Email etiquette rules dictate what’s appropriate and what’s not when you’re sending a message to a prospect, business partner, coworker, manager, or acquaintance. They help you avoid miscommunications and mistakes which can reflect poorly on you and the organization you represent.

So, to avoid prospects coming to those negative conclusions, here are a few email etiquette tips every professional (especially client-facing ones) should know and follow.

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Oftentimes, email etiquette for business communication will start off straightforward and professional. As you develop a relationship with the person you’re emailing (in this case, a prospect), you can use more casual language while still maintaining a professional tone. This allows your personality to shine through so the future client can get to know you better and feel comfortable doing business with you.

1. Keep your tone professionalemail etiquette tip: keep your tone professional

Since you still don’t know your prospect well after the discovery call, it’s best to keep your subject line descriptive and your greeting formal.

In the example above, you’ve reminded them of your earlier conversation and kept things personal and friendly. You’ve also confirmed your scheduled meeting and called out the tidy agenda attachment, so it doesn’t get lost below.

Finally, you’ve signed off formally, which is fitting for this stage of the sales process. This email example shows a high level of email etiquette that just about anyone would appreciate.

2. Avoid vague subject lines

email etiquette tip: avoid vague subject lines

The subject line of this email doesn’t tell the prospect anything about the contents — so why would they open it? Also, the greeting is too casual, there’s nothing personalized about the email itself, and no meeting confirmation has been included.

Sending long URLs is also an email etiquette no-no, the sign-off is too casual, and the typos make it clear the person writing it either has very poor grammar or didn’t take the time to read it through.

Instead, use a subject line that gets straight to the point — something like “Follow Up to Our Call”. Then, address the prospect by name in your greeting and hyperlink the agenda. This makes it easy for the reader to click the link rather than copy and paste it into their browser. Finally, read through your email one last time to check for grammar and spelling errors, like “you’re”.

3. Use proper email punctuation

Punctuation is subtle when you use it correctly and obvious when you don’t. Don’t make your recipients cringe — memorize these rules and follow them religiously.

Terminal Punctuation

Every line should end with a terminal punctuation mark, i.e. a period, question mark, or exclamation mark. If you skip terminal punctuation, it’ll look like you never completed your thought.

Here’s an example:

  • Incorrect:

“I talked to Finance, and they approved the agreement”

  • Correct:

“I talked to Finance, and they approved the agreement.”

Use question marks sparingly. If you use too many question marks in one email, you’ll sound like you’re interrogating the recipient.

“What’s your status? Have you talked to your team yet? Are you free for a call tomorrow at noon so we can discuss any potential changes?”

Semicolons (;)

A semicolon can also connect two unique, but related sentences. It cannot act as a comma.

  • Incorrect:

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

  • Correct:

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

Comma (,)

One of the most common bloopers is adding commas where they don’t belong. While I could devote an entire post to proper comma usage (English major talking), here are the most important rules:

  • Use a comma before a coordinating conjunction (and, but, for, or, nor, so, yet) that connects two independent clauses.

“I worked with a similar client last year, and their open rates went up 20% in one month.

  • Use a comma after a dependent clause at the beginning of a sentence.

“After improving their subject lines, open rates improved dramatically.

  • Use a comma to separate items in a list.

“I focused on email length, readability, and content.

Salutation Punctuation

There are a few different ways to punctuate your salutation (the first line of your email where you address the recipient by name).

  • If it’s a formal email, use a colon.

Dear Ms. Frost:

  • If it’s a relatively casual email, use a comma.

Dear Aja,

  • You can also use an em dash.

Hi Aja —

Exclamation Mark

Use exclamation marks as sparingly as you use question marks. You’ll come across hyper and overexcited if you go overboard with exclamation marks.

“Thanks again for a productive conversation yesterday! Good news, I talked to Finance and we’re good to go! Can’t wait to work together!”

In general, exclamation marks aren’t considered professional. So, leave them for your happy hour text messages to friends.

4. Practice good grammar

Unless you devote your full attention to studying grammar (which is much less lucrative than sales), you’re bound to make the occasional mistake. But no one will care if they’ve never heard of the rule you broke, either. Just steer clear of basic mix-ups that your prospect will definitely catch, such as:

Know the difference between:

  • There/they’re/their
  • Its/it’s
  • Effect/affect
  • Your/you’re
  • Too/two/to
  • Loose/lose
  • I/me/myself

Pro tip: Do you ever wish you could have an editor reading over your shoulder? You can — kind of. Grammarly is a free tool that scans everything you write for grammar and spelling mistakes. Not only will it catch issues in real-time, but it’ll also send you a weekly report highlighting trends in your most common mistakes.

5. Resist emojis in email

I understand the urge to add a smiley face to a potentially harsh sentence or cap off a joke with a laughing emoji.

However, unless your recipient has already used one, resist temptation. Research reveals including emojis in work emails is bad for your reputation: They make you look less competent (and they don’t have any effect on how friendly you seem).

6. Keep subject lines descriptive and short

I understand the urge to add a smiley face to a potentially harsh sentence or to cap off a joke with a laughing emoji.

However, unless your recipient has already used one, resist temptation and keep things a bit more formal.

6. Keep subject lines descriptive and short.

Your subject line should be descriptive and relatively short. Ideally, it should give the recipient a good idea of whether they want to open your message.

  • Bad subject line:

“Hi”

What are you emailing them about? It’s completely unclear.

  • Good subject line:

“Summary of December 2 call”

This line leaves no doubt about the contents of the email.

7. Choose your email salutation carefully.

Above, we covered which punctuation to use in the salutation. You also need to pick a greeting — which can be formal or informal, depending on whom you’re emailing and what your relationship is like.

Most of the time, a casual salutation is appropriate. You’ll set a friendly, easygoing tone and communicate confidence.

Casual email greetings include:

  • Hi
  • Hey
  • Hey/hi there
  • Good [morning, afternoon]
  • [Name]

If you’re reaching out to someone for the first time — or if they work in a conservative industry — err on the side of formality.

Here are some formal email greetings:

  • Dear [first name]
  • Dear Mr./Ms. [last name]

And greetings you should avoid using:

  • Yo: Too informal
  • Hey!: Too intimate and eager
  • [Name]!: Too off-putting
  • To whom it may concern: Too impersonal
  • Dear sir or madam: Too stiff
  • Hi friend: Too creepy
  • Gentlemen: Too old-fashioned
  • All: Too cold

8. Leave the right impression with your email sign-off.

The right sign-off will complement the tone and content of your email. Since it’s the last thing your recipient reads, this line influences their lasting impression.

If your tone is lighthearted, end with a warm sign-off.

Informal sign-offs:

  • Thanks
  • Thanks again
  • Best
  • Cheers
  • Happy [day of the week]
  • Enjoy the weekend
  • Talk soon
  • Talk to you [tomorrow, on Wednesday, when you get back]
  • Looking forward to working together
  • Looking forward to our next conversation
  • Excited to hear your thoughts

If your tone is more reserved, your sign-off should be as well.

Formal sign-offs:

  • Thank you
  • Thank you for your time
  • Have a wonderful [day, weekend]
  • Regards

And here are the closing lines you shouldn’t be using:

  • Sincerely: Too outdated
  • Kind regards: Too unnatural
  • Warmly: Too relaxed
  • Respectfully: Too random
  • Xoxo: Too intimate
  • Cordially: Too stilted
  • – [Your name]: Too abrupt

9. Triple-check your recipient’s name

Triple-check that you’ve spelled your recipient’s name correctly. It takes two seconds: Just pull up their LinkedIn profile and compare their headline to the name you’ve used. (If you have Sales Hub, this step is even quicker. Their social profiles will show up in your inbox.)

And don’t shorten their name unless they’ve signed their email accordingly. You might assume “Michael” becomes “Mike”, but he could prefer going by the latter. Check his signature. If it reads “Mike”, you can use the nickname; if it’s “Michael”, that’s what you should address him by.

10. Use sentence case

When you’re texting or on Slack, you probably don’t capitalize much — if anything. But when you’re writing a professional email, use sentence case. In other words, capitalize the first letter of the first word in a sentence and all proper nouns.

Example:

Dogs are welcome at HubSpot.

11. Consider your email’s tone

It’s incredibly hard to get the right tone across over email. Research shows people dramatically overestimate how often their recipients would correctly identify if their tone was sarcastic or serious.

While they believed recipients would get it right 80% of the time, reality was closer to 56%.

Does that mean half of your emails will be misinterpreted? No. But it does mean you should think carefully about the words you’re using and how someone else would read them.

  • First, avoid negative phrases. They can make you seem more anxious, irritated, or worried than you truly are.

Examples: Mistakes, issues, failure, delay, problem, crisis, trouble, unfortunate, consequence

  • Second, don’t be sarcastic. There’s a good chance your recipient won’t get the joke — and you’ll seem like a jerk.

Example: “I’d ask my team to review it tomorrow, but as you probably know, no one actually gets work done on Friday.

  • Third, cut out adjectives. They can make you sound overly emotional — you’re shooting for calm and professional.

Examples: Very, really, extremely, highly, grave, serious, deeply

  • Fourth, copy your recipient. Following their lead ensures you won’t accidentally offend them. If they write short, straightforward messages, make yours concise too. If they usually include a rapport-building line (like “I saw you were in Bermuda; hope you had a great time”), do the same.
  • Fifth, when in doubt, pick up the phone. Whenever you’re having a potentially fraught conversation, it’s always a good idea to call, Skype, or meet face-to-face with the person.

12. Always use standard fonts and formatting

Want to make your recipient’s eyes hurt? Use wacky fonts, wild colors, and offbeat formatting.

Yes, your email might be more memorable, but you’ll look like you’re completely out of touch with communication norms.

Always use the standard font. Never use a color other than black. Stick to the standard font size. Don’t bold or italicize more than one word (or string of words) in a single email.

And if you’re copying and pasting text, make sure you highlight it and clear the formatting. (Command + on a Mac, Ctrl + Shift + N on a PC.) If you don’t, the snippet will appear differently than the rest of your email.

13. Shorten your URLs.

Pasting entire URLs into your email takes up valuable space and looks messy. Instead, create hyperlinks or insert a shortened URL.

  • Incorrect:

Check this out:

Check out this article on sales emails.

  • Correct:

Check this out: https://bit.ly/2sl3DDH

14. Call out attachments.

Indicate somewhere in your email you’ve included an attachment so your recipient doesn’t overlook it.

A simple “I’ve attached a [document, spreadsheet] for X will do the trick.

And make sure you’re reattaching files when you add someone to an email chain, or they won’t be able to see them. (An alternative? Simply forward them the thread.)

15. Perfect your email signature

A bad email signature can really do a number on your relationships. Even if you write the most eloquent, persuasive message in the world, a poorly designed signature will make you seem like an amateur.

Keeping in mind less is definitely more, yours should be relatively small, simple, and restrained. Now isn’t the time to include your favorite inspirational quote, headshot, or every possible way to reach you. Stick to your name, job title, LinkedIn URL and/or company website, and phone number.

16. Fill out your email fields properly

  • To: This field is simple. Add the email address of the person you’re trying to contact.
  • Cc: If you’d like to include someone else on the message Cc them. You’re essentially saying, “Hey, read this, but don’t feel obligated to respond. Ccing someone is necessary when there’s relevant information in the email or you’re connecting them with the actual recipient.
  • Bcc: Bccing also copies your contact to the email, but no one besides them will see they received it. In other words, if you send an email to Michael Scott and Bcc Jim Halpert, Michael won’t know Jim got it as well.

17. Use Bcc appropriately

To hide email addresses. Bcc can be 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: Bcc can let someone see a message without actually including them on all the threads to follow.

Common Courtesy: Bcc allows you to politely remove people from inbox threads. For example, if your boss is introducing you to someone, it’s common courtesy to Bcc your boss in the response (usually by saying, “Moving [name] to Bcc to save their inbox.) This shows you answered without flooding their inbox with the following back and forth.

18. Use ‘Reply all’ sparingly

  • Reply: When you click “Reply,” you respond directly to the 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 a certain issue has been addressed. It’s also helpful when you have information everyone cares about.

When in doubt, default to “Reply.” You don’t want to be the annoying person everyone is secretly rolling their eyes at.

19. Think before 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 than 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

20. Respond in a timely manner

We all have overwhelming inboxes and busy schedules, so it’s not always possible to respond to emails right away. The appropriate response window depends on the person:

  • Immediate Teammates: Respond within 12 hours. Your team relies on you to work quickly and efficiently; plus, most emails are about timely matters.
  • General Colleagues: For everyone else you work with, respond within 24 hours. Can’t address their request in that time period? Respond letting them know you’ve read their email and will follow up by X time.
  • 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.

21. Set informative 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 whomever 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:

  • DO: Include how long you’ll be unavailable.
  • DON’T: Create an OOO response for one day.
  • DO: Include another person to contact for more urgent matters.
  • DON’T: Include a colleague to contact without letting that colleague know they’re in your OOO reply.
  • DO: Include “OOO in your subject line so people can easily identify the automated response.
  • DON’T: 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 situations. Here’s an email HubSpotter Beth Dunn sent before her month-long sabbatical:

email etiquette tip: set informal out of office replies

Beth makes it clear she won’t be responding to email, but since she’s out for an extended period of time, she shared a clever and easy way to grab her attention when needed.

22. Track email opens and click-through rates

Rather than sending passive-aggressive “Did you see my email? messages, use an email tracking tool like HubSpot Sales Hub. You’ll know the exact moment your recipient opened it — and if they don’t reply reasonably quickly, you can find a non-irritating reason to follow up, such as, “I read an article on X that reminded me of you; here’s the link if you want to check it out.

23. Don’t add that ‘Sent from my phone’ caveat

Should you include “Sent from my iPhone or “Sent via phone — please forgive any typos? I wouldn’t. Many people take this as an excuse to be lazy and forgo a glance-over before you press “Send.

Email is one of the most essential tools a salesperson has in their arsenal. Make sure you’re using it well with these email etiquette tips, and you’ll be on your way to starting genuine relationships with prospects.

Editor’s note: This post was originally published in July 2019 and has been updated for comprehensiveness.

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