Business Email Horror Stories — Where you Really, Really Didn’t Mean to Hit Reply All


Noooo! No! No! No! You’ve got a dreadful feeling in the pit of your stomach. A cold sweat is breaking out. You really need to take a very deep breath, but you’re just gulping for air. Yes. You did it. You hit “Reply All” when really you should just have hit “Reply.” Now, the secret conversation you were having with your colleague is all over the department, or worse, the company. Oh no! Did you copy in the CEO AS WELL?!?! If it’s any consolation, we’ve all been there. Take a small crumb of hope that you’re not one of these poor souls. Enjoy the schadenfreude.

The “Bathroom Incident”

HR isn’t always your friend. Someone was attempting to deal with a “crisis” in the employee bathrooms and needed help with the plunger. They got their HR rep involved who helped out — everything is good, right? Until, later that same day, you email the rep to thank them, and they then reply accidentally ccing in the whole company. Cue being asked into the boss’s office to explain “the bathroom incident.”

Ari Gold Would Have Something to Say

Pity the poor person who once sent an email with the words “Jeremey Piven” and only the words “Jeremy Piven” to everyone at an enormous media empire. Thousands of employees across the country were reminded of the Mr. Selfridge and Entourage actor. In case you need reminding how great Ari Gold is, here’s a reminder. (NSFW)

Well, You DID Want to Get Rid of Them…

How about that time a manager emailed HR to find out how to get rid of their outsourced development department. And accidentally copied in the outsourced development department? Yeah, that problem sorted itself out pretty quickly…

You’ve Got the What Now?

Another poor guy was tasked with getting a large order of shirts with a company logo on them. They finally came in, so he excitedly sent an email to the whole business letting everyone know “I’VE GOT THE SHIRTS!” except he accidentally left out the “R.” He didn’t live that down for a while.

Ready to Move on to a New Chapter? Not So Much…

“Female co-worker emailed the whole company about her change of name so I accidentally reply-all’d with “Congratulations!”… which wouldn’t have been so bad if she had just got married. It turned out she had a divorce and was going back to her maiden name. My boss didn’t see the humor.”

Sending Salary Details to the Whole Company is Kind of a Thing

If you think back to our last installment of “reply all” blunders you’ll remember the person who accidentally emailed the salary details of everyone to the whole business. Not wanting to be outdone, here’s the story of a contractor trying to iron out the details of working at a new business, “we got a ‘welcome aboard’ email that went out to the entire team welcoming this consultant to our ranks. The email was essentially: “Reply All: Re: Re: Re: Re: Fwd: Fwd: Re: Re: Fwd: Job Offer Including Salary”. To make things even better, this young guy was starting well above the salaries of people who were decades his senior and who had worked there for many years.”

So, the next time you want to reply to an email, stop. Take a moment before you hit send. Double check the to, cc, and bcc recipients. If you’re using Gmail you can also set up a “delayed send” function so you can stop an email if you realize just after clicking “send.”