I can’t count how often I have sat in front of an email draft, palms sweaty, reading, re-reading, re-wording, then re-reading again on an email that is very important. Sometimes it has been a cold email, written to someone who does not know me, but I would like to connect with. Other times, it’s been when I am asking for something from the email recipient that feels like they might say “no” to. Most recently, I felt this way when I need to give strong direction to a group of important people; I don’t make it a habit of telling people what to do, but sometimes it’s gotta happen.

When I get in this knotty-stomach mode, there are a few tricks that I’ve relied on to make sure I’m still sending solid emails. Most of them I’ve learned from doing it wrong, and I’ve lived to tell the tale, so it’s not the end of the world if you mess up a little. Hopefully these tips below will save you from having to send a follow up damage control / “what I actually meant to say was…” email, and let you focus on achieving your dreams and changing the world! <3

A note: While these are important for every email, I do not follow each of these to a T for every email that I write. If I’m shooting off a quick note to a friendly coworker, I don’t stress about making sure that my grammar is 100%, for example.

Double check the spelling of people’s names

First things first, if you’re using the recipient’s name (and you probably should), double and triple check that it’s spelled correctly. This is a personal pet peeve of mine to see “Jaime” “Jaimie” “Jamey” when my name spelled “Jamie” is readily available for reference. This is a huge turn-off, indicating low attention to detail or lack of caring about the person the message is going to. If this is a high pressure situation, don’t miss this one.

Avoid the dreaded premature “Send”

Shortly after Gmail introduce a “handy new shortcut” to send your emails by pressing a certain combination of keys, I sent several partially completed emails on accident. While I appreciated the intent, I quickly turned off that feature and implemented these two strategies as well. Voila, no more rogue email fragments flying out of my outbox.

First, if it’s a new email, fill out the “To: ” field LAST. If you need their email address for quick reference, pop it into the first line of the body of the email to cut & paste later. This ensures that you can get all the content you want into the email without fear of an accidental mouse click or unknown keyboard shortcut sending the email out too early.

The second is if it is an email that you’re replying to, where the “To: ” field will autopopulate. You could erase out the recipients and add them back later, but my preferred strategy is to open up a new, blank email and type up my message there. When it’s all set, I’ll cut and paste into the reply, and send it away. The other bonus of the blank email approach is that if it’s a real dicey situation, it’s easy to send it over to a friendly coworker to review and get feedback on.

Make your point and make it clear

Whatever the main point of your email is, it should be within the first 1-3 sentences of the email. If you’re asking for something, get to the question. If you’re recounting action items, keep them at the top and bold names. The general principle here is that people are busy, and most people skim emails by reading the first bits of sentences and paragraphs or anything that’s highlighted. Help them identify what is important and what you need to make it easier on them.

Personally, I’ve gotten emails that were full of text with no differentiation; I thought I read it adequately, only to find out later that there had been a question or an action item for me that went inadvertently ignored. Use your formatting tools sparingly (bold, underline, etc.) because if everything is highlighted, nothing is.

Make it personal and personable

As a counter to the above, find ways to infuse a little humanity and personality into your message. It’s a delicate balance, but your email style is essentially a personal dialect: you want something that’s reflective of you. For example, I’m generally cheerful, positive, smiley person, so I can get away with using more exclamation points than your average bear! I also verbally say “y’all” — it’s a gender inclusive term with a hint of Southern charm — so it finds its way into my emails as well.

The age-old advice to “find something to connect on” is valid here as well, but I have a slightly different take: if this is the first time you’re emailing someone, give them context on who you are and how you came to be writing this email. Keep it short enough to get to the main point quickly.

Craft your subject line

Honestly, subject lines tend to give me the most pause when writing important emails. There’s a science and an art. It must be long enough to give context without being so wordy that it gets overwhelming. The keys that I’ve found are to identify immediately if there is action requested within. This could be as explicit as “Action Requested: blahblah” but I typically only reserve those for shit-just-got-real emails. I am a fan of the prefix “Request: ” but it’s definitely formal. You can also say “[Meeting Name]: Action Items” or “[Meeting Name]: Follow Up”. Direct, succinct, and not-too-formal is where I’m aiming; it’s a tough one to hit!

Bonus tips

• Set up your email signature. Depending on your context, it can provide extra information to your recipient about who you are and what you’re about. You can identify your full name; I typically don’t include my last name in the body of the email because it will come through in the “From: ” field and will be in my signature, so it contributes to the body feeling a bit more informal, which is often the tone I’m intending. You can also identify your position or title (for example: Project Manager, ProjectX) and your company or school. If you’d like the recipient to check out your personal website or Linkedin, include those links there.

• Download Grammarly or another spell check software to catch obvious typos.

• If you have time to spare, don’t send it right away. Take a break and reread; you’ll often catch typos or other not-quite-worded-correctly bits that a spell checker would miss, but — at best — look slightly unprofessional or — at worst — confuse the reader or miscommunicate entirely. I’ve picked up a nasty habit lately of omitting the word “not” when I’m in a hurry, which results in me communicating the exact opposite of what I’m going for. A reread typically reveals these easily and it’s a quick fix (and a self-directed eye roll).

• If you’re feeling extra nervous, send it to a coworker to read. They’ll be able to give you a fresh set of eyes on it and point out any odd phrasing or lingering questions.

Sample Emails

Sample Email #1

Situation: I’ve been asked to reach out to someone in the company that I’ve not met before to set up a meeting to discuss financial reports.

Subject: Request to Discuss ProjectX financial reports

Hi [person whose name is spelled correctly],

My name is Jamie, and I am the Project Manager on ProjectX. I was talking to [person we both know whose name is spelled correctly] about financial reports, and he/she said that you are the resident expert on that! Could we set up a time to meet this week and discuss? I’m happy to send a calendar invite over to get things rolling; let me know if there’s anyone else we’ll want to include.

Thanks,

Jamie

Sample Email #2

Situation: Action Items after a meeting, sent to a group of people

Subject: [Meeting Name] Action Items

Hi team —

Thanks for a great meeting. Below are the notes and action items I’ve captured. As always, please let me know if there is anything to add or edit.

• Action Items

  • Person 1: This deliverable by this date

  • Person 2: This deliverable by this date

    • Special note about this deliverable

• General Notes

  • Items that are good context to have documented or to share with anyone who wasn’t able to attend the meeting, but nothing critical for the people who won’t get this far when reading your beautifully crafted email. I’m still working on not taking that part personally — just because someone doesn’t appreciate art doesn’t mean that it isn’t art… and my emails are definitely art. 😉

Thanks y’all,

Jamie

I don’t have a crystal ball handy, but I fully believe that beautiful emails are in your future!

Jamie

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