Grading is more an opinion than the science it aspires to be, so developing your own standards is a must for any collector pursuing gem state Indian Heads.
The fastest way to earn your grading degree is by purchasing overgraded, unappealing coins and losing a sizeable amount of money when it comes time to sell them. The preferred method is to view large samples of other people's coins -- at local coin dealers, shows or even over the internet -- and create your own frame of reference for the "look" of high and low end before jumping into the market.