How to Ask for PTO (Without Issues or Awkwardness)

Picture this: you’re planning a vacation—maybe a beach trip, a cruise, or even skiing with friends, coworkers, or family. You’ve been grinding at work for months, and now it’s finally time to ask your manager for some well-earned PTO.

And then—boom—your request gets denied. Sounds like a nightmare, right?

Believe it or not, this kind of thing happens more often than you’d think. But the good news? You can stack the odds in your favor with a little strategy. Here’s your 5-step guide to asking for and taking paid time off the right way—plus a bonus tip that’ll keep your team and your manager happy while you’re away.

Know Where You Stand with Your Performance

Before you even think about putting in a PTO request, do a quick self-check. Are you crushing your goals? Hitting deadlines? Helping your team? If yes, you’re in a great position to ask.

But if you’ve been slacking or missing deadlines, now might not be the best time. Companies tend to remember who steps up and who disappears when things get tough. Make sure your work speaks for itself before you put in that time-off request.

Don’t Ask When Things Are On Fire

Timing is everything. If your team is in the middle of a huge, high-stakes project, it’s probably not the ideal time to check out. Even if you technically have the right to take time off, you don’t want to be known as the person who bails when the pressure’s on.

Plan around the natural ebbs and flows of your work schedule. Avoid high-traffic periods, and aim for the quieter moments when your absence won’t cause a domino effect.

Ask Early (Way Early)

One of the best things you can do is get ahead of the game. Think you’ll want to take a long vacation next spring? Start the conversation now.

A good rule of thumb: for every day you want off, give at least a week of advance notice. Taking five days off? Give five weeks’ notice. This might sound extreme, but it gives your team time to prepare and makes your PTO request way more likely to get approved.

Keep Track of Your PTO Days

Even if your company offers “unlimited” PTO, it’s still a good idea to keep your own personal log. This shows your manager that you’re organized and not abusing the system.

Create a simple tracker in Notion, Google Docs, or a spreadsheet. Note the days you’ve taken off and how many you plan to use for future trips. It’s a small habit that builds trust—and can be helpful if questions ever come up about your time away.

Leave No Loose Ends: Cover Your Work + Document Everything

Want to really impress your manager and teammates? Don’t just ask for coverage—make it easy for them to cover you.

Before you go, create a clear document outlining everything someone needs to know while you’re gone. What tasks need to be handled? What’s the status of your projects? What should they do if something goes wrong?

Bonus: Include contingency plans and point people. (“If X breaks, talk to Y.”) This kind of proactive handoff builds respect and makes your absence feel seamless.

Final Sip ☕️

PTO isn’t just a benefit—it’s a right. But asking for it without the right approach can backfire.

Make your case solid:

• Be in good standing

• Avoid asking during crunch time

• Plan ahead

• Track your days

• Leave a clean handoff

When you handle it well, your manager won’t just approve your PTO—they’ll encourage it. Because a well-rested employee is a better one. 🌴

Now go take that vacation—you’ve earned it.