Described herein are systems and methods for use in preparing holes in bones. In certain embodiments, the trajectory followed in preparing a hole in a bone is optimized by adjusting characteristics of rotation of a drill bit (e.g., an anti-skiving drill bit). In certain embodiments, a change in material is determined once a hard outer layer of a bone has been drilled. Subsequently, characteristics of rotation of a drill bit are altered to allow natural features of a patients anatomy to guide the drill bit. In this way, certain hard walls of certain bones can act to redirect a drill bit. The change in material may be determined, and/or characteristics of rotation altered, by a surgeon or a robotic surgical system (e.g., automatically). In certain embodiments, a robotic surgical system notifies a surgeon of a change in material to prompt the surgeon to alter the characteristics of rotation.
