In skateboard, we never use round heads. Indeed, we try to make sure that the screw heads sink into the deck and do not protrude so that we can rub our feet on the grip without any obstacle. Skate = flat head.
In longboard, depending on the board, we use screws with round heads. On Drop-Through mounts, round heads are mandatory. In addition, on a top-mount, round heads can provide extra grip at the foot, which is very useful for high speed.
Often you can't mount flat screws because the board isn't drilled the right way for the heads to sink into the wood.
On an already equipped board, take the same thing you already have.
On a new board, you have to check that the screw heads will disappear inside the board once tightened, otherwise they will stick out.