A surgical drill bit can include a body portion that defines a central axis that extends along a first direction. The body portion can be separated along the first direction into a distal cutting segment, and a guiding segment. The body portion can include a helical flute that winds about the central axis. The helical flute can define a first outer profile along the cutting segment and a second outer profile along the guiding segment, the first outer profile has a first leading edge and a first bearing surface and the second outer profile has a second leading edge and a second bearing surface. The first leading edge can be configured to cut into bone and can be spaced from the central axis by a first length. The second leading edge can be spaced from the central axis by a second length that is less than the first length.
