6 Ways to Convince Your Boss to Give You a Vacation You want time off during the holidays. So does everybody else. Here's how to make your request go smoothly, so you can be one of the people sipping hot cocoa in your bathrobe and relaxing with the newspaper on a weekday morning. Request time early. Ideally, you've already done this. If not, there's no time to waste. "Don't go to your boss with a request at the last minute or after everyone else already has done so," says Jobvite CEO Dan Finnigan. There will be no one to cover the bases while everyone else is out, so your boss will be more likely to say no. Give your boss a plan. "If you get push back from your boss when you make your request, be prepared with reasons why she or he don't need to be worried," Finnigan says. Outline for them verbally - and follow up via email - the details of who will cover your duties while you're out of the office and whether you'll complete projects early or wait until you return to finish them. In the last case, be able to explain why the work can go on the back burner until after the holidays, Finnigan says. Barter your time. "If you need Thanksgiving off and it's important to you, offer to work New Year's Eve for the colleague who's hoping to get engaged that night," writes Miriam Salpeter, a career consultant and owner of Keppie Careers. Find another person with an equally pressing need for time off. She adds that if this fails, try upping the ante by offering to swap a holiday weekend for Christmas day, for instance. You know to run this by your boss first, right? Negotiate with your boss. "Don't be afraid to ask for time off," says Shon Burton, founder of HiringSolved. Do make a reasonable proposal to the boss when making the request. Offer a trade-off, Burton suggests. In exchange for some time off, for instance, volunteer to turn in a project or two early. Ask if you can work from home. No, it's not the same as being off the clock entirely, but you'll spare yourself a hectic holiday-season commute. Depending on your job and the field you work in, you might be able to ask your boss to agree to give you a day off on the condition that you'll be available by phone or email during regular work hours if an important question comes up or a fire needs to be put out. Try the everybody's-doing-it argument. In some industries, work slows to a crawl around the end of the year because taking time off or closing up shop is customary, points out Finnigan. If this is the case in your line of work, it might be worth making the case to your boss that even if you were at your desk, you wouldn't be very productive if everyone you need to call or meet with is laying around their house in pajamas.