I order mine medium, but if it's going to be 'off' I'd rather it veer toward more done than less. I've only ever returned a steak once at a restaurant and it was because it was too rare for me to eat (like rare-to-medium-rare. I think I must have accidentally been served someone else's.)
I don't like steak well enough to pay restaurant prices for it, so I don't normally order it in a restaurant. (Too expensive for the amount of enjoyment.) When I have steak, it's usually a family member who's grilled it, so I try really hard not to be too critical. If it's overdone I'll grin and bear it. If it's way underdone I might ask if we could throw it back on for another couple of minutes. And my DH does a good job of looking out for me. He'll eat his rarer than I will, so he's been known to trade plates with me if his is more done than mine.