I'd also strongly recommend looking over that shared vacation calendar and identify anyone who may not be taking a reasonable amount of time off. Some people are just love their jobs ... I'm one of them, and it's not as big a deal (though, I believe nearly everyone benefits from some time off, even when forced). But make a point to ensure they don't think the "we don't track vacation time" equates to "we don't take vacation time".

I'd also steer clear of the "laptops to the beach" comments. I don't take frequent vacations, but when I do, I need to go places where I can barely get a phone call and have no internet (I fight with myself on this topic every time, but when I go on a cruise or camp in a remote part of the state that I live in, I always return more refreshed than when I go somewhere that I can keep up with e-mail). I don't know the culture of your company, but at my company "laptops on the beach" would be code for "obligation to carry your laptop with you at all times".

Just my 2p, you sound like a decent leader and I appreciate the transparency.

- If a company is really about "we don't care about how much vacation you take", then why not to give me minimum vacations? It seems intellectually dishonest.

- How I do know how much of vacation I can take and whether that amount is preventing me of getting raise/bonus/promotion?

- This policy means that my vacation will vary depending on manager and current project. I cannot commit to travel with my kids, I cannot commit to visit my parents... because who knows: I might have a different manager next month.

- If I take two weeks vacation and none of my teammates are taking vacations, am I going to be fired? Are they going to consider me that I'm not a team player?

- I can lose a job after working for year or so without taking any vacation, but if I did accure vacation I will get some money (kinda reward for working hard for a year and not taking vacation), while in case of "flexible vacation" I get nothing.

If you want to work remotely for the next month and nothing depends on your physical presence at the office, fine.

If you want to fuck off for the next month and you're not on anyone's critical path, that's fine, too.

Restricting things a bit, "not hosing the company" could be interpreted to mean that you can take off when you want, but for absences longer than x days you need to let your supervisor know y days in advance so s/he can take it into account when necessary. It doesn't sound like this would be an unreasonable thing to ask, as long as x and y are clearly stated by the company and respected by employees.

This whole thread reminds me of why I don't work for other people. The idea of someone demanding my physical presence for a portion of each day, for no reason other than the fact that they can, makes me frown and cock my head to the side like a puzzled beagle.

But if you can do this, maybe they and you will think about whether they need you the month after that, too.

The overriding goal is to run an outfit where the employees want to be there. If you do that, then vacation-policy abuse will not be a major problem. If you don't, then vacation-policy abuse is the least of your problems.