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Peldi-- I believe you to be correct in your fear. It doesn't scale unless you ensure the managers layers below you encourage their employees to take time off and are as flexible as you.

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.