This study sought to expand what is known about executive coaching by exploring how inquiry—as indicated by the conversational competencies of listening and questioning—interacts with trust (as a part of the coaching competency relating), and how these competencies influence the client's achievement of goals and attainment of outcomes. Specifically, the purpose of this case study was to explore the experiences of a sample of executive coaches and their clients as a means of identifying, describing, and furthering an understanding of how these conversational and relational factors (listening, questioning, and trust) interact and how they play a role in client interim outcome attainment. This dissertation is based on a qualitative case study of graduate level certified coaches and their clients. The sample consisted of 14 individuals involved in executive coaching relationships—4 executive coaches who participated in the coaching certification program and 10 total clients. Each coach and client participated in semi-structured interviews and a working relationship survey. The researcher analyzed these data along with the archival case documents. The findings indicate there is an interdependent relationship between how coaching pairs build relational trust and make meaning through inquiry. Results of this study also indicate that this interdependent relationship seems to have an influence on client interim outcomes. Variations of the following coaching pair characteristics and practices influence one another: (1) nature of trust and how it was built; (2) questioning and listening approach; and (3) quantity and quality of client interim outcomes. This study informs practitioners and educators about the role inquiry and trust play in helping clients succeed. The researcher proposes a Situational Coaching Model to address the variations in level of client self-directedness and subsequent coaching approach.