Need our top e-mail tricks?  We have you covered.  Working at a company with over 100,000 of your best friends teaches you NOT to Reply All to e-mails. Here are those e-mail tips and tricks. If you have your top email tricks, please share them with your neighbor!

Be Polite and Professional

You never know who your e-mail will be forwarded to and you might not ever know if it does get forwarded. Whenever you write an e-mail, you should assume your boss, the CEO, and your mother might eventually get a copy. If there is ANY question about the content, leave it out. E-mails are easy to track, copy and print out.

Being polite and professional does not require you to use big words and complex language. As a matter of fact, you should write e-mails using language that is easy to digest – say at a 10th-grade level or so. If you use Microsoft Outlook or Word, there's actually a grammar checker that will tell you how complex your language is! Don't use language that will make your recipients feel stupid because they don't understand the words, it's a great way to alienate them. Use only abbreviations and acronyms that are common in your business… and you should still spell them out the first time around. Here's an example:

“Terry, could you please sign and return the attached SOW (scope of work) to me by the end of the day today? The customer needs the SOW tomorrow and I will need to revise and get it approved in the morning.


Notice how the acronym for SOW was spelled out in the parenthesis () the first time? After the first time, you can assume that people will remember the definition. This is especially important when your audience might not be familiar with the terms. In some cases, terms are so common this doesn't make sense to do, but it certainly cannot hurt.

Don't Store and Send Large Attachments In E-mail

Putting large attachments in an e-mail makes a copy of the attachment. The more recipients you send to, the more copies are made and the more storage is required. You lose your “single version of the truth”… that is, all the sudden there are many un-linked versions of your file floating around.

Especially if you're collaborating on a document, you want to use something like SharePoint for sharing files. SharePoint allows you to track versions of documents, restore earlier versions easily and you sync a local version or send a link to the file rather than the file itself, so you track everyone's changes in a single place rather than having to merge multiple documents manually.

Services like OneDrive for Business, Dropbox, can also help with file sharing, allowing you to send links instead of actual files. If you need to send something securely use an encrypted file sharing service instead. Here's how those services generally work:

a. The attachment is uploaded to a service or removed from your e-mail automatically in some cases and then hosted on a secure server
b. The recipient receives an e-mail with a link to the secure, hosted file
c. Credentials to access the secure, hosted file are provided to the recipient separately from the file-sharing link
d. The recipient securely logs in and downloads the file

Don't Reply All

As I mentioned at the top, you do NOT want to be the one that e-mails the whole company the large file that crashes the e-mail system… keep an eye on who your recipients are and remove any that really don't need to receive the e-mail.

The side effect is that people are more likely to open e-mails addressed to only them or to just a few people in a small team than they are too large group e-mails.

How To Notify Your Manager And Co-workers About Vacation Time

Many companies have a vacation calendar you can access through Outlook. The problem with vacation calendars though is that people have to go look at them for them to be useful. Here's how you can put your vacation on the calendar and notify those you work within a meaningful but non-intrusive way:

a. Highlight the vacation time on your calendar, right-click on it and choose New Meeting Request.

b. Add your co-workers and vacation calendar to the recipient list and type in a subject that includes what it is (vacation) and your name. In the location box indicate that you'll be OOO (out of office).

c. Change the Free/Busy status to Free. This will ensure that when your coworkers accept the invitation it doesn't block off THEIR calendars. They'll see that you are out of the office but it won't affect their ability to schedule items during that time.

d. Click the Response Options button and uncheck Request Responses. This way the recipients of your invitation don't need to click to accept the invite and you don't receive back a response from them.

e. Click the Send button to send the invite. It should look like this on your calendar and theirs.

You just notified your coworkers and the vacation calendar that you would be on vacation and out of the office with minimal interruption to them and without affecting their own calendar availability.

*Update suggested by a reader – create another regular meeting entry on your personal calendar for the same period and select an option such as Busy or Out of Office so that others see that you are unavailable when inviting you to meetings!*

Highlight Important Information

One of the problems with e-mails is that people include too much information and don't properly call out what is important and what is not. If you have 3 long paragraphs of introduction and then at the bottom of your e-mail there is an action required, you may not get your reader to scroll their screen down and see the action at the bottom of the e-mail.

Here are three guidelines that'll help you keep your e-mails to the point:
– Keep your e-mails to 6-8 sentences if possible.
– Get to the point in the first two sentences.
– Place important content at the top of your e-mail – where it's more likely to be read.
– Use bullet points or numbered lists to highlight action items and important facts.

I'm going to get on my soapbox for a minute regarding bulleted and numbered lists – all items in your list should be full sentences or they should all NOT be sentences… don't mix sentences with list items composed of individual words or short phrases. And end all sentences with proper punctuation. If it's not a sentence, don't include punctuation at the end.

For example, here is a list of fruits and their attributes:
– Apple – usually red or green, hard
– Pear – usually green, hard
– Peach – light orange to pink, soft
– Grape – green or purple, hard

This list is composed of short phrases and not sentences. It has no completing punctuation and the list is consistent and looks good. Notice that my previous list (the guidelines for keeping e-mails to the point) includes properly formatted full sentences that are completed with proper punctuation.

The Shorter, The Better

Long e-mails get ignored. It doesn't matter how well written they are. People don't have time to read a book… they want to get in, deal with your e-mail, and move on. Keep e-mails short, to the point, highlight important information, and as I mention in #3, call out required actions.

Here's an example of a good e-mail where important information has been highlighted well:

“*Action Required Today* – Signature Needed on ACME Brick Accounting Report”

“Bob, the ACME Brick Accounting Report ran successfully this morning and requires your signature by 3:00 PM so we can send it to the customer by the end of the day, today.

*Required Actions*
a. Your Signature
b. Scan & send signed doc to Processing by 3:00 PM


Evaluation – this e-mail is good because it's short, to the point, and clearly states what actions are required, why, and when. Even if someone didn't read the introductory paragraph, they could look at the required actions and understand at a glance what actions are necessary.

Use the Subject Line Well

E-mail subject lines serve three purposes:

a. Provide information about the contents of the e-mail so that recipients can understand its relevance to them.

b. Help recipients prioritize reading your e-mail among all of their other competing activities.

c. Act as a teaser to encourage others to actually open and read your e-mail.

First of all, you should only send e-mails to those for whom the content is relevant. As I suggested in Don't Reply All above, this will make it more likely that your e-mails actually get read when you send them. Don't cry wolf!

Second, when you include the right language in the subject line, your recipients will understand how important your e-mail is, whether it requires an action on their behalf, and whether they need to address it sooner or can wait until later.

Third, you WANT people to open your e-mails. If you can make the subject interesting in addition to being informative you'll increase your “Open” rate.

Finally, as I mentioned above, the subject should be short… under 35 characters.

Here are a few examples – I'll give you a sample and then tell you why it's good or bad:

Subject: “Spotlight on the options for dealing with problems in company systems due to environmental conditions that I have found.”

Good / Bad: BAD – it's not specific, it's too long, there's no teaser, even as long as it is the wording is too general and I can't tell what it's about, how important it is or whether it would be relevant to me – nobody will want to read that e-mail.

Subject: “*Requires Action Today* – Need your signature on ACME brick contract

Good / Bad: GOOD – it's short, to the point, you can judge how important it is to you and that an action is required and when. You should be careful with punctuation in subject lines, however… don't overdo it. Be especially careful with exclamation points – they can be considered rude or as shouting. Asterisks can highlight something important or call additional attention to something particular if you don't overuse and overdo it… don't use them in every e-mail or they become less effective and you're back to crying “Wolf!”

Subject: “ACME Brick Company Schedule”

Good / Bad: BAD – while it's short and clear on what the contents are about, it doesn't give you any information about how important the e-mail is, whether there is an action required and in what time frame it needs to be dealt with. If there's anything important in this e-mail, you couldn't tell at first glance.

Next Steps

Review our case studies and engagements where we helped companies just like yours solve a variety of business needs.

About Oakwood

Since 1981, Oakwood has been helping companies of all sizes, across all industries, solve their business problems.  We bring world-class consultants to architect, design and deploy technology solutions to move your company forward.   Our proven approach guarantees better business outcomes.  With flexible engagement options, your project is delivered on-time and on budget.  11,000 satisfied clients can’t be wrong.