Your examples don't sound natural. Usually, the phrase is a fixed phrase "He/she goes against the grain."
"go against the grain" refers to woodworking with a plane. Removing a small amount of wood with a plane is easy "with the grain" (in the direction of the wood grain). It is hard "against the grain" (in the opposite direction of the grain).
By analogy, "go against the grain" can mean "to go against" the traditional approach (leading to opposition). Also, it can have the general meaning of "to upset people" (like stroking a cat's fur the wrong way) and "to do things the hard way."