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Design has always been seen as an inherently human activity and hard to automate. It requires a lot of traits that are seldom attributable to machines or algorithms. Consequently, the act of designing is also hard to assess. In particular in an educational context, the assessment of progress of design tasks performed by individuals or teams is difficult, and often only the outcome of the task is assessed or graded. There is a need to better understand, and potentially quantify, design progress. Natural Language Processing (NLP) is one way of doing so. With the advancement in NLP research, some of its models are adopted into the field of design to quantify a design class performance. To quantify and visualize design progress, the NLP models are often deployed to analyze written documentation collected from the class participants at fixed time intervals through the span of a course. This paper will explore several ways of using NLP in assessing design progress, analyze its advantages and shortcomings, and present a case study to demonstrate its application. The paper concludes with some guidelines and recommendations for future development. [ABSTRACT FROM AUTHOR]