More training, more training, more training and try hiring a few plow operators from up north or out west with a lot of experience. We get large snow storms every few years and it seems like we have to learn all over again every year.
Planning: mark the edges of streets with tall poles so that plow operators know where the edge of the street it. It was immediately apparent from what I saw that more of them had no idea where the edge of the road was. This is especially important when many of our roads are curbed.