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Illustration: Oscar Ramos Orozco

Email Strategy

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.

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Illustration by Oscar Ramos Orozco.
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