A self positioning cutter element and cutter pocket for use in a downhole tool having one or more cutting elements. The self positioning cutter element includes a substrate and a wear resistant layer coupled to the substrate. The cutter element includes a cutting surface, a coupling surface, and a longitudinal side surface forming the circumferential perimeter of the cutter element and extending from the cutting surface to the coupling surface. The cutter element has one or more indexes formed on at least a portion of the coupling surface. In some embodiments, the index also is formed on at least a portion of the longitudinal side surface. Hence, the coupling surface is not substantially planar. Additionally, at least a portion of the longitudinal side surface does not form a substantially uniform perimeter. The cutter pocket also is indexed to correspond and couple with the indexing of the cutter element.