Help! I want more vacation this year
Here's the right way to ask for extra time off. And what to watch out for if you get it.
By Anne Fisher, FORTUNE senior writer

Dear Annie: I've just completed a promising round of interviews with a prospective employer, and I'm pretty sure I'll get an offer. This is great, as I am really excited about this job. There's just one problem: In my current job (after 10 years here), I get a month's vacation time per year, and I've heard my new company will only give me two weeks. I had planned a three-week trip with my family for this August and would hate to have to cut it short. Can I ask for more vacation time, or should I keep quiet? -Yosemite Sam

Dear Sam: As you've no doubt noticed, vacation time isn't what it used to be. Most managers now do some kind of work while away from the office, whether it's checking e-mail, staying available to clients and colleagues by cellphone, or catching up on paperwork.

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This isn't necessarily a bad thing. "The change in the way vacation is perceived brings with it new opportunities for job seekers to negotiate more vacation time," says Richard Bayer, chief operating officer of The Five O'Clock Club, a nationwide coaching and networking group. "With so-called tethered vacation becoming the rule rather than the exception, job hunters need to figure out a company's unwritten vacation policy and individual managers' expectations."

Bayer offers these tips to help you make the case for more time off:

Get a firm offer first, ask about vacation last. "Vacation is the last thing you want to bring up when interviewing for a job. It comes after salary," says Bayer. "Hiring managers are turned off by candidates who seem more interested in benefits than in the job itself."

Check out the employee handbook. In many big companies, vacation time is determined by rank and is often accrued for each month worked. "But these policies are old and were based on the assumption that employees would stay a long time," Bayer notes. "If you are at a certain level, you can sometimes ask for - and get - the same vacation time as others at your level, even though they have obviously been there longer."

Try to find out what your new boss will expect from you while you're out of the office. "Will you be working for someone who will want you to call in frequently, check e-mails often, and be available for conference calls? If so, you may be able to negotiate for extra days or more frequent vacations," Bayer says. Makes sense, since you'll essentially be working the whole time anyway.

Emphasize that you're willing to earn the extra leisure. Bayer recommends saying something like, "I expect to work long hours" or "I plan to put in a significant amount of overtime in the first six months here to get the project up and running, so I'll need time off to decompress and recharge." In other words, the chance to rest up from all that effort will make you more productive, not less.

Be prepared to give as much advance notice as possible for special plans. "Everyone has weddings, graduations, or pre-planned vacations they don't want to miss," Bayer says. In your case, that three-week trip in August is worth bringing up as soon as the topic of vacation time arises. Since it was planned before you knew you'd be changing jobs, it would be only fair to let you take it. In the worst-case scenario, if your new employer absolutely refuses to budge on the two-week limit, you could offer to take the third week without pay. (Let's hope such an extreme tactic won't be necessary.)

For anyone thinking of trying to get out of the office more, Bayer has a word of warning: "Too much vacation has a downside. When you're away, you can't defend yourself against colleagues who want to undermine you or steal the credit for your work. And some organizations default to an 'out of sight, out of mind' posture that can limit your ability to get plum assignments," he says.

One solution: Have a spotter. "It's always a good idea to choose one colleague you can go to for regular updates on what's going on - someone you can trust to keep you informed so you're not blindsided when you get back to work." Good luck!

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Most stock quote data provided by BATS. Market indices are shown in real time, except for the DJIA, which is delayed by two minutes. All times are ET. Disclaimer.

Morningstar: © 2014 Morningstar, Inc. All Rights Reserved.

Factset: FactSet Research Systems Inc. 2014. All rights reserved.

Chicago Mercantile Association: Certain market data is the property of Chicago Mercantile Exchange Inc. and its licensors. All rights reserved.

Dow Jones: The Dow Jones branded indices are proprietary to and are calculated, distributed and marketed by DJI Opco, a subsidiary of S&P Dow Jones Indices LLC and have been licensed for use to S&P Opco, LLC and CNN. Standard & Poor's and S&P are registered trademarks of Standard & Poor’s Financial Services LLC and Dow Jones is a registered trademark of Dow Jones Trademark Holdings LLC. All content of the Dow Jones branded indices © S&P Dow Jones Indices LLC 2014 and/or its affiliates.