Not everyone is big hitter guy. If you can only get it out 250 yards and you've got a big hitter, let big hitter go out last so if you don't have 1 in play, he can take his hybrid and put it 250 in the middle. If you got one out 250, let big hitter go last and see if he can get one out 300+. If not, NBD.
If you're not a good putter, nothing wrong with show the line guy. If the break is unclear, go right at it and just try to get pace so the other 3 guys can give it a good shot. If you're the first up, don't try to "take out the break" by flying it past the cup. Your job is to show the line and get it within 3 feet.