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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)
  • Bjarte Edvardsen

    I had the same issue with emoticons in emails as you. I thought they were more appropriate for SMSing (rather than emailing) and feared to use them in business related messages – and especially towards people I had never spoken to before. Now I think they can be quite effective as long as they’re not overused and carefully placed after a sentence where the receiver might get concerned about the tone. An emoticon often fit quite well at the end.

    Other than that, I just try to write as I would speak. And if I have something negative to say I feel it’s better to meet face-to-face or on Skype to make sure the other person doesn’t take it the wrong way.

  • Chris B

    Great article.

    Setting the tone of the email is something I spend a lot of deliberating over, I recognise that my email communication can come across as cold because I tend to write quite formally.

    Still can’t quite bring myself to use emoticons in an email unless I have been working with the recipient for a while. Internally is ok, but externally I will only do it if the other person does it first.

    #6 is something I’m firmly in favour of. Often instant messenger, or (god forbid!) walking over and talking to the person is much more effective. You can then send a follow up email to confirm and formalise the discussion.

    #4 I’m on the fence over – “Are you planning to take care of that issue?” can very easily come across as condescending. Sometimes a more direct “Please can you send over x when you get a chance’ does the same job of letting the other person off the hook in terms of not having completed the task (the inference being that they just haven’t got round to updating you), but reinforces that they still need to do it.

  • Andre

    Great Article! Email is a great tool to communicate content, not so great for communicating emotional content. A good rule of thumb is to never send an email when you are in a negative emotional state. Write the message, sleep it over and, if you still feel you should send it after re-reading it, by all means click the send button. Once you click send, it is out of your control.

  • Tabatha Bourguignon

    Fantastic article! I honestly find myself staying away from using emoticons – I was “taught” they were unprofessional – but I’ve always felt they have their place, provided they’re used correctly. Maybe I’ll have to start trying to use them more effectively – thanks for the insight! 🙂

  • Sean

    I’m wondering who the “we” is who assume the tone of an e-mail is negative. It may just be that I’m young enough to have grown up knowing and trusting e-mail, but I don’t recall ever having an innate distrust or innate pessimistic view of e-mail messages any more than I would a print message of the same content. I’d be curious to see a study that also included factors like age and personal disposition- e.g. people who use e-mail primarily when they have something negative to say but are too evasive to say it face-to-face or put it in a more “formal” context vs people who consider e-mail second nature for any content, and people who are inclined to make the best of any news or situation vs people who feel put upon by any change in their workflow or knowledge state, which e-mail is so quick to deliver.

  • shaun

    I used to be fully against exclamation points, but I’ve found they add a air of friendliness to an email. As long as they don’t start making it into official copy. I’m slowly accepting emoticons. They work. Also, it never hurts to just call the person on the telephone when I suspect an email might start a chain of exchanges. A phone call gets it all done at once.

  • Scott McDowell

    Hey, thanks for the thoughtful comments!

    I totally agree–when in doubt phone or a quick chat can clear up many issues, and that many of us have a tendency to hide behind email. At least I do. 🙂

  • Kim Norvard

    That was a great read.

    I often look over my emails to see if I’ve set a positive or negative tone depending on the issue at hand.

    This article changed my view on emoticons in emails.
    From, like you state, looking at them as silly additions, to a tool to set the actual tone.

  • Jake Shakespeare

    The use of emoticons is an admission that the writer is incapable of expressing himself clearly in the language, and has to resort to pictures to clarify the message. Spend more time composing an email that matters, or enlarge your vocabulary–do anything but resort to cute little pictures.

    Try including emoticons in an email to a prospective employer or a university administrator, or anyone else whom you hope will take you seriously. Your message will go directly into the trash folder, as it should.

    Emoticons are emphatically not a tool; they make the writer look like a tool.

  • Josh Davis

    Amazing article.

    I worked for over five years as an online mediator, and I found that I adapted most of these practices to my work based on trial and error.

    Starting conversations by highlighting positives and then providing direction with questions, has to be considered best practices. You can get more pointed with familiarity, but I always try to keep those approaches in mind.

    Emoticons have helped set the early tone for some of my longest online relationships. Emoticons can be appropriate, but I would never start out a professional conversation with them. Once a rapport has been built, emoticons can function as a short cut to tone. They can be effective and keep messages from being overly wordy. Not everyone has the time to read a book in the form of an email. A winking or big smile emoticon might not convey a thousand words like a picuture, but it can be good for 100 words to set a tone.

    Great article. Really made my day to see these concepts written out and explained.

  • Moo

    You’re a tool. 🙂

  • elenacpotter

    Using emoticons correctly is a matter of familiarity or formality. I use them all the time in short, informal emails to colleagues I work closely with, or am on the same level with. Your implication that it’s a form of shorthand is true— so I think a good rule of thumb would be to ask, “am I comfortable using slang with this person?”

    If it’s someone with whom I have a less convivial relationship, or no existing relationship at all, I’d certainly not use them! And those are also cases where most people would spend a little bit longer working on the email.

  • David

    I think emoticons are a great idea, as long as they make sense :{(> (man who is unhappy about his ridiculous facial hair)

  • Filip

    I’m a student, and the last 2 years I started using emoticons ( mainly smiley) when communicating with my professors , and contrary to what I expected, they do react better, and tend to answer in a positive.

  • Tim

    YOU ARE TOO! >;)

  • Casey Armstrong

    Thanks so much for the Mavenlink mention.

  • pingsandneedles

    Whilst I agree that it is important to craft your writing so that communication is as clear as possible, I’m afraid I disagree with your claim that a message using emoticons would ‘go directly into the trash folder’ if received in an educational setting – it is simply not true and highlights a misunderstanding of their use.

    I teach at a Higher Ed institution and have taught at university. I also train teachers to use VLEs and to run online and classroom courses, where the communicative register is generally ‘neutral to informal’.

    In some situations the emoticon can come in very handy, especially when those involved don’t know each other very well, but need to communicate quickly and clearly.

    Emoticons are not ‘pretty pictures’ they are universal symbols which cross language barriers. I do not advocate the use of them willy nilly, but a smile, wink and frown can be incredibly useful when getting your point across to students AND teachers/tutors/professors.

    Tone of voice is notoriously difficult to communicate through email; the 😉 winking emoticon was invented to express irony in written communication.

    Language change is unstoppable. No amount of pedantic harrumphing will change that.


  • caesuras

    “Are you planning to take care of that issue?” could sound passive aggressive to some people. Perhaps an alternative is “Could you please take care of that issue? Thanks.”

  • 99U

    A very good point. We decided to tweak that recommendation, adding in some better language. Thanks for the feedback.

  • 99U

    A very good point. We decided to tweak that recommendation, adding in some better language. Thanks for the feedback.

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  • Stacey Acevero

    Nice post Scott. I am often apprehensive when putting emoticons in my emails, but am also often worried about the tone of the email coming off too neutral or negative. Infusing exclamation points makes it seem cheesy, so the tips you listed above seem like great alternatives and I’ll be sure to give them a shot. Thanks!
    –Stacey Acevero, Social Media Manager @PRWeb

  • Robin Kemp

    I am the Help Desk at our college, and I have to deal with frustrated students all day long. Some help requests come through email directly to me and some come through a chat forum. We use Google email (which has cute animated emoticons) and I use these emoticons in my replies to diffuse the frustration and let the student know “Hey, I’m on your side.” It pays off when students write that “the Help Desk person was very friendly and helpful”.

  • Talton

    I totally support the use of emoticons! While others may think it’s childish, it definitely helps break the tension in written communication. Skype has some good emoticons that help me out on a daily basis. Especially the hidden ones. 😛

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