A critical aspect of information system development (ISD) projects is identifying, interpreting and specifying the requirements for a proposed information system. In this article we focus on the reasoning process employed by the stakeholders of the RE process. We argue that new insights in RE may be gained by trying to explore the reasoning process that underlines RE. Specifically we argue that a deeper understanding of this process can be developed by exploring it through the Naiyayika system of inference. During the course of this paper we explain the special nature of this school of inference; which relies on empirical observation to create a rule based mechanism for assisting one’s understanding of the context. Initial insight is developed from applying the lens of Naiyayika school of inference to the qualitative data collected from Indian IT services organizations is discussed from a perspective of seeking new insights about the RE process.