Follow These 6 Steps for Negotiating With Your Boss for More Vacation Time

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Editor’s note: This article was originally published in March 2018.

Want more vacation days? (Who doesn’t?)

Then make yourself irreplaceable. 

That’s the advice of Amanda Basse, and she should know.

She negotiated for nine extra vacation days during her employee review as outreach coordinator for Alan David Custom in New York City.

Actually, Basse negotiated for nine additional vacation days, plus her birthday off, plus work-from-home flexibility when her kids get sick or a snow storm hits.

So how’d she do it? And how can you? 

6 Steps for Negotiating for More Vacation

Asking your boss for extra vacation days might seem like a tough ask, but these six strategies will help put you in the position to enjoy a little more of the sweet (non-working) life.

1. Know What’s Negotiable

Because she worked for a smaller business, Basse noted that there was more flexibility when negotiating and that her boss, as the owner, had the authority to make this kind of decision.

Depending on the company you work for, your ability to negotiate could initially be limited, explained career coach Loren Margolis, CEO of Training & Leadership Success

Pro Tip

Before you even consider negotiating, investigate whether your employer is in a good enough financial position to offer you anything — even days off.

“Smaller, more nimble companies can be more flexible in terms of certain perks,” Margolis said. “For structured, more established companies, you need to know their policies.” 

But policies aren’t necessarily written in stone.

“Talk to HR, knowledgeable colleagues who’ve done something similar and read the employee handbook,” Margolis advised about making your case that your company should change a policy. “Do some research.”

2. Prove Your Worth

Don’t start planning that extended European vacation just yet.  

Basse said it took her a year of documenting concrete examples of her accomplishments on a Google doc. 

“Start by writing down your wins,” Basse said. “Document everything, even if it’s small. Little things amount to big things.”

Benefits are more than just add-ons and fun perks — they account for 37.7% of an employee’s total compensation, according to the Bureau of Labor Statistics.

Next, she assigned a monetary value to each accomplishment, from the extra hours she put in on the weekends to her assistance on projects that fell outside her assigned duties.

She totaled those numbers and compared it to what she expected to get for a raise that year.

Then she considered how much that money was really worth to her.

“I was expecting a 4% to 5% pay raise, which turns out to be only a few hundred bucks — I would pay for that just in childcare,” Basse said. “I could make more money elsewhere, but I also wanted to be present in my children’s lives.”

Money is only part of the equation, Margolis agreed, noting that you should also request a breakdown of all your benefits and add it into your total compensation package.

“Know their value as you prepare your case,” Margolis said. “The better armed you are with facts, the better you can make the case with your boss.” 

3. Get Your Boss on Board

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You don’t know what you got ’till it’s gone.

Let your boss ponder the wisdom of Joni Mitchell when you present your case for more vacation.

“Companies are competitive with each other,” Margolis said. “When you’re in there, weave in what competitors are doing.”

Basse said she completed an analysis of what her company’s competitors were paying before she started negotiating.

“I didn’t have any intention of leaving, but I started fishing for other opportunities,” Basse said. “I looked elsewhere so I could see what others are making to know what I’m worth financially in the marketplace.”

To find out what you’re worth, check out salary comparison calculators on sites like Glassdoor and search for jobs similar to your current position in your area for a salary comparison.  

4. Don’t Be Afraid to Haggle

You’ve prepared your spreadsheet of accomplishments, you’ve figured out your position’s market value and you’ve found three competitors who pay a higher salary for your position.

Now how much paid time off should you ask for?

Basse’s advice: Aim high.

“I’ve never gotten everything on my first ask,” she said. “I went in asking for 40% to 50% higher, then worked my way down.”

Her boss’ reaction?

“He was a little shocked I didn’t ask for a raise, but for days off,” Basse said. “He had to think about it, and it took a little back and forth.”

Margolis advised that if and when you reach this point, the next step is crucial: Make it clear your boss’ opinion matters.

I’ve never gotten everything on my first ask. I went in asking for 40% to 50% higher, then worked my way down.

“Ask your boss their thoughts — ‘Do you have any reservations?’” Margolis suggested asking. “Make it a two-way conversation so your boss can address concerns.”

Basse added that it’s also essential to get everything in writing.

“Right after the meeting, I emailed a follow-up,” Basse said. “I wanted to be clear what I was communicating.”

5. Close the Deal

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By going into the negotiation knowing what she was willing to accept, Basse said she could clearly communicate her needs to her employer — as well as herself.

For Basse, that meant trading more money for spending her vacation with her family doing things she loved instead of having to squirrel away days to care for a sick child or for a snow day.

“I had to think of ways to feel compensated other than monetarily,” she said. “I realized I wanted time to enjoy my time off.”

Margolis also noted that what’s important to you at one point in your career (and life) could change over the years.

You may even end up realizing more paid time off isn’t what you really want.

“As you get along in your career, you may ask if I want to get more professional development, tuition reimbursement,” Margolis said. “That can be worth thousands of dollars.”

6. If at First You Don’t Succeed…Asking for extra paid time off could have potentially hurt her career, Basse admitted, but she ultimately decided it was worth the risk.

“There was some fear since women with young children can be considered a liability,” Basse said. “I decided that more time to travel and volunteer at my children’s school is more important.”

And if her boss had ultimately said no deal?

Pro Tip

Regardless of the outcome, remaining calm and professional throughout the negotiation is essential for maintaining a long-term work relationship with your employer — even if you decide to leave.

“I would have stayed, but I think long-term, it would have been a deal breaker,” she said.

If your boss says no to more vacation time, it’s not necessarily the end of the discussion, Margolis pointed out, but it’s up to you to keep the dialogue going.

“Who knows, it could be the timing of your request, and you may be able to expand your vacation time after the company’s busy season,” Margolis said. “Or it could be that your manager or peers might see your longer vacations as you not pulling your weight.

“But you won’t know that you have to move on to negotiating something different unless you ask.”

No matter what the outcome, the knowledge and experience you gain translates to a valuable skill, Margolis said. 

And that skill could come in handy the next time you ask for those extra vacation days.

Tiffany Wendeln Connors is a staff writer/editor at The Penny Hoarder. Read her bio and other work here, then catch her on Twitter @TiffanyWendeln.