Why a wink and a smile won't wash

Q I sent my boss an e-mail informing him of the results of a pitch we recently did. Due to the downturn in the economy, there has not been much new business to go for and so I thought that as the pitch seemed to go well, I would try and cheer him up with a bit of good news. I mentioned that the marketing director of the company we pitched to was flirting with me and that I might have to "take one for the team" if we were to win the business.

David Emin is director of advertising at Mirror Group Newspapers
David Emin is director of advertising at Mirror Group Newspapers

I signed off with the emoticon ;-) but he e-mailed back straight away saying that my e-mail was very unprofessional. I'm confused, as I am not sure if he was referring to my reference to the fact that I suggested sleeping with the marketing director to secure the business or to the "I'm winking" design. Which do you think upset him?

ATo some of us older generation, emoticons are often considered a bit of an enigma. This is surprising as they have been in existence since the 1800s, but with the advent of text messaging, online games and web forums, they have increasingly become used as a textual way of demonstrating a writer's mood or facial expression.

However, it is not always obvious to the recipient of the message what is actually meant by a particular emoticon.
I used to get e-mails from a certain individual who would always sign off with (_x_). I used to think this was a term of endearment until someone pointed out this actually meant "kiss my arse". Needless to say, I was not impressed.

My guess is that your boss wasn't either. Save the smiley face for friends and keep your e-mails succinct and business-like. After all, he might well have wanted to forward your message to his boss, but was unable to because of its content.

As for "taking one for the team", I'd like to think you were just joking and that this was a throwaway remark. If this was the case, might I suggest this kind of remark is best said face-to-face, rather than via e-mail.

Even using an emoticon might not get across the fact that you were not serious. And because you were not face-to-face, it is not always easy to detect how a statement has gone down with the person on the receiving end of the information.

Being in front of someone enables you to immediately judge their reaction and explain immediately that you were not serious.

Of course, if you were serious, I shall forward you the date of when our business is next up for review. 

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