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Email Etiquette II: Why Emoticons (And Emotional Cues) Work

Did you know humans are hard-wired to mistrust email? We reveal why, along with 6 simple tips on how to increase the emotional intelligence of your email messages.

Earlier this year I attended a presentation with Daniel Goleman, author of Social Intelligence and godfather of the field of Emotional Intelligence. According to Goleman, there’s a negativity bias to email – at the neural level. In other words, if an email’s content is neutral, we assume the tone is negative.

In face-to-face conversation, the subject matter and its emotional content is enhanced by tone of voice, facial expressions, and nonverbal cues.  Not so with digital communication.


echnology creates a vacuum that we humans fill with negative emotions by default, and digital emotions can escalate quickly (see: flame wars). The barrage of email can certainly fan the flames. In an effort to be productive and succinct, our communication may be perceived as clipped, sarcastic, or rude. Imagine the repercussions for creative collaboration.

Tools are already emerging to address this phenomenon. See ToneCheck, a “tone spellcheck” app that scans emails for negativity and then helpfully suggests tweaks to make your communication more positive (featured in The New York Times Magazine’s annual Year in Ideas issue).

I’ve been experimenting with simple ways to encourage positive digital communication. Here are a few best practices I’ve found useful:

1. Heed the negativity bias.

In this case, awareness and attention goes a long way. Consider how your communication may be perceived. Can you be more explanatory? Is your language positive as opposed to neutral?

2. Pay attention to your grammar.

Since monitoring my emotional reaction to incoming and outgoing emails, I’ve noticed that in our haste, meaning is often obscured by simple grammatical confusion. “That’s not what I meant” is emblematic of digital miscommunication, and can escalate a problem quickly. Re-read your emails before sending, and make sure your intended message is being conveyed clearly.

3. Consider emoticons.

Until keyboards can actually perceive the emotional content of our digital messages (not so far off!), emoticons may be the simplest method of clarifying tone. I’ve had to let go of my own perception that emoticons are silly. They may currently be our best tool for elevating the emotional clarity of digital messages.

4. Use phrasing that suggests optionality.

When gentle prodding is necessary, try using phrasing that empowers (rather than accuses) the receiver. Questions in particular tend to be better received than declaratives – a “Can you?” instead of “Do this!” approach.

5. Start things off on the right foot.

When the news is mixed, consider leading off your message with an expression of appreciation. Then follow with the meat of your response. It could be something as simple as, “We’re off to a great start, I just have a few small tweaks I want to suggest.” Such gestures may seem like fluff, but they set the tone. Effectively saying “I appreciate the work you’ve already done…” prior to bringing the feedback that means “back to the drawing board!”

6. Jettison email… maybe.

Ask yourself, “Is email the best carrier of this message?” Often a more social communication tool such as an internal project management space or messaging tool (Yammer, Action Method, or Mavenlink) can be more appropriate and serve as an emotional buffer. Reactive communication tends to be more measured in a public digital space. Plus an added bonus: knowledge sharing.


Because of the lack of emotional tone in emails, we often have to go the extra mile to convey a solicitous attitude – whether it’s rewriting a sentence, adding an emoticon, or offsetting bad news with a positive remark. Even if it seems a chore, it’s time well spent.

In the immortal words of a recent 99U commenter: Don’t treat others like a “DO IT” button, treat them like human beings.

What’s Your Approach?

How do you craft pitch-perfect emails?

What are your strategies for keeping digital communication friendly?

–> Read more email etiquette tips.

More Posts by Scott McDowell

Comments (66)
  • Guest

    Fascinating article but we must remember that emails are widely read on hand held devices now so it is evolving even further. I now do a 1. should this even be an email? check and 2. is this person highly likely to be reading on a mobile phone? check

  • Bill

    I think #4 and #5 are absurd. It’s so passive aggressive. Please! What ever happened to shooting straight and getting the information across without having to cater to someone’s insecurities and inability to focus on the task at hand and not the emotional poop. It’s exhausting to have to constantly worry about “hurting someone’s feelings.” In business, I can see making sure your point is accurately communicated and in personal emails I can see not being hurtful unless you are intending to be hurtful, but to have to spend so much time worrying that someone might be hurt by the way you write something? What a pain.
    I mean, what a pain. 🙂

  • 99U

    Hey Bill. I’m glad you commented. Scott (the author) & I actually had a bit of discussion about this one. Because I consider the 99% content to be “evergreen,” I’ve been mulling over adapting point 4, which I just did. I think the original published version could be perceived as creeping into passive agressive territory and that’s not the goal! The intention is more about not being accusatory or overly harsh, as opposed to pandering.

    With regard to point 5, I disagree. A lot of what gets lost in email is the vocal tone and body language that convey good intentions, friendliness, and, in many cases, appreciation. So the point here is less about strategically “couching” bad news than it is about making sure to express appreciation (assuming, you feel it), alongside of criticism or demands. I think considering the way someone else will react (or feel) about your email is completely relevant and necessary.

  • AJ

    i am also not comfortable using emoticons in official mails. what if the person on the other end is a disciplinarian who wants a crisp and formal text? won’t emoticons make things appear a little less serious?

    also, why should we start using emoticons now? there was a time when people used to send formal letters but we have never used smileys on those… an email is a digital form of a similar letter, how can the use emoticons help?

    this is the only aspect from the article that i am skeptical about.

  • Rice

    Do have one thought in mind that sure these things OFTEN HAPPENS, however in terms of professional emails, such as replying job offers or to your chief, would emoticon be a professional choice? adding a 🙂 at the end seems well, not professional.

  • Justin Threlkeld

    If I can figure out a way, I will always avoid using an emoticon. I mean, I can see emoticons having a place in ultra-short communications (think text messages), but isn’t relying on a collection of re-purposed punctuation marks a little bit lazy? Shouldn’t we try to use language to provide emotional cues?

  • John Choura

    I like this, it is a non verbal compensation.

  • genwilliams

    I wish more people would heed this advice. It’s so uncheering and demoralising to get emails just telling you ‘do this’ without so much as a “please” or “thanks”. Much more encouraging to get something that suggests some actual faith in the work you’re doing! 

    I probably overthink every email, which is unproductive, but my day involves asking for lots of info from comparatively inexperienced, young people. So I strive to be clear and friendly; I only get clipped and abrupt if I find myself asking for the 3rd time. (At which point I try to explain what the consequences of their inaction will be, rather than just “DO IT”). The more hostile I am, the more hostile they are – no good for anyone.

  • Eric

    I think it’s a great article and we think growing large lists will eventually give you a good ROI. Very good article!

  • Marvin Quianzon

    this should also work for text messages (sms) 🙂

  • 772rosemary

    Over the last couple of years I have seen fundamental leadership skills avoided by those who prefer one way communication. Often the relationship between workers is sabotaged by inappropriate and inopportune use of email. No emoticon in the world can convey the non-verbal communication which lays alongside the tapped out message. 

  • W. Michael Hsu

    Great write. Especially like the thought that emoticons can actually help clarify tone – thanks. 

  • Jonathan Manness

    Nice discussion about email etiquette, Scott. Having a positive tone in the subject of the email helps remove anxiety before it’s even opened. You can also add positive words in parenthesis when a subject has been established and is going back and forth. Credit goes to Leil Lowndes for this tip.

  • Alex

    Clearly this is a hot issue! I appreciate your bringing it to light. There’s something to be said, too, for exclamation points instead of periods (in moderation of course), as a way to show lightheartedness through written communiques. Consider my first sentence here, and how different it would seem with a period instead!

    One thing I would say is that this kind of thinking, while I agree with it, won’t propagate unless society agrees on the conventions you’re discussing. The fact that Q-Bob a year ago (!) had such a different perception of emoticons shows just how conservative some people still are about emoticons. But hey, someone just tweeted your article today, and if it keeps spreading maybe we’ll all get onto the same page. 🙂

  • patterdale

    i just keep seeing the <3 icon as a pair of boobs 80085 styley 😉

  • La Flaca

    Personally, I prefer hitting the old cap lock button when I write emails to my terrified, cowering employees. It makes me seem even more intimidating than I already am. It also helps to refer to myself in the third person, as in: YOUR WORK DISPLEASES LA FLACA. FIX IT IMMEDIATELY, SCUM!

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