The goal of assessment is to identify weaknesses in learner's knowledge. There are various types of assessment in which among them are the Quantitative and Qualitative assessment. This paper is concerned with the qualitative assessment. The underlying principle of qualitative assessment motivates the research. Qualitative assessment is not about assessing the domain knowledge but it is about assessing the learner's current and potential capacities related to the knowledge. Dynamic questions generation for qualitative assessment involves a strong degree of subjectiveness. Appropriate scoring mechanism is needed to assess learner's level of knowledge and to dynamically create a subjective question that is adaptive to the learner's current knowledge and understanding. The paper provides an overview of adaptive qualitative assessment and dynamic questions generation and a discussion on possible approaches found in the recent research as a guide to the development of an automated tool. © 2010 IEEE.