This achievement can be unlocked once you level any skill from the character screen to at least level 300. This will take a while, but it’s certainly doable throughout the course of a long campaign. It’s often easiest to do this with one of the weapon skills such as One-Handed and Two-Handed weapons. These are generally easier than others to level up, since using any one-handed or two-handed weapon will count towards improving that skill. The potential to level Polearm, Bow, and Crossbow skills quickly is more limited unless you’re using one of those weapons as your primary most of the time. You should focus on taking part in as many battles as possible to ensure that you get enough chances to improve the skill, rather than leaving them to simulations.