In this paper, we will use this textual fragment from an interview to demonstrate a set of approaches that allow us to critique the initial reading of events. In doing so, we come to a deeper view of the development process. We will see interpretations of the project from a variety of perspectives and in the process shed light on the conundrum of success and failure in Information Systems projects. Our primary goal is to increase our understanding of the Information Systems Development (ISD) change process and at the same time maintain openness of inquiry. Additionally, we use the textual analysis to illustrate the use of the hermeneutical circle. Finally, many research projects in information systems (IS) employ interviews of subjects and develop large corpuses of data transcripts. We believe that our approach adds an additional weapon to the armory of the IS researcher in making sense of such textual “databases” and producing more interesting and insightful readings.