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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)
  • Giovanni Cappellotto

    Great piece of news!
    I use a simple tool to track my “social mood”, it’s called Smood it (
    You can interact with it using a simple interface or connect your twitter account to convert every emoticon to a “smood”.

  • Lisa

    Hurray! So glad to hear some validation that emoticons and business email communication are not incompatible. I am a big supporter of making emails as friendly as possible—and phone texts too. Right on :0)

  • @SocialJamie

    I’m not a big fan of emoticons in professional emails, but I definitely use them in less formal communication. If I have a problem or less than positive news to convey, I usually start off with a positive affirmation and then offer some preliminary solutions or ideas with an offer for further discussion. If I feel that my email could be perceived negatively, especially by a client, I pick up the phone rather than risk my message being misconstrued. I’ve been bit in the butt too many times to take that chance again!

  • Brandon Baker

    As long as teenagers litter their emails and text messages with emoticons, the adult world will have to find an alternative in order to accomplish the same ends. I like the phone call method as well as using better language to overcome these barriers.

  • Justin Beeler

    I don’t use smiley faces, because I still believe they are silly. I agree with other commenters, it’s probably better if you feel what you’re writing could be interpreted negatively, to make a phone call. Your tone of voice goes a long way in keeping your clients from being upset at you. I always re-read before I send, and try to keep things light and positive.

  • Marko Pavlovic

    Great post, it proves some of my thoughts. Like everything else in life, one should know when and how to use them without overdoing it 😉

  • Robert

    I disagree with number 4. You’re dangerously walking the passive aggressive line – if you truly had a conversation with someone concerning a project and do not know where you left things, you already have multiple problems. Stick with the truth or or more straightforward questions. Example: Having any luck with that new content? Is there anything I can do to help? Steer clear of white lies and passive aggressive sounding statements.

  • Q-Bob

    Strongly disagree with the articles whole point on how emoticons can increase an e-mails emotional intelligence, would rather say the opposite, that it underestimates your recipients understanding of the written word. Plus, it shows that you’re insecure about your writing and language skills.
    If someone writes me an somewhat negative e-mail and inserts emoticons to ease the deliverance, they lack authority and it probably would provoke me more than the mail itself.

  • area-norte


  • Marc

    The phone call is easier, faster and more straightforward than the mail. I agree with you in that point.
    However, it may also be that teenagers have adopted technology better than adults have. And now it’s adult’s turn to improve it’s digital text communication skills.
    Will the actual teens still write with emoticons when they reach that parallel world you describe that is only inhabited by adults? 😉

  • Robert Pizzo

    When in doubt, there’s a wonderful technical device that can convey your actual emotional tone fairly accurately. I’m not making this up! In fact, most of you probably have this modern miracle already. It’s called a “phone”.

  • schunk

    Of course, the average person with little attention can see the emotions that have been incorporated in the written word. But emoticons are still very common language of communication within the structure. 🙂

  • Jonathan Patterson

    I agree. I don’t use emoticons in client emails whatsoever. I do use them in personal communications, Facebook, Twitter etc.

  • Jonathan Patterson

    I don’t use emoticons in professional email but when I use them in personal email I tend to use the unconverted smileys… 8) (where it doesn’t show up as an image.) I feel they are more high brow (funny to see high brow and emoticon in the same sentence.)

  • drexel

    Eventhough the phone is faster. Email allows for the nearly unlimited storage of additions to a conversation which can be referenced at a later time.

  • Michelle D'Avella

    Great post! I use a lot of these as well. On the flip side, as readers we need to take responsibility of assuming negativity and begin to read emails with question and a more positive light.

  • Thailand Reisen

    Yes, I notice that emoticons are becoming more and more “acceptable” even in exchanges between “serious” business partners. Interesting post!

  • dean_l

    I like using emotions in my work emails. They make it sound more ‘real’, personal, better than usual corporate emails. Of course I don’t use them in corporate proposals and official emails.

    Great reading. As always major point for any good communications is – BE positive!


  • Eva

    Sorry Q-Bob but will disagree with you here, someone (of adequate emotional intelligence) is unlikely to insert emoticons when they’re delivering a truly negative message. If they did then yes they’d lack authority in that instance however I think this is more about the ‘reading between the lines’ that occurs and how more often that not people misinterpret neutral language as negative.

  • Eva

    Can I ask why we’re all so seemingly obsessed with portraying how grown up we are? If we’re really all ‘adults’ then why are we so fearful that the likes of an emoticon would reduce us to sniffling, simplistic, emotionally immature children?

  • Klaas Nienhuis

    I think I understand how emoticons may help add a positive flavour to any message. I too struggle sometimes to find the right wording in e-mails. However emoticons introduce a new set of issues: if I’d restrict my emotions in professional communication to the emoticon-range I’d be either smiling, frowning, winking and so on. This might seem silly, but with emoticons I think I iron out any nuance in a well composed written message.
    If I’m unable to write it down, I either talk on the phone or in person, if possible.

  • persimmons

    Q-Bob! Thank you for speaking out! Not that I entirely agree with you on this particular issue, but I totally admire the way you courageously stated your view. We need many more people like you who are not afraid of being contrarian. Our society is increasingly weighed down by the growing populace of young lemmings who can only repeat each other’s benign twitters.

    I’ve no idea how old you are, but in my days there was a subtle art of irony, wry humour and covert metaphor which would’ve been never reduced to the simplistic kindergarten emoticons.

    Having said that, emoticons have their use in the visual communication and I don’t entirely belittle them. Like any sign languages, albeit simplified, they can convey something quick and easy. Also it conveniently camouflages any temporary or permanent deficit in the communication skills. I use them. Why not.

    Whatever it is, we need to keep diversity and flexibility in the way we communicate each other.
    Subtlety and ambiguity, and precision and clarity have all their merits in our ever richer, rewarding world of world-wide human connections.

  • Opt In Email Marketing

    There’s a fine line between ‘silly’ and ‘intentionally light’. I’d prefer to be thought of as occasionally silly than rude. Re-reading your messages before sending to scan for potentially mis-interpretable contexts is key and if there’s any doubt about how your message will be received, pick up the phone and have a quick conversation to clarify your disposition…

  • Keliomatic

    It sounds like you might be a bit of a critic, so with that taken into consideration you are likely hard-to-please and look for the worst in all situations 🙂 <—-see how I did that?

  • Ellen

    I have been giving advice for years that if you have a problem or an issue you should never communicate by e-mail. It’s always faster, better and more likely to have a positive resolution if you have a face to face or phone conversation. Interesting idea that there is “tone checker.” Nothing wrong with tools to help the “positive challenged.” :-/

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