1. Wait 3-months.
Normally, we recommend going about three months at a new job before requesting any time off. Three months is usually treated as a probationary time for employers, so they can make sure hiring you wasn’t a horrible mistake.
2. Be upfront, but not presumptuous.
If you have a vacation planned before you’ve been offered the job or internship, you’ll need to tell them, but wait until after an offer has been made, like when you discuss start date, payment, logistics, etc, with your hiring manager or HR. Many people we’ve interviewed talk about how they have a vacation planned, and we haven’t even made it through their resume! Don’t do this. It’s tacky.
3. Timing is everything.
We probably don’t need to tell you this, but don’t ask your boss for time off on the same day she finds out the company is being sued. Find a time that is quiet, perhaps after a meeting or lunch, and ask politely, but directly. Don’t tell her you are taking the time off, ask for permission: “My cousin’s wedding is the week of July 4th and I’m really hoping to attend. Would it be possible to take two days off that week?” Most likely, it will be no problem.
4. Put it in writing.
After you get the verbal go-ahead, make sure to send a follow-up email with specific dates. If you have projects or tasks that interfere, this email is a good opportunity to explain how you will handle getting your work finished ahead of time.
5. Send a reminder.
A week or two before your vaca, send a brief reminder to your boss, and highlight once again the tasks that will be completed before you take off. It’s also a good idea to ask your boss what will be expected of you while you are gone—will you be on-call? Will you be expected to answer emails? The answer is most-likely “No,” but double-checking shows that you are responsible and awesome.
6. Use an away message.
You may find that you get a million emails while you are on vacation, making it hard to enjoy yourself and actually relax. We recommend setting an away message on your computer, something like: “I will be out of the office on Thursday July, 4th and Friday, July 5th, with limited access to email. I will return your email as soon as I can. Thank you.”
