A drill bit comprises a shank extending along an axis and an interface comprising at least one outermost drive portion spaced at a first interface distance from the axis. The drill bit further comprises a resilient arm extending from a proximal end of the shank. The resilient arm comprises an outer arm surface facing away from the axis and a retention surface facing toward a distal end of the shank. The retention surface may be radially aligned about the axis with respect to the outermost drive portion. The resilient arm is movable between: a first position where the outer arm surface is spaced from the axis at a first arm distance greater than the first interface distance, and a second position where the outer arm surface is spaced from the axis at a second arm distance less than or equal to the first interface distance.