In sales-oriented service encounters like financial advice, the client may perceive information and interest asymmetries as a lack of transparency regarding the advisor’s activities. In this article, we will discuss two design iterations of a supportive tabletop application that we built to increase process and information transparency as compared to the traditional pen and paper encounters. While the first iteration’s design was “enforcing” transparency and therefore proved to be a failure [Nussbaumer et al. 2011], we built the second iteration on design rationales enabling more “casual” transparency. Experimental evaluations show that the redesigned system significantly increases the client’s perceived transparency, her perceived control of the encounter and improves her perceived trustworthiness of and satisfaction with the encounter. With these findings, we contribute to (1) insight into the role of transparency advisory encounter design; (2) design solutions for establishing particular facets of transparency and their potential instantiations in tabletop systems; and (3) insight into the process of designing for transparency with socio-technical artifacts that are emergent as a result of design activities.