Pin Me

Oops! Did I Hit the Send Button on That Email?

written by: Donna Cosmato • edited by: Tricia Goss • updated: 8/27/2014

Loose lips might sink ships, and fumbling fingers could sink your career. Most people are careful to watch what they say out loud at work as they realize inappropriate conversations could damage their career prospects. However, what happens when you send an inappropriate email to the wrong person?

  • slide 1 of 4

    Did I really hit the reply all button? 

    A while back, Steve Yegge made the viral history books as the person who committed what he called in his own words, “…what must be the great-granddaddy of all Reply-All screwups in tech history."

    If you missed the story, Yegge accidentally emailed a rant about a former employer, Amazon, and his current employer, Google, to the digital universe instead of to a more selective list of internal recipients.

    If you have ever experienced that feeling of dread following the realization that you just sent an embarrassing email to the wrong person, you can empathize with Yegge. As it turns out, rather than being in the minority he is in the majority. It seems this is a rather common technology goof.

    According to a survey conducted by security vendor Sophos that asked if respondents had ever sent an embarrassing email accidentally, “The numbers were shocking as 50 percent of the employees said they already sent embarrassing messages to another person."

    Okay, the damage is done, so what happens next? Let's talk about that next.

  • slide 2 of 4

    I Shouldn't Have Done That!

    Oops! I bet I'm in trouble now! 

    Okay, so the unexpected has happened and that embarrassing or highly confidential information is sitting in someone’s inbox like a ticking time bomb --waiting to blow up your reputation or your relationships. What is the potential fallout?

    For starters, depending on the message’s content and who actually received it, you could be looking at consequences that range from short-term egg-on-the-face to long-term, extended court battles:

    • If you inadvertently share confidential or proprietary information, you could be liable for prosecution.
    • If you expose the fact that you are having an affair with someone, you could face an ugly, expensive divorce.
    • If you offend or insult someone, you could lose a friend or damage a relationship beyond repair.
    • If your remarks are derogatory or libelous, you could be sued.

    The list could go on and on, but let’s not belabor the point. There is a simple formula that we teach the kids in our children’s church to help them avoid embarrassing situations like this. Even though this is designed for elementary students, you might want to try it. It could save your job or your relationships. Before you say or write something about another person, put it through this filter.

    1. Is it true?
    2. Is it necessary?
    3. Will it help or hurt the other person?
    4. Would your parents approve of it?
    5. Would God approve of it?
    6. Would you say the same thing if you were face-to-face with the other person?

    Obviously, if you cannot answer “yes" to all of the above, it is best not to write (or say) it.

  • slide 3 of 4

    I'm Sorry

    I'm really sorry.... 

    Just as you can't stick your hand into a mailbox and pull out a letter you didn’t intend to mail, you cannot stick a virtual hand into the digital world and retrieve an email that is headed to the wrong person. (In most cases, that is. We’ll discuss this aspect more in a minute.)

    What's done is done, so how do you mitigate the damage? Well, when you are swimming and start to drown, if you panic, you will probably die. Therefore, keeping calm and assessing the situation logically is your first step. You know the email didn’t go to the right person, so to whom did it go? Figuring out where it is and how that affects you comes next.

    Contact the recipient(s) immediately because the longer you wait, the worse it could get. With any luck, you can reach the other person before he or she opens the email. If you grovel enough, they might just delete it without reading it. In this scenario, you have learned a valuable lesson but you escaped the situation relatively unscathed. I bet you double-check the “To Field" the next time you send an email.

    However, if the worst has happened and the other party has read the email, now you have some damage control to do fast:

    • Confess. I know it hurts and it is embarrassing, but this is a case where honesty is really your best policy.
    • Just admit you made a mistake and take the heat without making excuses or trying to justify what happened.
    • Ask for forgiveness.
    • Saying “I’m sorry" is hard.
    • Saying, “I’m sorry. I was wrong; please forgive me" can be extremely painful but it sure shows your moral character.

    It takes guts to admit your failures, but it could be the key to salvaging what is left of a career, friendship or relationship.

    While I can’t speak to all email systems as I’m not familiar with them, there is a way to set your Google Gmail to give you a chance to retrieve an unintended email before it wrecks your life.

    1. Open your email and navigate to the settings at the upper right hand corner.
    2. Click mail settings.
    3. Click the lab tab.
    4. Enable the undo send function.
    5. Save your changes and exit.

    Before you write that rant, send that email, or post that inflammatory blog post, pause and think about how it could affect you. After all, you'll be living with those words for a long, long time. How will they taste if you have to eat them?

  • slide 4 of 4

    Share Your Thoughts and Experiences

    How about you? Have you ever inadvertently sent an embarrassing email to the wrong person? Even worse, have you ever received an unflattering email about yourself or a friend or relative? Please share your experiences with us and let us know how you handled the situation. We're waiting to hear from you!