You can add all the smiley faces you want: what really leads to miscommunications is a lack of empathy.

When speaking face-to-face, it’s the verbal and nonverbal social cues that allow us to gauge the best way to arrange our wording in order to get our point across clearly. In email, we don’t get such real-time feedback. Once our message is in the hand of the recipient, we’ve lost all control.

This, of course, often leads to miscommunications, guessed intentions, and a total unawareness of whether an email was typed in red-faced anger or while sipping a martini by a pool. What really leads to those miscommunications is a lack of empathy.

Crystal is a brand new (still in beta) email extension that operates as a spell check for empathy. As you write to your colleagues, it tells you the way in which your intended email recipient communicates best, and then offers you suggestive edits in their preferred style of email—thus, hopefully, removing the likelihood that someone misreads your intended message.

“The most important thing is understanding each other’s language,” founder Drew D’Agostino said. “It’s not me completely adapting the way I communicate with you, but being aware and considerate of how you communicate best. Everybody’s different, and if we can just learn to recognize the communication styles of each other we can create much clearer interactions and productive communications.”

So how do we write emails that enable empathy—especially with people we might have never met in person before? And how can we be more empathetic when reading the emails of others? We asked D’Agostino to share Crystal’s best tips on how to bring more empathy to emails; both in the ones we receive and in the ones we send.

As the Recipient:

If They Write Their Entire Email in the Subject Line, You’re Better Off Just Calling Them Directly

The infamous “Subject-Line emailer” is the type of person who writes the email entirely in the subject line, with nothing more than their signature in the actual email body. This person is very direct, and either feels very busy or that the problem can’t be solved simply in an email, so it’s too much for them to go into it all.

“If you respond with more than two to three sentences, they are probably not going to read it,” D’Agostino explained. “You should probably just get on the phone or get over there in person.”

If They Write “Please Advise,” They Are Looking For Very Specific Instructions

It’s fun to quibble over what our email signature says about our intentions, but according to Crystal’s data there’s one in particular that demands a change in behavior: the ever-demanding “please advise.” D’Agostino explains, “When people write that in an email you know that you’ll have to write very specific instructions back. They want to have everything written out.”

If it annoys you that someone has shifted the burden to you, talk about it in person. Or, if it doesn’t happen that often, acquiesce. After all, there are likely some email habits of your own that folks find irksome, but it’s all part of the give and take required when emailing. “It is just normal, non-rude behavior for a lot of people,” says D’Agostino.

If They Use “Hey,” They See You as a Peer

Your email greeting is the first thing after the subject line that your recipient will read, so the tone you establish here is key for the rest of your email to be received well. The trick in getting it right, D’Agostino says, lies in the context: Are you sending this to a peer, an authority figure, or a stranger? If it’s not a peer, skip “Hey” and go for the safe, but respectable, “Hi” or “Hello.” “If they see ‘Hey,’ more formal-structured, less-casual emailers will immediately discount the email,” D’Agostino explains. “Right away they won’t take it seriously.”

But don’t skip greetings altogether—that’ll make even more people anxious. D’Agostino says that for a lot of people, if the email starts off with only a name, “they immediately think the email has a negative connotation, and it comes off as more robotic.”

If They Use Emojis, Don’t Dismiss Their Credibility — They’re Just Providing You With Additional Emotional Cues

Though widely debated as professional or not, as younger generations age into the workforce, usage of emojis at work will soon become the norm. And that’s a good thing, says D’Agostino, “Because we now use emojis like words, or as substitutes for words. It’s not just a ‘fun’ thing anymore, it’s a way to communicate your intentions.”

Though easy to dismiss, emojis add context and social cues in text-only communications. However the true genius behind them is that, by design, “emoji have no in-built linguistic capacity for meanness,” as Adam Sternbergh explained in a piecefor New York Magazine. It’s hard to take an angry-but-still-cute cartoon face seriously.

Even D’Agostino says he uses them all of the time, even professionally. “If I’m worried that I might come off wrong due to the context of it being in an email or text-only based communication, I do fall back on a smiley,” he admits.

…But Emojis Can Also Appear as Insecurity, So Use Them Wisely.

Despite their upside, emojis can still sometimes run afoul of their intentions. Though it’d be quite a stretch for someone to get offended by an emoji of a smiley poop, the context in which they are used can work against you. While fine for most professional correspondence, D’Agostino advises that we leave them behind at the negotiation table.

“Emojis can be perceived as a weakness sometimes. If someone is using an emoji but we’re in a negotiating setting, all of a sudden I know that they are, or that they thinkthey are, in the weaker position,” he says. “Not necessarily ‘weaker’ as in less powerful, but as in they are uncomfortable and worried about my emotional state.”

If you notice someone using an emoji in this situation, it means they don’t feel the negotiating table is weighted equally. The conversation itself needs to be improved, because one side is feeling very unsure of where they stand.

As the Sender:

Don’t Ask Anyone For A Favor Without Also Giving Them Something In Return

Cold-emails are annoying to receive and are also difficult to send, but largely unavoidable. Even if it’s not part of your job duties now, you’ll have to do this at some point in your own life, whether it’s applying for jobs or reaching out to make a new connection or even online dating. But just receiving a cold-email can feel intrusive to start with.

“You’re essentially asking them to gift you their time and it’s important to be respectful of it,” D’Agostino reminds us. So above all, you want to make it easy for your recipient to say yes. “If you’re looking for an action to be taken by the recipient,” says D’Agostino, “That action should be able to be done in less than one click away from the email, without much thought. Every email you want an action to be taken on, make sure you would also want to take that action if someone asked it of you.”

And if you really want to land that big Ask, D’Agostino personally thinks you should turn your cold-emailing into something warmer. Personalize your email by providing not only your request, but also something they could use as well; an article relevant to their recent interests, a service you think would solve a problem you saw them tweeting about, etc. “All of a sudden they’re offering me value, thoughtfully, and directly to me—I don’t only get the sense that they’re only trying to take value from me,” D’Agostino says.

Try to Remind Yourself That On the Other Side of the Screen is a Real, Live Human

Traditional letter writing does have a few perks that email lacks, mainly in providing a tangible sense of distance and objectivity. When it takes days or weeks to receive a hand-written message, you’re acutely aware of the barriers between you and the sender. With that in mind, it can be easier to stay level-headed in both your perception and judgment (not to mention that handwriting can carry with it some emotional cues that typed words lack—there’s nothing more visibly angry than when the writer pressed down so hard on the pen when writing it that they almost tore through the paper). But with email’s instantaneousness, that visible, tangible barrier is gone.

However, short of putting up a banner that says “I PREFER EMAILS WITH FORMAL GREETINGS” above your desk, there’s not much we can do about it, yet. Email-helper extensions can provide a visual reminder that might work for some people, but no software is infallible. For now, the best course of action is to simply recognize and be cognizant of the communication hurdles within email—and trying to be a little more human.

If you think your miscommunications might be due to the pressure to immediately respond, blocking out specific parts of your day to answer can loosen some of that anxiety and allow for better judgment. If that’s not a feasible option, keep the negativity bias from creeping in with apps like ToneCheck. The extension flags negative tones as you write, but even the most positively worded messages can still be unclear in meaning or context. To bring in more context while you craft your message, Rapportive pulls your email recipient’s LinkedIn photo and stats into the window while you draft, which can help remind you of the real human you are emailing—but again, there’s no guarantee they will still read your email in the way you intended.

“I think it’s very rare that anyone is ever trying to actually offend or criticize you,” D’Agostino explains. “Usually people have good intentions. But much more often we perceive it, especially at work, as critical or rude—all these feelings we get immediately because we all take things personally, and in the way of our own communication style.”

Email is simply another tool we use to try and understand one another (albeit quickly, and often in rapid succession). Recognizing your own email behavior and working to improve it, in the same way you would recognize your own social behavior “in the real world,” might be the only lasting fix for communication issues both onscreen and off.

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This article first appeared in www.99u.adobe.com

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