How to add annual leave to your Outlook Calendar (2024)

In this post, we’ll show you how to add annual leave to your Microsoft Outlook calendar.

There are actually two ways of getting this done. The not-so-simple way, and the simple way:

  1. The not-so-simple way is to just use Outlook. We know, you’d think just using Outlook would be the simple way. But sadly, your Outlook Calendar wasn’t made to be a time off tracker. As you’ll see below, there are several steps you need to take to add annual leave to your Outlook Calendar.
  2. The simple way is using an annual leave app like Timetastic. It can manage all of your leave management needs (from booking holidays to doing absence tracking), and it automatically syncs with Outlook to share holidays, sick leave, and other types of leave across your organisation. This removes all the double work.

If you’re the kind of person who likes to see how things work in real life then I’d suggest jumping straight into the free trial of Timetastic. You can probably get it set up and feeding your annual leave into your Outlook calendar in less time than it’d take to read this whole article!

But if you’re looking to manually update your Outlook Calendar, keep reading below for our step-by-step breakdown.

Adding your own leave to your Outlook calendar (using only Outlook)

If your manager hasn’t set up and shared a separate “annual leave calendar” in Outlook (more about this later), you’ll have to jump through quite a few hoops to share your holiday plans with your colleagues using Outlook.

Step 1: Go to your own calendar and create a new meeting appointment.

This meeting time will be your time off. You can type in a description in the subject box, such as whether you’re on holiday or out sick, or you can leave it blank. You’ll need to pick the start time and end time for this “meeting”.

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Step 2: Click “Request responses”

Then you’ll want to click the “Response options” drop-down menu and click “Request responses.” This way, your team can acknowledge that they got your time off notification.

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Step 3: Mark your Time Off as “Free”

Then you want to mark this appointment to show as “free.” This is a critical step because this lets your team add your time off to their calendar without having it visually block up their entire day.

FYI: If you’re putting in an all-day event, Microsoft Office defaults to “free.”

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After you’ve done that, you will add who you want this notice to go to. It then pops up in their Outlook calendar and they get a notification in their inbox.

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But there’s still a bit left to do.

Step 4: Do it all again for your own calendar (yes, really!)

Because you marked that time away as “free,” that means it’s marked as “free” on your own personal calendar, too. That’s a problem, because you’re not free, you’re out of office on holiday.

To get around this, you need to create an additional appointment for yourself on your calendar. But this time, set yourself as “Away” and don’t invite any attendees.

Now, if someone on your team looks up your calendar, they’ll see that you’re on holiday.

If you’re managing a really small team, you might be able to get away with having everyone just add time off to their calendars (and sharing it with whoever is necessary).

But if you’re managing a larger team — or if you’re also trying to track your staff’s leave balances in Outlook — then you’re going to need to create a completely new calendar in Outlook that’s just for time off requests.

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Unfortunately, this is pretty complicated if you’re just sticking with Outlook calendar. In other words, if you’re not using a leave management app — like Timetastic.

You can find a full breakdown of the process from The Microsoft Outlook Ideas Book.

While this is a good resource if you want to set up a shared Outlook calendar for annual leave requests, if you click the link, you’ll see it’s still not an easy task if you’re not a developer.

And once you’ve gone through the dozen or so steps to create your shared calendar, you’re facing the same problem: You’ll still need to add everyone’s individual time off to the calendar (using the process we explained above).

Now, let’s look at the simple method for adding annual leave to Outlook.

Timetastic simplifies the whole time off process — everything from booking time off to keeping your team’s calendar updated.

When your team wants to book time off, they do it in Timetastic. They select the dates, pick the type of leave they’re taking (holiday, sick leave, etc.), and book their request.



Approved requests show up in your company’s Wallchart, which can have different departments to reflect your company’s organisational structure.

Everyone can access the Wallchart, quickly seeing who is off now or has a holiday coming up soon.

And you can set up your Timetastic Wallchart to share this information automatically with your Outlook calendar via our calendar subscriptions. This syncs everything in real-time.

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Simply take the iCal URL you need to add the bookings you want to your Outlook calendar.

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Now, when someone books a holiday in Timetastic, it shows up in your Outlook calendar.

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And when you click on someone’s approved time off, you can still see why they’re taking time off.

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Here are a couple of useful Help Centre links to help with implementing this:

  • How to use calendar feeds in Timetastic
  • How to sync Timetastic bookings into your Office365 calendar

It’s that simple. No double work is needed and you and your team will always have up-to-date and accurate information.

Extra benefits of using Timetastic to manage your team’s leave

Timetastic is a complete time off management tool (in fact, it’s simple enough to use from your smartphone). As well as syncing with your Outlook calendar, Timetastic also comes with several other benefits, including:

  • Easier approval of leave requests.
  • Automatic approval of leave requests (if you prefer).
  • An updated record of everyone’s annual leave.
  • Absence insights, so you can track patterns and trends.
  • Absence summaries, which are sent directly to your inbox.

Easier approval of leave requests

With Timetastic, it’s really easy to respond to someone’s time off request.

After a staff member submits their holiday request via the Timetastic smartphone or web app, you can choose to receive it in your email inbox or as a direct message via Slack or MS Teams.

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Once you get the request, you can approve or decline their request from there without having to log into Timetastic.

You can also set up Timetastic to automatically approve time off requests, while still keeping control over how many people you have in the office.

  1. First, you set your maximum absent levels. This is how many people your company can afford to have off on any given day.
  2. Then you lock your key dates. A locked date is when your team can’t take a holiday, whether that’s a particularly busy time or when you have certain deadlines.

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With maximum absence levels and locked dates all set up, Timetastic will be able to approve or decline holiday requests without you having to manage them manually. This saves you even more time, while having the system in place means you don’t lose grip of staff holidays.

Note: You can also set all types of leave to “Needs Approval” and this means you get notified of every leave request. It’s totally up to you and what works best for your business.

Updated record of everyone's annual leave

When a time off request gets booked in, your employee’s leave balance is automatically updated. So you always know how much leave everyone on your team has left to use.

You can find this helpful info in several places.

First, you can see people’s individual balances on your company’s Wallchart when you log into Timetastic. (In the left-hand corner next to everyone’s name is their updated annual leave balance):

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And you can also click on an individual employee to get a more detailed breakdown of how much time off they’ve taken in the year:

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You can also click on Insights to get a view of your entire team’s leave balances and trends.

On your “Absence Insights” page, you can see which type of leave is most popular with your team, and when is the busiest time of the year for your team taking off:

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And this is also where you get hold of your team’s Burnout Board, telling you who is overdue a holiday:

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Absences summaries sent directly to you

In this post, we’ve explained how you can hook up your Timetastic calendar with your Outlook calendar. Using this simple integration, you don’t have to log into multiple platforms to find out who’s off, when, or why.

You can also get this information sent directly to you through absence summaries. These summaries tell you who’s off for the upcoming week. They can be sent to your:

  • Email inbox
  • MS Teams account
  • Slack account

While you can use your Outlook calendar to share your time off and create a shared calendar for annual leave, we think it’s pretty clunky and burdensome. Even a small business with a handful of employees will find it to be inconvenient and time-consuming.

This is why thousands of companies choose Timetastic. Because it’s built especially for annual leave, and it plugs into your Outlook calendar without fuss.

You can try Timetastic now for free, using our one-month free trial. You can:

  • Book time off through Timetastic.
  • Keep track of everyone’s leave balances.
  • Automatically sync with Outlook calendar.
  • And much more.

Start your free trial today.

Did you like this article? You may also like:

  • A balanced review of 2 Excel templates for tracking staff leave
  • More information on connecting Timetastic to your calendars (including Outlook and Google Calendar)

Suggested reading

  • The best PTO tracker: 3 tools compared
  • The best paid time off tracking software (3 options)
  • The best vacation tracking software (2 options)
  • The best annual leave calendar for your business
  • The best way to track employee time off: plus, 2 alternative methods
How to add annual leave to your Outlook Calendar (2024)
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