This research methods case provides guidance on how to deal with the different practical aspects of conducting qualitative research, specifically case study in cross-cultural research, and highlights some of the challenges faced during the steps of the methodological process. In particular, it describes the study conducted by Rubens Pauluzzo, Marta Guarda, Laura De Pretto, and Tony Fang, in which we adopted a cross-case analysis to explore whether organizational and national cultures mutually influence each other, how they do so, and how this process of reciprocal learning may encourage organizations and individuals to balance cultural paradoxes and manage cultural dilemmas. For this study, we used Yin Yang thinking as the lens through which Western national and organizational cultures were examined and as a way to advance diversity and plurality in case study design and go beyond the dominant implicitly positivistic North American approach to conducting qualitative case study. We used multiple sources of evidence (interviews, field observations, and internal document analysis) to obtain a comprehensive insight into four subsidiaries of an Italian insurance multinational corporation, called Generali Group, each of which is located in a different area of Europe. This allowed us to ensure the validity and reliability of the data, thereby increasing the probability of our findings being credible. These sources of data also permitted triangulation, helping us ensure the trustworthiness of the research.