This Trophy is almost impossible to miss if you're playing as a Rogue.
Max out the Pinning Shot line of the Archery skill tree. It consists of Pinning Shot, Crippling Shot, Critical Shot and Arrow of Slaying.
The interesting skill here is Arrow of Slaying because of big damage numbers.
Have a decent amount of points pumped into Dexterity and use Arrow of Slaying on a standard enemy. You might be a few points short the first time you use it but with this it is no problem whatsoever to reach 500+ points of damage when you're a little higher in level.