A surgical drill bit configured to form a hole in an anatomical structure, the surgical drill bit comprising: an elongate cylindrical body portion that defines a proximal end, a distal end spaced from the proximal end along a central axis, and at least one flute that extends helically about the central axis from the distal end to the proximal end, the body portion further defining a cutting segment and a guiding segment that is proximal to the cutting segment, wherein the at least one flute defines: a first outer profile at the cutting segment, the first outer profile defining a first leading edge that is configured to cut into bone and, and a first bearing surface that extends from the first leading edge such that both the first leading edge and the first bearing surface are spaced from the central axis by a first length (L L1, L B1) that substantially defines a radius (R 1) of the hole, and a second outer profile at the guiding segment, the second outer profile defining i) a second leading edge that is spaced from the central axis by a second leading edge length (L L2) that is less than the first length (L L1), and ii) a second bearing surface that is spaced from the central axis by a second bearing length (L B2), characterized in that the second bearing length (L B2) is greater than the second leading edge length (L L2), and in that the second outer profile further defines iii) a substantially straight leading surface that is connected between the second leading edge and the second bearing surface. an elongate cylindrical body portion that defines a proximal end, a distal end spaced from the proximal end along a central axis, and at least one flute that extends helically about the central axis from the distal end to the proximal end, the body portion further defining a cutting segment and a guiding segment that is proximal to the cutting segment, wherein the at least one flute defines: a first outer profile at the cutting segment, the first outer profile defining a first leading edge that is configured to cut into bone and, and a first bearing surface that extends from the first leading edge such that both the first leading edge and the first bearing surface are spaced from the central axis by a first length (L L1, L B1) that substantially defines a radius (R 1) of the hole, and a second outer profile at the guiding segment, the second outer profile defining i) a second leading edge that is spaced from the central axis by a second leading edge length (L L2) that is less than the first length (L L1), and ii) a second bearing surface that is spaced from the central axis by a second bearing length (L B2), a first outer profile at the cutting segment, the first outer profile defining a first leading edge that is configured to cut into bone and, and a first bearing surface that extends from the first leading edge such that both the first leading edge and the first bearing surface are spaced from the central axis by a first length (L L1, L B1) that substantially defines a radius (R 1) of the hole, and a second outer profile at the guiding segment, the second outer profile defining i) a second leading edge that is spaced from the central axis by a second leading edge length (L L2) that is less than the first length (L L1), and ii) a second bearing surface that is spaced from the central axis by a second bearing length (L B2),