We have become aware of the coming together from a variety of sources of an assessment philosophy which acknowledges that those being assessed are not passive and that active participation in the assessment process is crucial in determining the quality of assessment and decision making. This acknowledgement is apparent in many different settings; for example, it may be seen in the moves towards greater patient involvement in medical diagnosis and treatment options. However, we think that if such participation is to be practically and effectively achieved, then a new interactive assessment system is needed. This chapter is about our work to develop such a system.