Former company had an unlimited PTO policy.
It was a mess.
Apart for the hidden threshold other people mention, I had several direct reports in different countries.
Each country had a legal vacation policy... and out 'unlimited' PTO didn't took that into account.<p>When I joined the company one developer had no vacation for more than eight months. She was Russian and was relocated to a country where she had no relationship... si she just worked. That was a huge liability until she took one week off to interview and left then company one month later.
I've been at several companies with unlimited PTO. I've it it go the following ways: 1) no questions asked until a secret limit (usually 3-4 weeks) and then you're likely to be denied based on your manager's judgment 2) As long as you get your work done and give enough notice, no one cares. This is my personal favorite variant. 3) you're approved as long as enough people are not taking off during that period.<p>The problem I've found is that you don't really know which you're gonna get. What's the limit is a secret few companies openly speak about to leverage the fact that generally speaking people take less PTO with unlimited PTO. Some of the companies I've been at combat this by having vacation minimums or official office closed days or having leadership leas by example, but it's honestly a hard problem to solve because a surprising amount of people will not take vacation without the pressure of use it or lose it because they are natural workaholics.<p>I have also found that people are generally more stricter about how good your performance has to be the more vacation you take. I've found that despite taking like 6 weeks (which is crazy for an American), most companies have been cool with it because I perform well, but people who take 3-4 weeks get way more pressure for average performance. Is suspect this bias is also why some people don't take off.