Business schools are often criticized for the inadequate writing skills of their graduates. Improving writing skills involves first understanding the current skill level of students. This research attempts to provide insights into the effectiveness of the current method of assessing writing skills in a school of business at a large regional university and to provide insights relative to how the assessment process can be improved. Three studies were conducted. Study 1 is a quantitative analysis of the full set of data based on the use of Criterion®, an online writing evaluation service developed by Educational Testing Service (ETS). Study 2 is a quantitative analysis of a coded subset of the data and Study 3 involves a qualitative data collection effort consisting of comments gathered from assessment proctors. While the overarching purpose of this research was to determine the effectiveness of the assessment tool utilized towards understanding the current status of students' writing skills, the results also offer recommendations to improve the assessment process such that a clear picture of writing weaknesses can be more effectively addressed.