How do we increase Player Skills at a position? Is this just a random practice increase?

It depends on the training schedule you have set and how much they play on the field at that position.

Thanks Brooks. As far as training goes would upping Positional help increase player skill? I have a rookie RB that has good stats besides Player Skill he is starting and we are 16 games in and no increase at RB Player skill.

Yea, that will help