Psychological assessment involves the use of validated measurement tools to answer specific questions. However, there are a wide range of available tools, a variety of reasons for choosing them in any given clinical context, and very little evidence to guide instrument selection. Experienced clinicians may have intuitions about which tests to use to answer specific questions, and psychoanalytic theory provides a structure within which to consider what kinds of tests to use in different clinical situations. In this article, we review common considerations for selecting tests in clinical assessment from a psychoanalytic perspective. We then use a case to illustrate how four expert assessors who work in different contexts and have somewhat different backgrounds demonstrate their approach to test selection in answering specific collaborative assessment questions. Similarities and differences between these experts are discussed, with an eye toward developing a more systematic model for test selection that could be helpful to psychodynamic assessors and provide a foundation for applied research.