Should you negotiate vacation? If so, how?

Happy Thanksgiving! 🦃

Hi there,

Happy Thanksgiving! 🦃

As you settle in around the table this holiday, you may have had to think about:

• how much time off to take now and/or for the end of the year holidays,

• when to take any time off,

• whether to even take any time off this year,

• whether to ask for more vacation days than what the company offered.

If you’re negotiating a new job offer, you have to consider how the vacation negotiations fit in with the job offer’s other compensation components (salary, equity, bonuses, etc.). And if you’re at a job already, you have to consider how the vacation negotiations will affect your potential promotion/raise and relationships.

Let’s talk about how to think about and execute this.

1. Know your priorities

In the long list of things you care about at a new job (salary, equity, bonuses, etc), where do vacation days or vacation timing fit in?

2. know your non-negotiables

If having more vacation days is extremely important to you, be clear with yourself that that’s the case, and negotiate that upfront.

When I got my first job out of college, I was offered only 2 weeks of vacation a year - yes, for the non-Americans reading this, that’s 10 vacation days a year.

My family however lives in Albania, which often take a full day to get to, and another day to get to the US from. So visiting them twice a year would mean wasting roughly 4 days of vacation just on travel. Not to mention dealing with jet lag, or even spending some vacation days for things other than just visiting family. The 2 weeks of vacation a year was not quite a deal breaker, but it was close. So I made sure to negotiate it early on.

Spoiler: I negotiated an extra week off. That’s a 50% increase. Win!

3. negotiate strategically

One thing at a time, unless it’s a non-negotiable. If you’re negotiating a new job offer and you care about compensation the most, do not start with negotiating vacation days, even if the conversation happens to be on that topic. Don’t even mention it in the same ask as a higher compensation, because in those cases, companies will pick the easiest thing to give and forget about giving you the other thing that may have been more important to you.

4. don't ask for the whole turkey

Sometimes, you don’t need a traditional vacation day to make it work. Get creative:

• Suggest remote work: “What if I stay connected while spending time with family?”

• Offer unpaid leave: If time off is critical, this shows you’re flexible without sacrificing priorities.

Win-win solutions make it easier for everyone to say “yes.”

5. be strategic, not pushy

Think of your requests like spending a little “social capital.” Make them count.

• Research your company’s vacation policy so you’re not asking for something way off-base.

• Frame your ask as reasonable: “I noticed others often take time off around [specific dates], and I’d hope to get the same privilege”

Be confident. No one’s handing out extra days if you don’t ask for it.

a quick thanksgiving tale

Alex once bundled a vacation ask with a salary bump during a job negotiation. The company said “yes” to the vacation (easy win!) but sidestepped the raise. They also made the vacation ask seem as if they had done Alex a huge favor.

After Alex started his new job, he learned that the vacation didn’t need negotiating—they’d have said yes anyway.

Moral of the story: Don’t spend your negotiating power on what’s easy to get. Use it for the things that really matter.

So, go ahead and ask. The turkey will taste even better when you know you’ve got time to enjoy it. You’ve got this.

Now go enjoy that pie. 🥧

Best,
Gerta & Alex
Co-founders of YourNegotiations.com​