Have you ever accidentally sent an e-mail before you were done? Or sent something that you immediately wished you hadn't? I had done this enough—and caused myself enough embarrassment—to think about ways to avoid it the next time. My first attempt was remembering to double-check my e-mail before sending it. This worked for a bit, but failed during busy days. My second attempt was more high tech. I created an Outlook rule that sends my e-mail two minutes after I click Send. That way, I have another barrier to catch e-mail messages that I mistakenly send. I have two minutes to recognize my mistake and delete the message before it goes public. I set up my rule about a month ago, and it's saved me three times. That doesn't sound like a lot, but those were three e-mail messages that would have been embarrassing at best.

The delay can be annoying when I'm having e-mail conversations with people and want to send a quick response. In those cases, I've come to rely more on instant messaging.

To create the rule in Outlook 2003:

1. On the Tools menu, click Rules and Alerts.
2. In the Rules and Alerts dialog box, click New Rule.

   

3. In the Rules Wizard dialog box, click the Start from a blank rule radio button. Under Step 1, highlight Check messages after sending. Click Next.

   

4. In Step 1, select defer delivery by a number of minutes. In Step 2, click a number of to set the number of minutes that you would like to delay delivery.

   

   In the next dialog box, select the number of minutes you would like to delay delivery. I choose 2 minutes. Click OK. Click Next.

   

5. Select any exceptions to your rule. I didn't choose any, but you might find some that are appropriate. Click Next.

   

6. In Step 1, give your rule a name. In Step 2, turn on the rule. Click Finish. Click Apply.

   

Now when you send a message, it will stay in your Outlook Outbox for 2 minutes before being delivered. If you send an e-mail by mistake, go to the Outbox and delete the message before your mistake goes public. Believe me, this may truly save your tail.

—Jason Kozleski