The New York Times: E-Mail Saves Time, but Being There Says More
“Emoticons are ‘intended to represent a facial expression and to convey the sort of emotion that plain text does not,’ it says in the Webster’s online entry about those typographical symbols that turn up in e-mail messages.
Emoticons may work in personal communications. But Don G. Lents, the chairman of Bryan Cave, the international law firm, said he doesn’t like seeing them in business communications. If you’re depending on a smiley face to communicate a thought to a client or a distant colleague, he tells young lawyers in his firm, you should probably step away from the keyboard, get on a plane and communicate in person. Especially if the communication involves any kind of dispute.”