This chapter analyses the relationship between the hermeneutical and dialectical traditions in philosophy, how Jaspers integrated some of their key insights into his psychiatric thinking. After introducing these concepts (e.g., understanding as contrasted with explanation) on a theoretical level, the question about the applicability in the psychotherapeutic context (i.e., in concrete encounters between doctors and patients), is discussed. The element of verbal communication in the encounter appears as a link and an important hermeneutical task. Then, the polar structure of psychotic and non-psychotic syndromes is introduced and described in a phenomenological framework. In a concluding section, the element of negativity in experience as well as the importance of hermeneutical and dialectical knowledge for the vocation of psychiatry are addressed.