9 Embarrassing Email Mistakes That Can Hurt Your Business

9 Embarrassing Email Mistakes That Can Hurt Your Business

9 Embarrassing Email Mistakes That Can Hurt Your Business

Email is a modern wonder in many senses. It took the time to deliver a message down to a fraction of a second and negligible cost. But it also opened businesses up to a whole slew of problems. Email takes up far too much time and effort for the average worker today, but it is even worse when the person on the other side of the message doesn’t understand proper email usage. If you are the one making embarrassing email mistakes, it could come back to hurt your business. Avoid these 9 embarrassing email mistakes that can hurt your business.

1. Messed Up Mail Merge

We often blame technology for not working right, but when it comes to mail merge mistakes it is often user error. One simple mistake in a mail merge can turn into a major embarrassment when the bulk email goes out to your entire customer list or sales funnel.

Mail merges require very precise bracketing and labeling for the names to get mapped to the right place in an email. In many cases, it is simply a missing closing bracket or misspelling in the mail merge forms that causes the issue. Whenever you send a mail merge email to any group, always double and triple check everything before clicking the send button.

2. Reply All

Moments after hitting send, realizing the message went to more than the intended audience can cause a feeling of despair. Avoid it by setting your default button to “reply” instead of “reply all.” Because if you do hit reply all and send to too many people, you might find yourself among a growing number of people who have lost customers, contracts, jobs, and relationships from one wrong click of the mouse

In most cases, an email that goes to the wrong audience shouldn’t be enough to damage a career or relationship. One way to avoid that even if you do accidentally hit the reply all button is to never send an email you wouldn’t want in the newspaper. In this day and age, that should be the standard for all emails, as we can see from the fallout for some business executives and politicians after an email gone wrong. Here is one harrowing story of a reply all that led to a job loss.

3. Not Personalizing a Templated Response

When applying for jobs, recent college graduates often write one form email in their Gmail or Outlook account to a group of businesses and simply customize the name and a paragraph or two. Forgetting to change the name in a templated response shows lack of attention to detail and a level of carelessness that means the applicant isn’t getting the job.

But that same scenario can happen in business under many scenarios. After all, a mail merge doesn’t always make sense and sometimes you want to personalize a portion of an email without rewriting the entire thing each time. Make sure to pay attention to that detail, or it could lead to an embarrassing reply. In the worst case, you could give up the name of another customer or target on the list, making it that much worse for your business.

4. Using Text Message Grammar

OMG, LOL, and LMAO are arguably appropriate acronyms when sending text messages to friends. However, they virtually never belong in the business world. While some sayings like LOL might have made it into your office lexicon, do not send email messages that look like a text message between two teenagers.

You should always use proper spelling, grammar, and punctuation in email messages. You don’t need to maintain the high standards of a newspaper editor, but when in doubt you can take a few moments to look up proper usage.

5. Missing Important Messages

Everyone gets lots of email in the business world these days. Depending on what you do, that can be hundreds of messages every single day arriving in your inbox. But too many junk and unimportant emails are not an excuse for missing an important message from a boss, coworker, or client. When you are the boss, a missed email could mean a missed project or job that will go to a competitor instead. You certainly don’t want that to happen!

To make sure you never miss an important email, you have a few great tools and strategies available. Consider unsubscribing to email lists and talk to any repeat offenders that CC you on emails way too often. If an FYI is TMI, it doesn’t belong in your email. You can also setup rules to flag or highlight emails sent only to you, from important people, or from outside email addresses.

6. Inappropriate Reply Length

Don’t write an essay where a simple paragraph will do just fine, and don’t write a sentence or two where something a little longer and more thoughtful is appropriate. It may be easier said than done, but you should work to understand each relationship and message to make sure your reply is appropriate for the task at hand.

At one past company in my career, some managers had a reputation for only reading the first paragraph of any email, so you should always put everything important into one paragraph. But if the paragraph is too long, they might glaze over and miss important messages there. But if something is really important, don’t send a short and unhelpful response. Knowing the sweet spot takes a little experience, but if you pay attention you should get there quickly.

7. Bad Subject Lines

A blank subject line might as well say “this is an email about nothing important.” On the opposite end of the spectrum, a subject line shouldn’t be too long or detailed. The idea of a subject line is to offer a brief, clear explanation of the email’s main topic. According to email deliverability company ReturnPath, the ideal subject line is about 65 characters in length. That equates to about a sentence.

If you send an email with a truly terrible or blank subject line, it may not be opened at all. That means everything contained within goes to waste, even if it is vital information. When an employer asks for “excellent written and verbal communication skills,” this is part of what they mean by written communication skills. You need to be able to succinctly explain what the email is about with just enough information to get the recipient to click and open it.

8. Improper Emails

Chain emails, anything of a sexual nature, and anything that may be construed as offensive (even by people who are easily offended) do not belong in business. There are just too many stories of sexual harassment, phishing, and workplace discrimination to risk sending any email that may be taken out of context or taken the wrong way.

One would think business leaders can easily identify appropriate and inappropriate behavior, but we see stories again and again of “bro culture” and other workplace culture and email issues that shouldn’t be happening today. If you wouldn’t send it to your grandmother and religious leader, don’t send it to a business associate.

9. Email overload

Last but certainly not least, do not send too many emails. Everyone is busy these days, and email takes an inordinate amount of our time. Do your best to gather up information and send it in one email rather than a string of emails. Also, avoid oversharing by sending too many minute details on a regular basis.

Email should be a “need to know” platform. Don’t send business emails without a business purpose. If you can keep your emails focused and limited to priority issues that impact everyone involved, you are on track for email success for years to come.

This article was originally written on February 26, 2018 and updated on February 2, 2021.

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