This is something I learned in my on and off side career as a sailing instructor. I used to start off as a navigator and walk people through a course, telling

This is something I learned in my on and off side career as a sailing instructor. I used to start off as a navigator and walk people through a course, telling them exactly where to tack for an ideal path. Then I started setting buoys and letting them figure it out for themselves. Buoys start out perpendicular to the wind, which is not terribly challenging. When students do well enough and gained enough confidence I set them in line with the wind, which is incredibly difficult for someone new. I give them hints pointers, but I never make the decisions for them. Without fail, everyone screws up the upwind and downwind buoys on the first lap but they eventually make it around. Gradually they screw up less and less and start to get it.