Trust. You know it when you feel it, and you value it when you receive it. But what exactly is it, is it important in the surgeon-patient relationship, and how does it develop? The essence of commonly encountered definitions of trust is the optimistic acceptance of vulnerability wherein the truster believes the trustee will care for their interests. Patients in surgery are in a situation of extreme vulnerability and intimacy with their surgeon, often preceded by a relatively limited time to develop such a consequential relationship. On a surface level, preoperative evaluation involves making an assessment, developing a surgical plan, and obtaining informed consent. At a much deeper level, the process of counseling, dialogue, and shared decision-making among physician, patient, and family members provides a critical opportunity for the development of trust. Once established, this trust is foundational to the ongoing surgeon-patient relationship. This chapter will discuss the preoperative evaluation and its importance in the development of trust in this unique relationship.