In this article, we outline a methodological framework for studying the inter-organizational aspects of paradoxes and specify this in relation to grand challenges. Grand challenges are large-scale, complex, enduring problems that affect large populations, have a strong social component and appear intractable. Our methodological insights draw from our study of the insurance protection gap, a grand challenge that arises when economic losses from large-scale disaster significantly exceed the insured loss, leading to economic and social hardship for the affected communities. We provide insights into collecting data to uncover the paradoxical elements inherent in grand challenges and then propose three analytical techniques for studying inter-organizational paradoxes: zooming in and out, tracking problematization and tracking boundaries and boundary organizations. These techniques can be used to identify and follow how contradictions and interdependences emerge and dynamically persist within inter-organizational interactions and how these shape and are shaped by the unfolding dynamics of the grand challenge. Our techniques and associated research design help advance paradox theorizing by moving it to the inter-organizational and systemic level. This article also illustrates paradox as a powerful lens through which to further our understanding of grand challenges.