5 Professionals Share Their Biggest Email Blunders

You’re moving quickly, hoping to eliminate some of the backlog from your inbox. You tap out a response to an unanswered thread and quickly hit ‘send…’ then it dawns on you. You accidentally hit ‘reply all,’ and now the entire organization received your two cents!

Luckily, this is one of the more benign email blunders, and one most of us have committed at least once. But some snafus involving electronic correspondence are slightly more embarrassing.

Here, five professionals share stories of email mishaps that serve as a gentle reminder to all of us—always give your message one more once-over before hitting the send button!

1. The Feline Faux Pas

Alexis Chateau is the founder and managing director of her own PR firm. She also doubles as primary caretaker for the office pet.

“One day, I got up mid-email to grab a snack, and didn't lock the screen,” Chateau says. “I returned to find that Shadow the PR Cat had tap-danced across the keyboard, and sent off a rather interesting email to a journalist I was speaking with on an important piece.”

Whoops! A furry faux pas to be sure, but surely one that anyone with a sense of humor would get a laugh over, right? Not so much.

“I don't think the journalist ever believed our cat was the culprit, and they did not reply to our apology. Our team had a good laugh about the mishap.”

Shadow’s mischievous activities aren’t limited to sending off unintentional emails; you can follow along with all his office antics at his dedicated twitter handle, @ShadowThePRCat!

2. The Unintentional Forward

Before launching his own search engine optimization company SEOJet, Adam White was doing client work for a large agency. One day a sales rep forwarded him a conversation with a client we’d describe as, um, *high maintenance.*

“He needed me to help answer her questions, which to me, seemed condescending and belittling,” White recalls. “Because I was only responding to our sales rep, I may have said something like ‘if this stupid woman would actually implement the changes I gave her…’ and then of course I answered the question.”

We all know where this one’s headed. The sales rep wasn’t too technically savvy, and ended up forwarding along the entirety of Adam’s message to the client, insult and all.

“Needless to say the client was not happy with me. I don't think they retained our services for much longer.”

Perhaps the golden rule of email is this: never write anything in a message that you wouldn’t feel comfortable with the world seeing!

3. The Mistaken Identity

When you manage multiple clients, sometimes they admittedly start to blur together. But in the best case scenario, a client always feels like she’s the only one.

That wasn’t the case for Howie Jastrow of Braniactive when he was simultaneously corresponding with two different clients.

“I was just typing too fast and doing too much and I called them by their opposite names,” he says. “It was pretty embarrassing, considering I run a small business and need to keep a positive reputation with all my clients.”

Don’t worry too much, Howie. Stellar customer service should make up for a name slip-up—so long as it’s a one-time blunder.

4. The Unfortunate Addressee

This is hands-down my email nightmare: sending an email about someone, to that person by mistake. It’s exactly what happened to Christoph Seitz, CEO of transport and shipping firm CFR Rinkens.

“A couple years ago, I accidentally sent an internal email laying out my grand strategy of how to decimate the competition to a key competitor,” he recounts. “It was one of the absolute worst moments of my professional life.”

Understandably so! The good news is Christoph used it as a teachable moment, sharing the blunder with his staff and even creating a new staff-wide mandate.

“I preach to everybody who will listen to check the send-to email addresses before hitting “send”. I also made it official company policy.”

A wise policy for all of us, indeed.

5. The Missing Word

Sarah Nelson is a customer service manager with B2B SEO firm Staylisted. She remembers an incident where she gave a customer a harsh dose of reality—unfortunately, it wasn’t what she meant to say at all.

“I was emailing back-and-forth with a difficult client who was requesting to cancel her services but was still within contract,” she says. “She said something to the effect of ‘is it your intention to upset me through email?’”

Sarah replied promptly, but one missing word changed the entire meaning of the message.

“I replied, ‘I am trying to upset you.’ Not only did I forget the word 'not', but I also sent the email without the rest of the response!”

I think we’ve all been there with a missing word or a premature send, albeit not in such drastic circumstances. Sorry, Sarah!

What have we learned here? Email at your own risk! Take your time, choose your words carefully and always, always double-check the recipient.

For more articles and humor created exclusively for entrepreneurs, subscribe to our blog.

You Might Also Like...

7 Crazy Ideas People Turned Into Businesses

17 Ways Being An Entrepreneur Is Exactly Like Being A Parent