It can be mathematically computed. For example, if I wanted this tool here http://www.harveytool.com/ToolTechInfo.aspx?ToolNumber=905624 to cut to .03" deep into my part (or create a .03" bottom side chamfer), I would start with the data shown in the image below. Once i gathered that data, I would program that tool to a .375 Dia, the Toolpath depth would be set to -.032 Incremental from bottom Edge of part and the toolpaths Stock To leave on walls would be programmed to -.044. 
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