I had a student that could fly the airplane just fine. In fact I had soloed him and his training was going along quite well until... we started the X-C phase. This guy could not correllate what was on the sectional with what he saw on the ground. Radio Nav was ok, but he just could not get pilotage. I worked with him for a long time, but I was stymied. Of course, there was no way I could let him go X-C solo.
I then started making some phone calls and ended up having a long talk with a Profeesor of Education at Long Beach State. What I learned was that there are some people that just have a hard time reading maps. Kind of like dyslexia, but can't read maps. She gave me several excercises to do with my student. One of them was we went into a classroom, and I had him draw a map of his home town. Then we made paper houses and roads, then I had him place those on the floor, copying what he drew on the paper. Then we did it in reverse, then we took a sectional and did an area, then we flew over that area.
My proudest moment was the day he passed his PPL checkride.