Describing the processes of trusting empirically, at the micro level, is a challenging affair. One way to focus and nuance our understanding of trusting is to pay attention to how expectations are negotiated and changed. The suggested framework of symbolic interaction is explored in the chapter through an empirical example in the form of rich description of the ongoing and challenging relationship between an investment manager and an entrepreneurial team. The ethnographic narrative offers a rich description of how expectations are negotiated and changed as part of trusting interactions. It provides readers with insights into the relationship between expectations and trusting and how the developed framework based on symbolic interactions constitutes a productive framework for studying trusting from a process perspective.