Do you have a “Reply All” horror story? Have you ever realized, seconds after hitting “Send”, that your message was going to someone who really, really, really  shouldn’t get it?

Most of us have — Reply All is simultaneously a wonderful convenience and an easy way to damage your career by sending sensitive information to the wrong person.

Photo Credit: Ed Yourdon via Compfight cc

When one of my sons was in middle school, we had an extended email argument with the Vice Principal about a 7th grade teacher assignment. Eventually the Principal joined the email chain. Vice Principal got fed up with me and sent an extremely candid assessment of my personality to his boss.

Of course, he used Reply All to do it, and I received his colorful assessment in my inbox. Five minutes later, I received an abject apology… and the next day he caved in on the argument.

Although I benefited from that particular fiasco, I’ve been on the other side of that issue on several occasions, and often wished that there was a way to take an email back after sending it.

About three years ago I discovered the next best thing: Reply All Monitor by Sperry Software. It’s a $14.95 add-in for Outlook that pretty much does one thing: it warns you when you’re about to reply to everyone. That “one thing” can be a biggie.

For example: you get a group email from your manager, asking if everything’s okay with the Bainbridge account. You want to tell your boss, in confidence,  that one of your team members is a butt-head. You’re trying to multitask, and you hit Reply All by mistake.

That’s when Reply to All Monitor kicks into action:

“Hang on just a minute there, Hoss!”

Reply to All Monitor does a few more things as well: it will notify you when you are about to Reply All when you’ve been BCC’d (so that you don’t inadvertently give up your anonymity), and tip you off when you just hit “Reply” on a group email (in case you genuinely wanted to reply to everyone).

The big picture is this: it slows you down and makes you take one more step before you do something stupid. That one extra step has saved me from heartache and despair an average of three times a year since I bought it.

Question: What’s the worst message you ever sent, or received? Got a Reply All horror story? You can leave a comment by clicking here.