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Contest: The e-mails you wish you hadn’t sent

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This post is from Brooke Howell, a business editor at SmartBrief.

A couple of weeks ago my sister and I opened our e-mail to find an outrageous message from our father that ignited more than a little bit of drama in our family. He later said that he regretted sending the message — written in a fit of frustration and anger — the second the e-mail was whisked out of his sent folder.

Luckily for good old Dad, we’re family and won’t hold his e-indiscretion against him for long. But co-workers and professional contacts are unlikely to be so magnanimous.

The speed of e-mail combined with the minimal human contact it requires compared with a phone or face-to-face conversation makes it easy to send messages you wish you hadn’t. Still, there are some simple tricks to help avoid coming down with a serious case of e-mail regret. My personal prescription has three parts:

  • Address it last. I think it’s silly that the address field is at the top of every e-mail compose window. It makes people think that they have to fill in the address first, which puts them at risk for accidentally sending an incomplete, unpolished or ill-conceived e-mail. Whenever I’m typing anything that should be polished, such as to a superior, client or someone who doesn’t know me well, I  write and edit the message before I enter the address, so it can’t be sent early by accident. I do the same when I’m writing while angry or in some other heightened emotional state.
  • Let it sit. If you are writing while angry, frustrated, sad, etc.; don’t send the message as soon as you type the last character. Whenever you can, sleep on it for a night, then review and edit before you address it and hit send. If it can’t wait that long, give it at least 10 minutes. You may even change your mind and opt to hit delete.
  • Run it by a friend. Don’t hesitate to have a trusted friend or coworker read through a sensitive e-mail message before you send it. She’ll tell you if it’s too harsh, rude or unwise in some other way. This is especially useful if you, like me, are prone to telling it like it is in a not-so-gentle manner.

Do you have an e-mail disaster story to tell? Share it in the comments of this post, and we’ll pick our five favorites to feature in the brief.

Image credit, iStock