Drill assemblies and methods for drilling into bone are provided. In general, a drill assembly can have a flexible distal portion configured to move between a substantially straight configuration, in which a longitudinal axis of the distal portion is aligned with a longitudinal axis of a proximal shaft portion of the drill assembly, and a curved configuration, in which the longitudinal axis of the distal portion is angularly offset from the longitudinal axis of the proximal shaft portion. The drill assembly can include a proximal shaft, a drill tip, and a plurality of segments located between the proximal shaft and the drill tip. The drill assembly can include a connecting element extending from the proximal shaft, through the segments, and to the drill tip at a distal end of the drill assembly. The drill assembly can include a conformal covering on the distal portion thereof that is configured to curve.