The problem of comparing and matching different learners’ knowledge arises when assessment systems use a one-dimensional numerical value to represent “knowledge level”. Such assessment systems may measure inconsistently because they estimate this level differently and inadequately. The multidimensional competency model called COMpetence-Based learner knowledge for personalized Assessment (COMBA) is being developed to represent a learner’s knowledge in a multi-dimensional vector space. The heart of this model is to treat knowledge, not as possession, but as a contextualized space of capability either actual or potential. The paper discusses a system for automatically generating questions from the COMBA competency model as a “guide-on-the-side”. The system’s novel design and implementation involves an ontological database that represents the intended learning outcome to be assessed across a number of dimensions, including level of cognitive ability and subject matter. The system generates all the questions that are possible from a given learning outcome, which may then be used to test for understanding, and so could determine the degree to which learners actually acquire the desired knowledge