While the vast majority of assessments designed to measure noncognitive skills rely heavily on self‐report, concerns surrounding faking and response bias have led to an increased demand for the development of new and innovative methods by which to measure such traits, particularly in high stakes contexts. The focus of this report is to address one such method—the inference of noncognitive skills, namely personality, through nonverbal behavior—and the role contextual factors may play in influencing the validity of conclusions drawn from its application. Specifically, this report discusses the various ways in which characteristics of the task (e.g., level of cooperation, physical effort) may facilitate or hinder the assessment of personality when personality is being inferred through observable behavior. This discussion is dovetailed by a review of research from the nonverbal assessment and interpersonal task literatures, as well as a synthesis of these literatures to highlight the degree to which situational factors (as manifested through different tasks) influence the assessment of personality via nonverbal behavior. Additionally, the potential value of using noninvasive tools, such as the sociometer, to collect nonverbal behavioral data during these tasks is discussed. The report concludes with a brief commentary on the feasibility of using nonverbal methods to assess noncognitive skills, with a specific focus on the extent to which structuring the context to elicit certain behaviors may influence the validity and robustness of nonverbal responses as a measurement source.