Secret ingredients to quality software


Rules to Better Calendars

22 Rules

It's important to use your calendar correctly as it's your main organizational tool and how others view your time.

Since calendars are often used with emails, you should also have a look at Rules to Better Email.

  1. Appointments - Do you send Outlook Calendar appointments when appropriate?

    If you wish to organize a meeting that involves some of your colleagues and a client, instead of sending an email, send an appointment. Sending appointments is convenient because all the user has to do is click 'accept' and it is in their calendar.

    Figure: Use Outlook appointments to easily synchronise your calendar with your client's

    This way Outlook will remind your colleagues about the appointment and you can update them if any changes are made.

    If the appointment is for 3 days or less , send a separate appointment for each day. This is because multiple-day appointments appear at the top in your Outlook Calendar, so you risk missing the appointment (see below).

    Figure: Bad Example - Multiple-day appointments appear hidden at the top of your Outlook calendar, so you might miss it, thinking that the time is free

    Figure: Good Example - Send a separate appointment for each day so you can clearly see it in your Outlook calendar

  2. Appointments - Do you create appointments as soon as possible?

    A lot of people talk about appointments and plan to do it later. E.g. you’re at the dentist and they give you a card with your next visit’s time written on it. People take the card and plan to enter it into their calendar later.

    A better way is to stop, pull out your phone, and enter it immediately before leaving the dentist.

    Similarly, you might be on the phone with a client and arrange a date and plan to enter it in later. A better way is to say “Hang on a second while I shoot you an appointment for the time.”

    Locking in time as soon as possible is a big efficiency gain, and helps to avoid any possible mistakes or double bookings.

    ssw do it now
    Figure: As soon as you know you’ll need time with someone, create and send the appointment immediately

  3. Appointments - Do you make sure your appointment has a clear location address?

    Make sure appointments have address details unless it's obvious for all attendees.

    appointment location bad example
    Figure: Bad Example - Appointment field should have addresses in location when appropriate

    map example
    Figure: Good example - Address is clearly identified in the location field, meaning it can be mapped using applications on smartphones

    It's important to always add the address information in appointments when a third party is included. i.e.:

    • A client meeting at your location
    • A meeting at the client location

    The exception is for internal meeting appointments:

    You should invite a coworker to work with you in the boardroom (but not include the address)

  4. Appointments - Do you make sure your appointment has a good subject?

    When sending an appointment, it's a good idea to choose your subject/title intelligently so that people can see all the information they need to see on the Subject of the Appointment.

    For example, if the appointment is a meeting request you should include the names of the persons attending that appointment. Another example is flight bookings or hotel bookings. Including the flight number and/or Hotel name in the Appointment Subject so that you can see the information without having to open the item. Think about what the recipient sees in their calendar and try to make it as clear as possible.

    ApptSubjectBad small
    Figure: Bad Example - appointment subject with very little information

    ApptSubjectGood small
    Figure: Good Example - Appointment subject with all of the relevant information shown

    CRM users making bookings should keep their naming standards consistent.

    Related rules

  5. Appointments - Do you explain why you've deleted or updated an appointment?

    Whenever you have to modify the time, attendees, or subject of an appointment, always send the updated one with comments at the top to explain why you want to make these changes.


    UPDATED: Moving to Thursday as Adam could not make it

    Figure: Good example – changing the date or time

    UPDATED: Adding Uly since he may want to know that we are working on TimePro this day

    Figure: Good example - adding someone as per Do you know how to add or remove someone from the conversation?

    UPDATED: Change the subject as we will be taking about Marketing first

    Figure: Good example – changing the subject. Learn more on Do you know when you should change a subject?

    This will help to solidify the changes and alleviate confusion.

    Figure: Good Example - Explaining the change that has been made using the prefix "UPDATE:"

    Note: Using brackets is also an option

  6. Appointments - Do you know how to "Reply All" to an Appointment?

    Often your conversation flow with someone will go from a phone call to emails, to an appointment, and then back to emails.

    It's nice to be able to look back and see the whole history in one thread, so you will need to be able to Reply All to an appointment to continue the email conversation after the meeting.

    Outlook makes this easy:

    • Option 1: Right-click on the appointment in your calendar and click "Reply All"
    • Option 2: Left click on the appointment in your calendar and type "Ctrl + Shift + R"
    • Option 3: Use the ribbon as below

    Outlook 1
    Figure: Open the appointment in your Calendar (You should already have Invited all the required people to attend)

    Outlook 2
    Figure: Click on "Contact Attendees" | "Reply to All with Email" if you created the appointment, or "Respond" | "Reply All" if you were invited

    Outlook 3
    Figure: Good example – This friendly reminder has the right history (the appointment)

    Reasons you might want to "Reply All" to an Appointment include:

    1. Continuing the conversation after a meeting
    2. Reminding someone about an upcoming meeting (especially if you know they have unwieldy calendars)
    3. Getting more information before a meeting
  7. Appointments - Do you know to copy the email content into the calendar appointment?

    One of the great things about email is that as a conversation progresses, you always have the thread history that you can refer to for context. 

    Calendar appointments, on the other hand, don’t have this. Therefore, if you make plans via email, and that email conversation includes details like times, agendas, locations, etc. It’s usually a good idea to copy the email text into the body of the calendar appointment. That way you’ve got the history and context right there, so the attendees don’t have to go searching for it in their inbox.

    Warning: With calendar appointments, there’s also the risk that people will accept the appointment without reading the content – people don’t do this with email. So if you are initiating an appointment that has a task in it, where you would like a ‘done’... then duplicate the content of the appointment into an email.

    Figure: Calendar appointment with tasks should be copied from an email, so the items assigned get read via the email (better visibility), and also the email can get replied to with a ‘done’

  8. Appointments - Do you avoid putting the time and date into the subject or body of a meeting?

    Avoid putting the date and time into the text field of a meeting since these are often overlooked when changing the meeting time/date metadata.

    Bad calendar appointment
    Figure: Bad Example - The appointment with the date in the text

    Good calendar appointment
    Figure: Good Example - The appointment without time and date in the text

  9. Appointments - Do you use propose new time?

    When you would like to propose a new time for an appointment that someone has sent to you, use the Propose New Time button in Outlook instead of simply declining the message. By using the Propose New Time option, the requestor can easily accept your proposed time, rather than having to edit the previous appointment.

    Figure: Bad Example: The person who sent the appointment has to interpret your message, then go back in and edit the appointment

    Instead of simply declining the message and typing your proposed time in the message body, propose a new time as follows:

    Propose new time
    Figure: Good Example - Click one of these... and then...

    scheduling assistant

    scheduling assistant
    Figure: Good Example - The new time is proposed, and the person who sent the original appointment can easily accept your proposal (or view all proposals if there are multiple recipients)

    Figure: Good Example - The new time is proposed, and the person who sent the original appointment can easily accept your proposal (or view all proposals if there are multiple recipients)

  10. Appointments - Do you automate scheduling of meetings?

    We've all been part of that email chain... "Let's meet to discuss this", "When are you free?", "I can do Friday", "Friday's no good, what about Monday?", "I'm free in the morning", "Penny can't make that, how about Tuesday afternoon after 3?", etc.

    AI can make scheduling meetings with multiple attendees much easier.

    Note that both of the following solutions work best when you're dealing with people in your own organization, as they then have access to all calendar data, but with a bit of back and forth, they can still work for externals too.

    Microsoft Cortana Scheduler (formerly known as

    Sexy face This option is best if you're ok to meet any time that your calendar says is free.

    Instructions to use Cortana: Step 1: Register yourself at before you can use this feature. ** **

    Step 2: Open an email... not an appointment!

    To: [person] Cc: Body: after your normal text to a person, add some extra text like "Cortana, schedule a meeting."

    Cortana then handles all the back-and-forth emails to find a time when everyone can meet and then she sends out an invite on your behalf.

    More help for Cortana:

    1. More on and see the FAQ
    2. Watch the video here

    Figure: Speak to Cortana as you would a PA

    Figure: Cortana will find a time that suits everyone and send the appointment

    Step 3: To make it easier to add Cortana to your emails, create a Contact.

    Figure: Cortana added as a contact

    Mobile – works great ✔

    cortana scheduler mobile
    Figure: Microsoft Scheduler – Fully works on mobile phone


    This option is best if you want to be selective about a few options for when to meet, and send a poll to attendees to choose.

    FindTime shows what days and times work the best for you and the attendees when available using free/busy data.

    Propose your selected times to all attendees and allow everyone to vote and quickly come to a consensus... and you’re done!

    FindTime sends out the meeting invite on your behalf. More on

    findtime scheduler
    Figure: FindTime gives a nice UI for people working in the same org, as you can see times that might be available for all attendees easily (e.g. 8 am above)

    Mobile – does not work ❌

    As of Dec 2020, FindTime does not work on iOS.

    Vote at What features would you like to see in FindTime?

    Note: Findtime’s competitor is

    findtime mobile
    Figure: FindTime - No mobile support for iOS

  11. Appointments - Do you always put your join link for remote meetings at the top of the body?

    By default, when you click the button to turn an appointment into a Teams Meeting, it adds the link to join the call to the bottom of the body content. It’s generally a good idea to move this up to the top, as It’s the 1st thing you’ll want people to do when they open the appointment on the day of the meeting.

    join link bad
    Figure: Bad Example – join link gets lost

    join link good
    Figure: Good Example – easy to know what to click on

  12. Calendar Permissions - Do you share your calendar?

    Within a company, there are occasions that you are not able to access your computer to send sick emails, or you get a call from your client on the way to the office that you have to drive to a client site straight away; when such things happen, you need someone else to update your calendar when you call in, so others are aware of your availabilities.

    Always make sure that:

    • Admin people are able to access your calendar with full permission in order to add/edit/delete appointments for you.
    • The whole organization can see your full calendar details.

    Do this to allow Admins to edit your calendar permissions:

    1. Open Outlook (or Outlook Web) | Click Calendar | Click "Share Calendar" | Click "Add..." | Add the Admin group | Select "Can edit"

    Share Calendar
    Figure: Click on "Share Calendar" in Outlook

    Figure: Give admins full access to your calendar in Outlook with "Can edit"

    Now do this to allow the whole organization to see your full calendar details:

    1. Open Outlook (or Outlook Web) | Click Calendar | Click "Share Calendar" | Click "My Organization" | Select "Can view all details"

    Figure: Give the whole organization access to your calendar in Outlook with "Can view all details"

    Once the permissions are given, opening other people's calendar is as easy as 2 steps:

    1. Go to the Calendar tab in outlook and click "open a Shared Calendar"
      Shared Calendar
      Figure: Opening a shared calendar
    2. Choose the calendar you want to open in the pop-up form
      Figure: Find the calendar you want

    Then you can have this shared calendar shown in your Outlook.

  13. Calendar Permissions - Do you check someone's calendar before booking an appointment?

    If someone has shared their calendar permissions with you, you will be able to check their calendar directly without needing a conversation.

    Imagine someone wants to book some time with you. Offer to look up the calendar and book in time straightaway.

    Bad Example - "Try calling him."

    adams calendar
    Good Example - "Sure, I'll just look up Adam's calendar and see when he's free. Obviously, it's not a good idea to call Adam now as he is on a plane."

  14. Calendar Permissions - Do you know how to send an appointment on behalf of someone else?

    If someone has shared their calendar permissions with you, you will be able to send appointments on their behalf.

    If someone wants you to send an appointment for them, but you don't want it to appear in your own calendar, this is the way to go.

    When sending an appointment from someone else's calendar, you should always include that person as an attendee so that they also receive the same appointment email that their guests do. It shows them that the invitation has been sent, and also allows them to check for any mistakes or additional information that needs to be added.

    shared calendar

    Figure: Step 1 - Open the person's shared calendar

    Send on behalf of

    Figure: Step 2 - Make sure you invite the person you're sending for

    on behalf of

    Figure: the attendees will receive an appointment that says you sent it on behalf of the other person

  15. Calendar - Do you know how to share your availability via email?

    Sometimes your schedule is chockers and you want to be transparent!

    Have you ever needed to send your calendar schedule to someone to figure out the best time to schedule a meeting with them? Figuring out when someone is available within your organization is usually easy, as Outlook can show you automatically using the Scheduling Assistant.

    If you're trying to coordinate with someone outside of your organization, this can be more challenging. In Outlook you can easily include a copy of your calendar schedule to make this process easier.

    To insert a nice looking calendar and .ics file attachment into your email in Outlook, do the following:

    1. New email in Outlook, go to the ribbon and select Insert / Calendar
    2. Select your options to insert the fancy HTML calendar and .ICS file in to the email:
    3. You now have a nice looking calendar showing your availability, ready to send: share-availability.jpg Figure: Pick your calendar, date range, and amount of detail
  16. Calendar - Do you know the ways to see others' calendars?

    While working in a team, there are three ways of seeing others' or team calendars.

    Option 1: Using Outlook Calendar Permissions - See a person's calendar

    You can share your Outlook calendar with another person or a group in Outlook. This option is useful when you want to share your personal calendar with others.

    See for step by step instructions on how to share your calendar or see another person's shared calendar.

    outlook calendar example
    Figure: The Outlook calendar

    Option 2: Using the Dynamics 365 CRM Service Calendar - See everyone's calendar

    When you want to see what's your colleague is doing, you can use the CRM Service Calendar.

    This can keep track of important things like client work and leave. See Scheduling - Do you know how to book developers for a project? on how to add a booking to CRM Service Calendar.

    Note: The CRM Service Calendar is deprecated; Microsoft are now moving to Dynamics Universal Resource Scheduling

    ServiceCalendar Figure: The CRM Service Calendar shows everyone's booked in client work and leave

    Note: This will only show appointments that have been tracked in CRM.

    Option 3: Using SharePoint's calendars - See a team's calendar

    You can also create a calendar in SharePoint which will be shared with the team on that SharePoint site. By sharing a calendar using SharePoint, new developers who have just joined the team can immediately look at the project's events (e.g. Daily Scrum meeting).

    In this scenario, the scrum master of "SSWSugarLearning" wants to share the calendar called "Team Calendar" with his team.

    To share a team calendar, you just need to give the calendar URL to the person in your team.E.g.

    Tip: You can also connect the SharePoint calendar to your Outlook. Here's how to do that:

    sharepoint sharing calendar   using outlook
    Figure: In SharePoint 2016: On the "Calendar" tab, click "Connect to Outlook" to show the calendar in your Outlook account

  17. Appointments - Do you make your team meetings easy to find?

    When joining a new team, it's easy to be lost and not know when the important meetings are (like the Daily Scrum, or the next Sprint Review). If you run the meetings from Microsoft Teams you can make them easy to find!

    team meetings   bad example
    Figure: Bad Example - When I look at my calendar, I don't know when the meetings are

    team meetings   good example
    Figure: Good Example - A SharePoint page allows me to see my Team's meetings before I have been invited (and invite myself if required)

    1. Open up the Team's SharePoint site (you can find this easily by going to the Files tab and clicking Open in SharePoint)
    2. Go to the SharePoint site's Home page (from the menu on the left)
    3. Add a new page
    4. Add a Group Calendar web part to the page
    5. Publish the page

    Figure: Some easy to follow steps to create the SharePoint page

    1. In Teams, click add a new SharePoint tab to the Team
    2. Select the newly published SharePoint page
    3. Click Save

    Figure: Adding a tab to a Team is an indispensable skill

    1. All done 😀

    🔥 Make sure you pick "SharePoint" tab (as opposed to "Website" tab) for best possible integration:

    ![](Bad One.jpg)

    Figure: Bad Example - using the Website tab

    ![](Good One.jpg)

    Figure: Good Example - using the SharePoint tab

    Suggestion to Microsoft: This is an unnecessary extra hoop to jump through. If you create an appointment from a Team then this tab should be automatically created.

    team meetings   add yourself
    Figure: As a bonus, I can the event to my calendar

    Warning: Only the organizer of a meeting can make changes to it and Teams offers no ability to transfer ownership of that meeting. To be fair you also can’t change meeting owners in Exchange.

    Vote for this UserVoice item (that describes that the Teams team is working on delegation for Teams meetings but no ETA).

  18. Calendar - Do you set your work hours in CRM and your calendars?

    You should always set your working hours in your Outlook calendar so others knows when you are working, this will help us to do resource scheduling. This is especially important for people who are not working as full time, e.g. part-time, contractors etc.

    You can find this setting in File | Options | Calendar Options, it looks like below:

    Outlook work hours
    Choose your working hours
    Figure: Outlook Calendar options for working hours settings Once you set this up, you will be able to see the grey area in "Scheduling assistant" so you know what's the best time to book that person.
    You can see the working hours in Scheduling Assistant.
    Figure: Working hours will be shown in Scheduling Assistant CRM set work hours 1 Figure: In CRM, Click on the cog in the top right | Personalization Settings CRM set work hours 2 Figure: Go to the Activities tab | Enter your default work hours

  19. Calendar - Do you use a centralised leave calendar?

    People take leave all the time, and it can be frustrating to find out that someone is not in the office after you've already sent an email to book them for a meeting. You should have a centralized system to check for everyone's availability.

    The easiest way to do this is to use a shared calendar that is just used for leave. At SSW, we have the SSWAbsence calendar for this. This requires people to send their leave requests as an appointment to SSWAbsence .

    Since this is just a calendar, you should also have these leave requests automatically to your admin managers (SSWAdmin), so they are always notified of what's going on, although normally these managers will decline the notification rather than add it to their own calendar by accepting it.

    Figure - Good Example: You can see everyone's leave in one place

  20. Calendar - Does your website make it easy for your users to add an event to their calendar?

    If you have a date for any event appearing on your website, you should make it as easy as possible for the user to add it to their Outlook calendar. This is why we use ICS links for all dates on our site.

    Next User Group Meeting: Wednesday, 15 February 2006 5:45 PM

    Figure: Bad Example - User cannot add a reminder

    Next User Group Meeting:Wednesday, 15 February 2006 5:45 PMAdd Outlook reminder

    Figure: Good Example - User can click and add a reminder

    By clicking the calendar link, users can easily add the event to their own calendars.

    You have 2 options - VCS and ICS. Both let you add appointments to your calendar. We use ICS because it allows collaborating information between personal information management programs like Microsoft Outlook, Mozilla Calendar, Mac OS, etc. over the Internet, independently of differences between program vendors or operating systems, which is not allowed with VCS.

    It is always preferred to use icons to give users a proper idea about the file. Users can quickly get the idea by just looking at the icon.

  21. Metrics - Do you track your initial meetings?

    When creating an appointment email for an initial meeting, make sure you include the words " initial " and " meeting " on the subject.

    Subject: Northwind project with SSW and Bob

    Figure: Bad subject - not clear it is an initial meeting

    Subject: Initial meeting with SSW and Bob from Northwind Subject: Initial phone meeting with SSW and Bob from Northwind

    Figure: Good subjects - Make clear it is an initial meeting by having both words

    The Appointment should also be tracked (without regarding) in Dynamics 365 so that this information is readily available and reportable.

    initial meeting dynamics
    Figure: Initial Meeting created in Outlook and tracked to Dynamics 365

    The idea behind it is that Power BI can then track and show this.

    initial meeting graph
    Figure: It's clear to see that there is no yellow in the past couple of months, which may indicate work drying up for Stephen's area

  22. Calendar - Does your calendar always accurately show where you are?

    The following steps will help you to setup your calendar to allow us track your current availabilities and improve our team collaboration.

    Step 1: Set your work hours in Outlook Read rule: Do you set your work hours in your Calendars?

    Step 2: Share your outlook calendar with everyone Read rule: Do you know the ways to see others' calendars?

    Step 3: Allow calendar admins to have full access to your calendar Read rule: Do you share your Calendar?

    Step 4: Send your leave appointments to a centralized leave calendar Read rule: Do you use a centralized leave calendar?

    calendar accurately show where you are
    Figure: Keep your calendar up-to-date and set to share, so people can always find where you are

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