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Why this Twitter leader plans vacations a year in advance and schedules a meeting her first day back

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Courtney McMillian is the vice president of Total Rewards at Twitter and plans vacations as much as a year in advance.
Courtesy of subject

Working for a company with an unlimited vacation policy isn't always as great as it seems. Some reports indicate people with unlimited PTO end up taking fewer days off than those with a fixed policy. And the free-for-all could leave people wondering how much is too much time to request off. Roughly 1 in 3 American employees with an unlimited PTO policy is afraid of abusing it, according to an April survey from New View Strategies, a management consultancy.

For what it's worth, Courtney McMillian says she's never denied an employee's PTO request. More often than not, she's more concerned with people not taking enough time off.

McMillian, 41, is head of Total Rewards at Twitter, which has "unaccrued PTO for most employees," as well as a monthly day of rest.

She thinks of it this way: "I manage work, not people," she tells CNBC Make It. "As a human being, you are accountable and responsible for yourself, and I respect your needs. I don't think anyone likes to be micromanaged or told that they can't take the time they need and when they need it."

She wasn't always good at setting her own boundaries until she realized the only people who benefited were the ones taking advantage of her overextension.

As a mom to a 17-month-old son, she's now a pro at planning vacations, sometimes a year in advance. Here, McMillian shares why she bookends her time off with meetings, and why you should take time off even if your plans fall through.

What she covers in a pre-PTO meeting: My team shares a PTO calendar for the global Total Rewards team, so everyone can see when we're trying to plan time off. I'll give my team as much notice as possible, even if it's six or eight months in advance, so leading up to that time we can prioritize our work.

I like to make sure my team can get me in a meeting where I can give a red light, green light or yellow light on any projects that they are working on so they're able to keep moving forward in my absence. This way, they can get really clear on what they may need from me before I step away, and it helps to have that transparency across the team.

Why she plans a meeting right when she's back: Things move so fast, so one of the first things I have the first day I'm back is a meeting with my leadership team so they can brief me on what's been happening and where I need to jump in and help. It helps me get a sense of what's at the top of the priority list that needs my attention.

Why she's OK with working late before vacation: I try to finish all the things that I need to get done before I leave, otherwise mentally I'll be stewing while I'm on vacation and still thinking about work. Even if it means I have to work really late into the evening a few nights before I go, just putting everything to bed really allows me to feel good about the time that I'm about to step away.

Why she shares her vacation plans, even when they fall through: I sometimes hear people on my team who are hesitant to take time off. That's why it's really important for me to share with them what I did on PTO once I'm back. It could be something small. Recently, I was planning to go to the spa for my birthday, but the technician got sick, so my plans fell through. I ended up spending the day in my garden. And I shared that with my team, that I still took my time off and did something else that was meaningful to me. We work in front of our computers all day, so to be able to work on my vegetable garden was really renewing and refreshing. I try to encourage that dialogue as a part of our team and lead by example.

What she'd tell her 25-year-old self about taking time off: Set boundaries and actually take vacation. The only people who have an issue with you setting boundaries are the people who've been taking advantage of the fact that you're not setting boundaries.

In all my years of working I've never been like, "Man, I should have worked that extra day and skipped that day of vacation."

This interview has been edited for length and clarity.

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