A walking beam conveyor (54) delivers drill bits (B), one at a time, into a feed position. A pushrod (52) moves a drill bit (B) from the feed position into the nosepiece (36) of a robot arm (28). The drill bit (B) enters the nosepiece (36) shank end first. The shank (84) enters into and is gripped by a collet (38) in the nosepiece (36). A stylus (66) is then lowered down onto the point end portion of the drill bit (B) and the drill bit (B) is rotated about its axis until the stylus (66) drops down to the bottom of the drill bit flute (70). Rotation is immediately stopped and the robot arm (28) is retracted and swung into a position of alignemnt with a drill bit holder (18) of a sharpening machine. The robot arm (28) is then extended to place the drill bit (B) into a collet (C) in the holder (18). The collet (C) is operated to grasp the drill bit (B) and the collet (38) in the nosepiece (36) is operated to release the drill bit (B). The holder (18) then moves in position to in turn move the point of the drill bit (B) into contact with a surface of a rotating grinding wheel (14). The drill bit (B) was rotated while in the nosepiece (36) to in that manner orient the point surfaces of the drill bit for proper contact with the grinding wheel (14). Oversized and undersized drill bits (B), and drill bits (B) with excessive material buildup, are detected and rejected.