My previous job had unlimited PTO and that team sucked mega-donkey balls. It worked despite the culture, here's how:
- large vacation time was scheduled around projects. The SPM gave large priority to devs over the business. Thus priorities were reduced to meet resources for that sprint (SCRUM).
- We had a flexible work schedule so if you needed to be home because the guy fixing your water heater is coming at 3, we made that possible. The philosophy was that as long as you were meeting your targets, everything was peachy.
- We had one guy who would occassionally go on two/three day breaks and not tell anyone - including the SPM. As a team, we just left him alone and if he can't finish his task, oh well, we didn't bail him out.
- Ironically, most of us took fewer vacation days with unlimited PTO. You have the outliers who will gladly abuse it, but prior to my departure, I took a total of four weeks (20 days) of total vacation time. Most companies give that anyways.
Simply put, as long as we gave a long enough notice and put things into the engineering calendar, no one gave a crap. A lot of our unlimited PTO success boils down to prioritizing resources and expectations with the business. This company is around 300 people, so not a small company by all means. We just ensured that we all gave appropriate notice. For me, my formula was 1 month advanced notice for every week I wanted to take, so three weeks off meant three months ahead.