I’m confident most of you are probably pretty clear on email etiquette. You know when to forward a memo to a colleague and when to CC your boss on a thread. You even know when to implement the sometimes confusing BCC option (or do you?). And, depending on who you’re corresponding with, you probably also know when to respond and when not to.

And yet, it turns out that CC/BCC/Reply All still trips people up—and not just recent grads who are just getting the swing of things. After listening to my colleagues talk about their embarrassing email “oops” moments, I reached out to my network to see what other incidents have occurred over the years. Turns out? Well, those little email labels can have a big impact, both good and utterly disastrous—and big lessons for the rest of us.

Let’s kick it off with this anecdote from Felipe, a web developer, whose co-worker learned the hard way that thinking before you CC and press send is not only prudent, but career-saving:

For the one-year anniversary of 9/11 my co-worker Judd took off from work. Because it was for 9/11, one of his colleagues, Larry, illustrated a cartoon depicting Judd as a scared child-fearing terrorist. It showed Judd hiding under his bed squeezing a teddy bear. Larry sent it around to a small group of co-workers and their manager as a joke. For some odd reason the manager on the thread emailed the cartoon and CCed the entire company. The company had over 500 employees. A couple of hours later the CC-everyone manager was fired and escorted out the building for good. Oops!

So, lesson one: If you’re going to CC a whole bunch of people, make sure it’s going to be well-received.

Danielle, a director of career services in higher education, does just that. She uses the CC field to celebrate her colleagues’ accomplishments. “Sending out emails to our entire campus giving shout-outs where needed is good for morale,” says Danielle, who also likes the CC option for helping someone stay in the loop and encouraging him or her to be proactive.

A word of warning, though: While the shout-outs typically result in piggy-back shout-outs, sometimes enough is enough. Amanda, a talent acquisition coordinator, recalls a job at a bank where “They had this one guy who was infamous for replying all to say ‘thanks’ or ‘much appreciated’… Every. Single. Email. Even if there were 50 people CC'd. There was a running joke about him and really got people annoyed,” she explains. Eventually one of her frustrated co-workers called the offending responder out and explained the basics of email.

James, a copy editor, knows all too well the problems that can arise when too many people are messaged. He recalls an incident from his college years when the off-campus student council once accidentally sent a message to its entire listserv, rather than BCC all of its members. The result? A week of reply-all chaos for 3,000 students. “Good times,” says James, shaking his head, no doubt remembering the fullest inbox he ever had.

To some individuals, however, BCC is just bad business. Jessica, an early childhood specialist based in Brooklyn, has this to say about it:

I don’t like BCCing. I like transparency. It’s always the people who are ‘reply all’ happy that ruin it. In my current role I need to send out group emails to communicate time and location info as well as request feedback periodically. Even if I write in bold italicized letter at the top of the email, ‘Do not reply all to this email,’ inevitably, someone always does. Sigh. Therefore, I’ve taken to BCCing everyone and only CCing my team. That way, if someone ‘replies all’ not everyone will be subject to their thoughts, opinions, and feelings.

Writer and editor Sara doesn’t feel as strongly about the use of BCC as some, but she believes there’s a trick to it:

Anytime you want to BCC someone for the purposes of showing him an email meant for someone else, ask yourself: Could I send the email to the intended recipient (without a BCC), and then forward it on to the additional contact? It feels a lot more honest, because instead of looking like you’re hiding who you’re sharing the email with, it looks like you sent it per usual and then thought, ‘Oh, maybe I should share this with my boss for her reference.’ It's more ‘Let me make sure my manager is looped in’ and less ‘Spy on my communication with so and so,’ which is always nice. Plus, that way you’re covered if the BCCer ever brings it up!

It’s not just CC and BCC that causes confusion. The deceptively simple ‘Reply’ has been known to make more than a few people sweat. Rebecca, an account executive, admits to pressing ‘Reply’ when she meant to hit ‘Forward.’ As president of a club in college that was putting on a big event, Rebecca was dismayed to learn that the space the club planned on using was double-booked. In her haste to share her fury with the rest of the exec team, Rebecca typed out a slew of expletives aimed at the club owners but intended for her colleagues’ eyes only, and instead of forwarding, she accidentally replied! Rebecca learned a lot of things from this incident, including, “Make sure you’re sending your messages to the correct person,” “Don’t send emails when angry,” and, most importantly, “Don’t be an immature idiot when sending emails to real people.”

Make sure you’re sending your messages to the right person is advice Mark, a sales manager, wishes he had paid attention to several months ago before he sent redlined contract edits to the wrong person. Upon realizing his error and freaking out that he’d lost not one but two deals, Mark sent out the requisite apologies and hastened to patch up the damage he’d caused by being careless. He landed only one of the two deals and is quick to say that the company that pulled out for budget reasons didn’t do so because of his mistake—“though I’m sure that didn’t help.”



While there may be a difference of opinion in when to use which field, there are some lessons to be learned from these colorful anecdotes. And if you want my opinion? Don’t be that obnoxious reply-all person, avoid the power CC, and don’t forget to actually move someone to BCC if you say you’re doing so.


Photo of shocked man looking at computer screen courtesy of Shutterstock.