We all know that sinking feeling. We hit “send” and realize we made a massive mistake. Oh yes…we all are guilty of email fails.
But once it hits cyberspace? It’s gone. There’s no going back.
Yes, you can hit “recall this message.” But this only works BEFORE your email has been opened, IF the email is on Microsoft Exchange Server, and PROVIDED you sent the email to a user within the company. I mean, what are the odds of THAT?
Sometimes the mistake is as innocuous as forgetting to add an attachment. Sometimes it is as egregious as hitting “reply all” when you really want to only reply to the one person to say how difficult your boss (also on the email chain) is to work with. Oops.
We’ve all been there but by literally taking a five-second pause to scan your missive, you can avoid most email snafus.
1. Check the “To” line. Check it again. Check it ONE last time.
I have learned this the hard way. Complaining about a coworker. In vivid, vibrant language. Wondering why our boss doesn’t do something. Sending it to another co-worker. I think. But since I’m inadvertently thinking about the boss, somehow her name ends up in the “to” line. Oops.
Or it could be that as you type “K-e-n” your email program fills in “Kendra,” whom you had emailed earlier that day to get some financial information. But Kendra was so slow getting it to you that you really are trying to email Kenneth to complain about Kendra. Oops. Sorry, Kendra. Now I’ll never get that information.
2. Know the difference between “reply” and “reply all.” Make “reply” your default choice unless you know for sure you want to “reply all.”
This is similar to the “to” line above, but sometimes “reply all” can include hidden names. For example if the “to” line says “Jennifer” and the “from” line says “Jennifer,” then Jennifer sent a huge list of bcc emails. And your response is going to all of them.
Even after all these years of being a savvy emailer, “reply all” can trip up even the smartest professional. Make it a habit to never click “reply all” unless you have checked each and every name on the list.
3. Is your attachment included?
Duh. Seriously, how many times have you sent or received an email that needs an attachment and it’s not there? Two seconds later (hopefully) the sheepish “Oops, forgot the attachment” email comes through. Or, if you are the sender who forgot to send the attachment, bam, here comes the flood of messages: “What attachment?” “I don’t see an attachment!” “Where’s the attachment?!”
4. Double-check the attachment.
After you have attached the attachment, OPEN it as it sits in the attachment line. Many times what you think you have attached isn’t. It might be an older version. It might be a similar-sounding document. Track changes might show up. You might have thought you modified it but then didn’t save it correctly.
5. If you are replying or forwarding, scroll all the way down to see what else has hitched a ride.
Sometimes you think you are just replying or forwarding the initial message, but below your long email signature could be a whole separate string that might not be appropriate for all eyes.
Bonus tip: Check the “To” line. Oh, did I already say that? Well, check it again!
The five seconds it takes to double-check each of these common email mistakes can help you avoid embarrassment or career suicide.
What’s your best/worst email fail? C’mon, share! Misery loves company….

