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“When can I ask for more paid vacation?”

How to prioritize and negotiate non-salary benefits

by Josh Doody

“When can I ask for more paid vacation?” is a valuable question that you need to get right so you don’t leave anything on the table when you negotiate your salary.

Ask too early and you may wind up with a lower salary. Ask too late and you may miss your chance.

You should list your priorities for your salary negotiation

Here’s a short list of things you might want to maximize in your salary negotiation, listed from most valuable to least valuable:

  1. More salary
  2. Additional paid vacation
  3. Signing bonus
  4. Equity
  5. Relocation stipend
  6. Flexible work schedule

Your list may be different depending on what you value the most. You may want to maximize your base salary, work remotely, or even take long weekends to spend with your family..

Your instinct will be to make sure you ask for everything you might want so you don’t miss out on something you do want.

But what’s important is that you identify which things are most valuable to you so you can focus the negotiation on those things. If you don’t explicitly do this, the company will do it for you.

The company also has a list of priorities for the salary negotiation

Their list is ordered from the least to most expensive things for them to give:

  1. Flexible work schedule—This costs them almost nothing
  2. Relocation stipend—A one-time expense that they can cap
  3. Signing bonus—A one-time expense
  4. Equity—A future expense that could be reduced over time
  5. Additional paid vacation—A recurring expense that will grow with your salary
  6. More salary—This is expensive and recurring

Notice their order, driven by what’s cheapest for them, is almost the exact opposite if yours.

To get the best compensation package, focus on one thing at a time, and start with what’s most valuable to you. For most people, that’s base salary. Once you maximize base salary, move on to something like paid vacation or whatever is the next-most-valuable thing on your list.