You're about to slam that laptop shut for two weeks when the boss messages, “See you Monday!”

We've all been there, staring down a manager who has forgotten about our paid time off—even though we told them!

When we communicate something that's important to us, we can forget that it's not necessarily as meaningful to the recipient. Surely you've been on the flip side, too, annoyed at a coworker who hasn't replied to your messages, until someone mentions that they're on holiday.

A key to efficient communication in the workplace is to repeat yourself. It sounds counterintuitive, but it's true. We're all better off when we overcommunicate by saying the same thing two or three times.

The trick is how and when you do it. Think of all the avenues you have for requesting, recording, and reminding people of your PTO. Use all the channels, and spread out the messaging so that each instance has relevant context and timing.

If you like to plan in advance, you might request time off four to six months out. Not all managers appreciate this much notice, however, because they might not know what the workload will be when your vacation rolls around, making it hard for them to approve your dates.

How far in advance you should request time off is a conversation to have with your direct boss. It depends on them as a person, the type of work you do, the size of your team, and other factors. If this conversation doesn't give you much clarity, four to six weeks before your time off is probably about right.

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