email! It’s great that you’re so enthusiastic about the media industry, but if you can’t spell our editors’ names correctly, I’m not sure you’re ready to intern here yet. I’m not telling you this to be mean, but rather because once you fix that, your enthusiasm will surely get you an opportunity in the future.
When I called my friend to ask if she could dig up the email for me, she had a moment of reflection: “You know, that was actually the best email I’d ever gotten, because it forever changed my attention to detail.” As long as there’s a learning curve, take a deep breath and let the little things go. That was in 2012, and now she’s on the fast track to fame, fortune, and success—honest to God.
Do know your CCs and your BCCs.
CC works when you’re sending an email to various employees in your company and you need them to see the responses, but make sure you “organize the recipients either alphabetically or by seniority. Some high-level executives are very sensitive about being important,” says Napier-Fitzpatrick. Use BCC when sending a mass email that doesn’t require responses. “Especially,” she notes, “if you’re emailing people outside the company. Respect people’s privacy—they might not want their email addresses shared with those who otherwise do not have it.”
Don’t skimp on the details.
Specificity is key—especially when it comes to the subject of the email. “People get so many emails,” says Napier-Fitzpatrick. “It’s important to be very clear and pertinent in the subject line. If you write ‘RE: Meeting,’ it’s like, what meeting? Put the date of the meeting and what it was regarding.” Even when reaching out about jobs, “it’s not enough to put ‘Staff Intern’—put ‘NYU Graduate Applying to Staff Internship’ instead.”
Do pay attention to your tone.
It can be challenging to show personality through email. Napier-Fitzpatrick explains, “If I say something during a meeting that might read a little harsh on paper, but when I say it I have a smile on my face, you’re not going to take it negatively.” Slang and abbreviations can be interpreted as informal, and sarcasm can too easily be misconstrued. Also, limit your exclamation mark usage to one—at most two. “Everything can’t be excitement, so use them sparingly,” she warns. Too many exclamation points “can come off as trying to be pleasing rather than credible.” Oh—and never write an email in all caps. It’s very aggressive.
Do say thank you.
It doesn’t matter whether you met someone in person, chatted on the phone for five minutes, or engaged in a quick email exchange. It is crucial to properly thank anyone who has been generous with their time and knowledge—and do it quickly! “The sooner you send it, the more sincere it seems. You have a 24-hour window, but really it should be sent within 12.” Bonus points if you follow up your thank-you email with a handwritten card.
Millennials, it seems, have a tendency of thinking it’s optional to answer an email. Perhaps because we’re used to getting (and ignoring) emails from our parents, or maybe, muses Napier-Fitzpatrick, “millennials aren’t as empathic as other generations. They don’t consider what it would be like if they were on the receiving end of that email, or lack thereof.” Bottom line: The only thing more important than writing a good email is responding to one.
Written by: Isabel McWhorter-Rosen for Vogue Magazine