This case study describes a variation of cultural, technology, and other probes, called a “perspective probe.” The perspective probe consisted of multiple activities that participants completed on their own and then discussed with the researcher. The participant’s responses to the individual activities added up to their whole perspective. The probe’s activities helped guide the conversation around a sensitive topic instead of asking directly about it. This paper illustrates how the perspective probe methodology was used to gather information for Google Finance. The focus is on the method rather than the particular findings from the study. The perspective probe methodology was useful in getting rich data from participants and building a holistic understanding of the participant’s perspective on a difficult topic, in this case money and investing.