THE 3 most embarrassing business emails/texts: Can you beat it?

In my selling skills programs, I almost always spend at least a few minutes with the group talking about what email etiquette is today. One thing groups always ask is how to deal with humiliation like when you send an email/text to the wrong person.

Here are some examples of the most embarrassing messages sent (but you may be able to beat these!):
As a new catering manager, figuring out attrition charges seemed really difficult. So when her client emailed her asking about the costs due, she wrote the following email to her director: “I am so dumb and I am sorry. Can you figure this out for me?” But instead of sending it to her director, she sent it to the client. Wait, it gets worse. She didn’t realize she had sent it to the client until she received an email back saying: “I’ll try but I really thought this was your job.” What an amazing client!

And there is the text-er who intended to text her husband, “Why am I still at work? She won’t let me leave. FML” and yup, texted it to the boss. Her boss texted back, “What does FML mean?” Neither she nor I knows how she kept her job, but she did.

My worst story happened years ago (but I still cringe big time): I worked on a proposal until about 2a for a new client. I was so proud of myself for getting it done, and still awake, so I rewarded my good behavior by writing a long email to a friend asking if she agreed that it was time to break up with my then boyfriend. I was extremely graphic in my descriptions of why I thought it was time to break up. Then I sent the email to the new client. In the morning, I received a brief email from him that simply said, “I concur. Break up.” No, I didn’t book the business but it was a good thing because there is no way I could have met him face to face!

What about you? What is your most embarrassing email/texting story?

Oh, and the solution? Check the to line before sending or be smart enough to add the recipient’s name after you write and review the email. It is so worth it!

And if you do send the wrong email to the wrong person, immediately – do not stop to talk this over with your manager, your BFF, yourself – pick up the phone and fess up. “Hi Name, this is me and I am mortified that I just sent you an email that was intended for someone else.”

Do not try to recall. That just makes it worse and doesn’t make the message disappear.

Depending on your relationship with the person (like with my new prospect, all I did was send a thank you for being gracious about this and I never followed-up, and neither did he), you can continue speaking the truth, “Can we talk about the email? I was feeling really frustrated and never should have said what I did.”

Let them talk. It’s very likely that they’ll say something like, “Thanks for your honesty. I did this myself once and know how it feels. By the way, I still want my concessions plus X and Y.”

Business and relationship saved!

What is your most embarrassing email story? The best one gets a free copy of the ” title=”Power Sales Writing: 2nd Edition”>Second Edition: Power Sales Writing. It may be too late for you for the last time but you’ll learn lots of awesome ideas for your next email!

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