Abstract: Risk data generation for an organizational network involves a risk assessment server that communicates with organizational computing devices. The server transmits risk data request and receives responses identifying organizational risks. The server generates and transmits assessment templates, and receives risk evaluation data from a plurality of computing devices in response. The server automatically generates a risk assessment score for an organizational risk based on the values in the plurality of risk evaluation responses, the risk assessment score defining an expected organizational impact of that particular organizational risk and transmits the risk assessment score to an administrator. The server collects benchmark risk data and risk outcomes from similar networks and generates the scores using the benchmark data. The server also provides comparative results between similar organizational networks.