Author Archives: TheLeader

The Six Worst Business Email Etiquette Mistakes Ever

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Proper Business Email Etiquette – Part 2

If you’re in business, it’s time you learned how to properly send an email. Just because you can open Outlook and click “send” doesn’t mean you’re qualified to use email as a business tool.

This is the second part of a two part series covering the Twelve Worst Business Email Etiquette Mistakes Ever. In this article, we will explore the Top Six Worst Business Email Etiquette Mistakes Ever, to see numbers 7-12, follow this link.

6) Text Messaging – omg ne1 w/brain noz that email n txt msging r 2 difrent things    txting is 4 persnl coms n email is 4 biz   we r rotf over the use of txt msging 4 email

Attention Generation Whatever, email is not just a cumbersome way to send a text message, and business email should never be confused with “texting.” Regardless of what you believe the recipient wants to see, you can never go wrong with properly written, grammatically correct verbiage.  

If you must send email from your cell phone, get a BlackBerry or some other email-ready smart phone with a QWERTY keyboard, activate your spellchecker, and send emails we can all understand without having to ask a 5th grader for help.

5) Attachment Names – Consider your audience, the recipient. What does the filename “my_resume.doc” mean to an HR manager who receives hundreds of resumes each week?

TheManager once received over 500 resumes for a single position posted on Monster.com. In that mix, there were more than 50 attachments with some variation of the name “my resume.” Needless to say, none of those 50 attachments were opened, and TheManager filled the position with someone who understood this basic tenet of email etiquette.

Naming your email attachments for yourself and not for your audience shows a certain level of inconsideration that borders on disrespect. Of course, most of these attachment missteps are more the result of simplemindedness than they are utter rudeness, though all need to be banished.

Filenames should be as descriptive, yet also as short, as possible. Where you have a file that includes date sensitive information, include a date in the filename. Great examples of this are “…_Aug_08” and “…_081308” (today’s date).

When you’re sending an attachment to a customer, include your company’s name somewhere in the filename. Of the 802 email attachments received in the 4,000 emails examined by the editors of AskTheManager.com, 135 contained just the name of the receiving company in the filename. Hey, we know who we work for – we don’t need 135 documents on our hard drives that remind us of this.

4) Email Stationery – Ugh. Nothing sucks the professionalism out of a business email more than a pretty blue background. Just as email and text messaging are two different communication media, email and wedding invitations are also very different. 


Your business emails should never, ever be set to include stationery (sometimes called “email backgrounds”). While there were only twelve examples of stationery usage (from four senders) in the 4,000 emails examined, when those emails were replied to or forwarded, the stationery took over the layout and color of the new email. This required the original recipient to make adjustments to their outbound email, or risk sending out something that was unreadable.

Stay professional, drop the stationery and, while we’re at it, limit your business email signature to name, title, company name, address, contact information and confidentiality verbiage. Including a quote from some long dead philosopher may impress your mother, but it does nothing for a business colleague.

3) Carbon Copy (Cc) – Be careful with this one. Somewhere along the way the initials Cc began to mean “copy carelessly.” Let’s review some email basics:

  • The “To” line represents the primary recipient(s) of the email. This line also indicates who must take action, if action is required.
  • The “Cc” line is used for any secondary or tertiary recipients who must be informed about what is in the body of the email. Think of the cc line as sending an “FYI-Only” email to these people. They should not be expected to take any action on the email, nor even be required to read it.
  • The “Bcc” line, which stands for “blind carbon copy,” is intended to allow the sender to mask the list of recipients. To see the acceptable uses of this line, check out Number 12 on this list by following this link.   

The Cc line is not a license to copy the world. Too often, business people get carried away and include a dozen or so colleagues that couldn’t care less about the email. Unfortunately, the overuse of the Cc line grows the amount of email we all receive exponentially; and it slows down the real productivity of all who are “Cc’d.”

The most egregious instances of Cc occur when it’s used to throw someone under the bus (by copying their boss) or to make you look good (by copying your boss). We’re hopeful that the great business leaders of the world do not reward the use of Cc for personal gain. (If you’re so determined to grow your career, buy a book on career development rather than over-copy your boss in emails – if your boss has half a brain, she sees through it anyway.)

Of the 4,000 emails we examined, 3,013 (a whopping 75%) included at least one recipient in the Cc line. Of these, the editors determined that a Cc was only required in 210 – the other 2,803 emails were basically manual SPAM, created by business people with no business email etiquette.

2) Reply To All – Please, for the love of humanity and the sanity of the editors, learn how to use this simple, intuitive button installed in every email program in the world.

The Reply To All button was included in email programs for the primary purpose of allowing one of the recipients of an email sent to many people to respond to everyone else included in the address lines. Unfortunately, there are two instances when this is misused; one is annoying and one can be hilarious, though both are inadvertent.

The annoying misuse of Reply To All occurs when someone copied on an email string with multiple addressees fails to use Reply To All when they intend for everyone to see their response. This is frustrating because it often creates a new branch of the email string complete with its own conversations and conclusions.

The hilarious misuse of this occurs when someone copied on an email with multiple addressees intends to reply only to the sender, and inadvertently hits Reply To All. While we only had one example of this in the 4,000 emails the editors examined, it was still pretty funny.

A colleague (we’ll call him John) of one of the editors was copied on an email sent to most of the top managers at the editor’s company, including a VP that no one respects (we’ll call him Carl). John intended to simply reply to the sender with the following message, but inadvertently hit Reply To All:

You’d better send this by carrier pigeon to Carl, I doubt he knows how to open his own email. – John

Now, unless you’re Carl or John, you have to admit that that’s pretty funny. Carl didn’t find it amusing and John has since been “reassigned.”

1) Using a Non-Business Email Address – While we found only 62 instances of this (from 14 senders) in the 4,000 emails we examined, using a personal email address for business purposes is such a clear violation of proper business email etiquette that the editors almost felt compelled to name the 14 offenders in this article just to shame them into acquiring real email service for their companies.

If you would like both you and your company to appear completely bush league, please continue to send emails from addresses that end in @hotmail.com, @earthlink.net, @aol.com, @comcast.net, etc. And, although people once thought having an @gmail.com address was pretty cool, it’s not so cool for a business email account.

Additionally, if you’d like to look like a complete nincompoop, then continue to use “mustang,” “godawgs,” and “bucnut” before the @ in your emails. (All three of these were actually received by the editors.) The consensus of the editors is that these email handles will guarantee that you will receive no response to your “revolutionary new product” emails. 

While we’re on the subject of email addresses, the AskTheManager.com editors mandate that only the following naming conventions (and minor variations of these) should be used for business emails:

  • FirstName.LastName@BusinessName.com
  • FirstInitialLastName@BusinessName.com
  • LastName_FirstName@BusinessName.com

While many startups once thought it was cute to allow employees to use just their first names in their email addresses (pretty convenient when you only have five employees), these look a little silly today. So, bob@, george@, ralph@ and jeff@, please add your last names to your emails if you want to conduct serious business moving forward.

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These are our twelve worst – what did we miss? Do you have an example of something in email that just drives you crazy? Please send us a note at themanager@askthemanager(dot)com, or leave a comment below.

(We think it’s important to note that there are resources to help you write better emails. Understanding how to use all of the features of Microsoft Outlook is a great first step. Outlook 2007 For Dummies is the best Microsoft Outlook training and reference guide available.)

The Twelve Worst Business Email Etiquette Mistakes Ever

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(Editors’ Note: This is a follow-up article to a post by TheManager on August 7, 2008 that detailed the most common mistakes in emails. To read that post, follow this link.)

Proper Business Email Etiquette

If you’re in business, it’s time you knew how to send an email. Just because you can open Outlook and click “send” doesn’t mean you’re qualified to use email as a business tool.

Though email was invented in the 1970s, our use of it as a business communications tool has never quite evolved. It seems that the streams of business emails received by the editors of AskTheManager.com aren’t getting better with time.

Poor grammar, typos and everything in between have become an epidemic among businesspeople. Even when someone is smart enough to employ their spellchecker, it’s clear they don’t understand the first thing about their audience.

The editors of AskTheManager.com argued endlessly, but finally created this list of the Twelve Worst Business Email Etiquette Mistakes Ever. (Perhaps we should have spent more time coming up with a better title for this post, though it’s important to note that we rejected some really terrible names.)

In reverse order, here are the Twelve Worst Business Email Etiquette Mistakes Ever (to assist our readers, we provide links to the best business writing books, tools and resources available throughout this list):

12) Blind Copy – The use of blind copy or “bcc” has, thankfully, been only a minor annoyance in business email. Proper usage is limited to including a colleague in your own company on an email to someone outside your company. Any other use is disingenuous, at best, and displays a very clandestine intention. Managers should read between the lines when they’re blind copied on an email – whatever you do, don’t reward the sender, and perhaps use this as a development opportunity.

The editors of AskTheManager.com examined 4,000 business emails received from individuals (we discarded anything that was sent from an automated program), and we discovered we were blind copied only 3 times, though we did receive a reply from someone who was blind copied on an email where one of the editors was the primary recipient.

Holy crap, we thought. This idiot didn’t realize he wasn’t supposed to let the rest of us know that he was blind copied.

It should go without saying, but don’t ever, ever respond to an email on which you were just a bcc. If you’re the sender, consider eliminating the bcc and simply forwarding the email (after it’s been sent) to those you intended to bcc. This way they can never expose you by replying to everyone on the original email.

11) Spelling – Weird, with virtually every single email program available providing a free spellchecker, that this would even make the list. Among the 4,000 emails we examined, we noted misspelled words in 486 of them (that’s 12%). TheManager’s solution is to check the Help or Options sections of your email program and set up automatic spellchecking. If that doesn’t help, perhaps a dictionary might.




10) Grammar – Of the 4,000 emails we examined, we counted grammatical errors in 544 of them. That’s almost 14%, and that’s too high. Basically, 1 in every 7 emails we received in our business life contained some grammatical misstep.

There’s only one solution for this and that’s education. Buy a book, take a class or hire an editor, but do something to stop the onslaught of crap coming from your email program to your business partners. (We all thank you in advance.)

9) The Subject Line – The editors have two issues with subject lines: first, include one; and second, write a subject line that makes sense. Believe it or not, we received 43 emails without subject lines. While that’s only 1%, we also received 605 emails with confusing, misleading or “lazy” subject lines. Combine these, and over 16% of the emails we examined did a poor job of conveying the true intent of the message they were meant to describe.

A subject line should always be used. Silly to even have to write that, but with 1% of our emails arriving without one, it must be stated.

Additionally, try to give some consideration to the recipient. For example, if the recipient works for ABC Company, don’t send them an email with only “ABC Company” in the subject line – they know the name of their company! Do you want them to guess at the real subject of the email? How do you expect them to file this email to refer to it later? Are you just a selfish person who wants to organize your emails without regard to the recipient?

It’s important to note that TheManager deletes email from unknown senders that contain only TheManager’s company name in the subject line. Not because he’s afraid of SPAM or viruses, he’s just a very particular SOB.

8) Attachment Sizes – Rule number one for the novice email user: Email programs do not allow attachments of unlimited sizes. As crazy as that sounds, it’s true. Typical email programs limit attachments to around 6-8 MB, some less, some more. Even a company’s own email servers will limit the size of an email inbox, making it impossible to receive messages that have extremely large attachments.

The largest attachment received in the 4,000 emails examined was 11 MB. Interestingly, it was a PowerPoint document that consisted of only 15 pages. Why was it 11 MB in size? The sender didn’t know how to properly use PowerPoint and they didn’t bother to compress the images in the document. Once the images were properly compressed, the file size was a manageable 1.3 MB.

The largest attachment the editors never received? Of course, we don’t know what we didn’t receive, but one sender did wonder why TheManager never responded to an email with an attachment. When he asked the attachment size, the sender replied “sixty-two megabytes.” Yikes! The worst part about an email of this size is that any sender dumb enough to think that a 62 MB file will be received successfully, obviously has no idea on how to send something via ftp.

It’s not just email programs that create limits on what someone can receive. All of the editors at AskTheManager.com use wireless CDMA cards from cell phone providers on our laptops. These cards enable speeds about twice that of dial up, which means large attachments can literally crush you when you’re sitting at the airport trying to access email.

The editors all agreed, the largest email attachment anyone should send should be 4 MB, with anything larger being transmitted via ftp. If you thought ftp was a floral delivery company, check out this link. For those of you who don’t know how to compress images in documents, perhaps you want to check out this link.

7) Email Quantity – We all receive too many emails – it’s a fact of business life in 2008. Our issue isn’t really with the amount of diverse emails we receive, it’s with the few senders who don’t know how to walk down the hall or pick up a phone.

Quick Tip: Not every communication needs to be documented in email.

Between these few email offenders and the dreaded email string that goes on forever, we are running out of time to do any real work. The solution? File every email where you are not the primary recipient without reading them, and resist the temptation to keep long email strings alive.

Interestingly, the longest string the editors found in the 4,000 emails examined for this article had only 41 messages included. Everyone predicted the winner would include somewhere closer to 100 emails. Oh well, 41 still seems long to most people.

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While we’re sure none of our readers have ever committed any of these egregious errors, we felt they needed to be reported so that we can, collectively, destroy the offenders with ridicule.

These were the first six in the Twelve Worst Business Email Etiquette Mistakes Ever. Please follow this link for the Top Six.

(We think it’s important to note that there are resources to help you write better emails. Understanding how to use all of the features of Microsoft Outlook is a great first step. Outlook 2007 For Dummies is the best Microsoft Outlook training and reference guide available.)