Do you think what you send across the Internet is private as long as you’re careful? Think again. Here are just a few things that have happened over the years to some of my friends, and to myself:

I didn’t realize Auto-Complete would send my mail to the wrong person

We’ve all misdirected mail when we have people with a similar name in our address books. Steve Laube shared a story with me that happened years ago:

Many years ago I sent contract questions, in an attachment, to an author instead of a publishing executive. The problem was that the author was not associated in any way with that particular deal. Both had the same first name and the computer filled in the rest without me checking carefully. The author was gracious and let me know he did not open the attachment and deleted the email.

A lesson we have all had to learn, the hard way. One way to prevent it is to turn off the Auto-complete feature. Or better yet, double check everything before hitting the “send” button.

I thought the message I sent in response to a loop post was just going to one person but it went to the loop.

Maybe. Maybe not. I’m on several loops, and I can never remember without referring to the address field. Always, always, always check before dashing off a message meant for one pair of eyes only. And while you’re at it, think about the message itself. If it’s a deep, dark secret, should it be addressed in an email? Again, maybe going offline would be better.

We’ve all made this mistake, and I’ve seen people write a second message saying, “So sorry I sent a message to the whole loop saying that Felicity and I are supposed to meet at Holy Grail Grille after the book signing in Richmond on Saturday. That was just supposed to go to Felicity.” While the first message isn’t an embarrassment, by sending a second message apologizing for the mistake, you’ve created yet another reason for 800 people to press the delete key. I say don’t worry about it. I understand the impulse to apologize, and as much as I advocate being the epitome of politeness, I think this is one time you can let it go. Everyone will figure out that the original message was meant for Felicity and move on to the next email.

I thought I could trust the person I emailed not to share with anyone else. 

Sometimes you can. Sometimes you can’t. And you won’t know if you can’t until it’s too late. Too often someone will share with someone else if he promises not to share with anyone else. But even then, your unflattering words were spread to a third party. The second party has violated your trust, and the third party may be in a position to cause you damage. The real disadvantage here is that by putting negative opinions and feelings in writing, you’ve unleashed the potential for private thoughts to be spread all over the Internet without your permission. And, since the missive is in writing rather than a retelling of a conversation, it’s hard to refute with, “I’m sorry, Felicity misinterpreted. Let me explain.”  Feelings expressed in writing don’t have the advantage of voice inflection or facial expressions to tone them down. They are bare, and if angry, can seem even more brutal than you ever meant. Again, better to take hurt feelings offline.

But I must be honest.

Of course you should be honest. And sometimes you need to make points in writing for the person’s reference. One technique I learned years ago is the sandwich. Open with something positive, then move into the thoughtful and careful expression of whatever negative thoughts you need to share, and then close with a sincere compliment. No matter how bad a situation is, there is always something good you can say. Engaging in the sandwich method will also make you feel more positive. Everybody wins.

Most of all, whether you are talking in person or through email, always show love and compassion. One day you’ll need both, and will be glad for the understanding and consideration of others.

Your turn:

What’s the worst email you’ve ever seen misdirected?

Have you ever seen reconciliation and forgiveness occur as a result of misdirected mail?

What tips do you have about sharing negative thoughts in a kind way?