How to Remind Your Boss of Your PTO Without Pissing Them Off
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.
6 Weeks to 6 Months Out: Get It on the Books
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. Start there and adjust as necessary.
Occasionally, you need approval well in advance for an event that cannot move and will cost you a lot of money to cancel, like your own wedding or a nonrefundable trip. In those cases, six months or more is not unreasonable, but bring it up from time to time so no one forgets.
Whenever you put in your initial request, it must be recorded. Log it into a time-off system if your organization uses one (human resources software, a shared calendar) or write it in an email with a clear subject line, and make sure your boss replies saying it’s approved.
2 Weeks Out: Verbal Reminders
About two weeks before your time off, remind your boss and colleagues verbally in meetings. The ideal settings are in a weekly one-on-one meeting with your direct manager and in a team meeting.
Save your info for the end of the meeting after all pressing business has been discussed. If you need to make sure your responsibilities are covered while you’re out, raise that point privately with your manager rather than in a team meeting so the boss has time to decide how to handle it.
1 Week Out: Email or Message Your Contacts
If you need to tell someone beyond your team—such as clients or another department—about your planned time off, do so in writing a week before you leave. This gives them plenty of opportunity to reach out while you’re still available.
Email is fine, though if you usually communicate with these people through Slack or Microsoft Teams, that may be a better option. How you format the message matters—see the next step for tips.
2 Business Days Out: Send Formatted Messages
Two business days before your time off begins, send a short, clear message to everyone who needs to know that you will be out. If the norm is to use Slack or Microsoft Teams, use that.
How you format this message makes a huge difference. The first sentence should say something like, “Just a reminder, I will be out beginning DATE. I will be back on DATE.” This sentence can be in bold. The second DATE is the day you return to work, not the last day of your PTO. What’s relevant to your colleagues is the day you are available.
If you need to give more information, such as who is covering for you, put that in a new paragraph. Do not go overboard with detail. It will make people crazy. Should you need to leave detailed instructions, put them in a shared document and link to it.
Why send this message two business days out? Simple: If your first PTO day is Monday, you send this message on Thursday so that anybody who takes off or calls in sick on Friday still sees it in time.
The Day You Leave: Set Your Status
My favorite PTO reminder is the status indicator in a team messaging platform. Set it to show you’re out and add an appropriate emoji, like a palm tree or airplane.
Even if you dislike emoji, they are extremely efficient and effective communicators here. At a glance, everyone who sees it is reminded that you’re out.
You can typically set a status message too; use this to tell everyone the date you’ll be available again.
Your First Day Off: A Final Reminder for the Extra Forgetful
For those supremely forgetful bosses and coworkers, you might set up an automated message that appears at 8:30 am the first day you’re out. Slack, Teams, email, or even a text message will do the trick. Be concise. Be kind. And have a sense of humor. The point of the message is to be helpful—not make someone else feel like a forgetful jerk.
