Eastern European transformations have captured the interest of a myriad of scholars, who have studied them from a variety of perspectives. Many global, European and internal challenges, such as a shift towards populist and authoritarian politics, will keep the focus of comparative research on transformations. This is further enhanced by the increasing availability of (mainly) quantitative data. However, comparative research is dominated by the positivist paradigm, which allows for a scientifically rigorous search for robust and complex general explanations, but fails to reach context-specific configurational conclusions. In this chapter, we argue the applicability of Charles Ragin’s fuzzy-set qualitative comparative analysis for comparative research on transformations. We use the analysis of socio-cultural factors of developmental performance in Eastern Europe to present this method and reflect on the problems of the accessibility, validity, reliability and transparency of empirical data for comparative research on transformations. We then describe the inclusion algorithm and truth table algorithm, and we present the latter with an analysis of differences in innovative performance between West and East European Countries.