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Punctuation, Grammar, and Copy

Section 1

Proper sentence structure may sound overrated, but think of this way: After someone reads our email, do we want the main takeaway to be the core message or the fact that we misused a semicolon? We’re guessing the former.  

We'll start with six punctuation-specific tips to keep our emails punctuated pristinely, and then dive into other copy tips. Don’t worry, we won’t use any fancy grammatical terms such as “clauses” or “compound adjectives” - just plain English tips. 


" " Quotation Marks

We all know when to use them, but the most common mistake is where to place them.  Periods and commas go inside quotation marks.

  His book, “Design for Puppies”, releases tomorrow.
  His book, “Design for Puppies,” releases tomorrow.


( ) Parentheses

Periods and commas go outside the parentheses, except for when the parenthetical sentence stands alone. 

  I got a bonus last week ($150.)
  I got my bonus last week ($150).
  think you’re one in a minion. (Ha, get it)?
  I think you’re one in a minion. (Ha, get it?)


: Colon

A colon can connect two independent sentences. Many people, however, don’t realize that the latter sentence should be a capitalized with Sentence case

  Her conclusion was simple: the ducks are mad cute.
  Her conclusion was simple: The ducks are mad cute.


; Semicolon

A semicolon can also connect two unique, but related, sentences. It cannot act as a comma. The Oatmeal has a great comic on its proper use.

  She can call me tomorrow, she can give me an answer then.
  She can call me tomorrow; she can give me an answer then.


; Commas

Many people go comma crazy. A comma is used to mention additional details or build a list.

  The author Sam Smith, was very nice.
  The author, Sam Smith, was very nice.


! Exclamation Points

Hey!!! Are you trying to exclaim in your email? If not, it may be best to avoid the exclamation point. Not sure? Use the flowchart below from the HubSpot Blog.

(click to enlarge)




In a world of acronyms - omg, btw, lol - it’s easy to let proper grammar fall to the wayside. Our recommendation is to avoid such shorthands when communicating with external contacts and, depending on who, some internal contacts. Grammarly is a great free tool that helps ensure you're writing emails free of fundamental garammar issues.

That said, there are workplace appropriate acroyms; here are some common ones to know:  

For a complete list of 20 email acronyms you should know, click through the presentation below.





Use emoticons sparingly. The only one typically accepted in business email etiquette is the standard smiley face :)



Subject Lines

Interestingly enough, our data on one-to-one email correspondence has shown that emails with no subject all together were opened 8% more than those with a subject line. [CLICK TO TWEET]


While this may be worth testing, our general recommendation is to still use a brief subject line that’s descriptive of the core contents of your message. If you’re looking for more pointers, this presentation has 19 stats to help:


Sentence Case

While email correspondence with our friends or peers can neglect sentence case and be written in all lowercase, business emails are a different story. To maintain professionalism, stick with sentence case (just like every sentence on this page).




Tone is the most misunderstood aspect of business emails. Many writers end up with a far-too-formal tone (HelpScout has a great guide on this for the support world here). Meanwhile many others end up overcompensating with extra exclamations or emoticons. The best approach here is to use friendly language with simple punctuation.

Here's a sample email with basic, proper punctuation that still conveys a friendly tone: 


Fonts and Formatting

Section 2

Take a look at this email and think about how much it pains you to read it:

Let’s help make inboxes everywhere a better place by avoiding any of the faux pauxs in the email above and instead keep these basic formatting tips in mind:



Font Size

Avoid any alternatives to the standard email font size. This includes font choice as well. If you're questioning a font choice, refer to this guide to email typography from MailChimp.


Font Colors

Refrain from using multiple font colors. Our email clients default to the standard black color—in HEX codes, #00000—we see on this web page. Some people try to “mix it up” with a navy blue or by emphasizing a word in red. Stick to simplicity to keep the focus on your actual message and not on your funky formatting.





Avoid highlighting the copy of your message as you would avoid font color variations.




Rather than pasting full URLs into the email body, a better approach is to either shorten the URL or hyperlink a set of words. 

 Check out this article
  Check this out: http://bitly.com/1Gn6pN0


We recommend hyperlinking specific words within your email copy. By doing so, you can use email link tracking to know when your recipient has actually clicked on that URL. 




Underline / Bold / Italicize

Each of these font formats are used to provide further emphasis. Examples:

If there is one hotdog you eat this week, let it be this one.

No matter what we do, one person just has to leave a negative comment.

need those french fries on my desk by morning.

Using them in excess can clutter our message. Using more than one at a time can harshen our tone. Using one when necessary can keep our message clean. 




There’s an old rule that says we should “request” to send an attachment before actually sending one. That email etiquette tip is out-of-date. For internal contacts, we shouldn’t worry about including a quick document or excel sheet.

When communicating with external contacts, it may be worth a quick heads up. This could be as simple as the following: 


Bonus Tip: We all get irritated when someone adds us to an email chain and says, "see the attachments Rachel sent below!"

Then you look below and realize there's nothing there - the attachments must not have gone through. That's because email attachments don't remain attached when we reply in thread. This issue can be easily resurrected with email forwarding. Take a look at our two email attachment solutions.

Greetings and Signatures

Part Three


Email Salutation

We all know we should start our emails with a greeting. Depending on who we’re communicating with, this greeting can be formal or informal. We’d say that 90% of the time, an informal greeting is perfectly appropriate. Occasionally, a more formal tone is required. Here are some examples of the difference: 



Email Ending

The formality or informality of your email ending should match the tone of the greeting. If you use a formal introduction, use a formal ending.




Email Closing

Even when the rest of our email is formal, we usually never need a formal email closing. Simply signing off with “-Name” suffices. 



Email Signature

One of the core problems with email signatures is that we overthink them. If your signature does any of the following, it’s likely doing nothing more than distracting recipients from reading the actual content of your email:

  • Includes every possible way to contact you. We’re already emailing someone, so shouldn’t the best possible way to reach you to be to email back at the same address? Why do include emails in email signatures?! The only contact information needed in a signature is a phone number - which if you’re not in a services-role, can often be kept out and shared if you want the person to actually call you.  
  • Uses an image of any kind. Not only can images get blocked by image blockers, but images typically render much larger on mobile opens than desktop. Highly visual signatures can also distract our contacts. Headshots are not critical elements of an effective signature.
  • Includes heavy marketing information. While including a web URL or a quick call-to-action for an upcoming event can be helpful, an email signature is not the most effective home for mission statements, business pitches, or detailed bios. Save that for the social profiles or website URLs that you can link to in the signature - just be cautious of how many links to include. The more options, the less likely any will be clicked. Here are 10 example marketing links you could include - be wise in selecting which makes it into your signature!


Fall into any of the above traps and your email signature may end up looking like this horrendous example: 

BCC, Replies, and Forwarding

Section 4


Email Sender Fields

Every email has three main sender options for including an email address: To, CC, and BCC.


To: This field is simple. It’s simply where we place the email address of who we’re trying to contact.

CC: If we’d like to include someone else on the message, but not necessarily indicate that this is message is being sent specifically “to” them, we can CC - or carbon copy - them. Sometimes this lets a CC’d recipient know they’re not obligated to respond.  

BCC: A BCC - or blind carbon copy - copies someone on the email just as a CC does. However, BCC’s cannot be seen by anyone in the “To” or “CC” field. Example use cases:

Protect an email: Sometimes a BCC is used to protect someone’s email from being exposed to others. For example, if you’re emailing a group of people about an upcoming event, you may opt to BCC all emails so you’re not exposing emails without permission.

General FYI:
Sometimes a BCC is just a way of letting someone see a message without actually including them on all the threads to follow.  

Common Courtesy: Sometimes a BCC can help you simply be polite in email threads. For example, if your boss is introducing you to someone, it’s common courtesy to BCC your boss in the response. That way, they can see you responded to the thread, but don’t have to see their inbox flood with the back and forth responses in the thread. 


Reply vs Reply-All

Incorrect usage of the reply vs reply-all is among the biggest pet peeves in email etiquette. Everyone thinks they get it, but do they?

Reply: When you click reply, you respond directly to the last person who emailed you last. If you respond directly to the initial message, your reply will go to the original sender of the email. But if you respond to someone else’s email in the thread that follows, you will end up replying just to that person:


Reply-All: When you select reply-all, you email back everyone who is either in the “To” or “CC” fields. The benefit of reply-all is letting those in the thread know that a certain issue has been addressed. The irking factor is when people reply-all to emails where everyone on the thread does not need to see the response. 

For more on how to properly employ the reply-all, check out this post on Life Hacker.


Email Forwarding

There’s a few key pointers to keep in mind for proper email forwarding etiquette:

  • Some emails are not intended to be forwarded. If a contact is sending you private or sensitive information, use high caution before forwarding it along.
  • When forwarding a long email thread, a common courtesy is to summarize what’s being discussed below so the recipient knows exactly what you want from them. There’s nothing worse then getting forwarded a 50-chain thread with a note that just says, “see below.”
  • If you’d like your forwarded email to start a new email chain (rather than being a part of your current thread) simply include your own commentary in the subject line.

Same Thread Subject Line:
FW: notes from tuesday
New Thread Subject Line: Check this out! FW: notes from tuesday


Follow Ups and Mobile

Section 5


Email Response Time

We all have overwhelming inboxes and busy schedules, so it’s not always possible to respond to emails right away. We try to think of email response times in the following buckets:

  Immediate Teammates:

Respond within 12 hours. Our team relies on us to work quickly and efficiently. Most often our team is emailing us about day-to-day tasks that require our attention. Everyone on the team is more productive when communicate is quick and crisp.

    General Colleagues:

To all other colleagues at your organization, a 24-hour response time is considered appropriate. If you honestly do not have time for a particular request that comes over email, respond and say so. It’s better to respond with transparency than to let an email go ignored and leave your colleague in the dark.  

      External Contacts:

Unless marked as an urgent email or one that needs an ASAP response, responding to external contacts by the end of the week in which it was sent is perfectly appropriate - so if you received the email Tuesday, respond by Friday of that week. For high value contacts, it may be worth responding within a 24-hour time frame.

The exception here is for any emails to customers. For more on an acceptable response time to customer emails, refer to this HelpScout post

If you truly can’t respond properly to any of the above categories within a respectful time frame, send a quick email that acknowledges you’re busy and will get back as soon as you can. Example template:


Out-of-Office Replies 

If you’re going to be unavailable for an extended period of time, an automated “OOO” reply - or out of office reply - can let whoever is contacting you know that you won’t be able to respond to their message until the date you’ll be in the office again.

Some do's and don'ts for OOO replies:

Include how long you’ll be unavailable.

Create an OOO just for being unavailable for one day.

Include another person to contact for more urgent matters.

Include a colleague to contact without letting that colleague know they’re in your OOO reply.

Include “OOO” in your subject line so people can easily identify the automated response.

Include more detail than needed - such as the exact location of your vacation.

If you're taking a vacation for an extended period of time, it may be helpful to have a way of earning your attention for truly urgent, require your attention, situations. Here's an email HubSpotter Beth Dunn sent before her month-long sabbatical:


Email Follow Ups

With the response times from point 25 in mind, follow up to unresponded emails when appropriate. If three days has gone by and you’ve yet to hear from a colleague, it may be worth nudging them again with a follow up.  

That said, follow ups are a tricky category and can vary based on your specific needs. Here are a few helpful resources:



Email Tracking

Repeatedly sending our contacts the, “did you get this email?” email can be obnoxious. Meanwhile saying nothing and waiting on a response for satisfaction that our email delivered is equally stressful. To avoid getting irritated - or irritating others - simply track your emails.  


By tracking our emails, we can easily see when the emails we sent are opened, giving us the the guarantee that our recipient received the message without irkingly asking them to confirm that they did. That’s why we built Sidekick - to provide a free tool that will track your emails for you.




Mobile Autocorrect

While some go as far as turning off predictive text when emailing over mobile, we recommend at least trying to avoid using autocorrect when typing a message on your phone. Since our mobile devices are smart in understanding the various slang words or acronyms we type repeatedly, it's easy to have autocorrect change an innocent word to something with a meaning inappropriate for your correspondence.  


Mobile Email Tracking

Since emailing from a mobile device can lend itself to innocent errors, a custom email signature can help cut us some slack. The classic, but simple and effective, example we all see is "Sent from my iPhone." Employing a similar technique can let email readers know you're typing the note on your mobile device.