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Rules to Better Outlook - 17 Rules

  1. Do you know how to search Outlook effectively?

    Some people are really good at using Outlook search to find the emails they need, while others have a hard time. Searching for emails can be a real struggle, sometimes you want to find emails from months ago but you aren't sure exactly what to search for.

    Being able to find an email quickly in Outlook is an important skill. Here are some tips and tricks about how to find that email buried in your inbox...

    Video: Searching Outlook Effectively with Ulysses Maclaren (9 min)

    Note: These tips will also help you in your Google/Bing searches too.


    Let's take an example scenario and see what tips we can use to search. Last month, you got an email in your inbox from your manager Bob about making changes to how you see data in his Northwind website.

    Tip #1: Give the person you are talking to the focus

    If you get 10 calls a day, you should be using this tip 10 times a day. When you get a call from Bob, before he has finished saying "how are you" you should have already typed in the search box and be looking at his most recent emails.

    To get Bob's most recent emails the best thing to do, is to limit Outlook to only your inbox folder and only emails from Bob by:

    • Change the folder to "Current Folder"
    • Search for:    from:Bob

    Note #1: You can change the folder scoping to fit your specific needs.

    search scope
    Figure: There are several scoping options available

    Note #2: You can change the default to always be "Current Folder".

    outlook search options
    Figure: Outlook Options for Search, have been changed to “Current Folder”

    Tip #2: Focus on the person (i.e. to: from: cc: bcc:)

    There are many different ways to focus on people. If know that the email was sent to Adam, from Bob, Luke was CC'd and Chris was BCC'd then:

    • Search for:    to:Adam from:Bob cc:Luke bcc:Chris

    Tip #3: Focus on the subject (i.e. subject:)

    If you have a good idea of what the email subject contains, then the "subject:" scope can help a lot. For example, if you know that the email had Northwind and Bob in the subject then:

    • Search for:    "Subject: Northwind Bob"

    Tip #4: Use negatives (i.e. –)

    Negatives are a great way to remove results you know definitely won't be relevant. For example, if you know Luke and Adam frequently work with Bob but weren't involved in that email then:

    • Search for:    -Luke -Adam

    Note: Start with a broad search, and then, when you start seeing irrelevant results about invoicing, add -invoice to your search

    Tip #5: Use quotation marks (i.e. “”)

    You can search for a direct match in an email using quotation marks. For example, if you know that "days outstanding" was written in the email then:

    • Search for:    "days outstanding"

    Note: Particularly useful when using common words but you know they were written in an exact phrase. E.g. “on top of this”

    Tip #6: Combine 2 searches into 1 (i.e. OR)

    Sometimes you might know a specific thing was referred to, but aren't sure what terminology was used. For example, let's say you know the email mentioned either "web app" or "website". In that case:

    • Search for:    "web app" OR website

    Note: Must be upper case... lowercase “or” won’t work

    Tip #7: Find a file (i.e. hasattachments:yes)

    Emails can be filtered to only include ones with attachments. If you know the email has an attachment then:

    • Search for:    hasattachments:yes

    Tip #8: Find a file’s content (i.e. attachment:)

    File contents can also be searched. If you know that there was an attachment that contained the text "20/07/2021" then:

    • Search for:    attachment:"20/07/2021"

    Note: You must enter dates in USA format #ouch

    Tip #9: Focus on the date received (i.e. received=<>)

    You can filter on a specific time period or date. For example, If you know that the email was received after 07/20/2019 then:

    • Search for:    received>"07/20/2019"

    Note #1: You must enter dates in USA format #ouch

    Tip #10: Recent Searches

    If you know you found an email before, but you can’t seem to find it again, try clicking on Recent Searches to scroll through your latest searches.

    outlook recent search
    Figure: Easily find your recent searches

    More Info: Outlook has a heap of other properties that you can filter on.

    email metadata
    Figure: Outlook has a lot of meta data filtering options

    Learn more: How to search in Outlook.

  2. Do you minimize your Outlook Distractions?

    Getting in the zone is pretty challenging in any work environment. Outlook in particular likes to offer as many distractions as possible to ensure you can never forget you've got it open. Set your options so that Outlook:

    Figure: Good Example - Turn off Outlook distractions on Windows

    minimize outlook distractions mac
    Figure: Good Example - Turn off Outlook distractions on a Mac

    • Doesn't play a sound
    • Doesn't briefly change the mouse cursor
    • Doesn't show an envelope
    • and DOESN'T display a New Mail Desktop Alert

    Here are a few more distractions tips:

  3. Do you use Autocorrect in Outlook to insert links?

    You just received another email from a client asking for your company's Terms and Conditions. Instead of navigating through your files or searching your website to find the link, wouldn't it be more efficient to simply type a shorthand code like #+ T and have Outlook automatically insert the URL for you?

    This is where the Autocorrect feature in Outlook can become a huge time-saver.

    Why Use Autocorrect for URLs?

    • Efficiency: It saves time by eliminating the need to find and copy-paste URLs
    • Consistency: It ensures that everyone is using the same URL and reduces the risk of errors

    How to Set It Up

    1. Open Outlook and go to File | Options | Mail | Spelling and Autocorrect
    2. Click Autocorrect Options and add your shorthand and URL link.

    Outlook image uly
    Figure: Make sure you use short key combinations that are unlikely to be used normally, but still easy to remember

    T - Adds a link to the company’s Terms and conditions. E.g.

    B - Adds a link to your Bookings

    Figure: Good example - Using shorthand codes to represent commonly used URLs

    By using Autocorrect in Outlook effectively, you can speed up your workflow. It's a small change with a big impact. Make sure to choose shorthand that is both unique and easy to remember.

  4. Do you use spelling and grammar checker to make your email professional?

    Improper spelling, grammar, and punctuation on your emails give a bad impression of your company. It looks unprofessional and can result in your message not being conveyed correctly. To ensure this doesn't happen, use Microsoft Outlook Spelling & Grammar Checker on the 'Editor Options' window.

    outlook spelling
    Figure: You should also check “Always check spelling before sending” to ensure your message doesn't have mistakes

  5. Do you give yourself a 2nd chance by not sending emails immediately?

    How many times have you clicked “Send” and within a minute or so realized you made a mistake and wished that email had not sent yet?

    Microsoft Outlook has the option to "recall the message", but this is not recommended mainly because you cannot guarantee the recipient hasn't seen the message already. If your recall does work, then the recipients don't know the reason the email was recalled as there is no spot for an explanation.

    Also, it's not a good experience for the users who receive a recall, as it does not even send it on the same thread.

    What you need to do is to set a rule to delay sending your emails in 15 minutes for example, which gives you time enough to correct it in most of the cases. If you only realize your mistake after this amount of time, just use "reply to all", mentioning your changes or send a v2 when changes are too substantial.

    Here is how you do it in Outlook:

    1. Click the File tab.
    2. Click Manage Rules & Alerts .
    3. Click New Rule .
    4. In the Step 1: Select a template box, under Start from a Blank Rule, click Apply rule on messages I send, and then click Next.
    5. In the Step 1: Select condition(s) list, select the check boxes for any options that you want, and then click Next.
      When you don't select any check boxes, a confirmation dialog box appears to confirm that the rule you are creating will be applied to all messages that you send.
    6. In the Step 1: Select action(s) list, select the "defer delivery by a number of minutes" check box.
    7. In the Step 2: Edit the rule description (click an underlined value) box by entering the number of minutes you want the messages to be held before it is sent. Delivery can be delayed up to 120 minutes.
    8. Click OK, and then click Next.
    9. Select the check boxes for any exceptions that you want. Click Next.
    10. In the Step 1: Specify a name for this rule box, type a name for the rule (E.g. "Delay sending emails").
    11. Select the Turn on this rule check box.
    12. Click Finish.

    Now when you click Send, each message remains in the Outbox folder for the time that you specified and you can make changes to it until then.

    recall message
    Figure: Bad example - Recalling a message when you want to change an email after sending

    create rule to delay sending
    Figure: Good example - Delay sending in 15 minutes (make it less or more if necessary)

  6. Do you know when and how to send a v2 of an email?

    Sometimes you will need to send a new version for an email. This often is due to 2 main reasons:

    • You received substantial feedback about the email you've sent that requires a new version
    • You realized you've made a mistake and want to send an updated version of an email

    Having an entire new version of an email is important as it:

    • Ensures that you understood feedback and incorporated it immediately
    • Cleans up the email thread history to only have relevant content

    Video: Fixing An Email Mistake with Adam Cogan (3 min)

    Note: Not every feedback will need a v2. Some may be in the form of:

    • Hints for what could be better for next time, in which case all that's required is you take the feedback on board
    • Changes or clarifications to the content, that can act as the latest version of the thread, without needing a re-send

    How to send a v2 (Outlook)

    1. Open your v1 email in Sent Items
    2. Click Actions | Resend this message
    3. Include (v2 - {{ REASON }}) on the first line of the email body
    4. The reason should include a summary of what was changed

    Warning: Do not add "v2" to the subject as we want to keep the thread.

    1. If the email is a reply, then keep the email history leading up to your original email.
    2. Replace your v1 with your v2 email, as if the v1 never happened (same for v3, v4, etc)

    Note: For v3 emails replace the (v2 - {{ REASON }}) on the first line of the email body with (v3 - {{ REASON }}). Repeat this for v4, v5, etc.

    For appointments, the procedure is different, see do you explain why you've updated or deleted an appointment?.

    Figure: Good example - Sending a 'v2' when you need to make an update

    Note: If all the feedback you received is incorporated into the new version, there is no need for an additional done email. However, if you've got other tasks in the feedback, it may be necessary to reply 'done' to those separated from the content of your v2.

    Tip: If you are doing a lot of these, you can add the 'Resend This Message' button to 'Quick Access' toolbar in Outlook.

    microsoftteams image
    Figure: 'Resend This Message' on the 'Quick Access' toolbar

    Video: Some jobs give no chance for a v2

  7. Do you know how to recall an email?

    Do you know it is better to send a v2 rather than recall the email, see SSW Rule Do you know when and how to send a v2 of an email?

    Even though you may check your emails before sending, use SSW lookout to help you avoid mistakes, and even if you send/receive manually, there will still be times where you will send out an email with mistakes or incorrect content.

    But all is not lost.

    With Outlook 2007

    If you go into your sent items, open up the offending email, and go into Actions | Recall this Message, outlook will attempt to delete the message from the recipient's inbox before he has a chance to read it.

    Recall a message
    Figure: Actions | Recall this Message (Outlook 2007)

    With Outlook 2010

    If you go into your sent items, open up the offending email, and go into file | Info | Resend Or Recall | Recall this message, outlook will attempt to delete the message from the recipient's inbox before he has a chance to read it.


    Figure: File | Info | Resend Or Recall | Recall This Message (Outlook 2010)

    Outlook will tell you whether it was successful or not

  8. Do you know how to duplicate an entire email draft?

    Sometimes it can be useful to have multiple copies of the same email.

    If you want to duplicate a particular message in Outlook, place the cursor in any of these fields: To, Cc, Bc, or Subject, and press CTRL+F.

    Video: Duplicate an entire email in one keystroke in Microsoft Outlook (3 min)

    Note: This works on Outlook for Windows only. Unfortunately, it doesn't work on Outlook for Mac nor Outlook on the web.

    It will open a new draft message with the very same information as the original one.

    This is handy if you want to ask different people their opinion. Easily get multiple copies of the same email for each of them.
    E.g. Subject: Scrum - what is the best length of a Sprint?

    Figure: Place the cursor into "Subject" field and press CTRL+F to create a new copy of your message

  9. Do you avoid Outlook Rules?

    Some people make extensive use of the rules wizard so that as email messages arrive they already appear in the appropriately created folder.

    "I basically think this doesn't work as you never look at these emails."- Adam Cogan

  10. Do you avoid using Auto Archive?

    If you use Exchange Server, Auto-Archive moves the archived items from the Exchange Server to a local drive on your notebook or desktop. While this keeps your Exchange Server nice and small, if you happen to use email to store legal documents, or want to search for emails you've sent a year ago, Auto-Archive is like throwing data away.

    Outlook Auto Archive
    Figure: Turn off AutoArchive so your emails do not get thrown away I promise you'll be thankful you never deleted your Sent Items.

    We have a program called SSW LookOut! for Outlook to check for this rule.

    SSW LookOut! for Outlook can tell you if you have archive on.

    Contact or No Aging
    Figure: SSW LookOut! for Outlook warns you if Outlook is set to archive your emails

  11. Do you group your emails by Conversation and Date?

    You may be involved in different tasks simultaneously every day. The best way to organize your tasks and follow each task individually is grouping your emails by conversation. By default, Outlook groups the emails by Date.

    Figure: Bad example. Email messages are grouped by Date

    Figure: Good example. Email messages are grouped by Conversation

    Follow these steps to group by conversation:

    1. Open Outlook and select the Mail View.
    2. Right-click any column and choose the "Customize Current View..." option.
    3. Select the "Group by..." option as displayed in the image.

    Figure: Steps to group by conversation field

    1. Select the "Conversation" field from the list. (Leave empty the remaining groups)

    VIDEO - Top 10+ Rules to Better Email Communication with Ulysses Maclaren

  12. Do you know how to make your CC’s grey?

    Cut down the noise in your inbox by visually filtering emails not sent directly to you.

    Figure: Good Example - Cut down the noise in your inbox by visually filtering emails not sent directly to you

  13. Do you manage your Deleted Items?

    Your deleted items can become quite out of hand if you don't manage them. First, it can waste a lot of space on your hard drive, and second, after accidentally deleting a mail item, it can take days to find it again amongst the 30,000 messages in your Deleted Items Folder.

    Here's a couple of solutions:

    • Permanently delete your deleted items. This is based on the theory that once you have deleted a mail item, you should NEVER HAVE TO LOOK AT IT AGAIN. This is a good theory, but unfortunately, we don't always follow it in practice and there's no recovery
    • Move the items into subfolders under Deleted Items. This is a good solution as you can manually archive items, making it easier to search. You can permanently delete items when they reach a certain age.

    Figure: Good Example - Deleted Items ordered into time periods

    Note: A hot tip for making it easy to search for an accidentally deleted item is to add the "Modified" field into your Deleted Items view and sort by "Modified". The item from two months ago which you just accidentally deleted will be sitting at the top.

    Figure: Sort by "Modified"

  14. Do you sort your emails by "Received" and "Important"?

    OK - so now you've got your important emails identified, don't let them get lost in the quagmire. If you use Outlook make use of its inbuilt functionality. Always sort your emails by the Received, but add a secondary sort by "Important". This way your important emails always stay at the top to haunt you until they are done.

    Figure: Good Example - Sorted by Important and Received Date

    The Red Exclamation Mark is a good start, but the Blue Arrow keeps getting my attention.

    Use sort by importance to sort the items with the blue arrow to the bottom.

  15. Do you use the security options in Outlook?

    When you distribute important information by email all you can do is put "Do Not Forward this please". Important corporate information should be protected better than this.

    Figure: You can protect your email messages

    This solution exists in Microsoft Office and is built into Outlook. Entitled 'Information Rights Management', a file level security application built onto Windows Server. The capability enables you to prevent recipients of your emails (and attachments) from forwarding them on, copying any text, or printing the document (be aware that determined chaps could use a lower level screen shot program to get past this).

    Additionally, it encrypts the file as it's sent away. As an added basis - you can secure on a group level (based on Active Directory groups). To prevent an email being forwarded simply create a new email and select the "options" tab and click on "permission" in the ribbon and select "do not forward".

    outlook prevent FW
    Figure: How to prevent emails being forwarded in Outlook

    Note: You may be interested to know that every mail item that you send gets a file saved with these credentials so you can still open the emails when you are offline. To see: go to Start - Run %USERPROFILE%\Local Settings\Application Data\Microsoft\drm.

  16. Do you use the voting option appropriately?

    Usually when an employee from the company wants to make a decision about either a naming convention, a button style, using user-controls or forms, or even something as simple as changing a font; there should always be reassurance from the rest of the team that it should/should not be done.

    Outlook Voting
    Figure: Good Example - using the voting buttons option.

    1. The subject should start with "VOTE: ..."
    2. The sender should reply with a summary after either everyone has replied or after a certain period of time to let the group know how significant their input was.
    3. The voting options should be short, to the point, and provide a distinct difference for each option.

      i.e. option1;"option1";option2;"option2" is not appropriate.

    4. There should also be an extra option to allow a flexible result if a member of the email group does not want to vote. i.e. yes; no; un-opinionated.

      This will provide an accurate result of the vote and will not force anyone to select an option just for the sake of giving a reply.

    5. Voters should be allowed to add their extra comments along with their vote when replying to all, regardless of whether or not they think it is their "two cents", simply because the person who initially voted is looking for any and all opinions to assure the right decision is made.
    6. When making a vote, try to make the options clear enough so that voters would not have to spend too much time deciding.

      A good voting system is one that allows the voters to choose an option quickly and carry on with their work, unless of course it is controversial.

  17. Do you minimize the use of Out of Office?

    When you are on leave, you need to make sure that your mailbox is monitored. The best way to do this is by either:

    • For extended periods off the grid, asking someone (nicely) to check your mailbox if you are away for 3 days or more. This ensures that any important emails from clients are actioned,
    • Make sure all client emails are handled before you leave; either delegate the task, or inform the person taking care of your inbox or,
    • Check it yourself every 3-4 days from home or wherever you are (a Hawaiian beach or Himalayan mountain maybe!). People are generally OK waiting a couple of days for a reply. For extended periods off the grid, the use of ‘Out of office’ is good , but when you expect to have partial connectivity and anticipate replying, don't set your ‘Out of office’ on at all.

    The use of 'Out of Office - Automated Response' emails should be avoided unless you plan to be away for more than a week, and unable to check your emails while away. In this case, it is also good to mention one or two alternative contact(s).

    owa auto reply
    Figure: Bad example – Outlook OWA setting the automatic reply

    bad out of office
    Figure: Bad example – This appointment has “Out Of Office” status which will change other peoples Teams status (unless every person was to change it to "Free")

    step1 good
    Figure: Good example - Step 1 - Click on "Schedule out of office"

    step2 good
    Figure: Good example – Step 2 – Enter your reason and an end date. This message will be seen by your colleagues when they email or message you in Teams

    Use Teams to let people know you are not around

    If you are on leave or unavailable for a period and want your team to know, you should set your status to Out of Office. A recurring problem when doing this in Outlook is that if a user selects their meeting to show them ‘Out of office’, whoever accepts the appointment will also have their status changed to ‘Out of office’.

    In case you use Outlook and Microsoft Teams, there’s a quick way to do this. You can use Edit status message | Out of Office feature on Teams.

    By using this feature, your Teams status will be synchronized to Outlook, showing the whole organization that you are not available for calls or meetings. You can even set up an automatic message to be sent when someone tries to reach you on Microsoft Teams.

    teams status
    Figure: Good example - Your new status on Teams will be shared across your Outlook calendar, and your team will see you are not around

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