Have you ever accidentally sent a too-honest email to the wrong person? I have. But never so egregiously as a friend of mine — I’ll call him Curtis –did years ago. I was working at PC World and he had just joined the staff. On Curtis’ first day, the publisher sent out a formal announcement of some kind that Curtis found ironic. So he forwarded it to me with a funny – but not very flattering – comment about the publisher. Curtis ended his message with a tongue-in-cheek invitation (intended only for me) to a party. He joked about topics inappropriate to the work place — drinking, dancing on tables, and other forms of hilarity – that made him seem like a post-fraternity party animal — living in a blur of beer pong and keg parties. I knew Curtis was joking and that he is a serious, intensely intelligent, and gifted man. I also knew he was inviting me to what would be a quiet and civilized party. But I was familiar with his particular brand of humor. Unfortunately, he copied the entire company – including the publisher he was making fun of – on the message. And, this being his first day, no one else was familiar with his wit. The publisher responded – copying the entire company – with a rather public spanking about appropriate use of corporate email. And for days afterwards, people accepted his party invitation– each one making a joke at his expense. It was very funny for all of us who were not Curtis (or the publisher). But — to this day — bringing up that incident gives Curtis a stomach ache and a bout of anxiety.

This sort of incident — I’m sure it gives Curtis no comfort to know – is extremely common. According to the Risky Business: Reputations Online survey of 703 senior executives conducted by Weber Shandwick 87 percent of executives reported they have mistakenly sent or received an email or other electronic message. Many of these mistakes were much worse than Curtis’ blunder. “The head of human resources at a major advertising company,” says the report. “Mistakenly sent an e-mail intended for senior management to its entire employee base. The e-mail included information on impending layoffs and talking points that management should use in delivering bad news to the organization. The e-mail was later leaked to the media. This fiasco generated more than 3.5 million hits on Google one week later.”

Ouch!

Even if you aren’t likely to leak anything as sensitive as that to an audience of millions, it is nonetheless embarrassing – and potentially dangerous to friendships — to accidentally copy someone on a conversation they weren’t meant to hear. If you use Gmail for email, there is a new safety valve for this sort of thing. The Google folks recently rolled out an experimental feature called “Undo Send.” Just hit “Undo” in your email confirmation to return the email to draft form so you can remove the recipient (or recipients) who shouldn’t get the missive or fix a typo – or take out that reference to beer pong. This feature gives you only a 5-second window to call back the mistake. But those five seconds would have saved Curtis a world of hurt — if he’d been using Gmail.

Another Google Labs tool that could save you embarrassment of another sort is Google Mail Goggles. Personally, I have a rule: Never drink and click. If so much as a sip of wine has passed my lips, no email, no blogging, no Facebook. But some people haven’t learned this. In fact, according to one survey, 39% of people surveyed email while they are at bars or clubs. Those people should seriously consider wearing goggles. Here’s how it works: If you try to send an email late on a Friday evening, Gmail will ask you to do a basic math test before allowing your email to go out. Can’t do the math? Don’t send the message! If you have another danger time or are a nerd for math, you can tweak the time of day when you get tested as well as the difficulty of the math.

To turn on either of these features, and many others, go to Settings from your Gmail account, click the Labs tab, and click “enable” next to the features you want.