A system and method for facilitating on-line generation and assignment of evaluations for entities of a particular organization comprising: a web-based server device for generating web-based communications for delivery to web-enabled devices over a communications network, and receiving web-based communications via the network; an evaluation build module for initiating a web-based communication via the server device for receipt by a user device, the communication comprising a first interface for receiving user input to generate a customized evaluation for a particular organization including input for specifying a target audience (evaluator) for the evaluation, specifying a subject (evaluatee) of the evaluation, specifying associated evaluation questions for the target audience, and specifying potential answer choice types to be entered by evaluators when completing the evaluation; and, evaluation assignment module for generating an evaluations assignment interface via a web-based communication for receiving user input to selectively assign and schedule by date and date range the generated evaluations to one or more evaluators for receipt at web-enabled devices, wherein the assigned evaluations are capable of being viewed and completed on-line by the evaluators.