Always get it in writing
You don’t need a formal contract drawn up or anything, but you should never leave the details of a successful negotiation up to memory. If your boss doesn’t offer to get the increased PTO in writing themselves, politely follow up over email so you have receipts.
“Email’s fine,” Lee said. “What you want is, if you’re negotiating with your boss, then you want to get it in writing from the boss.”
Unionize your workplace
Your boss may well be a lovely person, but they are not your friend, or your family, or whatever else they assure they you they are in your onboarding packet from HR. The best way to ensure that you have equitable benefits and protected PTO and comp time is to be a member of a union. (Disclosure: Thrillist's editorial employees are unionized with the Writers Guild of America, East.)
Don’t think about PTO just in terms of number of days -- get creative
“Frankly, what we hear about even more [than number of days] is flexibility of schedule,” Lee said. “What comes up a lot is, ‘I have a long commute and I want a flexible schedule to minimize that,’ or, ‘I have care responsibilities and I want a flexible schedule so I can get home by 4 every day to meet my kids.’”
You might want to ask about specific schedule modifications that make things easier for you to manage your other responsibilities. Or, depending on your personal preferences and the nature of your job, about modifications that even come out to the same amount of PTO as before -- like working four 10-hour days four days per week instead of five eight-hour days.
“Remember, for a lot of people it’s not taking extra time off because they’re going to the beach,” Lee said.”It’s because they've got to care for a parent or a child or have an obligation of some sort.”
That said, there’s nothing wrong with using extra PTO to go to the beach. Spend the time how you like -- it’s yours now.