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5 People Share Embarrassing Work Emails You'll Be Glad You Didn't Send

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Workers today rely heavily on emails, but mistakes can happen. We asked professionals to share the most embarrassing work emails they've ever sent.

We've all sent an email and then cringed when we realized we spelled someone's name wrong or forgot to include an attachment. But mistakes like that won't seem like a big deal once you read about these embarrassing work emails. You can even learn from their mistakes.

Don't Offer Preemptive Congratulations

''I once congratulated a coworker on being pregnant over email. Turns out she was not pregnant. It was by far the most embarrassing email I have ever written, but I smoothed it over by offering to cover for her when she needed to take a day off.''

-Zach Hendrix, Co-founder of GreenPal

''Aside from running my own business, I help others market their businesses. One of those people owns a company, Dekomats, which makes printed custom golf cart mats. I sent out an email blast to 7,000 people at The Villages in Florida about the golf cart mats but put a link by mistake to my business that offers a medical device for women who suffer from pelvic pain! Let's just say we got a lot of phone calls and emails from surprised customers. It blew over in about a week. It was so embarrassing then, but something I can laugh about now.''

-Tara Langdale-Schmidt, Founder of VuVatech

A man is embarrassed

Be Careful When Reusing Materials

''One of the most embarrassing mistakes I made early on was sending a client a proposal and on one slide I had accidentally left the name of the prior client on the proposal. I was mortified when I was walking through the proposal with the client. Fortunately, he laughed and didn't think it was a big deal. That said, to this day, I double and triple check proposals or anything of the sort to ensure that doesn't happen!''

-Carlos Castelán, Managing Director of The Navio Group

Beware of Typos

''Me: That is exciting news! We are grateful for the opportunity to work with you. I will have Jill, my dance manager, send you an updated contract with the changed signature line.

Me: I am so embarrassed. That's what I get for quickly typing while I'm on set on a video shoot! Jill is actually not my dance manager (though I could use one). Jill is our finance manager.

Client: Haha I was just thinking we'd be getting more than we're paying for if Jazzercise is included! :) I'll keep an eye out for the updated contract.''

-Jeff Terpstra, President of Scott Allen Creative

Someone has received a new work email

Forward Emails with Caution

''Once I received a pestering email from a client. The client requested that her file be sent immediately, though we had already discussed that it would be available by the end of the week because of more pressing matters. I clicked 'forward' and added an eyeroll emoji and thought I had sent it to my coworker. Unfortunately, I didn't; I sent it back to the client. Gmail has the new 'Undo' feature on its mail, but that's only helpful if you notice your mistake as soon as it's sent. For me, I didn't realize my mistake until I went to respond to the initial email several hours later. I figured it would be best to not bring it up, and thankfully, she didn't bring it up either. However, she was not a repeat client.''

-Lauren Crain, Digital Marketer at HealthLabs.com

* Submissions have been edited for clarity and/or length

Do these stories having you feeling like you want to brush up on your workplace skills? Check out Study.com's business courses, including business communications, to develop important knowledge.

By Jessica Lyons
September 2018
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