A performance management system for use a plurality of machines operating at a common worksite is disclosed. The performance management system may have at least one data acquisition module configured to monitor performance of the plurality of machines, and a controller in communication with the at least one data acquisition module. The controller may be configured to collect machine performance data from the at least one data acquisition module, and detect a performance irregularity based on the collected machine performance data. The controller may be further configured to analyze the collected machine performance data, and determine which of a machine condition, an operator condition, and a site condition is the predominant cause of the performance irregularity based on the comparison.