Does this situation sound familiar?

You’re writing a business-related email, which you conclude with a sarcastic remark. Consequently, you feel the need to use—yes—the smiley face emoticon.

What do you do?

Emoticons like the smiley face have made tremendous headway into businesses the last few years. It seems that only a few years ago, smiley faces were merely for text messages. Soon, they started showing up on social networks such as Twitter and Facebook. Now, they appear regularly in business emails.

Is that devaluing business communication?

Does it impact your perception of the sender of that message?

Does it make the sender of the message seem younger or more immature? Or is it a way to humanize our email communications throughout the day?

Is it a way to have a little fun in what can be an unbearably dreary workday—put a little personality into our business communication?

Bottom line: Are emoticons OK in the professional workplace?

It depends.

If I’m writing an email to the CEO of a key client, an emoticon is not acceptable. I want the email to be taken seriously, so it needs a buttoned-up, professional feel.

If I’m writing an email to a client I’ve known for years—a client that’s also a friend whom I see outside the workplace—and the note is more lighthearted in nature, then yes, it’s perfectly OK to use an emoticon.

I probably err on the side of being extra chummy with many of my business contacts. In some cases, people might say I lack professionalism. But I would say I’m building relationships.

As a consultant, I know clients want to work with people they like. It’s hard to do that if people see me as a robot who’s incapable of having fun or showing personality. So, I see smiley faces and the like as a way to lighten up business conversations from time to time.

What do you think? Are smiley faces OK to use in your business email communications?

A version of this story first appeared on Communications Conversations.