A system and method for generating a schedule for multiple employees in a complex environment. In one embodiment, the method includes generating a schedule for multiple employees with varying skill sets for a time period, wherein the plurality of employees have varying overlapping skill sets that enable them to perform various tasks, and wherein employees are shared across tasks within the time period. In one embodiment, the method includes receiving a plurality of user inputs to a scheduling program, including a number of employee designations that each refer to a unique employee, and a number of skill sets that each correspond to one of the employee designations. The method further includes receiving a user input that changes the number of employee designations by indicating at least one changed employee, and estimating an effect of the at least one changed employee on effective staffing levels for each of the various tasks. The method further includes generating estimated effective staffing levels for each of the various tasks.