The 10 Embarrassing Emails We’ve All Regretted Sending

Oh no. You didn’t really hit “send” on that did you? You did? Oh no.

We’ve all been there, staring at our screen, face turning red, and wondering when our unfortunate recipient is going to read the message you never should have written in the first place. Embarrassing emails are a calamitous yet inescapable feature of any workplace, and you’ll be grateful to know even the best emailers among us have likely encountered the occasional embarrassment.

But if you want to improve your reputation in the workplace, and minimize your chances of humiliation, it pays to learn more about these email archetypes—including how they’ve happened in the past, how they could happen in the future, and most importantly, how to prevent them altogether.

In this article, I’ll be covering the 10 most common types of embarrassing emails, complete with amusing real-life examples and a detailed explanation of how you can prevent them from happening to you in the future. Who knows? You might even boost your email productivity in the meantime.

Golden Rules

Before I dig into all those juicy, embarrassing emails, I’ll start with a handful of blanket fixes, which can prevent the majority of these email archetypes from ever going out.

A combination of these “golden rules” can prevent almost any email on this list, so be vigilant, and use them consistently!

Proofread.

Proofreading doesn’t take much time unless you’ve written a practical novel in the body of your email. Before hitting Send, give your work a cursory glance to make sure you’ve included everything, make sure you’re sending to the right party, and double check things like wording and spelling.

Gmail has a built-in proofreading service, giving you helpful red lines to indicate possible mistakes, and you can use a service like Grammarly to double down if you feel you need it.

Turn on “Undo Send.”

“Undo Send” is probably the best Gmail trick I know, and it could save your ass if you end up hitting Send before you finish proofreading your email. The feature works like you expect it would; after sending an email, you’ll have several seconds to click an “Undo” button at the top of the screen.

If you do, it cancels the email before it ever reaches your visitors. To turn it on, head to the Settings menu, and look for “Undo Send” under the General tab. It used to be a Gmail Labs feature (an experimental addition), but it must have saved enough people from embarrassment that they needed to promote it to a general standby.

Wait.

It’s easy to fall into a rhythm when you’re writing and sending emails all day, but if you want to spare yourself from as much embarrassment as possible, it’s better to wait. Draft your emails carefully and methodically, but give them a minute or two before you send them off—preferably longer, for more important emails.

That extra time will help you achieve a calmer mind state, separate yourself from the material, and give your work a glance over with fresh eyes.

That said, even the most cautious among us can fall victim to a poorly timed, ill-considered, or hastily sent email. So let’s at least bask in the catharsis of reading others’ misfortunes—and maybe learn something along the way.

1. The email you thought was a test.

via GIPHY

If you work in marketing, or any other role that requires you to send emails through various apps and platforms, you’ve likely had to send “test” emails in the past. Maybe your company has an internal email address for testing, or maybe you send it to yourself. Typically, these emails are simplistic; something like “Dear Test, This is only a test email. Thanks, –Test” is acceptable, unless you’re including images or other media. But if you’re bored, or are sending a test email to your friend in the department, you might feel the urge to get more creative.

That’s where the trouble comes in. Using inappropriate language, gibberish, or anything other than professional content can get you in serious trouble if that email goes to a live audience instead of the test inbox you thought it would.

Take, for example, when Fetchnotes accidentally sent the message “This is my test bitches” to its entire user base.

Image source: TheNextWeb.com

As the company explained in a blog post: “Needless to say, we were using far worse language as we began running around our office screaming and panicking like chickens with our heads cut off.”

Thankfully, this incident worked out well for them—they actually saw an uptick in app usage—but it could have gone much worse if their customers didn’t have a sense of humor.

Why It Happened

So why does this type of embarrassing email happen?

It could be one of a few root causes:

• You thought you were in a test environment, but you weren’t.
• You used the wrong email address, such as a customer list instead of a test list.
• You got too comfortable with your language.
• You sent the email too soon.
• A glitch in the system (or someone else) forwarded your message to the wrong audience.

How to Prevent It

Obviously our three “golden rules” could prevent this from happening, but there are two easy steps to take that can stop this from ever occurring to you:

• Keep your test language testy. I like swearing and silly humor as much as the next person, and if you want to send a lewd joke to your coworker, by all means do so. But if you’re in a test environment, your general policy should be “better safe than sorry.”Keep your test-related language simple and to the point; that way, if customers or supervisors get your email by mistake, the damage will be minimal.
• Always verify the correct testing procedure. It also helps to have a consistent testing procedure in place. If there isn’t one already, create a series of steps every test email should follow, and a checklist you can run through to verify your test emails will be sent the right way to the right audience. Then, consult that checklist every time you send a test email, no matter what.

As long as you keep one (or both) of these habits, you shouldn’t ever run into this problem.

2. The accidental reply-all.

via GIPH

You’re probably already cringing, because if this hasn’t happened to you, it’s probably happened to someone you know.

Reply All is an awesome email feature, when used appropriately. It makes it easy to respond to a group of people all at the same time. But what if you want to send a message, privately, to only one person in the group? That’s where the Reply All button can become your worst enemy. Click it by mistake, and that tongue-in-cheek dig you sent to your buddy is suddenly going to be on 20 different computer monitors.

But take comfort here—it’s not just the little guys accidentally slipping up. A few years ago, the CEO of Spirit Airlines, Ben Baldanza, mistakenly replied-all to a message forwarded to him from customer service. A couple had requested reimbursement for a trip after a flight delay and poor treatment from Spirit Airlines staff, and an employee forwarded the chain to Baldanza, CCing the couple (unbeknownst to Baldanza).

The CEO replied, “Please respond, Pasquale, but we owe him nothing as far as I’m concerned. Let him tell the world how bad we are. He’s never flown us before anyway and will be back when we save him a penny.” Needless to say, the company got its fair share of bad press after the incident.

Why It Happened

Again, there are a variety of factors that could lead you to make this mistake:

• You were busy, and replying to emails in a rush.
• You didn’t recognize an email address in the CC line, and though the message was purely internal.
• You fat-fingered the Reply button, resulting in a Reply All without your knowledge.
• Your email thread layout was confusing, making it hard to tell what was a group conversation and what was a solo interaction.

How to Prevent It

As always, the golden rules apply here, but there are some extra measures you can take to make sure this doesn’t happen to you:

• Use a Gmail trick to display threads differently. Thanks to Gmail productivity hacks, you can rearrange your Inbox to display threads more conveniently, so you can easily distinguish group threads from one-off conversations. In the Settings menu, under the General tab, you can turn “conversation view” on or off.
• Get in the habit of checking the CC line first. When you get a new email, the first thing you should do is check the CC line—long before you read the rest of the message. Establish context for who this was sent to, and why it was sent to them.
• Write messages like everyone can see them. Write messages under the assumption that clients and people outside your company are going to read them. That way, even if you Reply All by mistake, you’ll spare yourself the majority of the embarrassment associated with it.
• When in doubt, Reply. If you want to play it safe, get in the habit of clicking Reply. The worst-case scenario is you cut the conversation thread short, and unproductive email threads between large groups of people are a bad email habit If someone’s left out of the loop, the originator of the thread can take point on reconnecting it.

Once you get in these habits, they’ll be hard to break.

3. The wrong list.

via GIPHY

Sending an email to the wrong list can take place in a few different ways.

First, there’s the internal error. Oftentimes, companies create catch-all names for different departments, like “marketing@company.com”, or “customerservice@company.com”. These are super convenient, because they allow you to email multiple people at once, and spare you the time of looking up individual people—which is fantastic if you’re chronically busy. However, all it takes is one error to produce a royal screw-up.

For example, if you mean to send an internal memo to the “customerservice” list, you might accidentally send one to the “customers” list due to auto-fill.

Then, there’s the marketing error. If you’re mass-emailing your customers, you’re probably using multiple segmented lists, so you can target each section of your audience a little differently. Again, it’s a brilliant strategy, but one that can go terribly wrong with an ill-timed message.

One of the best examples that comes to mind here is a Shutterfly debacle from 2014. Intending to send an email to new parents who had purchased baby-related items in the recent past, the company accidentally sent a “Congratulations” email to their entire customer base. Pregnancy and motherhood aren’t issues to be taken lightly, and understandably, many mistakenly emailed customers were offended.

Here’s the entire note, below:

Image source: HuffingtonPost.com

Shutterfly had a great response, however; upon realizing the error, they immediately sent out a concise, sincere apology email explaining the situation, and took full accountability for the mistake. Still, it would have been a lot better had that email never gotten sent.

Why It Happened

So let’s look at the precipitating factors for this kind of episode:

• You were going too fast, like the email renegade you are.
• The names of your email lists were unclearly named or are easy to mistake.
• A miscommunication led you to believe you were supposed to send to the wrong list.

How to Prevent It

Now we can work on prevention:

• Name your email lists clearly. Everything starts with how your lists are named and organized. If multiple lists have similar names, such as “customers,” “customerservice,” and “customerteam,” someone’s going to get them confused. Instead, make each name unique, and painfully obvious. Longer names might seem bulkier, but they’ll be far less confusing.
• Avoid using email lists as an individual. I believe email lists are best reserved for automated tasks; for example, you might have the contact page of your website go to a group of salespeople. If you’re emailing people one-on-one, stick to using individual names whenever you can. You might run the risk of forgetting to include someone, but that’s far better than mistakenly emailing more people than you intended.
• Keep your marketing email lists manageable. If you’re managing multiple marketing email lists, try to keep them limited and well-organized. Every segment you add is going to increase the complexity of your ongoing management responsibilities, so think carefully before you add it.
• Designate specialists, if you can. If possible, assign one point person to each email segment, to serve as a specialist for that segment. This will make it far less likely for a person to mistakenly email the incorrect list, since they’ll only be working with one list and one type of content.

If you’ll excuse me, I have some lists to clean up.

4. The forgotten (or wrong) attachment.

via GIPHY

After the examples from the past few embarrassing emails, the forgotten attachment seems tame. You email someone, intending to send an attachment like an invoice or a printing proof, but hit Send before you include the attachment. Don’t fret too much here; the worst-case scenario is the person will email you back asking for the attachment, and you can include it then.

The only time this is a problem is if your attachment is time-sensitive, and you aren’t around to get the reminder from your recipient. Thankfully, if you include the word “attachment,” or any variation of it, Gmail will give you an automatic prompt before your email goes out. That’s right—Gmail’s looking out for you, so you won’t have to worry much here.

The real embarrassment usually comes with the close cousin of the forgotten attachment—the wrong attachment. This one’s a bit of a gamble; you might get off with an innocent mistake, or you might send something capable of destroying your reputation.

For example, you might send an invoice from last month instead of the most recent invoice—or you might end up like Dirty Larry.

Back in 2002, Larry kept a “secret” folder on his computer full of dirty jokes and images for his personal amusement. The problem was, the title of the folder suggested it was related to his profession, and he ended up sending it as an attachment to a list of customers—who happened to be conservative professionals.

Larry lost his job for that one.

Why It Happened

Why does this kind of thing happen?

• You were going too fast (are you noticing a pattern here?).
• You grabbed a mislabeled attachment.
• You spent too long on the body of the message.
• Your files are disorganized.

How to Prevent It

For the forgotten attachment problem, Gmail has you mostly covered. Instead, these tips will be meant to help you prevent incorrect attachments:

• Avoid keeping inappropriate content on your work devices. This one should be obvious. What you do in your personal time is your business, but your personal tastes shouldn’t bleed onto your work devices. This should at least keep you from sending the worst types of material from your clients.
• Title your files uniquely and visibly. When you download a file, don’t keep its title as a string of random alphanumeric characters. Also avoid writing something generic. Instead, have a formal system of titling files, which includes a unique description of which client the file is for, and what the file contains. This should clear up the majority of your accidental clicks.
• Create a clear system of organization. Titling is a good start, but accidental navigations may still occur. Create a clear hierarchy for your files, including subsections and folders that clearly state what type of content is contained within.
• Reference the attachment in your body content. Make a conscious effort to reference the attachment you’re sending in the body of your message. This is going to force a mental check; are you attaching the file that matches your description? It’s also a verbal trigger that will ensure you get Gmail’s last-ditch notice if you forget the attachment altogether.

The “proofreading” golden rule is especially important here; don’t neglect it.

5. The wrong name.

via GIPHY

The wrong name is a mistake that can affect you in a real-life conversation as much as it does over email, but that doesn’t make it sting any less. The premise here is simple: you wrote an email to the right person, but you called that person by the wrong name, typically in the header, but possibly in the body as well.

A clear typo shouldn’t be considered a major breach unless you’re dealing with a picky client; for example, calling “Thomas by “Thomsa” is clearly a result of fingers tripping over keys. Things get tricky when you have someone with a preferred name spelling; for all you know, “Sara” hates to be called “Sarah”—yet that’s what you accidentally typed out.

Calling someone by the wrong name entirely is a next-level problem. Try not to think too much about the psychological implications here. People love their own names, and calling someone by the wrong one can range from awkward to offensive. At the very least, you’ll stand to make a worse impression for yourself.

The other potential problem is getting too chummy with someone prematurely. You might shorten their name, like from “Nicole” to “Nicki,” without knowing what their real preference is, or give them what you think is a charming nickname—only to find out it disgusts them.

There’s a range of bad outcomes here, including appearing forgetful, offending someone, and creating a more awkward dynamic that might last for years if you work in close capacity.

Why It Happened

Since there are a variety of ways to get someone’s name wrong, there are a number of possible contributing causes:

• You forgot the person’s name.
• You wrote the wrong name down.
• You went off of memory instead of your records.
• You had someone else in mind when you wrote the message.
• You got distracted and typed the wrong name in pure error.
• You made an assumption about the person’s name without verifying it.

How to Prevent It

Thankfully, this one has some easy strategies to help you prevent this mishap:

• Check your contact info before sending. You have to include an email address to send an email, and chances are, it’s already in your contact list. Hover over that name and make sure you get the spelling right. If they’ve emailed you previously, check their email signature and see how they’re spelling it. Otherwise, check your business card or whichever medium you used to get the name in the first place. By the way, now’s a good time to make sure your email address is top-notch! See our guide to email address ideas for some tips and tricks on choosing a perfect email address.
• Avoid overusing someone’s name. As human beings, we like the sound of our own names, so you might be tempted to pepper in someone’s name multiple times throughout your email as a form of subtle flattery. However, you should only do this if you’re 100 percent confident you’re getting that name right. Otherwise, ease off the gas pedal and keep that name in the header only.
• Never use an abbreviated name or nickname without permission. This is a breach of etiquette, so just don’t do it—even if you’re trying to be friendly. If and when someone introduces themselves as a specific name, or if you’ve been working together for years and you’re confident you’ll get a positive response, then you can move forward with a name alteration.

There’s one more problem to solve here. What if you’re calling someone the wrong name for months, or even years, but they never end up correcting you on it? At that stage, I have no advice to help you. You’re way beyond single email territory—though if you ask me, they’re just as much to blame for letting it keep happen.

6. The critical typo.

via GIPHY

Typos happen. I don’t care how much of a perfectionist you are or what type of proofreading software you’ve invested in; eventually, you’ll slip up and something will get past those fancy filters.

For the most part, these fly under the radar. Email veterans understand the vulnerability of the medium, and have dealt with the fallout from their own typos, so they’ll probably forgive you for missing an apostrophe or flubbing the occasional preposition. The problem is, not all typos are created equal—and ill-timed or unfortunate typos have the power to take things into next-level awkward territory.

The imagination runs wild with possibilities here. Maybe you forget the word “not” in an explicit warning to avoid a specific action. Maybe you forget or add a letter to a common word, turning an email to a conservative client into something profane. Maybe you added or left out a zero in a friendly discussion on price. In any case, typos can cost you—literally in terms of money, and figuratively in terms of reputation.

Though not related to email, this is a perfect moment to recount the anecdote of NASA’s Mariner 1 probe, which was set to launch in 1962. The goal of the probe was to get close to Venus, to report on the planet’s composition and behavior. However, programmers missed a single hyphen—and that one character caused the probe to explode minutes after takeoff because it caused incorrect guidance signals to be sent to the aircraft. Consider yourself lucky that none of your email typos will cost $80 million.

Image source: Wired.com

Why It Happened

Nobody makes typos on purpose. They all share a similar root cause: error-prone human nature. There are several potential influencing factors here; for example, you might have purchased a new keyboard you aren’t familiar with, or you might have suffered a finger injury that makes typing more difficult, or you might be using your smartphone and dealing with autocorrect. But the most likely cause is clumsy fingers, since they can happen to all of us.

How to Prevent It

These are the best tips I can offer to help you prevent this tragedy from occurring:

• Utilize your device’s spell check. Most platforms and devices, including Gmail, have a built-in tool that alerts you to any mistakes you’ve made, so take advantage of it. In Gmail, if you want to run a check manually, you can click the arrow in the lower-right corner, and click “Check Spelling.” Just be aware that this can only check for spelling errors and grammatical typos; it won’t save you if you spell a company’s name wrong, or relay the wrong instructions by omitting a word.
• Read backward and aloud. We tend to make typos when we get used to the text we’re writing, so one of the best ways to catch typos is to confront our text in a different way. For example, reading the text aloud, rather than relying on your eyes, can help you hear mistakes rather than seeing them. Reading your message backward, line by line, can help you catch sentence-level mistakes you might otherwise skip past.
• Enlist someone else’s help. Your coworkers are likely busy with their own work, but that doesn’t mean they can’t spare a few minutes to help you out. Ask a coworker or friend to look over an email—especially if it’s an important one. They may be able to spot some details that you’ve missed.
• Put your text in a different font. Another way to make your brain more sensitive to the details in your text is to put the text in a different font, or new font size. It will appear novel to you, and you’ll be more likely to pick out specific details that shouldn’t be there (or that weren’t intended).

You might still run into the occasional typo after using these tricks, but they’ll be fewer and further between.

7. The emotional response.

via GIPHY

The workplace can be stressful for everyone, and sometimes those tensions boil over. But I think I speak for all of us when I say the things you want to say most when you’re angry aren’t typically the best things to commit to a permanent communication medium.

In other words, if you let your emotions get the better of you, you could fire off an insulting, immature, or dickish email to someone who has the power to crush your career where it stands.

This can happen no matter what position you’re in, or what the circumstances were. For example, Binary Capital co-founder Jonathan Teo, in a tirade-level response to negative press coverage, sent out an email stating to his staff (and investors) that he was “tired and indignant” against “whiners” who were constantly demanding his attention. Teo later resigned.

After sending an emotional email, you’ll likely feel a sense of righteous fury, or of catharsis, depending on the nature of the message. You took all your feelings, bottled them up, and sent them off, and while those feelings are still burning in you, it feels good.

A few minutes to a few hours later, when you cool off, you’ll read that response you sent and feel a little less sure of yourself. Depending on how heated you were, you might be downright embarrassed—or worried about your future with the company.

Why It Happened

Two things have to happen for an emotional email to be sent.

First, you have to be emotional. Something in the workplace has to get you so worked up that you stop thinking clearly, whether it’s a threat to your reputation, the neglect of a fellow coworker, or a new responsibility that’s going to make your life hell. Second, you have to channel that emotion in to a message and hit “send.”

The bright side is you can prevent either of these things from occurring to prevent the emotional email from being sent.

How to Prevent It

It’s hard to unsay things that are hurtful, impulsive, or unprofessional, so all you can do is prevent this from happening:

• Learn to master your emotions. Anything you can do to stop yourself from getting to that heightened emotional state is going to be beneficial. Anger management techniques are highly effective here; when you feel overcome with emotion, leave the room and talk a walk. Hold your breath and count to 10. Take a moment to practice mindfulness, and do something you enjoy (or talk to someone you love). Experiment until you find one or two tactics that work especially well for you.
• Write a first draft and let it sit. If you’re still feeling salty, go ahead and write that email—but do it in a document file, rather than an email draft, so you’re not at risk of sending it by mistake. Then, walk away from it for a while. Whenever you feel calmer, whether it’s in an hour or in a day, look at the draft again and see if you still feel the same way. Chances are, you’ll want to tone down the aggressiveness or tone of your message, which will spare you from its worst effects.
• Ask another person’s opinion. If you want to make your email productive, and send a response that states how you feel, ask for another person’s opinion on your message. A third party will be a less biased indicator of the harshness and appropriateness of your tone, and they may be able to make suggestions on how to communicate your point more effectively.
• Talk it out; don’t write it out. If you still need to express your anger or disappointment after trying the above steps, consider having a conversation, over the phone or in person. When facing a person, you’ll be less likely to use inappropriate language, and you’ll get to hear another side of the story. On top of that, a verbal conversation is far less likely to be recorded—so if you slip up and say something you don’t mean, it may be treated as a temporary outburst, and not stared at and re-read, as it could be in an email.

You’ll likely get emotional in the future if you’re passionate about your work, but that emotion doesn’t have to manifest as an embarrassing email to someone important.

8. The wrong thread.

via GIPHY

Email threads can get confusing, I know, but if you end up responding to the wrong thread, it can be both embarrassing and destructive.

Let’s illustrate this with an example. You started an email thread a few weeks ago with your coworkers about how much you hate the new time tracking system—mostly so you could find ways around the features you don’t like, but also as a cathartic way to express your true feelings about it. Earlier this week, you got included on a thread by your boss about how to allocate hours for an upcoming project. One of your coworkers was the last to respond on both threads, and they bear similar subject lines, so you accidentally send an email to the thread your boss is on, venting about the inefficiency of the new system. Ouch.

There are much more innocent mistakes to be made here, of course. You might send an email to an old thread instead of its new counterpart, or mix up a couple of internal dialogues. But even at its tamest, this mistake can waste your and your coworkers’ time, and make you appear less professional.

Why It Happened

This usually happens when your email threads aren’t being used or managed efficiently. For example, you might see multiple new threads a day; if you’re dealing with dozens of threads, it’s only a matter of time before you get a couple of them mixed up. If those threads don’t have strong subject lines, or if many of them include the same group of people, the problem grows even worse.

How to Prevent It

You can nip this possibility in the bud by improving your ability to handle and organize email threads.

• Organize and start email threads responsibly. There isn’t much you can do about the email threads you’re included in; these are started, named, and managed by other people. But you can take control of your own email thread use. Start email threads only when you need to, and think carefully about who to include. Make sure to give the thread a clear, concise subject line, and keep the thread focused and on-point so it doesn’t take up unnecessary space or give unnecessary alerts. For help crafting the perfect subject line, see our post on subject lines for networking emails.
• Archive or mute threads you no longer need. As you engage in email threads, you’ll realize there’s a threshold where each thread no longer applies to you. When you get to that point, consider muting the thread in Gmail so you no longer get notifications from it; this way, you’ll be less likely to mistake it for another thread.
• Turn the conversation view off. I mentioned this in an earlier section, but Gmail will group your email threads into “conversations” by default. For me, this format is easier to manage and keeps things tidier in my inbox, but it isn’t for everybody. If you prefer to view your threads message by message to keep things straight, head to the Settings menu, and in the General tab, you can turn “conversation view” off.
• Always check the last few messages. Before hitting Send, scroll up for a few messages to make sure you’re on the right thread. It only takes an extra 30 seconds, and it could save you from a world of embarrassment.

Email threads will always have the power to trip you up, so use them and interact with them cautiously.

9. The fast fingers

via GIPHY

“Hey Dave! This week, make sure you”

Have you ever received an email like this? You’ve written an incomplete message, but accidentally hit the Send button anyway, and your recipient is going to be confused. If you realize your mistake, you can quickly send a reply that contains the rest of the intended message, but the damage may already be done.

Fortunately, this mistake has fewer large-scale consequences, compared to the other embarrassing emails on this list. You’ll lose face, but you’ll be presenting the correct recipient with incomplete information—which is better than sending to the wrong recipient, or sending the wrong information. It’s manageable, but annoying, so you’ll still want to take efforts to prevent it.

Why It Happened

There are two potential reasons for this type of embarrassing email. First, and most commonly, you were typing too quickly or you got too excited about the message, and you clicked Send before the message was complete. This can also happen if you work on your email in separate sections, completing the closing paragraph before you return to finish the introduction, then going on autopilot for the Send button.

The other potential option is simpler, and easier to control. If you have keyboard shortcuts turned on, you can accidentally make the keystrokes necessary for the email to slip through your fingers.

How to Prevent It

There’s a good Gmail hack for the keyboard shortcut problem, but otherwise, this is purely an effort of self-discipline:

• Change your keyboard shortcuts. If the shortcut is the problem, you can change it. Remember, you can create your own custom Gmail shortcuts by heading to Gmail Labs in Settings and creating your own commands. If you find you still have the problem, you can always change them again.
• Get in a habit of delayed sending. This is much easier if you have a habit in place. After writing any email draft, take a few minutes before sending it. Chances are, even an emergency situation can wait a minute or two, and Gmail will automatically save your draft so you don’t lose any work. Use this time to review what you’ve written, and separate the “draft” and “send” steps of the process.

With enough time, you should be able to prevent the majority of your premature email sends.

10. The wrong message.

via GIPHY

I’m concluding this list with one of the cringe-worthiest emails I can think of: sending the wrong message. With an incorrect email attachment, it’s usually obvious there’s a mismatch. With an incorrect recipient, the recipient usually understands immediately that the message wasn’t intended for them.

But when you send an inaccurate message to the intended recipient, they could be left with the wrong impression. From there, any number of social tragedies could unfold.

Take, for example, a notorious accidental group message from MIT back in 2014. Every applicant on the list received a message with the tagline, “You are on this list because you are admitted to MIT!,” despite this not being the case. The intended tagline was, “You are receiving this email because you applied to MIT and we sometimes have to tell you things about stuff,” notifying applicants that they had been added to an email list for ongoing notifications from the university.

This happened as a result of automatically combining two separate lists of email subscribers—MIT staffers had proofread the text of each email, but software platform confusion led to crossed wires, so to speak.

Fortunately, MIT was quick to try and rectify the mistake. Admissions counselor Chris Peterson wrote, “I’m incredibly, incredibly sorry to everyone who received this and read it and felt the mixture of confusion, elation, frustration it must have engendered,” going on to ask recipients of the email for forgiveness for the mistake.

Still, that’s a big pile of embarrassment to deal with, both as an individual responsible for the message, and as an organization. In other scenarios, your incorrect message might mistakenly notify a vendor that they’ve won a contract, or approve a proof that hasn’t been formally approved by a client, or give instructions to an employee to proceed with a job that’s been canceled.

All these messages are humiliating, some of them are costly, and some of them could hurt your reputation.

Why It Happened

In the MIT example, the root of the problem was an error in list management, but there are a variety of reasons why this could happen:

• Software issues that cause you to mistake a group’s identity.
• Improper fact-checking.
• Distraction with other emails.
• Confusion about the nature of the message.

How to Prevent It

So what can you do to prevent this from happening?

• Clean up your email lists. Take some advice from #3 on this list, and spend some time organizing your email lists. Having clearly named, clearly partitioned lists can keep you from sending an inaccurate message to all or part of those groups.
• Check your information before sending. This requires an extra step for each email you send, but for sensitive emails or high-profile projects, it may be worth it—even on your busiest days. Confer with your original source, whether it’s physical notes you’ve taken, another email from higher up, or a chat log, to make sure you’re reporting the right information.
• When in doubt, pause. Some situations call for you to respond as quickly as possible, but if you’re unsure about the accuracy or validity of your information, it’s best to hold tight. Evaluate your own confidence on the information you’re about to send, and if it falls below a certain threshold—like 80 percent certainty—delay sending the email, and request some time to clarify your information.

Because it’s impossible to have a truly perfect network of information, incorrect messages are still going to happen to you—but you can prevent the majority of them with these tips.

The Rebound

Let’s face it. No matter how many times you’ve been embarrassed in the past or how committed you are to improving your email performance, you’re probably going to send an embarrassing email in the future. When that happens, your only option is to try to recover as gracefully as possible, and these steps may be able to help you:

Act fast, if you can.

Assuming you’ve missed the “Undo Send” window of opportunity, there’s still a small chance you’ll be able to recall the message if you’re using Outlook and a number of other conditions are true. This is unlikely. It’s also inadvisable to stage an elaborate heist to log onto someone’s device and delete the email manually, but if you’re feeling bold, I won’t judge you for taking that step.

Even if you can’t recall the message, you can act quickly to own up to your mistake and, hopefully, correct it. The sooner the receiving parties hear from you, the sooner you can stop the bleeding.

Admit to your mistake.

You’re probably already cooking up an excuse like your toddler grabbed your phone, or autocorrect screwed you over, or you were misinformed by someone else, but it’s almost always better to admit to your mistake. Telling the truth and admitting fault shows both integrity and humility, and it’s hard to hold negative feelings toward someone with both those traits.

You may have to accept the consequences for your actions, but unless your email was truly devastating, it’s unlikely those consequences will be life-altering.

Apologize, but keep it light.

Do apologize for the mistake, but don’t spend too long dwelling on it. Sending five follow-up emails about how you messed up may only annoy the other person. If you keep it light, you’ll acknowledge that the mistake was significant—but not so significant that it warrants further attention.

For help, see our post on how to apologize professionally in an email. Embarrassment tends to stand out in our brains, making us remember that cringe-worthy moment for years to come, but the people around us aren’t nearly as invested.

In other words, your email recipient is probably less negatively affected by this incident than you are. The less attention you draw to its severity, the better.

Know your audience.

Think about the person you sent this to—are they fairly easygoing? Or are they the type to hold grudges? Do they email constantly, or do they prefer face-to-face conversation?

These qualities should shape the tone, medium, and timing of your response. If you don’t know the person you sent the email to, stick to neutral territory.

The better you understand your emailing habits, the more professional and productive you’re going to be. That’s why we created EmailAnalytics. It can’t save you from every embarrassing email you type, but it can help you analyze your email usage, take note of pain points, and ultimately find ways to improve your everyday use of email.

Sign up for a free trial today and you’ll get 14 days of free access to see how it can work for you!