The convergence of multi-disciplined technologies to address and support the rapid evolution of e business is critical to the success of many ventures. There is an increasing demand for the availability of tools to assist in the evaluation and processing of information as it flows between the bodies involved. A tool that could predict and forecast expected occurrences with a stated level of confidence is considered to be extremely valuable and well worth pursuing. The area of Web based learning is rapidly becoming a fundamental component of corporate training areas and educational Institutions, with an increasing reliance on the delivery of their programs via the Internet or Intranet. The success of such programs is dependent on the marrying of Internet technology, Information systems, Human Computer Interaction and Educational Strategies while catering for the individual student.This research investigates and evaluates the design of an innovative approach to a formative assessment that permits the participant to register their level of confidence. The system then provides enriched feedback and can predict the performance of the individual, reducing the number of failures. The system is based on the traditional Online Multiple Choice Questions format, but it facilitates a method of registering the level of confidence of the student's response to each of the options available, generating a score that reflects their level of understanding of the topic being considered. The iterative process of design and the results of a pilot program are discussed, and directions for further studies suggested.