Interactive Voice Response (IVR) is a popular and one of the most deployed technology interventions in the developing countries. One of the primary business drivers is that it does not mandate the user to use any technologically advanced device. On the other hand, IVR has been studied for its usability issues. Even for the service providers, IVR costs are higher than services on data channels. However, given the sunk costs and low-technology investments, they are an attractive business proposition and continue to garner support. In this field trip, we propose to have an “experiential” trip of manning and experiencing the system when in use by a less-literate user. Our field trip would allow the participants to “listen” onto and experience first-hand the roller coaster experiential ride when using an IVR system. This will help us to reveal a lot of contextual data such as performance of a low-literate user with IVR, turn taking behaviour, machine and user relationship building, ambiguities etc. This will lead to interventions in the development of dialog structure personification, emotional value association, interaction design and user experience design. The methodology used to conduct the study would be wizard of context, and field observations followed by an affinity analysis.