Despite the importance of reflection as a crucial element in stimulating successful student experience in study abroad, attempts to define and measure this construct have been fraught with difficulty. This article describes one approach to defining and validating a measure of the reflective process. University students who participated in a semester-long reflection course wrote weekly reflective essays. Four, multi-scale factor analyzed cognitive complexity factors derived from the Linguistic Inquiry and Word Count (LIWC) content analysis software formed key study variables: Immediacy, Interaction, Making Sense, Making Distinctions. These four factors aligned well with key components of reflection. The cognitive complexity factors were related to pre and post student intercultural effectiveness using the Intercultural Effectiveness Scale following a criterion validity framework. The LIWC cognitive complexity factor profiles fit well with student intercultural effectiveness scores when evaluated against reflection theory and previous research. The LIWC offers a measurement alternative that is objective, easy to use, and scalable to larger samples and more frequent administration. Thus, measurement may be harnessed in the service of formative evaluation and evidenced-based program development.