Secret ingredients to quality software


Rules to Better Email

72 Rules

Often emails are rambling and unorganized, forcing the reader to wade through blocks of totally useless text. When it comes to written communication, less is more. Having hundreds of emails in your Inbox is not uncommon. But it's very uncommon to find people who successfully manage their Inbox. Instead, they let their Inbox become a great black hole with no business value. Email has a bad name in business primarily because people don't treat email correctly.

Email can be a vital tool to your company and your software development project, but it has to be managed. Email should be an accurate record of requests, conversations, and decisions. Emails are legal documents and should be treated with the same care as any other correspondence with clients or employees. Email is also an extremely effective task tracking tool, and requests made by email should be treated with the same seriousness as Project Plans and other directives, for email can be seen as the protocol between the sender and receiver. Here is a series of email rules/etiquette that govern how we use our inbox.

  1. Do you keep your inbox as a task list only?

    Most people don’t manage their inbox effectively. Emails should be treated as a list to do. As you complete a task you can just delete the email.

    Your inbox should only contain 'tasks', that are actionable items on your list of things to do . Everything that is in your 'Inbox' (including sub-folders) should only be to-do items.

    So do it now, delete all emails you have done. If you want to keep some for reference, move them to a new folder that is not in your inbox.

    inbox tasks list
    Figure: Good example - All inbox items are tasks

    In fact, you could go so far as to say you should not do anything unless you have an email telling you to do it (which is why we send ourselves emails). However, very simple tasks can be requested and replied 'done' via IM.

  2. Do you use email for tasks only - not chatting?

    Email is a very powerful business tool. The main problem, however, is that for most people it is out of control - emails build up until they are impossible to manage. To help minimize mailbox clutter, try these tips:

    Using your mailbox as a task list also saves you from having to use inefficient paper-based cards to track your tasks.

    Figure: Bad Example - A bad email is one that gives no clear action items and will probably lead to a back and forth thread (potentially with people misunderstanding each other)

    Figure: Good Example - A good email has a clear task to be done (decision was made in-person or via call)

    Tip 1: It is better when email is not used as communication. Of course, if the person is unavailable, you may have to. In this case, also follow the "as per our conversation" rule E.g. "As per the message I left on your phone... I want to make a decision on... My suggestions is..." and detail the questions you would like answered.

    Tip 2: Make sure to number your tasks, if there is more than one, as per "Do you number small tasks related to 1 topic?"

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

  3. Dones - Do you reply 'Done' and delete the original email?

    If someone asks you to perform a task by email, don't reply "OK, I will do that" or fail to reply at all. Instead, do the task and reply "Done" when the task has been completed, and then delete the email. This way the person requesting the task knows that it has been done, and doesn't waste time following you up.

    Read "Definition of Done" for more information about the steps that need to be finished before replying to a done email.

    Only say "Done" when the work is completed.

    • If you have added the email to your backlog or to-do list, then say "Added to backlog – URL is XXX". You should still reply "Done" when you complete the task.
    • For tasks that will take time to be completely done (E.g. Producing a long video), you may send a "work in progress" email. This way you avoid giving the perception that no action was in relation to the task. You should still reply "Done" when you complete the task.

    Alternatives to classic "Done" emails

    • If the task is already done, then reply "Already done - the reason is XXX"
    • If you don't agree with the task or are unable to complete the task, reply "Not done - the reason is XXX"
    • If there are multiple tasks (some "Done" and some "Not Done"), reply to each item individually "Done" or "Not Done"
    • If the task can't be 100% completed at the time, you may reply "Partially done - the reason is XXX"
    • If you have already sent a "Done", then the client asks you to undo the change, reply "Undone"

    Figure: Good Example - "Not Done" email

    Tips for your "Done" emails

    Tip 1: Say "Done" first

    For clarity, "Done" (or "Not done" / "Already Done" / "Partially Done") should be the first word(s) so the reader knows the status straight away.

    Tip 2: Provide details in your "Done"

    In any reply, include relevant information, such as URLs, screenshots, and pieces of code/text that have been updated. This allows others to check what was done straight away.

    Extra tips:

    Figure: Bad Example - "Done" email lacks details

    Figure: Good Example - "Done" email has a link and a screenshot

    Tip 3: Replying "Done" to multiple tasks

    It is important that you clearly reply to each of the multiple tasks.

    Figure: Original email with the client request

    Figure: Bad Example – It is not clear which tasks have been done and which haven’t

    Figure: Good Example – You can see which tasks have been done and which haven’t (Note: you have to scroll to the original email to know what the tasks were)

    Figure: Bad Example – It is clear which tasks have been done, however, replying inline sucks

    Figure: Good Example – It is very clear which tasks have been done and which haven’t. Quoting the original task is only necessary when some tasks are done and some are not

    Extra Tip:

    What do you do with the "Not Done" tasks?

    If there are multiple items of work in an email and you can't do them all at once, reply to each item individually ("Done" and "Not Done"). With the "Not Dones" you should add a plan to action: a. Put yourself in the "To:" if you are going to do the remaining items later. b. Add another person if you are reassigning. c. Give a reason if it won't be done.

    Figure: Good example – If multiple tasks are 'done', then only the URL is needed. This is clear that all tasks have been done and they can read the history of the requests below

    Tip 4: Replying "Done" to huge tasks

    Ideally, all PBI's should be done in less than 2 days. If you are given a task that is going to more than that, then split it by following breaking up monster tasks.

    Tip 5: Don't consolidate emails

    If you get multiple emails or tasks, don't consolidate them. Reply to each email individually as you go. This way the person requesting the work hasn't lost the email history and can understand what the work is done relates to. It also means that testing and/or feedback can come in as soon as possible after the 1st completed task.

    Tip 6: Delete "Done" emails - Aim for 0 inbox

    There is no point in keeping emails that just clutter your inbox. You don't need to keep the original email because after you have replied "Done", there is a copy in "Sent Items". If you must keep an email, then move to your "Saved Items" folder.

    Tip 7: When appropriate, use text instead of images

    Figure: Good example - This "Done" uses text instead of an image so it is easier to search; to copy and paste; and to reply with a modification

    Tip 8: Handle an email once

    Follow a tip from Adam Cogan:

    “During my accounting days we had large physical in-trays and you were always picking up papers, 
    looking at them, deciding it’s ‘too hard to do right now’, and then picking up another piece of paper...
    I learnt that a sign of an efficient person is that they handle a piece of paper once". 

    Likewise, when you get an email - don't just open it, have a quick look and close it with the idea that you will go back to it later. Read it, make a decision and do the action. Delete as many emails as you can on the first go. In the same vein, when you complete all tasks in an email, delete everything in that thread.

    Tip 9: Consider alternatives in a team environment

    In a development team environment, it is better to move emails to tracking systems. E.g.:

    1. Azure DevOps Work Items
    2. GitHub

    Tip 10: Include a video when appropriate

    See how to record a quick and dirty "Done Video".

    Tip 11: Remember to thank people - don't be too brief and icy

    When replying 'Done' to a bug or issue someone reported, remember to thank the person for taking the time to send it. A short "Thank you for reporting this" helps to make your 'Done' warmer.

  4. Do you send "As Per Our Conversation" emails?

    Implement a policy of following up important conversations (usually by phone or IM) with an email that begins with the words "As per our conversation". The intent is to document what was said and agreed upon.

    When possible, the even better way of confirming requirements is to actually share screens of the drafted requirements and add the words checked by XXX.

    Watch the video below and see how a single email can make your job easier.

    Figure: Good Example - using "As per our conversation" email

    This is not just a 'cover my ass' email. This is for several reasons:

    • To make sure that you did not get the message wrong
    • To keep an audit trail of agreed decisions
    • To keep people, who were not a party to the conversation, informed about the progress

    Use this approach internally and with clients. As a result, expect to see "as per our conversation" emails that:

    • Require a task to be completed
    • Explain the logic of the decision
    • Include URLs that were referred to
    • Can be referred back to in the future

    Sometimes you might not reach the client or Product owner via phone and have to make a decision by yourself. In this case, it's still important to record everything in an email, starting with "I tried calling you but didn't get through":

    Figure: Good Example - for when you can't reach the person by phone 


    It's easy to fall into the trap of sounding rather robotic if you start every email with "As per our conversation", or "As per the message I just left on your mobile", etc. Here's a list of nice email openers that have the same effect:

    "As per our conversation" alternatives:

    • Thanks for the chat
    • Good talking to you
    • As discussed...

    "As per the message I left on your mobile" alternatives:

    • I couldn't catch you on the phone today.
    • I just left you a quick voicemail.
    • I called earlier but couldn't get through.
    • Hey I just called earlier to say...

    Other cases exist, include your reason at the top

    Figure: Bad example - reason at the bottom

    Figure: Good example - reason at the top

    VideoTop 10+ Rules to Better Email Communication with Ulysses Maclaren

  5. Do you number tasks/questions?

    It is good practice to be clear on what you want. One way you can make things clearer is to number tasks or questions.

    Note: Receiving an email with just numbered items is cold - An email starting with a paragraph of context is much nicer

    Bad example - the different tasks/questions may be skipped if the reader does not read very carefully

    Good example - the different tasks/questions are clear

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

  6. Do you know the four standard email types?

    All business emails (that are useful) should be in one of the four following formats

    1. FYI- to spread information

      • Daily Scrum - to report on daily progress in a Sprint
      • Sprint Review/Retro emails
      • Sprint Planning emails, etc
    2. Tasks- Sending someone numbered tasks

      • To Myself - to send yourself a task, and CC interested parties
      • Tasks to one or more other people
    3. Test Please - to ask for testing and acceptance of a task
    4. Done - replying to a task email, to show details of what has been done

    If your email doesn't fit into one of the above categories, it probably doesn't need to be sent.

  7. Do you ask for content changes using from X to Y?

    When asking for changes to be made to any file like a web page, Word document, PowerPoint slide or code, always include the original version of the content ("X") together with the changes you require ("Y"). This means you have at hand a history of the page or file as it currently stands allowing for convenient future reference and also makes it very clear to the person doing the changes exactly what the new file is meant to look like.

    Make the changes even easier to see and understand by highlighting in red what you want to delete (only do this on the "From" section) and in yellow what you want to be added/updated (only do this on the "To" section). All text we do not write ourselves should be indented, so this includes paragraphs we are copying and pasting (see Do you use indentation for readability?)

    From X...

    Figure: Bad example - original version of content has not been included in the email Y

    Figure: Good Example - it has 'From' and 'To' with changes highlighted... so it is clear what needs to be changed

    What if there are too many changes?

    Sometimes you have a lot of content and too many changes, making the process "from X to Y" too arduous. In this case is recommended to use Word 'Track Changes' functionality.

    word track changes
    Figure: A Word document with 'Track Changes' ON is recommended if you have too many changes

    Video: Top 10+ Rules to Better Email Communication with Ulysses Maclaren

    What if you have a website managed by GitHub?

    Some websites use GitHub to manage their files (e.g. SSW Rules). GitHub makes reviewing changes easy through "pull requests".

    A pull request is a request to make changes to 1 or more files. GitHub provides out of the box functionality for reviewing changes in a pull request. This process is as follows

    1. Open the pull request
    2. Examine the changes using the tabs

      • Conversations: see comments people have made about the change
      • Commits: see comments associated with the changes the requester has made
      • Checks: You can ignore this if you are not a developer
      • Files changed * Important *: see the difference between the old and new files being changed. Red highlighting indicates deleted parts and green highlighting indicates added parts.

      Figure: Review 3 of the 4 tabs in a GitHub pull request

      Figure: The best view is via the "Display the rich diff" button. This visual preview of the changes to a markdown file is accessed via Files changed | Display the rich diff

    3. Next is to approve or ask for changes.

      1. Files changed | Review changes

      2. Add a comment with your feedback.

      3. Choose "Approve" to mark it as ready to go live.

      If it is not ready, then choose "Comment" for general feedback or "Request changes" for mandatory changes.

      4. Press "Submit review" so that the requester can see it.

      Submitting a pull request review

    Congratulations! Your review has been submitted ⭐

  8. Do you know how to send a v2 of an email?

    If you receive feedback about an email you've sent, it will likely be in one of 3 forms:

    1. Hints for what could be better for next time, in which case all that's required is you take the feedback on board
    2. Changes or clarifications to the content, that can act as the latest version of the thread, without needing a re-send
    3. Changes or clarifications that are so substantial that they require you to resend your email in the form of a v2

      1. This ensures that you understand the feedback and incorporate it immediately
      2. It also cleans up the email thread history to only have relevant content

    The other reason for a v2 would be if you realise you've made a mistake and want to send an updated version of an email.To send a v2:

    1. Reply to all, to keep the same email thread
    2. Put v2 on the 1st line of the email body

      Note: Do not put v2 in the subject because we want to keep the threading.

    3. Only keep the email history leading up to when you sent your v1, so this v2 will essentially replace the v1, as if the v1 never happened
    4. If all the feedback is incorporated into the v2, there is no need for an additional done email. However if there are additional tasks in the feedback, it may be necessary to reply done to those as well as sending a v2 (i.e. 2 emails)
  9. Do you CC everyone and reply to all when necessary?

    When emailing external parties, it is a good idea to CC the other colleagues within your organization that may have an interest in the email. Some of the benefits of CC'ing others are:

    • It can save time
    • Gives the email more credibility if you have CC'd others in your organization
    • Colleagues may correct your mistakes

    In addition, I often see people replying only to the sender of the email, ignoring the fact that there were other persons included in the original email. Obviously the original sender intended to keep everyone in the loop, so it would be polite to CC everyone included on the original communication. The converse is true also - don't cc people unnecessarily - you're just adding to the email problem!

    2021 04 12 11 22 09
    Figure: Good Example - Reply All so that everyone is kept in the loop

    What if the other person drops people

    Sometimes the other person will 'little r' reply instead of 'Reply All'. It is not a good habit to little r reply aside for when there are any exceptions noted below. This can be problematic as those dropped off the loop are needed as part of the decision making. Decisions will be harder to be made in a timely manner or end up being made without a full team agreeance over.

    At this point if you are still Cc'd, you should reply and add all those dropped from the loop, back into the loop as soon as possible.

    2021 04 12 11 22 10
    Figure: Bad Example - 'little r' reply should be rarely clicked

    2021 04 12 11 30 35
    Figure: Good Example - Adding back those dropped from the loop incorrectly


    • If not all recipients need to be informed
    • The opinions of the rest of the recipients do not matter as they are unlikely to disagree
    • If the original email was to an alias with many subscribers, in general you should not Reply All.
    • Also, if the sender requests a 'little r' reply, then you should not 'Reply All'.

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

  10. Do you know how to handle duplicate requests?

    Sometimes you get the same task from 2 different people. Sometimes even the same person sends over-lapping emails. Sometimes you find duplicated PBIs.

    Whether you keep a backlog or are just using your email inbox as a to-do list, you have a choice to make:

    A: Get rid of the duplicates and only keep one (you need to spend time informing everyone about the merge)

    B: Recommended - Keep them all and when you do it, reply to all the emails with your ‘Done’ OR close each of the PBIs. (Of course it is a good idea to relate those tasks by adding links or the email subjects)

    Figure: Bad example – This email will never get a ‘done’ when completed

    Figure: Good example – Both emails got a ‘done’ reply and were referenced to each other

  11. Do you know how to reduce noise on a thread by using a survey?

    Reducing noise in email threads is easy now we have Office365 and OneDrive.

    Sometimes when organising or planning you will need to gather responses from a lot of people, but having many people reply to the email can create a long and messy thread.

    An easy alternative to this is to use Office365 in OneDrive to create a survey in Excel, and then send an email invitation with the link to your participants. They respond in the survey instead of by email, and the long, cluttered thread is avoided.

    Bad Example too many emails

    Figure: Bad example – a simple “X or Y?” question thread generated dozens of responses that clogged up the inboxes of the recipients

    Good Example Invite to Survey

    Figure: Good example – send an email with a link to a survey instead of asking for replies

    For a quick introduction to how to use Office365 from OneDrive, watch this video:

  12. Do you follow up tasks effectively?

    Sometimes you're not able to complete a task right away or anytime soon. In this case, people usually just say:

    "I can't do this week, but I should have it done by the end of next week"

    Another scenario is when the task should be done or will expire after a period of time. For example:

    "Send Google Analytics data after a month" or "Remove course banner after the course is completed"

    Efficient people don't rely on their memory and instead, use some way to make sure they don't forget to do that task. The most common ways are to either make a note in a paper diary, stick a post-it note to his screen. But there are better ways.

    postit screen
    Figure: Bad example - using stick notes

    To ensure you follow up any task like these, there are two ways to set yourself a task to follow up in the future:

    #1 Delayed Email

    Write yourself an email in Outlook.
    Before pressing send, click Options | Delay Delivery , and then specify when you want to be reminded.

    The email will sit in your outbox until the required time, when it will be sent to whoever you specified (you in this case)When you receive it in your inbox, action the task.

    delay emails outlook
    Figure: Good example - Use delayed email on Outlook

    #2 Email reminders -

    There is a brilliant service called FollowUpThen which can do all the administrative work for you.

    Simply BCC or email <period of time> and it will send you an email when that time expires, reminding you to follow up with another email.

    Figure: Good example - Use to be reminded of this email in one week

    Note that you are sending this email thread to a 3rd party, so if you're dealing with any confidential information, strip it out before using this tool.

    #3 Follow Up flag feature in Outlook

    When you require a reminder to follow up on an email by a certain date:

    1. Click the Follow Up button

    Figure: Set a follow-up date

    1. Select an appropriate date from the drop-down or choose Custom to add additional reminders

    Figure: Add an additional reminder to follow up

    * You can even set a custom reminder for the recipient :)
    1. Outlook shows an info tip with the exact follow-up date you chose.
    2. A To-Do item is also added to your Outlook To-Do list

    Figure: An item is added to your To-Do list

    * To-Do list can be found in the Tasks pane
    1. On the due date you will receive a Reminder popup from Outlook
    2. If you chose to add a custom reminder you will also receive a Reminder popup from Outlook
  13. Do you know when to do use 'Checked by xxx'?

    There are times you should have your email checked by someone else before sending. Simply ask for that person to come over and check it on your computer or IM him/her if the person is not close by (e.g. in a different room). This way you are guaranteed instant feedback and you won't clog up someone else's inbox with unnecessary emails.

    Examples are:

    • Where you are a little unsure
    • When you are new to a company and sending an email to a large distribution list
    • Sending a complicated email
    • Sending a sensitive email (where the content could be perceived as confrontational)
    • In application development, when you need a quick 'test please', and the person is immediately available. This provides you a chance to check and collaborate on the finished change before the 'done email' is sent

    Doing this will ensure:

    • You avoid grammatical and spelling errors
    • The layout and tone of the email is professional
    • You haven’t forgotten anything important
    • The receiver knows who else agrees with the content

    (Checked by Peter)

    Dear Adam,

    [email content]

    Regards, Phil

    **Figure: Use 'Checked by xxx' when sending a complicated email to a group of people**

    Reply to the "Done" email like below and CC the person who checked the email for you. In this way, you show it was double checked.

    Figure: Reply Email with "Checked by XXX"

    When you action a task for adding web content (such as a rule or suggestion), firstly paste the content into a new Word file and run the "Grammar & Spelling Check" to check if there are any errors. After the "Grammar & Spelling Check", you can add it to your website. After that, run Link Auditor in order to keep 0 bad links on that page.

    Figure: Reply to the email with grammar & spelling check and CA check results

    four eyes
    Figure: Consider this the '4 eye check' (four eye principle)

  14. Do you know who to put in the "To:" field?

    Make sure that anyone tasked in emails is explicitly added to the "To:" line. This helps them identify emails where they have tasks.

    A fair percentage of people open an email and don’t read who is on the "To:" or "Cc:" lines.

    Figure: Bad example - Mark can’t search for tasks that have been assigned to him

    Figure: Good example - Mark can filter his emails based on whether his name is on the "To:" field

  15. Do you seek clarification via the telephone first?

    We've all received a cryptic email at some point. Don't just reply saying "I don't understand". Chances are if the sender of the task couldn't explain the task well enough the first time then it's likely conversation is needed to clarify the issue. Pick up the phone or Skype the person who sent the email.

    putin phone
    Figure: If an email isn't clear, a phone call generally sorts problems out quickly

    Having clarified the issue by phone, reply but update the original email with the new details arising from the conversation (Remember to start with an "As per our conversation" line).However, sometimes you cannot immediately reach the task owner. In this case, you need to keep trying to contact the person for 24 hours. If you are still not able to contact the person, you need to reply to the email and put the following in red in the first line:

    Figure: Good Example - Send this email and now move on to other tasks and leave this task to next release

  16. Dones - Do your 'Dones' include a URL?

    Always include the relevant URL to your "Done" emails, like when you make a change to a web page. This way people can check the work that was done.

    If you are using a task tracking system like Azure DevOps, GitHub or Jira, also include the link to the PBI/issue/task.


    Figure: Bad Example - how can we check the task was done correctly?

    Done -

    Figure: Good example 

    Done -

    Figure: Good Example - easy to check what was done

    Video:  Top 10+ Rules to Better Email Communication with Ulysses Maclaren

  17. Dones - Do you reply 'Done' using Team Companion when using Azure DevOps?

    Before you do the task – say if the task requires a code change and you are using Azure DevOps, make sure it goes in as a work item.Follow the rule to happy clients - triage rule.

    After you do the task, the perfect workflow is to follow the rule to better project management with Azure DevOps - use TeamCompanion to send your ‘done’ and reply ‘done – changeset xxx’.

  18. Dones - Do you include useful details in your 'Done' email?

    Including images is a good idea, in addition when appropriate include code snippets, and ideally have the code that changed highlighted in yellow.

    An email with just the word "done" can often be enhanced with a screen capture or code snippet... provides evidence educates

    This has several benefits:

    • Improved visibility and transparency - The client can see the work actually being done
    • Reduced cost of fixing a bug - the cost of a bug goes up based of the length of time taken for the client to ask for a change. If you tell a developer to change something he did today, it is many times cheaper for him to fix, than if he got the same request 2 months later (when he has forgotten was it was about)
    • The client can raise questions based on what he sees in the code
    • Finally, in the very unlikely case that the code repository and backup goes corrupt, your emails are a backup!

    Let's look at some examples and tips:

    Figure: Bad example - the client cannot see any detail of what was done

    Figure: Good example - the client can see the image + the code changes highlighted in yellow

    **Tip #1: Include the URL** If you are using TFS, you can also include a URL to the work item in TSWA

    **Tip #2: Include a .diff file** You can include the code as an attached text file.

    Figure: Good example - this is a Text file with a .diff extension that includes the code change from TFS. If opened using NotePad2, the client can view the code changes with green and red color (added and deleted code).

    Tip 3#: Do you have force a link between the code and the requirement?

    For those developers lucky enough to be using Microsoft Team Foundation Server (TFS 2005, 2008 or 2010) you can associate your code changes with a work item. This means that future developers can work out not just *what* changed, but *why*.For those using TFS, enable the Checkin policy and force all developers to associate every check-in with a work item.

    Figure: Make developers associate all check-ins to a work items

    Figure: Enabling the Checkin Policy (via Project | Team Project Settings | Source Control | Add)

  19. Do you keep the history of an email?

    Often we receive a reply to an email and it has one word - "Yes."

    If the sender can't remember what was asked and the respondent has deleted the history, it's hard to tell what's going on. It's not possible to check whether all questions were answered, or what URL was in the original email. Also, we can't CC someone else on the new reply because the email is missing half the information.

    So the only way is to go back into 'sent items', find what was asked for and copy and paste it into my reply, which can be very frustrating.

    Crazy. Just don't delete the history ! Geezzzzeeeee, surely we aren't that hard up for disk space ;)

    Related Rule

  20. Dones - Do you include relevant info from attachments in the body of the email?

    When someone sends you a .doc file or images that are attached when you reply 'done' they (and others CCed) won't be able to see the appropriate history. If it is a word .doc or an image; open it and copy and paste the text/image into the history, where the image should have been. Don't leave it as an attachment.

    **Warning: ** iPhones strip inline images. If someone has replied to a beautifully crafted email (with inline images) with their iPhone, it will now be a clipped plain text email with your image as an attachment and would not be included in the "Reply All"...Grrrr

    So in such a case, you will want to skip that email and go back to the last HTML email and paste in the extra response. For clarity, add something like:

    "(fixed history to put back images - caused by Adam's iPhone)"

    Related Rule

  21. Dones - Do you know how to do a perfect 'Done' (replying to a bug)?

    To reply to a bug effectively and efficiently in your emails, you need to include:

    • Current Status - the bug is fixed (screenshot of working application) or not fixed (ask for more detailed information from the client)
    • Investigation - the reason for the bug, or if you don't know, what you investigated, e.g. checked Windows event logs and found nothing helpful
    • Solution - how you fixed the bug (code snippet if necessary)

    better emails reply bug small
    Figure: Good Example - Reply to a bug showing all steps

  22. Do you add context/reasoning to your emails?

    When sending an email it is very important to give context and reasoning. This way anyone can understand what was done at any time in the future. Never assume that the other person will get it anyway, and always try to give details and make yourself as clear as possible.

    Figure: Bad Example - There is no context or reasoning

    Figure: Good Example - There is both context and reasoning

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

  23. Do you avoid replying to all when you are only Bcc'ed?

    If you receive email via BCC, other recipients are not aware that you were sent a copy so it's actually a VERY BAD idea to Reply All in this case. It's ok to reply to the message you were BCCed on, but it's not ok to send your reply to the people on TO or CC list. Only the sender should receive replies from BCCed people.

    This extends even further to the person using BCC in the 1st place. Generally when using BCC, you should always pause to make sure you are doing the right thing. DontReplyAll

    9 times out of 10, you will find that your motivation for using BCC is something less than fully candid... and it's almost always better to use CC or forward instead.

  24. Do you include the name of the person you address as a heading?

    If you have to address an email to multiple people (including to yourself), include each person's name as a heading. This helps them quickly locate which part of the email that applies to them.

    Figure: Good Example - When addressing multiple people, include each addressee's name as a separate heading

    Tip: You can add a heading in Outlook by typing Control+Alt+3.

    Video: Top 10+ Rules to Better Email Communication with Ulysses Maclaren.

  25. Do you know how to add or remove someone from the conversation?

    If you think someone should be involved in a conversation but they're not on the recipient list, all you need to do is "Reply All", put the new recipient in the 'CC' field and include one line at the top to inform people for clarity

    e.g. (Adding Drew)

    Be aware that it is easy to over CC people. Try not to CC people without thinking as every person added to a thread costs $$$. So when you add someone, it is a good idea to state the reason why they are being added, so it will justify the cost of their time.

    e.g. (Adding Drew to the loop as during the daily scrum today he mentioned he has worked on similar issues and might have some input)

    Figure: Good Example - Adding someone to an email thread

    If you need to remove someone from the loop, for example to have an internal conversation about an email to a client, put (Removing xxx from the loop) at the top of the email.

    Figure: Good Example – Removing someone from an email thread so you can talk about the them in private

    You can delete people from an email thread, but what often happens is:

    • The people being dropped won’t know and won’t be able to say "I don't want to be dropped from this thread"
    • The people who added them in the 1st place don't know that they included unnecessary people
    • The others on the thread might not notice the change in email addresses

    To fix all these issues, instead of deleting people from the email, you:

    • Move them to the BCC
    • On the top line of the body say "(moving George and Bob to BCC)"

    Figure: Good Example – Moving someone to BCC

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

  26. Do you know how to follow up an unanswered email?

    Sometimes the person you send your email to may not reply immediately because they're busy or just may have forgotten about it. If you need an answer, reming them by adding a PING to the thread:

    1. Reply to ALL
    2. Put (PING) in 1st line of the Body
    3. Plus any other instructions - such as "Hurry Up!" or "following-up, and looking forward to your reply" or "Need an answer please"

    Figure: Good Example - (PING) written at the top of the email

    Of course you might use slightly friendlier language following up a client or a third party compared with following up a colleague! If it's really important and you need an answer you might like to consider using the phone instead of email.

  27. Do you know that less is more?

    Often emails are rambling and unorganized, forcing the reader to wade through blocks of totally useless text. When it comes to written communication, less is more. Be concise and to the point, listing only what is relevant. People tend to ignore reading larger emails if they are on the run and leave it until a later time when they are not as busy.

    "I didn't have time to write a short letter, so I wrote a long one instead."Mark Twain

  28. Do you know what to do when you get an email that you don’t understand?

    Sometimes a task will not be clear, or you won't have sufficient context to understand what is required.

    A bad approach is to simply delete the email or to reply with “?” and then delete it.

    What you should do is call the sender and ask for specifics, then reply to the email with an as per our conversation, documenting your new understanding of the task.

    If you can't get hold of the person, email them back asking specifics of what you don't understand.

  29. Do you know when you should change an email/appointment subject?

    Some email threads go on forever... sometimes the topic subtly changes... so when should you change the subject? The answer is "cautiously". The reason is email threading.

    So when do you change it?

    • When the original email theme has been superceded by new content
      You should change the email subject to a more relevant description of the content of the thread.

      E.g. From
      "Field of Study"

      "Next Years Conference WAS: Field of Study"

    • If the original subject was too generic, like "Reminder" or "Invoice" (especially when automatically generated)
      Change the subject by adding the client or project name to the email subject.

      E.g. From

      "Northwind invoice for website - March WAS: 'Invoice'"

    Remember, never forget the importance of a good email subject in improving communications.

    Figure: Keep your email subject description up-to-date. Sarah Palin isn’t even a governor anymore

  30. Do you link similar threads with similar subjects?

    Often there are two email threads that have separate tasks in them, but that both relate to a very similar topic. In this case, it can be useful to give them the same subject, with a number afterwards to differentiate them.


    SSW Rules - Add 'please update this rule' button #1

    SSW Rules - Add 'please update this rule' button #2

    Read Do you realize the importance of a good email Subject? for more on good email subjects.

  31. Do you know when, and when NOT, to use email?

    As all these rules indicate, email can either be a blessing or a curse. One of the most deadly of all the potential curses of email is when people choose to use email when it is just not the right tool for that particular task. Absolutely avoid email in the following situations:

    1. When you want to discuss an issue and make a decision
    2. When you are dealing with a 'delicate' problem

    Figures: a Meta Group survey found that 81% of respondents preferred the phone above email to build relationships, but 80% preferred email generally

    Making a Decision

    If you want to make a decision, asking for opinions via email is the best way to ensure one isn't made. Email discussions get off-topic, lose track, and generally go nowhere, with every email ending with "Yes, but what about..." or "Just my 2c". This leads to a lot of time-wasting.

    You should either pick up the phone or have a meeting to discuss the issue, make a decision then and there, and then confirm the decision via email. The first line in your follow-up email should be "As per our conversation..." This records that a conversation was held.

    The issue becomes even more important internally when you email someone in the next office and ask them a question. This is a great way of creating unnecessary emails. Instead, stand up, walk to their desk and ask them the question. Otherwise, have a folder called "AskDavid" or similar, file all your emails that you need to ask him about in there, and when he next comes to visit you, go through them and get an answer.

    Dealing with Delicate Situations

    Similarly, never bring up a tricky topic with someone by email. It's very easy to misunderstand or misrepresent via email. We always pick up the phone and speak to the person first when discussing important, sensitive, complex issues, or issues where some serious convincing is required. This is the standard we follow:

    • Draft the email covering the issues we want to confirm
    • Call the person covering every issue outlined in the draft
    • Adjust the email according to the decisions made together, adding "As per our conversation..."
    • Send the email

    This way you can review issues together, and, importantly, decisions are confirmed in writing.

    Figure: Are you in the right frame of mind?

  32. Do you prepare, then confirm conversations/decisions?

    Ideally all phone conversations and meetings should be confirmed afterwards so you have a record of the decisions and action points. Meetings and phone calls should have adequate preparation so they are efficiently run. The reality is, after the meeting or phone call, we get busy on the next call. So this is the workflow that should happen:

    1. Prior to speaking to a client, speak to relevant people to help you formulate your recommendations e.g. speak to a developer about the proposal
    2. Draft an email with bullet points for each issue (don't send)
    3. Call up the client (or have a meeting)
    4. Modify during conversation
    5. Send the email to the client (cc relevant people e.g. the developer) saying "As per our conversation..."
  33. Do you realize the importance of a good email Subject?

    Just as we should not 'judge a book by its cover' - we will not judge an email by its subject. But, we do! Because users get so many emails, getting your clients and suppliers to take notice of yours in their inbox can be quite a struggle.

    Subject: 6:30PM Tonight! See you at the User Group

    Figure: Good Example - Definitely going to read this email

    Use the email Subject to grab your recipient's attention. Choosing the right subject can give an email a sense of urgency or importance that choosing the wrong subject won't!

    The best way of doing this is to ensure that your subject includes either an ACTION POINT (E.g. "6.30 TONIGHT! See you at The Oaks Hotel...") or a RESULT of a task you were asked to do (E.g. "Here's the 5 mins. of FEEDBACK you requested from our meeting with Charles Merton"). You'll note from this that including the date and time in the subject gives immediacy to the email.

    If there's anything to be learned from spammers, they know how to get your attention. Spammers use very tabloid based, or headline-grabbing subjects, to try and coerce you to open that email. But don't make your email subjects tabloid-tacky, instead follow a good broadsheet paper's style of attention-grabbing lines.

    Never leave the subject blank! It's like writing a book and failing to give it a name!

    Good Subject Examples

    Always use a descriptive email subject to make it easier to find later

    Consulting:::: greyboxSubject: Northwind - Future - Meeting to get your software solution rolling, next Monday 2PM :::

    Dinner:::: greyboxSubject: Dinner Tonight, 6.30PM at The Oaks ::: greybox

    Bugs:::: greyboxSubject: BUG - Northwind form - Button not working :::

    Call someone:::: greyboxSubject: SSW User Group - This month needs a speaker - Call Tom Howe pronto! :::

    Feedback on a product:::: greyboxSubject: Northwind app - User Interface feedback :::

    Test please (see test please rule): ::: greybox Subject: **Test Please - Product Name v1.11 ** :::

    Of course, we also use a structured approach for emails - especially when sending them internally.

    We use the following format for the subject internally and encourage clients and external contacts to use this format as well.

    Subject: [Client Name/Product Name] - [Project Name] – [Object Name/Description]


    Subject: Northwind – IOP – Customer.aspx - Add email address validation

    The advantage of this is that when you sort by the subject in Outlook, you get all of the emails grouped together, and it is easy to recognize the client/product, because the subject contains the relevant information.

    Tip: When referring to a website, it's a good idea to include the URL in the email subject.

    Additionally, you should be able to determine which emails are the most important. Using a meaningful subject with keywords makes it easy to identify and categorize emails without actually opening them (and it also makes it easy to find them in "Sent Items"). When emails are really important, write IMPORTANT in the subject. Other emails considered important or urgent should have the following in the subject field:

    • BUG
    • URGENT

    Other words to be used are:

    • TO-DO - for tasks pending
    • FYI - information you want to keep around for a while, for yourself or for others (never for a task)
    • FUTURE - ideas for the future
    • IGNORE - for the rare occasion when something is requested and you really don't want to do it yet
    • Product name - Registered User Support
    • Product name - Pre-Sales Support
    • Project name
    • Client Name

    ::: greybox

    Remember: For external emails, it is acceptable to change an email subject in certain circumstances.

    For internal emails, the subject should generally not be changed as it will break the threading of emails.

  34. Do you respond to each email individually?

    (AKA - don't respond to a series of emails in one email) If you receive separate emails, respond to each email individually. Don't answer a few emails in one email.

    • Each email is a little job (eating the elephant one bit at a time)
    • You get a steady flow back as bits are achieved (can get a feel or monitor employees efficiency)
    • You can move to 'todo' list folders
    • You get a email history for that one topic
  35. Do you know when to send tasks one email at a time?

    Do you sometimes find that people don't follow all the items you have listed in a long and carefully drafted email?

    Make it easier for everyone by sending unrelated (independent) tasks one email at a time. Also, don't forget to make your requests very clear.With separate emails, When a person has completed a specific task they just have to reply "Done" to that email, delete it, then move on to the next task.

    Breaking up unrelated tasks

    If you have a list of things to be done, have a second look, you may find that your requests are not directly related (don't depend on each other OR are not to be done in the same environment). In this case, it is better to break it up and send separate emails.

    Grouping related tasks

    As per the examples above, if you are requesting many smaller tasks under the same topic, you should group them in the same email. In this case, number each task that you wish to be completed.

    Figure: Bad Example - One email for multiple unrelated tasks (Domains and CSS)

    Figure: Good Example - Separate emails for unrelated tasks. A few related tasks in the same email

    Breaking up monster tasks

    If you have a very large task that requires days of work, it is also better to break it up and send separate emails. So that big task "Boil the Ocean" would become several emails with consistent subjects:

    • "Boil the Ocean #1",
    • "Boil the Ocean #2",
    • "Boil the Ocean #3" etc.

    The advantages are that you get an email history for specific parts, making it easier to include someone else and follow up.

    Figure: Bad Example - One email for multiple separate tasks

    Figure: Good Example - Separate emails for separate tasks

    TODO: Make grey boxes with clear separated emails - change from IIS to Git Repo + will become 3 emails

    Replying 'dones'

    When replying to emails, always reply to each email individually. Don't consolidate them all into one as it leaves unfinished email threads.

    Read Do you reply 'Done' and delete the original email? to see the best ways to reply "Dones".

  36. Do you use indentation for readability?

    Written communication can easily cause misunderstandings. Help the reader understand your message better by:

    • Using “>” and indentation when quoting the text from others, like the original email you are replying to, or a web page, etc.
    • Your new text should be kept to the left
    • Optionally, use a different text color in your reply
    • Add numbers if the sender didn't and it is appropriate

    This way you won't forget any questions in the original email.

    Figure: Bad Example - there's too much information here

    Figure: Good Example - You can clearly see the context of each part of the reply

    Note: For those using mobile devices the indentation function is not available, try instead using 3 spaces to indent manually.

  37. When asked to change content, do you reply with the content before and after the change?

    Your boss asks you to change a page on your website. You discuss it with your team and come up with the changes. Wouldn't it be nice if your boss could see exactly what was changed? Always keep a copy of what the page (or document) looked like before you make the change, and reply to the original email with the before and after.

    Note: SharePoint has version histories, giving you the ability to compare to previous versions out of the box.

  38. Do you use a different color when replying an email?

    Warning: there is very rarely a reason to use inline – avoid it.  You should copy the tasks and paste in your response area instead.

    Replying inline can mess up the history of the email thread. What you should do is to copy and paste the entire email in your reply and comment on each issue at a time, keeping the history intact.

    It's important to write your comments in a different color. You might want to mention what color your comments are in (sometimes there is more than one person making in-line comments).  Make sure what you type should always be aligned left, not indented. Remember, if you write emails with one issue at a time you won't need to do this too often.

    -----Original Message-----

    From: Daniel Hyles Tuesday, 28 May 2002 7:31 AMTo: Adam Cogan Daniel Hyles - Morning Goals

    I have replied inline

    -----Original Message-----From: Adam Cogan Monday, 27 May 2002 8:00 AMTo: Daniel Hyles Subject: Daniel Hyles - Morning Goals

    • TimePro Online pages Done
      - Double check backups (get backup today on both drives, I configured the other drive last night) Done
      - Make sure Exchange is backing itself up... Check Google on why not. Not Done
    • Access reporter Not Done

    Figure: Bad Example - Replying inline and using the same color can mess up the history + no indentation 

    From: Daniel Hyles Tuesday, 28 May 2002 7:31 AMTo: Adam Cogan Daniel Hyles - Morning Goals

    My answers in blue

    > 1. TimePro Online pagesDone

    > 2. Double check backups (get backup today on both drives, I configured the other drive last night)Done

    > 3. Make sure Exchange is backing itself up... Check Google on why not.

    Not Done

    > 4. Access reporterNot Done

    -----Original Message-----From: Adam Cogan Monday, 27 May 2002 8:00 AMTo: Daniel Hyles Subject: Daniel Hyles - Morning Goals

    • TimePro Online pages - Double check backups (get backup today on both drives, I configured the other drive last night) - Make sure Exchange is backing itself up... Check Google on why not.
    • Access reporter

    Figure: Good Example - Replying in a different color + keeping history intact + using indentation

    See Top 10 Rules to Better Email video for more details on how to reply to emails.

  39. Are you aware of the importance of a client's email attachment?

    Sometimes clients will add attachment files into emails. Those files could be documents or images, which may contain details or solutions of the issue, or some helpful information.To keep the history, it is very important to embed the attachment files into the email since it's easy to lose those files when responding.

    EmailAttachImage 1 small
    The image is in attachment.
    ::: bad Figure: Bad Example - The image is in attachment.

    EmailAttachImage 2
    The image is included in the context

    Figure: Good Example - The image is included in the context.

    PS: Clients make attachments because they are using OWA and you can't paste an image in - see suggestion for OWA

  40. Do you know to always be careful with your spelling, grammar, and punctuation?

    Improper spelling, grammar, and punctuation gives a bad impression of your company and can result in your message not being conveyed correctly. Emails with no full stops or commas are difficult to read and can sometimes even change the meaning of the text. And, if your program has a spelling checking option, why not use it?

    Web Content

    When on a web page, install Grammarly Addon for Chrome so you can automatically check web content. For example, while editing in a CMS.

    grammarly plugin
    Figure: A typo caught by Grammarly plugin


    When on Word, press F7 (or on the ribbon go to Review > Spelling & Grammar ) to check your .docx text.

    Microsoft Word has a spelling and grammar checker
    Figure: Click on "Spelling & Grammar" button to check your web content


    When on PowerPoint , press F7 (or on the ribbon go to Review | Spelling & Grammar ) to check your .pptx text.

    ppt review f7
    Figure: Click on "Spelling" button to check your web content

    You should also keep "Check grammar with spelling" checked in your PowerPoint Options | Proofing :

    ppt check spelling
    Figure: Make sure "Check grammar with spelling" is enabled

    Web Content

    Any other text can be checked manually. Go to Grammarly, create a New Document and Paste your content to check your text.

    Figure: A typo caught by Grammarly

    Related rule

  41. Do you avoid attaching emails to emails?

    Sometimes, in order to add someone in to the loop on something, you might write an email and attach another email as reference material.Generally this is not a good idea and you are better off replying to the original email instead so you can keep it in the history of ongoing threads.

    The exception is when you are already in a conversation thread with important history and you want to add more reference material to the email, although even then it's a good idea to also quote the particular line of interest as well.

  42. Do you avoid emailing sensitive information?

    Never email sensitive information such as Credit Card details, PINs or passwords. Not only does it present serious security problems, it looks like you don't care two-hoots about other people's information.

  43. Do you avoid huge images or attachments in your email?

    When your attachment is too big, you should think twice.

    1. Avoid large attachments. So if you are sending an email that is >1MB you need to take one second to think:

      • Could a URL be better than this attachment? (see example on the right)
      • Could I send this as a UNC to an internal share?
      • Could I .zip this?
      • Could I put this picture on Flickr or Picasa?

    Dear Mike,

    Thank you for spending time with us to come to a better understanding of your business requirements. Please review the new version of the specification at

    PS: The .docx was 4MB so I didn't attach a copy.

    Regards, Adam Cogan

    PS: An added advantage is that the document stays alive. If the URL has been updated and a user takes a week to get around to this email, they will view the latest version.

    1. If you have to attach the document, always use WinZip - it is common courtesy - I'll assume you already know that.
    2. Never use Rich Text inside Outlook. As a software developer, most large messages I receive are screen captures. By all means use screen captures - pictures do tell a thousand words - but don't include unnecessarily huge images or attachments in your email. Generally the only time you will have serious size problems is if you are using Rich Text instead of HTML inside Outlook.
    3. If you are sending screenshots then just send the region of the screen you need. Use a screen capture utility like Fullshot so you can use the region tool and get only the relevant part of the image you need. PS: Don't send screenshots as .bmps use .jpgs .gif or .png
    4. If you are sending pictures (every year digital cameras are making our photos bigger and bigger) you may need to resize them down. You can either use Photoshop or for something quicker try Office Document Imaging.
      compress pictures
      Compress Pictures
      Figure: "Compress Pictures" options dialog
    5. SharePoint was built with sharing files in mind and is a great way to collaborate. If you are using SharePoint to send a file you simply need to open the context menu, click "send to" and "email a link" as shown:
      sharepoint context menu
      SharePoint Context menu
      Figure: If using SharePoint 2010 you should use this context menu

    When should you break these size rules?

    Basically, you should be practical:

    1. Keep history
    2. Paste images into the email - not into a Word document and attach (so it stays with the customers' reply)
    3. When you paste a URL, also paste the section of the web page you are referring to (allows for offline reading)

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

    Contact or Mail Size
    Figure: SSW LookOut! for Outlook warns you if your mail size is large

  44. Do you avoid sending unnecessary emails?

    Every email you process takes time. Sifting through unnecessary emails becomes really frustrating. Don't clog up someone else's Inbox with unnecessary emails.

    A good rule of thumb for whether an email is unnecessary is if your email comprises of less than 5 words (e.g. "OK" or "See you then") it's likely it doesn't need to be sent.

    Merely saying "thanks" is often not sufficient to warrant the email but an exception to this rule is when positive reinforcement should be used when someone has done a specific behaviour that you like and want to encourage. E.g.

    "Thanks for being proactive and pointing out that improvement."

  45. Do you avoid sending your emails immediately?

    How often have you clicked "Send" and then wished you hadn't? It's a common problem. It can be easily solved by unchecking the "Send Immediately When Connected" option in Tools/ Options/ Mail Setup. We guarantee this will save you, one day!

    do not send immediately
    Figure: Don't send emails immediately - you will often remember something you needed to add

  46. Do you avoid using images in your email signatures?

    As useful as email signatures are for promoting your brand, using images in your signatures is a bad idea. To many recipients this can appear to be an attachment to the email. This will annoy some users, so it's better to keep your signatures as HTML or just plain text.

  47. Do you minimise 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 okay 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.

    2016 07 27 15 42 13 OOO
    Figure: Bad Example – Avoid using the Outlook Out of Office Assistant - This can fill up your clients' mailboxes with annoying auto-replies.

    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).

  48. Do you avoid using words that make your email like junk mail?

    Outlook by default reads your emails and can flag your email as potential junk email, or adult content email by examining a list of Sensitive words. This list is not available to the public.

    You should avoid any swear words or be using an angry tone as well.

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

    Contact or bad word
    Figure: SSW LookOut! for Outlook checks that you don't use bad words.

  49. Do you add branding to screenshots?

    You can communicate better by using screenshots with balloons and other visual elements (arrows, shapes, and highlights) instead of only text. Read the benefits of using screenshots.

    We recommend you define a standard style for your visual elements by changing the default colors and shapes according to your branding.

    More Information on SSW Branding

    2019 10 14 Snagit No Branding Example
    Figure: Bad example - shapes being used and branding not followed

    2019 10 14 Snagit Branding Example
    Figure: Good example - using balloons and arrows instead and brand colours used

    2019 10 14 Snagit Themes
    Figure: SSW theme already includes all tools you need with our branding

    Instructions to create and use Snagit themes can be found at Quick Style Themes Tutorial.

    Tip #1: You can automatically have your SSW Snagit presets on sign-in via a script. See Tip #2: Save your images in PNG instead of JPG for better quality.

  50. Do you know how to hand over tasks (aka Emails) to others?

    This rule is a variation of the popular rule Do you send "As Per Our Conversation" emails?

    The most dangerous time in a task's life cycle is in a handover. This is the most likely time for a misunderstanding to occur leading to a task getting lost and not being completed.

    Always make sure you clearly reallocate a task with an email to the person who will complete the task like the good example below:

    Figure: Bad example - task not clearly reallocated

    Figure: Good Example - Clear reassignment from Andy to Sergei

    If you need to hand over an entire project there are more details here: Do you know how to hand over a project?

  51. Do you know how to reduce spam?

    Problem: Spam. It wastes time and resources. In most cases, the amount of spam received by an organization far exceeds the amount of legitimate email.

    e.g. Average volume of spam received daily at SSW

    Total Email ReceivedSpamLegitimateSpam %


    1. Software Spam Filters Microsoft Outlook Junk Filter GFI MailEssentials Red Earth Policy Patrol Websense Email Security
    2. Hosted Spam Filters Google Apps Gmail (Free) Google Message Filtering Websense Hosted Email Security SpamSoap Core Filtering Microsoft Exchange Hosted Services

    **Solution:**At present, all email is filtered at the local Exchange server by GFI MailEssentials 12. While it removes a large amount of spam, an unacceptable amount still reaches user inboxes. The current architecture is shown here.

    Previous email architecture.
    Figure: Previous email architecture. GMail's basic service is the only free hosted solution, so it is naturally the first one to try. With Gmail as part of the solution the architecture changes to the following. The number of emails caught by each of the filters are averages.

    Current email architecture with GMail.
    **Figure: Current email architecture with GMail. ** **Process:

    ** The following steps need to be taken:

    1. Register for a Google Apps Standard Edition account. Go to and register with your domain name.
    2. Setup a catch-all account in Gmail and enable POP3 access to it. This means that only one account will need to be checked to retrieve filtered mail.
    3. Setup QSS Exchange Connector ( on your local Exchange server. This software bridges Gmail with Exchange. It logs into Gmail via POP3, retrieves the messages and then distributes them to users' individual accounts based on the header recipient fields.
    4. Switch over your MX records to point to Google's servers. This takes around 24 hours to take effect. When the change fully propagates, email will be delivered to GMail and retrieved by Exchange Connector.
    5. Monitor the GMail spam folder for false positives. Move false positives to Inbox. After approximately a week, GMail should have learnt enough to be left unmonitored. Emails can then be retrieved by user request.

    **Results:**The following report was generated by GFI MailEssentials 12. Note that the MX records changed over on 12/02/08.

    SpamGFIReportWithFullshot small
    GFI spam statistics over the architecture change-over periods.
    Figure: GFI spam statistics over the architecture change-over periods.

    It can be seen that after the MX records changed over, there were a couple of days of unusual data. This was due to the MX record change over and filter learning period.By the 16th, only 20 emails were marked as spam by MailEssentials. It can also be seen that the percentage of overall spam dropped from as high at 78% to mostly single digit percentages. GMail was now catching the vast majority of spam.

    It must be acknowledged that, while these figures do not represent the amount of spam actually reaching mailboxes, they do give a good indication of how effective Gmail's filters are.

    From further investigation, it was found that info[at], which receives more spam than any other account, was now receiving around 5 unsolicited messages a week, as opposed to a hundred or more prior to GMail implementation.In the first two weeks after implementation GMail caught 23124 spam emails, an average of 1652 per day.Apart from the obvious benefits, this also saved 641 MB of bandwidth allowance.In the case of info[at], a modest calculation of time saved reviewing spam would be 10 hours per year. This estimate is based on an average of 25 emails per day and 4 seconds spent reviewing each one. Actual times will obviously fluctuate, as will the amount of spam other users receive.

    Possible Issues:

    A third-party has access to your email.False positives. The GMail filter is very accurate but it is possible legitimate emails will be caught. In the Standard (free) Edition of Google Apps, spam emails are only retained for 30 days before being permanently deleted. With Premier Edition (US$50 for one account for a year) you have 90 days with the inclusion of Postini message management.Inbound emails will be limited to 20MB per message.In the current stable release (3.5.9) of QSS Exchange Connector, mailing list emails from Yahoo Groups and the like are not correctly delivered to mailboxes when "Automatically detect recipients" is turned on. This has been addressed in beta release and should make it to a stable release soon.Using this method, all spam is delivered to one mailbox. This has the advantage that one person can easily review all spam. The disadvantage is that each user doesn't have easy access to his/her spam messages. If users do not personally their own messages, legitimate email is more likely to be lost. Google Message Filtering would be a solution to this issue.

  52. Do you know not to send attachments in emails?

    It's better to use links to a portal or document store instead of having attachments in your emails.

    If you're sending to a fellow employee, use a link to a document store on your intranet (e.g.

    If you're sending to a client, it would be a link to a document store on their project portal. (e.g.

    Email Attachment 1 small
    Figure: Bad example - Don't send attachments by mail

    Figure: Bad example - Don't use location / filename in the link (URL)

    Tip: If you're using SharePoint, then an even better way to do this is to use a tool like OnePlaceMail to insert a link from SharePoint

    insert link in email to sharePoint item png
    Figure: Good Example - Use OnePlaceMail to send a link to a document in SharePoint

    Using the Document ID Feature in SharePoint will help minimise broken links under the following scenarios:

    1. Company Restructures / SharePoint restructures
    2. Records Management – when items are moved to the Record Centre

    insert link in email to sharePoint item with document id png
    Figure: Good Example - The use of the SharePoint Document ID as part of the link (URL) formation

    If you are using a shared DropBox, then put in a reference like so:

    I've moved the file to our DropBox at: 
    SSW_Designers/Project – FireBootCamp/Admin/FireBootCamp-USA-Ultra-Advert.pptx

    Related Rule

  53. Do you know that people misunderstand sarcasm in email?

    According to Sydney Morning Herald's "Flame emails missing the mark":

    "The senders of email messages expected their partners to correctly interpret their tone nearly 80% of the time, but in fact, they only scored just over 50%... Those attempting to interpret the message believed they had scored 90% accuracy".

    Because there is no "tone of voice" in an email, sarcasm can easily be misinterpreted by the receiver. You can use a smiley face to soften it up a bit

    Bad example: This is bad because it may seem like John is being reprimanded, even though the sender may just be giving him a "heads up" for next time

    Good example: Be friendly by adding a greeting. When in doubt, use a smiley face at the end of the comment

  54. Do you know when to use +1?

    When someone makes a suggestion or a complaint. Usually, you only hear from the ones who disagree. It helps to let others on the thread know you agree, by replying with "+1" and a quick sentence.

    From: Adam Cogan To: Code Auditor Team Subject: RE: Rule files

    +1 on this. It can be quite frustrating ________________________________________ From: Uly To: Code Auditor Team Subject: Rule files

    Hi, I saw two clients today that complained about Rule files being created even though one had already existed. They were all named x.SSWCodeAuditor where x was a number from 1 to 13 in one of the cases. Why do these keep being created?


    Figure: Good Example - using +1 to show you agree

  55. Do you link emails to the rule/template they follow?

    Having standards and email templates is great. It helps keep consistency, and the recipients know the format of the information they’re receiving and so can process it quickly.

    It also saves time if another employee needs to send one of these out later, as they may not know the processes that go into its construction.

    In order for other people to recognize emails following rules and standards, it's a good idea to include something like "<This email was sent as per XXX>" at the end of your email.

    Even when the rule or standard doesn't include an actual email template, but you want to empathize you are following it, it is still valid to include that link at the bottom, so the other person can get easily get more information.

    Figure: Good Example – the email links to the standard it follows

  56. Do you make sure every customers' (and prospects') email is in your company database?

    Most companies keep all their customers' (and prospects') contact information in a database (e.g. CRM, SQL Server, Access, Oracle). This allows all staff to easily locate contact details about a particular person. So when you get an email, make sure you check that email address and it is in the company database.

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

    Stephen Koop not in database
    Figure: Stephen Koop needs to be put into the database
    Not in database
    Figure: SSW Lookout! Can also check the emails that you are sending and tell you if the email address is not in your database.

  57. How do you reply to free support requests which would need more than 20 minutes work?

    You should reply like this:Dear Peter

    If it was a quick 5 mins I would do it straight away. However I need to do a little investigation - maybe a couple of hours.

    If that is OK then here is a link to purchase 2 hours and I will spend that time on this and let you know how I go.

    James Good Example - Reply like this if the free support request needs more than 20 minutes

  58. Do you manage your email accounts?

    When we have to use a local Email account, make sure we always CC our internal account on every email we send.

  59. Do you remember that emails aren't your property?

    The Australian Government Privacy Act permits employers to monitor employees' email (and web browsing) logs. While employers are encouraged to develop and promulgate a clear privacy policy, it's essentially a recommendation. Many employers may not have the resources to develop such a policy, but nothing prevents them from reviewing email records on the server. The Government admits that "system administrators are usually able to access everything on the network."

    The sensible response for employees is to be careful about what they say in email and abide by appropriate usage rules / etiquette even if they don't exist! Follow common sense on this one. Remember that your work email address should not be used for personal mail.

  60. Do you resist the urge to SPAM to an email alias?

    When you post to an email alias, you are posting to many, many people. Unnecessary emails are spam - only send emails that are valid or if there is a need for all to see.

  61. Do you send bulk email via 'Bcc' field if all parties are not contacts of each other?

    To ensure privacy, and not allow parties to get hold of each others' email addresses, emails to multiple parties should be entered in the 'Bcc' field (not the 'To' field).

    Figure: Good Example - Send bulk email via 'To' field

    Figure: Good Example - Send bulk email via 'Bcc' field

  62. Do you think when replying to emails it's better late than never?

    You should always try and reply to emails within a timely period, but this is not always possible.

    Sometimes people see an email 6 months old and just delete it because it's "too old" or refuse to reply because "the customer will think we're a joke taking this long to do something!" This is a great way to lose business, no matter how long it takes to do some tasks, it's always better to get it done. Of course, there are tasks that appear to be irrelevant with the passage of time, so reply and state that you don’t believe it is needed now.

    Example: A product suggestion might take 12 months to get around to, but when it's done the customer should be informed and get a link to the new version - it's possible that their need still exists, and they'll know that their ideas and suggestions are not ignored.

    delete outlook message button
    Figure: Bad example - Hitting the “Delete” button without replying

    Hi Bob, This is an old one. I tried to call you but you were not available. Please take a look and let me know if you want it actioned

    Figure: Good example - at least asking the question

    Hi Bob, Cleaning my inbox... Done - a few months ago

    Figure: Good example - informing a task was already done

    Hi Bob, Cleaning my inbox... This still looks relevant so I will start this old task today or tomorrow. Let me know if you don’t want that.

    Figure: Good example - giving the option to do it or not

    Hi Bob, Cleaning my inbox... I assume this is too late now. Sorry I missed this before.

    Figure: Good example - informing a task is not relevant anymore

    Reply to emails regardless of how long it takes to respond. It shows you value the sender's feedback.

  63. Do you avoid using "Request a Receipt"?

    Do you always demand a receipt for every email you send? This is the equivalent of crying wolf. People get prompted about receipts so often, that eventually, they change the settings to automatically ignore receipt requests. Then when someone really, really needs acknowledgment that an email has been received, you never get one, because they've turned off the mechanism.

    Turning this option on all the time effectively throws the option away, not just for yourself, but everyone else as well.

    Figure: Selectively request read receipts so as not to annoy your recipient.

    Warning: If you are using this more than once a year then alarms should be ringing!

  64. Do you use active language in your emails?

    Try to use the active voice of a verb wherever possible. For instance, 'We will process your order today', sounds better than 'Your order will be processed today'. The first sounds more personal, whereas the latter, especially when used frequently, sounds unnecessarily formal.

  65. Screenshots - Do you know how to show wanted actions?

    When using Snagit to show actions on a screenshot, follow this:

    1. To enter data – Use the yellow highlighting
    2. To click on a button – Put a square box around it
    3. To point out something – Use the arrow

    snagit actions bad
    Figure: Bad example – There is no visual difference between different actions

    snagit actions good
    Figure: Good example – This screenshot tells that the user should be on the "Message" tab, click on "Attach File" and edit the subject to be "Button types"

  66. Screenshots - Do you use balloons instead of a 'Wall of Text'?

    Some people communicate with a 'Wall of Text'. Communicate better by using screenshots and reduce your amount of words.

    You can take screen captures to the next level by adding balloons that have the appropriate text (aka speech bubbles). Sometimes you need only the text in the balloon and no text in the email.

    The balloon is great because you can point to a specific part of the image. It is much easier than reading the old ‘Wall of Text’.

    Let's look at bad and good examples:

    Figure: Bad Example – The email is using a screenshot so that is good, but you need to read the text and relate it to the image

    Figure: Good Example – The balloon with text on the screenshot, makes it quicker to understand

    See more details on how to configure balloons branding in Fullshot and Snagit.

    Now be aware not to go crazy with this balloon rule.::: bad

    balloon overload
    Figure: Bad Example – Balloon overload

    balloon not needed
    Figure: Good Example – See 3 balloons were not needed

    arrow example
    Figure: Good Example - Sometimes an arrow is all that is needed

    Figure: Betsy Weber Techsmith - Part 1 - Creator of Snagit. See full series here

  67. Bounces - Do you know what to do with bounced email?

    Having people report bounce back emails is frustrating and time consuming. The first thing to try when you get a report is to check that your mail server isn’t on a spam blacklist. An easy way to check this is via MX Toolbox.

    MXToolbox 1
    Enter the domain to check
    Figure: Enter the domain to check
    MXToolbox 2
    Then select Blacklist Check
    Figure: Then select "Blacklist Check"
    MXToolbox 3
    not blacklisted
    Figure: Getting a zero is good, so you know that you are not blacklisted… so Step 1 is good Next step check that you have primary and secondary (and even better tertiary) MX records setup and working.
    MXToolbox 4
    SMTP test
    Figure: Seeing at least 2 MX records is good... Run an SMTP Test to test mail servers. So Step 2 is good If success on both steps the error is most likely on the senders side. Send them the an email to check their mail settings.

    Dear xxx

    As per this rule on bounced emails

    • I have checked Step 1 – it is good
    • I have checked Step 2 – it is good The problem is likely your end

    Figure: What to send the person

  68. Bounces - Do you know how to correct a bounce?

    Let's say you press “Send” and get a bounce, e.g. An email in your inbox that reads:

    Delivery has failed to these recipients or distribution lists:

    Adam Cogan ( The recipient's e-mail address was not found in the recipient's e-mail system. Microsoft Exchange will not try to redeliver this message for you. Please check the e-mail address and try resending this message, or provide the following diagnostic text to your system administrator.

    Get the correct email address and ‘Reply to all’ with just this text in brackets:

      (Resending with Adam’s correct email)

      ---------------------------------   [Original Email]

    Figure: Good Example - Correct the email address and send again.

  69. Efficiency - Do all your employees know the quickest way to fix small web errors?

    Imagine this scenario... Mary notices a small error on a page in her intranet. She is a good employee... She opens up the backlog and reports the spelling error. As she sends it she says to herself "That took more time to report the error than it would have taken me to fix it".

    Small errors should be fixed by the person who found them. Text changes can be easily done in SharePoint or WordPress. If you know who the culprit is, it might be a good idea to inform that person, including the things you have fixed.

  70. Do you give your emails a Business Value?

    The problem with emailing a task, is that no one knows how important that email is, in relation to all their other emails. So, what is the solution?

    There are the 3 ways people can send tasks:

    1. Send an email only. Email sign

    Figure: Bad example - An email with requirements does not indicate the priority

    1. Put the task straight into the backlog, and send no email: straight to scrum

    Figure: Bad example - The developer does not get a chance to ask questions and refine it before it hits the backlog

    1. Send an email, the recipient reviews it and places it into the backlog, based off the specified Business Value. Developers often prefer this method if they like control over their backlog. Developer entered

    Good example - Email tasks with a Business Value, allow the developer to review before putting it in the backlog

    The perfect email workflow

    Before you email a task to someone, think about how important it is to you. Then draft your email, add the Business Value using the same scale that you would use to estimate your PBIs. Email Diagram

    Figure: Good example - The best workflow for sending an email

    Q: What if you need to write an email to multiple recipients? A: Assign each person a Business Value. In the case of "To Myself" emails, you can also add the amount of 'Effort' required too. Email screenshot

    Figure: Good example - The best workflow for sending an email (with multiple recipients)

    Related links

  71. Do you add a Bot signature to make it clear when an email is automated?

    With the advent of Microsoft Flow and Logic Apps, automated emails are becoming more common. And in fact any reminder or notification email you find yourself sending regularly should probably be automated.

    However, the end user should be able to tell that this was sent by a bot, and not a real person, both for transparency, and also to potentially trigger them to automate some of their own workflow.

    Figure: Good Example – you can clearly see this was sent by a bot

  72. Do you use great email signatures?

    Email signatures are a great way of adding some advertising and branding. You should always use a nice email signature for external emails . Internally, you shouldn't use any or just use a short one (just your name or initials).

    Full email signatures are great when they have:

    • A little branding and advertising (can be a tagline or company news), so people know instantly who it is from
    • Your phone number (in international format - it's important to add the country code so people from all around the world can easily add you to their contacts - as per Do you know the right format to show phone numbers?)
    • Your company website link (e.g.
    • Your work-related social media and blog link
    • Your position
    • Your location (city/country) where you are based

    Mobile signature are not easily customized so they can be simpler.

    Mobile Signature

    Use the "mobile signature" when sending emails from your phone.

    Get Outlook for Android

    Figure: Bad example - This default signature sucks

    Thanks, Adam | +61 4 1985 1995

    Figure: Good example – Add your name, URL and your phone number

    PC Long Signature

    Use the complete "long signature" when sending a new email or appointment to a client.

    This is created in HTML and goes well on emails with Word used as the email editor. Include some product advertising, like what's new on your monthly newsletter. It should have the company colors.

    outlook signature
    Figure: A great long signature for PC

    However, you shouldn't use your long signature on every sent email. It's recommended to have a simpler version for internal emails and appointments:

    PC Short Signature

    Use a really short signature (your first name or initials) or no signature at all in internal emails as people already know who you are.

    Note #1: You can see Ulysses using this rule in practice, along with other best practices, on this short demonstration video.

    More Information

    How to set it up in Outlook

    1. Open Microsoft Outlook and go File | Options
    2. Click the "Mail" tab as seen below
    3. Click on "Signatures..." and add in your signatures

    Outlook2013 signature
    Figure: How to add a signature in Outlook

    How to set it up in OWA

    1. Open OWA (e.g.
    2. Click "Options" on the top right side.
    3. Go Settings | Mail and make following changes:

    owa signatures
    Figure: Add your 'Email Signature' and save

    How to set it up in Office 365

    1. Open Outlook in Office 365 (
    2. Click the "Settings" cog on the top right corner of the Window
    3. Click on “View all Outlook settings” at the bottom of the Settings panel

    outlook settings signature
    Figure: Where to find "View all Outlook settings"

    1. In the "Settings" window that pops up, go to: Mail | Compose and reply.
    2. Add your email signature and click "Save"

    Warning: Unfortunately you need to setup up your signature in Outlook and OWA. There is no way to share this.

    SSW Only: You can automatically have your Outlook signature changed on sign-in via a script. See

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