Plan the best dates and make sure they're a few months from now
Lawrence Hedblom, founder and managing director of executive coaching firm Springboard Unlimited, recommends asking for time off at least two months in advance.
If you're trying to get time off between Christmas and New Years or another popular period for vacations, you might ask even earlier. Asking months in advance could ensure that you get that time off.
"With lots of lead time, it's harder for them to say no," Hedblom told Business Insider.
Be sure you don't plan the dates right before major deadlines, Echols said.
Ask your boss in person
The cardinal rule: Do not buy tickets, hotel rooms, or anything else before asking your boss for permission for the dates you planned.
Remember you are asking your boss for vacation time — not informing or demanding them.
"Pick a good time to ask such as when the office is relatively quiet or when you have just delivered a project," Hedblom said.
Don't ask in the midst of a deadline or after your boss just left a stressful meeting with his or her boss.
You could try:
"I would like to take off the second week of July. Does that work for you?"
Instead of:
"I'm going to San Francisco the second week of July. Just wanted to let you know. Thanks!"
Follow up by email
"An email provides both you and your boss with a record of what was agreed upon," Phillippi said.
Remind everyone a week before
Hedblom said a major mistake that many folks make before taking time off is not reminding their colleagues and bosses before they leave.
You should also make sure your coworkers know how to address any projects or clients that might need attention during your vacation.
"Don't assume the coworker who is going to cover for you is up to speed on your work," Hedblom said. "Be organized and make it as easy as possible for that person to cover for you so things go well and they'll do it again for you."
Finally, enjoy your trip — and don't forget to bring back your coworkers some treats from abroad.