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Kernberg's structural interview integrates exploration of elements of personality organization into the standard initial psychiatric evaluation. The structural interview approach, while essential to transference-focused psychotherapy for patients with borderline personality disorder, is not limited to use in that context. Following the model of the structural interview, clinicians ask a series of questions, which elucidate elements of personality pathology, thereby facilitating comprehensive diagnosis, guiding treatment, and informing prognosis. Direct questioning about finances and the clinician's general curiosity about issues related to money, in the context of the structural interview, can be high-yield lines of inquiry. Patients’ history with their finances, attitudes about money, and ways questions about finance emerge in the transference around fees and related concerns, can add an important, often overlooked, dimension to the assessment of personality organization and personality disorder pathology. This article proposes the utility of prioritizing questions regarding money, as might be integrated into the structural interview, as a template for a broader recognition of the value of this line of inquiry in a diagnostic assessment process.