How to Ask for Time Off Work

It’s time to play Good Cop, Bad Cop. When it comes to asking for a little time away from the office, you’ll have to learn when to be the nice guy or gal, and when to turn on the heat.

Photo Credit: © Ahmed Amir

I have worked a variety of jobs throughout my life and the culture in every work environment has been a little different. Every boss has come with a quirky personality. Every rule about vacations and time off have varied just enough that it’s hard to figure out what to say, and especially how to say it.

The Plan

Here’s a few tips to get you by in those tricky scenarios you’re almost certain to face.

1. Learn the Office Rules

Your office will have its own set of rules about how employees ask for time off work. You’ll probably have it figured out in a jiffy, but you need to understand how your boss expects you to request off and how the other employees actually do it. Sometimes they’re not the same.

For example, you may have to sign up for all your days off on January 1st for the entire year. Don’t be late to work that day. Days off can easily become a competition and you don’t want to lose your vacation to Europe because you overslept.

2. Learn How to Negotiate

The one with more information is the one who wins. Be that guy. If you know your boss expects you to be at work on the Friday before a holiday and you need that day off for a friend’s wedding, make sure you ask early.

Let your boss know that you’re aware of the rule and you’ve already found a solution to your absence. Be quick and don’t give your boss a reason to say no.

3. When to Play it Nice

Entry level jobs almost always put you at the bottom of the ladder when it comes to respect. In this position you’ll need to be REALLY nice when you’re requesting time off. If your boss is normally quick and mean when it comes to these things you’ll need to be extra careful and suck up like crazy.

Offer to stay late every day for a week, come in on Saturdays, wash her car, whatever it takes to get you out of the office and on vacation.

4. When to Play Hardball

Some supervisors will always say no if you ASK for time off. So don’t ask. Tell them you’re unavailable for work on Christmas Eve and that you simply won’t be there. They will have no other choice but to give you the time off or threaten to fire you.

In this case, offer to take the day unpaid, and reiterate that it’s not a matter of choice, you CANNOT be at work, so they will have to deal with it. Be careful not to use this strategy too often because it’s a guarantee to get you canned.

But, some bosses will respect you more for standing up for yourself and you may end up with a promotion. It happens. Just know when to say when.

5. When to be Honest

You may have already caught on to this one, but honesty is NOT the best policy in the working world. If you are always honest, you will almost never get what you want. Keep in mind that I’m not telling you to lie.

I’m telling you to guard the truth and be selective about what information you reveal to your coworkers and supervisors. It’s kind of like how you quickly removed all the Facebook pictures of you doing keg stands in the front lawn of that frat house in your underwear.

You remember that, right? Well, your boss shouldn’t. If you can be honest, then you should. You be the judge about how your boss responds to you asking for a day off to go to a concert, when you just as easily could have had a “migraine” that day.

On Permanent Holiday

The moral of this story is that vacation time in America is limited and tricky. Did you know it’s typical for some Europeans to have 6-8 WEEKS off of work every year? That’s right, weeks, not days.

In the United States you will have to learn to play the game if you want to get your way some of the time. The alternative is to work for yourself and take off as many days as you want.

You may have to work harder in the beginning to create your ideal business and lifestyle, but the end result is worth it.