How to Manage Your Team's Vacation Requests Without Drama
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How to Manage Your Team’s Vacation Requests Without Drama

Emily McGee Emily McGee Last Updated:

You’re sitting at your desk, daydreaming about the vacation you’re taking next week. You’ll get to sleep in, drink fruity drinks with umbrellas in them, and use your phone for jealousy-inducing selfies, not just sending frantic work emails at all hours of the day and night.

It sounds downright blissful… until your boss walks through the door and says, “Hey, I just realized we double booked ourselves for vacation. Can you reschedule yours and cover the office?”

And that’s when your vacation dreams crash full force into the reality of poor planning.

Of course, this could all be avoided if your team just had a better system for vacation planning.

Using a Shared Calendar for Vacation Planning

If your team isn’t using a shared calendar or timeline, it can be all too easy to lose track of who’s planning a vacation when. And if you don’t have a clear view on team member’s planned leave, the following things can happen:

  • Too many people plan vacation for the same time, leaving the office without proper coverage.
  • Key people plan vacation before a major project is due, setting the project timeline back.
  • A lack of transparency leaves some people feeling like the vacation policy just isn’t fair.

Planning a vacation from work shouldn’t be so frustrating. With a more transparent vacation planning system, you can avoid all these issues. 

The best vacation planning system needs to include all the relevant information in one place, available to everyone on the team, and in conjunction with your team’s plans. 

Using one calendar for vacations and a different calendar for work plans may be tempting, but don’t do it! When someone is assigning tasks for work, they need to be able to see who is in the office. Similarly, when an employee is planning for vacation, he needs to be able to see if there are any looming deadlines that will conflict with his plans.

Using a cloud-based tool like Toggl Plan is smart because it updates in real-time and everyone can access it, no matter where they are. We’ve seen teams rely on white board calendars, but as soon as someone has a business meeting or work trip off site, they no longer have access to all the calendar.

Similarly, we’ve spoken with teams who swore by Excel spreadsheets until they realized that people weren’t keeping it updated. Excel spreadsheets are such a hassle to save and people often forget to send out a new version of the calendar every time they make a change.

How to Set Up a Vacation Plan in Toggl Plan

Setting up a vacation plan in Toggl Plan is quick and easy. Simply create a new project labelled “Vacation” and assign it a bright color. Using a bright color makes the vacation pop on the timeline, so no one can miss it.

Any time someone is planning a vacation, they can add a new task to their timeline and label it with the project “Vacation.” This will automatically color-code the vacation in the color you chose earlier.

To see everyone’s vacations on one screen, use the project view and select the project “Vacation.”

Vacation view in Teamweek

To see how vacations overlap with day-to-day work, use the team view.

Vacation time, sick time, and time off in lieu for working overtime or weekends can all be labeled separately using project segments. This makes it easy for managers or the HR team to categorize and count the types of days off each employee has used.

Vacations are a necessary part of work. If employees don’t feel like they can take a break to rest and recharge, they’ll burn out, lose motivation, and eventually leave.

Make vacation planning more fair and transparent by using a shared calendar timeline like Toggl Plan. Toggl Plan’s easy-to-use drag and drop functionality makes it easy to react when plans change, while still being aware of everyone else’s schedule. With a system in place, you’ll prevent office drama and ensure that everyone gets to take a holiday without work grinding to a standstill.

Emily McGee

Emily is the former marketing team lead at Toggl Plan.

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