Money Talks, So Should You

How to ask for a vacation during the holidays

Kathryn Tuggle
by Kathryn Tuggle, Contributor (@KathrynLizbeth)

Asking your boss for a day off isn’t nearly as tough as asking for a raise, but during the holidays when many of your co-workers also want a break, those conversations can be tough to have. While vacation policies vary greatly from company to company, there are some things every employee can do to ensure absence requests go smoothly.

The early bird gets the worm

“As an employer, our policy was simply first come, first serve — ask before everyone else does,” says Richard Hayman, founder of marketing firm Hayman Systems.

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In order to ensure their requests were granted, Hayman says his employees would ask for a holiday up to nine or 10 months in advance.

“By using the concept of first come, first served, we were never put in a position of being unfair or playing favorites,” he says. “The vacation sign-up sheet was located on the wall in a public place for all to see.”

Stephanie Ciccarelli, co-founder and CEO of talent placement agency, also advocates for a first come, first served policy, and notes that it’s usually necessary to give two months’ notice when requesting a day off.

“People who plan ahead are rewarded,” she says.

Talk amongst yourselves

It may be easier to get your vacation days approved by a manager if you’ve already worked it out with a co-worker who is willing to cover your shift, says Ciccarelli.

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“Vacation requests that are accompanied by a note saying that the employee has arranged to have one of their team members cover for them are more likely to be granted during popular vacation times such as Christmas or Thanksgiving,” she says. 

Don’t jump the gun

Although it may be tempting to book a flight or a hotel before you get your vacation time approved, Ciccarelli says it’s a bad idea for all concerned.

“The worst way an employee could approach us for a day off is to present their request after they have already booked their travel arrangements,” she says. “This puts us in the awkward position of being the bad guy if we deny the request, or enabling the employee to sidestep our policy which could create resentment among other employees who abide by the policy.”


Once you’ve discussed your time off with co-workers who can potentially pinch-hit for you, don’t be afraid to barter, says Tony Goddard, CEO and founder of executive coaching firm Tony Goddard Consulting.

“If you can find someone willing to swap with you, this may be your best chance of getting some time off,” says Goddard. “I have seen people do this by offering a variety of favors including free babysitting or offering to cover time in the year when that person needs a day off.”

It’s all good

Believe it or not, many companies don’t mind being understaffed around the holidays because business is slower. If you see that many of your co-workers have beaten you to the punch with their vacation requests, don't stress.

“When it comes to holidays or the week in between Christmas and New Year’s, we don't mind being under-staffed,” says Ciccarelli. “Business tends to slow down for everyone at this time and there is less demand for customer service.”

READ: Why do some budgets fail during the holidays?

For those whose work is largely computer-based, Mark Anthony Dyson, CEO and founder of resume prep company, says that technology has paved a new way for time off.

“Certain jobs and careers are tougher than others to get that coveted day off — especially if you work retail and the holidays are the busiest time of the year,” Dyson says. “However, office careers are different because the workplace is much more transient than ever. If you’ve got internet access and a computer at home, you may find yourself wrapping presents with one hand and responding to e-mails with the other."

3 more tips to consider

When it comes time to pop the question, Dyson advises that no matter how you phrase the question, ensure your employer that they will benefit in a way that could improve the working relationship. He suggests three potential strategies:

  1. Offer to do your bosses' dirty work either before or after your vacation.
  2. Come up with a written proposal with a time line and very specific job duties that you commit to doing either before or after your vacation.
  3. Come up with ideas that would be more productive to work on from home than work. Sell the fact that you can work without interruption — even if you’re in your living room.


Kathryn Elizabeth Tuggle is a seasoned New York-based personal finance editor and writer who adores saving, investing and thrift store shopping. After getting her start writing about small businesses for the Inc. 500 at Inc. Magazine, Kathryn learned her way around the NYSE and NASDAQ while working at the The Financial Times. In 2007, Kathryn joined the Fox Business Network before its inception and was instrumental in launching the company's small business and personal finance sites. Obsessed with all things spending, saving and social media, you can find Kathryn tweeting her latest adventures with Dimespring at @KathrynLizbeth.