The Best Times To Ask Your Boss For Vacation

Just about everyone with a normal 9-5 job looks forward to their precious weekends and vacation days. It’s not that we hate our jobs, but we have a work hard, play hard mentality. We want to spent time with friends and family, so we work hard all week to have those opportunities.

The Best Times To Ask Your Boss For Vacation

While we usually have weekends all to ourselves, planning vacations is a bit more difficult. Asking for a day or two off is fairly easy as it doesn’t disrupt projects and short periods of time out of work should not cause big issues. There’s the guilt aspect of asking for vacation, too: your coworkers will have to cover for you.

Asking for a week or more of vacation time, however, can be much more problematic. You have to compete with project deadlines and coworkers schedules to find a time that’s convenient for you. It’s often very stressful asking for more than a few days of vacation at once because getting turned down can feel like a big letdown. Here are some of the best times to ask your boss for vacation.

Ask About Planned Vacations Before You Accept The Job

If you’re planning a vacation before you begin a new job, this can be the best time to ask about pre-planned vacations. Yes, you may want the job desperately, but employers also want you and understand that we’ve made commitments prior to getting an offer. Once they offer you a job, you can bring up commitments you’ve already made and ask if they can accomodate you. If they think you may not take the job if they say no (and they want to start off the relationship on a strong foot the same way you do), they have more to lose than to gain.

Ask For Vacation After A Successful Project

If your performance has been solid and you’ve gotten positive feedback about it, you’re more likely get your vacation request approved. It will be in the front of your boss’ mind just know how valuable you are to the team, and he or she will be more likely to accommodate your request.

Make It Easy For Your Boss To Say Yes

There are a few things you can do to give you the best chance for your boss to accept your vacation proposal. If you have been slacking off or your work hasn’t been up to snuff, put off asking until you’re in good standing. Ask far in advance, before your coworkers get a chance so there are no other competitors for your preferred vacation dates. And offer to work during popular vacation times, like Christmas week, and you coworkers will be more willing to pick up the slack when you’re out of the office.

Lauren and I are taking a big vacation starting this week, and I let my employer know before I even started. After being offered the job, I asked if they could accommodate the vacations I had already planned. One had already been booked, while the other I was still planning, and tried to find a time that worked well for everyone. They graciously allowed us to go, and we scheduled it partly during Thanksgiving so I won’t miss as many days.

2 Responses to The Best Times To Ask Your Boss For Vacation

  1. Time off is part of your compensation package. I’ve never worked in a place where taking time off is frowned upon or difficult. I think that would be a showstopper before even accepting a job, as a good work-life balance is very important to me.

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