How to create and improve group calendar use in Outlook – and other calendar planner tools

30-second overview:

So, your company uses Outlook and you want to view multiple employee calendars side by side, make bookings for other employees and manage calendar groups? If you’ve tried this, you’ll know there are a number of frustrating limitations in Outlook. In this article we show you how to setup Outlook to view calendar groups, discuss the limitations and offer ways to overcome them.

  • How do you setup Outlook shared calendars?
  • What are the limitations with using Outlook calendar groups?
  • How to configure Outlook in the best way for calendar planning
  • How to overcome all Outlook limitations with Timewatch’s calendar planning tools for Outlook

How to create a shared calendar in Outlook

We provided details in a previous post on ‘How to view someone’s elses calendar in Outlook’. In case you missed this, we’ve summarized how to do this here:

To setup Outlook shared calendars:

  1. In your Calendar, on the Home tab, in the Manage Calendars group, click ‘Add Calendar’, and then click the type of calendar that you want.
  2. Browse for names or type them in the Search box, click the name that you want, and then click Calendar. Repeat this step for each calendar that you want to include in the group, and then click OK. The added calendars appear in the My Calendars folder in the Navigation Pane.
  3. In the Navigation Pane, drag the calendar into the calendar group that you want.

To view Outlook calendars side-by-side, in overlay or schedule view:

  1. On the Home tab, in the Arrange group, click Day, Work Week, Week or Month. The calendars are arranged side-by-side.
  2. Click the View in Overlay Mode arrow on the tab on each calendar that you want to overlay.

What are the limitations with Outlook shared calendars? How can you overcome them?

Outlook shared calendars support basic multi-calendar management, but there are a number of limitations. Here we list the top 12 limitations, explore ways to work around them in Outlook as well as how to enhance Outlook and resolve or overcome them with add-on software:

1) Outlook views are limited by the number of people, and/or range of days

There are a number of ways multiple calendars can be displayed in Outlook. These vary depending upon the platform and version of Outlook you use, but the three main types of view are:

  1. ‘Overlay View’ – shows everyone’s appointments in your calendar, which is not ideal. Outlook color codes appointments by person, but as colors are used for three different things it can get very confusing. In the calendar groups example shown, the 3 yellow appointments are all for different group members!

The Overlay view in Outlook gets very confusing. Here, the yellow appointments are all for different people!

  1. ‘Split View’ – displays a separate calendar for each person. This works well when you display a 1 day personal calendar view for each person as you can scan across calendars to see who is free at a certain time (blue bars). However, this shared calendar view is very cluttered in 5, 7 and month views and you are limited to showing 5 personal calendars from your address book.

Split Views show a calendar per person. Week & month views can be cumbersome, a 1 day view for 5 people is helpful as you can quickly see who is available at a set time (blue bars).

  1. ‘Schedule View’ – displays each calendar as a row. This is a better layout for viewing multiple calendars as more than 5 calendars can be displayed, but again there are limitations. The view is limited to 2 days, it doesn’t show appointment type colors so you don’t know what people are doing, you can no longer see the subject or notes on the appointment, the view gets noticeably slower the more calendars you display and it is only available in the latest 2022 version of Outlook on Windows.

The Scheduling View shows employees as rows, which is better for viewing multiple calendars, but is limited to 2 days and loses the subject & appointment type colorization .

How to work around the multiple calendar limitations in Outlook

You can’t change Outlook’s view styles, but you can minimize frustrations. For example, for a team of 15 team members you’d have to use the new calendar check box to select 5 calendars to view from your contact list. You have to click the check box again to deselect them, then choose another 5 members and so on until you’ve seen all calendars. Instead, create a new calendar group for a block of 5 group members,  so instead of selecting and unselecting group members (employees) 15 times, you simply select and unselect 3 calendar groups. It’s a little faster, it’s not perfect, but it does work.

Another limitation is that you can only show time for a shared calendar over a date range of a couple of days. The combination of a limited date range and limited  number of group calendars that can be displayed, severely restricts the amount of calendar information that can be viewed. Timewatch can help overcome these issues with it’s Whitespace for Outlook system:

Timewatch Solution: Overcoming Outlook’s multi-calendar limitations

To overcome the limitations in Microsot Outlook, Timewatch’s muti-calendar Outlook view shows as many employee Outlook calendars as you need over as many days as you need.

To the right is an example of a view of 30 Outlook shared calendars over 2 weeks. The view is completely seamless – as new appointments are made in an Outlook personal calendar they are automatically updated in this Outlook group calendar view. The view is dynamic, you can filter employees by skill, tag or attribute, and sort employees by name, availability etc.

The Scheduling View shows employees from your address book as rows, which is better for viewing multiple calendars, but is limited to 2 days and loses the subject & appointment type colorization .

2) Outlook is limited to 5 appointment types

Outlook has 5 built in types: Free, Busy, Tentative, Out of Office and Working Elsewhere. Although these are valid categories for an appointment, they are not actually very helpful from a scheduling perspective.  In our experience, businesses need more types to correspond with the type of work or services they provide. Common examples include: Consultancy, Customer Meeting, Training, Design, Presentations, Team Meetings, Sickness, Vacation etc. Information that can help schedulers understand what people are doing. The Free appointment type is unnecessary as whitespace in the calendar indicates that time is free and takes no effort.

Outlook is limited to just 5 appointment types and you cannot rename them or change their color.

Timewatch Solution: How to overcome appointment type limitations in Outlook

Timewatch allows each organization to define as many appointment types as needed to classify the types of work performed. These types are also more powerful in Timewatch, with various rules, security, color-coding, default duration, reporting and other expanded features to help in resource scheduling and calendar planning. The free appointment type is not necessary as Timewatch provides availability information and can search and find free time, or “whitespace” in people’s calendars.

With Timewatch you can create as many appointment types (booking types) as you need and you can color code them as you wish, set security levels to control who can use them along with other rules.

3) Outlook has no effective color coding

Color coding can help people instantly assimilate an incredible amount of information and is incredibly helpful when people are viewing multiple calendars side-by-side. When you make an appointment in a Microsoft Outlook group calendar, it is colored according to the appointment type.

There are just 5 appointment types in Outlook. They cannot be renamed or their colors changed, which is very limiting and somewhat unusual for Microsoft who are usually very sensitive to the use of colors, particularly given the issues with color blindness. Colors are also used to represent different people’s calendars in multi-calendar views, but again you cannot control the colors used and the colors used for appointments are used for calendars. Categories are more configurable and you can set their color, but you are limited to a fixed color pallete that conflicts with appointment types and multi calendar colorization! Also, categories need to be set for each person and therefore can differ wildly by person. For this reason they are only really usable as a personal calendar tool.

The biggest issue with colorization in Outlook is that there are 3 completely different mechanisms that colorize appointments – appointment types, categories and shared calendars. These all conflict with each other and more often than not cause confusion.

Timewatch Solution: Make color coding more manageable, powerul and helpful

Timewatch allows customers to define the appointment types they need, they is no limit to the number that can be created and they can be color coded using the full color palette with control of both background and text color. This makes colorization a very powerful visual group calendar planning tool that allows schedulers to be able to instantly comprehend the activity of multiple employees over multiple weeks.

As a demonstration of this, look at the image to the right. ‘Vacation’ is colored purple and ‘Consultancy’ is pink – knowing this, take a look again and you’ll see that you can instantly see who is on vacation and who is doing consultancy work.

Timewatch’s multi-calendar Outlook view is clear, simple and easy to understand with powerful and fully configurable color coding.

4) Outlook appointment data is limited to Subject, Location and Notes

The information that can be allocated to an Outlook appointment is very limited. We are often asked to help companies add other information that critical to their business. Information such as: Customer, Project, specialist items related to a company’s industry or the way they work. For example: order numbers, yes/no answers, is catering needed, is setup time required and more. Often the information needed varies by appointment type! Again, Outlook is very limited in this regard.

Some companies resort to using the Location or Notes field to enter such information, but these are not viable solutions as there are data integrity, consistency and security issues.

Timewatch Solution: Allow new fields to be added to Outlook appointments

Timewatch allows important new fields to be created and added to Outlook appointments.

Fields such as customer, project, sub project levels and type of work are very common fields companies ask for.

Sometimes customers need special fields unique to their business, and in some cases fields that change depending upon the type of appointment, the customer or employee allocated. Whatever information is needed on an appointment, these can be added, they are visible in Outlook and are available in reporting.

Timewatch’s advanced booking screen can be as simple as Outlook is, or can have new fields added to suit your organization’s needs.

Add new fields to Outlook appointments
With Timewatch you can increase the number of Appointment Types you use. Most companies use this to better represent where people spend their time and the services they provide.
With the addition of a customer field on appointments you can finally see who work is scheduled for and create reports to analyse time by customer.
Projects, and up to two sub-levels, can also be allocated to appointments, which further enhances the ability to report upon the work people are scheduled on.
If you need to add specific fields to Outlook appointments, you can with Timewatch. This section allows you to create the fields you need, define their data type and attach them to appointments.

5) There is no easy way to find someone with availability at a set time or specific date range

This is best explained with an example: imagine out of a team of 20 people you want to find someone to work with a customer for a half day next week.

With Outlook you have to select 5 calendars, go to next week and look at each morning / afternoon. You might get lucky straight away, if not you have to uncheck those 5 calendars and choose 5 more and repeat the process until you find someone. You may need to repeat this many times and you may not find anyone free at all and need to start again looking at a different day!

There is a better way to do this in Outlook, but this has limitations. Timewatch also provides a solution to this need that completely overcomes Outlook’s limitations.

Improving availability searching in Outlook.

Outlook’s ‘Scheduling Assistant’ can help as it allows you to check people’s availability, but you need to know which people to search. This is not at all helpful if everyone is busy or you don’t know the people and their skills. Ideally the search should let you choose from a list of resources that are available on that date as well as specify the skills or the attributes of the person or persons you are looking for.

Timewatch Solution: How to overcome Outlook’s availability search limitations

With Timewatch you can use the view to show the employees with the attributes you need (skill, department, team, office etc.) and sort or search on their availability. In this way you can quickly see who can do a piece of work

You can also create an appointment but specify the skills and time you need and let the system do it all for you.

In the example to the right, the scheduler has filtered the view to only see “Designers” and can sort or search by availability to find their ideal resource.

Outlook Calendar Search
With Timewatch you can search for the employees you are looking for, then use availability search to find who is free.
The Availability sort allows you to show who has the most or least availability.
You can also filter the view to show only people who have more than a certain number of hours free. This makes locating people who have the skills and availability to do work simple and easy.

6) You can’t make an appointment for 2 or more people, without including yourself

If you’ve been granted delegate access rights to other people’s calendars, you can create appointments in their calendars, but only in one at a time. If you wanted to book 5 people for a meeting, you have to use the check box to select each person’s calendar, make 5 appointments, one for each person in their  personal calendar. It will take a while, and it’s prone to error as it’s all too easy to choose the wrong calendar, the wrong date or time. You can create one appointment and invite all 5 people, but you are included in the meeting request as the meeting organizer. As the meeting request organizer, the meeting  is in your calendar and cannot be removed without deleting the meeting for everyone. Your diary will soon become full of meetings that you are not involved in.

Outlook is geared toward organizations where people schedule themselves and their own meetings, but if you want schedulers to manage other people’s calendars, this is very difficult in Outlook.

Timewatch Solution: Make bookings for multiple resources from the appointment screen

Timewatch allows schedulers to make Outlook appointments for multiple resources without having to include themselves. The appointments are all linked together such that everyone can see who else is involved meeting.  Schedulers can choose specific people, or specify groups or skills of people that need to attend.

In contrast to the Outlook example we gave where the scheduler had to open 5 people’s calendars and make a booking in each, here the scheduler simply makes 1 booking for 5 employees. It’s much faster and removes the chance of error.

Timewatch makes booking multiple resources easy, just add the people or skills you need.

7) Timezones are by person not by the appointment or meeting

Outlook manages timezones by person not by the appointment. This can cause issues when making meetings with customers or others outside of your organization. Imagine you have a presentation with a customer this Friday at 10:00am but the customer calls to ask to shift it to Monday. No problem, but there is a daylight savings change in their timezone with the clocks going forwards but there is no change in your timezone. Net result, you miss the presentation..

Our Solution: Appointments have their own timezone

With Timewatch, appointments as well as people have timezones. It’s obvious when you think about it. If you make a meeting with a customer at 10:00am it should be made in the customer’s timezone and adjust in your calendar not theirs. With a timezone tied to the appointment, there are never any timezone mixups.

Outlook time zones
This appointment is for 4 attendees for a Customer Presentation. In this example, the customer is in New York and the people are other timezones.
The customer is in New York, but the people attending are in different timezones, but which timezone should the appointment be in? It should be in the customer’s timezone as they are the most important player here!

8) There is no Task or Project scheduling

Not all time commitments are diary appointments. Most people have tasks or project work where spend a certain amount of time, but it doesn’t matter when they spend it, or have a set amount of time to complete a project by a set date. There is no way of representing such time commitments in Outlook, which causes problems when other people need to view their calendars as they are not seeing a true representation of their time commitments.

Outlook’s ‘All Day’ appointments can be used to represent when such tasks exist, but there is no way of representing how much time is associated with these tasks. As a result, Outlook calendars, group views and the scheduling assistant incorrectly show people as free when they are not, which is a big problem for people wanting to use Outlook’s multi-calendar views to see people’s time commitments and potentially schedule them. Timewatch solves this problem.

Timewatch Solution: Add time commitments to Outlook calendars

Timewatch’s scheduling tools for Outlook solve project and task scheduling limitations by allowing the time associated with such scheduling commitments to be defined. This could be as simple as a set number of hours per day or week, a fixed amount of time to be spent before a set end date, etc.

With an accurate time value associated with tasks, each person’s calendar can provide a true and accurate representation of their time commitments and their availability, and for the organization it can show capacity and availability by skill, office, team etc.

Outlook Project Task Scheduling
Project Tasks look a lot like Outlook’s ‘All Day Appointments’. They have a start and end date and a Subject, but they also allow a Customer, Project and sub-project tags to be allocated. These
Time ratios allow you to specify how much time this task represents. Options include: hours per day, hours per week, total time to be spent by the end date, a %age of this person’s day etc.
This is the total time that this task represents, which will be taken into account in this person’s utilization, availability / capacity calculations and reporting.

The Task dialog box allows users to create non diary based entries – time commitments that the user finds the time to do.

9) There is no appointment security

Outlook calendar permissions do not allow control at the appointment level. Once someone is granted access to an Outlook calendar, they have access to all appointments in that calendar. If they are allowed to delete items, they can delete any item. There may be impoartant appointments that schedulers do not want employees to be able to create, edit or delete. Effective calendar planning requires a greater level of control over which appointment types people can access and what functions they can perform. Although Outlook does not allow you to change access permissions, Timewatch does.

Timewatch Solution: Enhance Outlook calendar permissions at the appointment level

With Timewatch, Outlook calendar permissions are expanded to the individual employee/appointment level. Not only can the types of appointment people can create be managed, appointments can even be locked or protected. For example, an individual may be able to edit internal team meetings, but not be able to edit, change or delete confirmed customer bookings. Employee / appointment level security brings increased levels of confidence to company resource scheduling and calendar planning.

Enhanced outlook calendar permissions

10) Outlook has no conflict management

Outlook allows you to create appointments that conflict with each other. These are shown in Outlook side by side at a reduced width. In some cases overlapping appointments is helpful, perhaps even desired, but having two commitments with two different customers at the same time is a big problem for any organization. This is a serious shortcoming in calendar planning, and one of the most common features customers ask us to help them with.

Timewatch Solution: Enhance Outlook with conflict management and resolution functions

Timewatch enhances Outlook with effective conflict management. As explained above, overlapping appointments are sometimes very helpful, for example for provisional appointments. However, as soon as one appointment is confirmed, the conflict is not desired. Timewatch’s conflict management system can allow overlaps for certain appointment types (e.g. for provisional appointments) but block them for other appointment types (e.g. confirmed customer appointments). Additionally the system highlights where conflicts exist and provide tools to help resolve them where they occur (e.g. the provisional appointments).

Outlook conflict warning

With Timewatch you can control conflicts at an appointment type level. Eg. allow for tentative appointments, disallow for customer work.

11) You cannot search or schedule by skill, availability, region, office or other attributes

In Outlook, calendars are displayed by employee name. This is fine for small businesses where when everyone knows everyone else, but as organization size increases, locating and viewing employee calendars and searching availability becomes harder and harder. Although you can use the create new calendar group  feature to create blocks of Outlook group calendars, it is not a very practical or scalable solution as it needs to be setup manually for each person and is prone to error. As we discussed in point 1 above, to be usable these group calendars are limited to 5 calendars over 1 or 2 days.

Timewatch Solution: Provide scalable views and grouping of employees by skill, office, team etc.

With Timewatch you can categorize employees by useful groupings such as skill, office, team, region etc. and then view calendars by these groups, find people with availability in these groups and book resources by group. A custom tag system provides a flexible way of allocating attributes to employees, and these tools can then be used to create views, search availability and make bookings by skill / tag. For example, you could create simple views by skill of “Consultants”, “Trainers” or any skills you use. You could even create more complex views such as “Consultants with skills in product X in Europe that speak French and English”, or whatever the various attributes are that you use.

The whole point of the Timewatch system is that you can define the employee attributes that your organization uses and then use this to find people that meet these skills / requirements and have availability to do the work that needs to be done.

Rather than searching calendars in Outlook, Timewatch can find the resource(s) you need with availability when you need them!

12) Outlook has no reporting or analytical tools

Perhaps the biggest limitation in Outlook is that it has no reporting, so it is impossible to answer even the simplest of questions without spending a lot of time and effort manually trawling through Outlook calendars. Take a look at the following questions and have a think about how long it would take to find out the following from Outlook for a Team of 10 people:

  • “Who is scheduled to work with company X next week?”
  • “How much time is scheduled for company X next month?”
  • “Which are the most utilized resources next week?”
  • “Who is free to provide Training to company Y on Friday?”
  • “How much time did we spend on customer X last week or month?
  • “How much time did we spend on project Y last week or month?
  • “How much time did employee Z spend on project Y last week or month?

Any of these would take hours and even in relatively small companies would not be worth the effort.

Timewatch Solution: Provide full, unlimited reporting facilities to organizations that use Outlook

Timewatch provides a full reporting suite on an organization’s employee calendars. We provide a library of standard reports that suit most needs. We also provide report writing and dashboard designer tools for customers to be able to create the exact reporting they need.

High level dashboards provide an instant overview of any aspect of employee Outlook calendar reporting. This example shows utilization performance by office, team and employee compared to targets.

Color coded Outlook availability views show in an instant employee availability by team, office, skill etc. over days or weeks.

Classic ‘print preview’ type reports are available as tabular reports, charts, maps, heatmaps, and with our Report Writer and Dashboard designers, pretty much anything you need!

How it works

Outlook was designed as a collaborative employee email and calendar system. Although it has some shared calendar features, the underlying data structure was designed and optimized for individual mailbox use, not company-wide scheduling. Whitespace&nbsp® was designed from the outset for employee and organization-wide calendar viewing, scheduling and reporting, and by integrating with Office 365 allows companies to overcome Outlook’s scheduling and reporting limitations.  Whitespace&nbsp® provides customers unparalleled access to view, analyse, manage and report upon employee Outlook calendars, and it does so without affecting Outlook or Office 365.

Whitespace&nbsp® for Outlook starts with a very simple, cost effective feature set that includes global Outlook calendar views and Outlook reporting. From here, customers can add a range of features to overcome and or all of the Outlook shared calendar limitations we listed above.

Want to Learn More?

Timewatch has over 20 years experience enhancing Outlook and helping customers use Outlook more effectively in their businesses. Even if you need help with just one or two of the Outlook limitations we have listed, we can help. We provide a configurable solution, so you can start with a simple configuration and add more  functions as you need them.

If you have any questions or want to see the system in operation, contact us via chat, or book a free call with a product specialist.

Speak with a specialist

Learn more about Outlook shared calendars, or Whitespace&nbsp® for Outlook

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