Abstract: A system and method are provided for portfolio risk assessment. A user is prompted for answers to one or more questions that each relate to the risk of aspects of a project. The questions may take the form of a customized questionnaire, and the answers may be quantitative or qualitative. Compounding effects among the questions are identified. Based on these compounding effects, a compound risk score for the project is generated. In some implementations, correlating effects between projects are also identified. Based on these correlating effects, a correlated risk score for a project is generated. Some implementations may generate output data that allows a user to view projects individually and in combination to highlight compounding and correlating effects.