A system is provided for programming workpiece feature inspection operations for a coordinate measuring machine (CMM). The system includes a computer-aided design (CAD) file processing portion and a user interface which includes an editing user interface portion and an execution time indicator. The CAD file processing portion analyzes an input CAD file to automatically determine workpiece features. The editing user interface portion includes an editable plan representation including an editable set of the workpiece features to be inspected. The execution time indicator is indicative of an estimated inspection program execution time for operating the CMM to execute a corresponding workpiece inspection program. The execution time indicator is automatically updated in response to a utilization of one of a first set of operations to modify the current workpiece feature inspection plan, so as to automatically indicate the estimated effect of the modification on the inspection program execution time.