A key element of the Army’s Human Dimension Concept is the need to prepare Soldiers to thrive in conditions of uncertainty while they contend with ambiguous and amorphous threats. To prepare for such conditions, advanced talent management strategies are needed to facilitate Soldier development across the cognitive, physical, and social domains. Comprehensive talent management systems must ultimately leverage assessment tools to gather large amounts of data to enable a detailed determination of Soldier strengths and weaknesses and facilitate continuous learning. The question remains, however, about how best to achieve this goal. This paper reports lessons learned from research with the Army Reconnaissance Course (ARC), Ft. Benning, GA, to assess and track student performance over time in both performance outcomes (e.g., fundamental skills, understanding information needs) and leader attributes (e.g., anticipation, accountability). The final ARC performance assessment system included a mobile application to record student observations, a method to link those observations to key competencies, and a method for presenting trends over time. The trending method enabled student data to be aggregated across instructors and over classes to demonstrate larger changes in performance over time. In this paper, we present the methodology for developing this assessment system, results from an evaluation of the system, and reactions to employing the full assessment system during a course. The findings reflect the results from the in situ testing and use of the assessment system to include additional features which facilitate future utility and promote usability. Implications of the research are discussed to provide suggestions and future research questions to inform the creation of a comprehensive Soldier assessment system as the Army strives toward effective talent management strategies.