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The ways in which natural language processing (NLP) can inform how veterans can improve effectiveness in translating military experience to workforce utility is underexplored. We design NLP experiments to evaluate the degree of explanation in veteran job interview responses as a proxy for perceived hireability. We examine linguistic and psycholinguistic features, context, and participant variability to investigate the mechanics of effective communication in employee selection. Results yield good performance when distinguishing between varying degrees of explanation in responses using LIWC features, indicating robustness of linguistic feature integration. Classifying Over- and Under-explained responses reflects challenges of class imbalance and the limitations of tested NLP methods for detecting subtleties in overly verbose or concise communication. Our findings have immediate applications for assistive technologies in job interview settings, and broader implications for enhancing automated communication assessment tools and refining strategies for training and interventions in communication-heavy fields.