I've seen companies set minimum time off, which can certainly simply the problem. (At risk of the Dilbert situation: "you need to get this done by end of year, and also take two weeks of holiday".) But ultimately, I think that's a road to this sort of cultural approach. Once people around you are taking time off, it becomes easy to justify taking time off. (And so, like most cultural things, you'd better have management doing it first.)

The best UPTO environment I've ever seen had managers who asked about time off in one-on-ones and pushed people who said "none" to take more. It also had a lot of acceptance for 'aimless' PTO; justifying your trip to the Andes is easy, but people take PTO more consistently if no one's expecting a better story than "sleep late and run some errands" or "play a new-release game".

> Once people around you are taking time off, it becomes easy to justify taking time off. (And so, like most cultural things, you'd better have management doing it first.)

Also once teams and management get used to people taking time off, the business processes also become more resilient to people missing for a week or two and taking PTO becomes less of a problem for everyone. Suddenly someone missing for a week is just not a big deal.

I'd never considered this explicitly, but it's an excellent point.

It occurs to me that Google somewhat famously adds artificial downtime to their services to make sure no one is relying on 24/7 uptime. I don't want to reduce people to server-equivalents, but I'll bet high vacation rates are a pretty good way of making sure no one relies too much on individual knowledge. Even from my personal experiences, lots of things get documented when the person who knows them well is heading out of town and there's a sudden scramble to formalize that knowledge.