4 Ways to Avoid an Outlook 'Oops'

Have you ever accidentally sent a sensitive e-mail to the wrong recipient? If not, congratulations; if so, welcome to the other 99 percent of the workforce.

I'm incredibly careful about sending out e-mail, since as a journalist I'm often under non-disclosure agreements, but even so I've still made the occasional gaffe. That's why I was happy to read Steve Levy's post at No Secret that suggested four ways to minimize "oops" e-mail in Outlook.

I'm pretty Outlook-savvy, yet two of them were new tricks to me -- and they're all worth sharing.

1. Get rid of unhelpful recipient suggestions. You know how when you start typing in a name or e-mail address in the "To" field, Outlook suggests some autocompletions? That's helpful most of the time, except when you hit "enter" too soon and your e-mail flies off to Jan, the problem client, rather than Jane, your best friend.

To get Outlook to remove an autosuggestion, open a new mail. Type the first few letters in the "To" box until you get the list of suggested names. Use the arrow keys to pick the one you want to get rid of, then press Delete. However, cautions Levy, make sure you type at least one other name in the "To" field before your cancel the name; Outlook apparently doesn't record the deletion until then.

2. Never use a current e-mail to look up a name. It's a nice feature, but if you accidentally insert that name into your e-mail, you're going to be sending it off unintentionally. If you have to look up a name, just create a new (blank) e-mail to do it. Then delete it when you're done.

3. Use an automatic delay when sending mail. Here's a cool trick: You can create an Outlook rule that automatically buys you some time. (By the way, this is also helpful if, like me, you sometimes send out e-mails that say something like "Here's the file, guys!" and then forget to attach anything.) Go to Tools â€"> Rules and Alerts â€"> New Rule â€"> Check Messages After Sending â€"> Next (leave the first part of the rule blank) â€"> Defer delivery by a number of minutes (I use 5) â€"> Next -- and then set any exceptions you want.

4. Think before you type. Don't diss your boss (or co-worker, or client) in an e-mail. Don't use off-color or sexist language. As Levy says, don't start a sentence with, "This might be illegal, but--".

Oh, and for non-work, "I wish I hadn't written that" e-mails, don't forget Google's Mail Goggles, which checks with you to make sure you really, truly, want to hit "Send."