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Rules to Better Calendars - 24 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. 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. 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. One of the least successful ways to get an appointment is to ask for one. The reason is that by asking for a meeting, you're creating hurdles. A hurdle for you to look at your calendar for available times, a hurdle for them to look at their calendar, a hurdle to reply to the email. And then there is the obstacle that arises when their proposed time conflicts with something you're doing, and the process begins again. Even for people who don't have busy calendars, these meetings often don't happen because they slip down the inbox.

    The better way to get an appointment with someone is to throw an appointment their way. You have a higher chance of it sticking if it appears in their calendar. You will be amazed at your success rate. That said, make sure you soften the appointment with something like “if there is a better time for you, let me know”.

    It is a good idea to send the appointment a few weeks out, it is less confronting and less demanding than finding a meeting in your calendar for the next day (or the same week).

    The obvious caveat is that you shouldn't send meeting requests to people who have no idea who you are, that's just spam in a different vehicle.

    Figure: Bad example - Leaving the ball in their court

    Figure: Good example - Sending the appointment first. They can change the time if necessary, but it's in their calendar

  4. 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. Example:

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

    The exception is for internal meeting appointments.

    In internal, you should invite a co-worker to work with you in the specific room and not include the address. Example:

    • SSW Boardroom Sydney
    • SSW Boardroom Brisbane
    • SSW Chapel Sydney
  5. 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 subjects are better when they can be read from both sides e.g. Include both names

    CRM users making bookings should keep their naming standards consistent.

    Related rules

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

    Examples:

    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: Changed 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 technique helps alleviate confusion.

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

    Note: Using brackets is also an option

  7. 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
  8. 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 is a risk of people accepting the appointment without reading the content – it doesn't happen with emails. If you are initiating an appointment that has a task in it (when you expect 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’

  9. 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

  10. 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.

    decline
    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)

  11. 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. There are some options.

    Microsoft Cortana Scheduler (formerly known as Calendar.help)

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

    Note: The helpful tool Scheduler has a portal too at https://calendar.help/user/dashboard

    Instructions to use Cortana

    Step 1 - Register

    Register yourself at Meet Scheduler before you can use this feature.

    Step 2 - Send an email

    Open an email... not an appointment!

    Figure: after your message, add some request to Cortana as you would a PA

    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.

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

    More help for Cortana:

    1. FAQ on calendar.help
    2. Watch the video here https://www.microsoft.com/en-us/scheduler

    Step 3 - Add Cortana as a contact

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

    CortanaContact
    Figure: Cortana added as a contact

    Mobile – works great ✔

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

    FindTime

    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 https://findtime.microsoft.com

    Note: Findtime’s competitor is https://calendly.com

    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.

    findtime mobile
    Figure: FindTime - No mobile support for iOS

  12. 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

  13. 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" Note: Check you are looking in the right address book using the "Address Book" dropdown if you cannot find a user or group.

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

    Permissions
    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"

    CanViewAllDetails
    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
      SSWAbsence
      Figure: Find the calendar you want

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

  14. 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."

  15. 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

  16. 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
  17. While working in a team, there are three ways of seeing others' or team calendars.

    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 Calendar Permissions - Do you share your calendars? 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 Dynamics 365 CRM Appointments - See everyone's tracked appointments

    If you do not have access to someone’s calendar, you can see their tracked appointments in Dynamics 365 | Appointments.

    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.

    dynamics appointments
    Figure: Appointments in Dynamics 365

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

  18. 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). Broadly, use Teams as the appointment source (rather than Outlook) then the benefit is that you can have a tab where you see it in the context of the team. Then, when a new member joins a Team they do not have to go looking for the appointment, and can easily join the call.

    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, now all you need to do is setup some meetings for the channel (see rule: Do you know how to create recurring teams meetings for a channel?)! 😀

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

    Bad One
    Figure: Bad Example - using the Website tab

    Good One
    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.

    --

    See this Microsoft Community entry that describes that the Teams team is working on delegation for Teams meetings but no ETA.

  19. Set your work hours in Outlook Calendar

    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
    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.

    SchedulingAssistant
    Figure: Grey means people are not available (so set your working hours to be accurate)

    Set your work hours in CRM

    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

    This only allows for times that are the same every day. You should also update the work hours field in your CRM Details Tab.

    Prems work hours
    Figure: Good example - Only update your work hours if they vary from the usual Mon-Fri, 9-6

  20. 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 (e.g 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.

    Leave
    Figure: Good Example - See everyone's leave appointments in one place

  21. 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.

  22. 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

  23. 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

  24. Do you use emojis to help text context?

    It's usually easier for users to remember where given information is when it is associated with an image/icon. This is especially true for non-technical people or the ones that are not very familiar with digital workspaces.

    An easy and fun way to alleviate this issue and boost user adoption to Microsoft Teams is to use Emojis in your channel names (using Windows Key + .)!

    Teams Emojis Bad
    Figure: Bad example - Teams Channel names without emojis

    Teams Emojis Good
    Figure: Good example - Teams Channel names have emojis

    control4 emojis
    Figure: Good example - Control4 automation Mobile UI is more friendly with emojis

    calendar emoji
    Figure: Good example - Some appointments can benefit from an emoji too, like a Sprint meeting in Scrum

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