A power tool control system connected with a drill press provides a system for determining operational settings for the drill press and/or structural factors of a workpiece to be operated upon by the drill press. For instance, the power tool control system may establish a visual indication of the axis of operation of the drill press upon a workpiece and/or determine the thickness, structural composition, and/or moisture content of a workpiece. The determined axis of operation and/or structural factor is utilized to determine the operational settings of the power tool.