In this paper, we present a mixed-method retrospective study of 360 digital transformations and the reasons for the respective success or failure in each case, as perceived and explained by 180 domain experts from 42 countries. The purpose of the study is to investigate why actual digital transformations succeeded or failed, in order to develop insights, critical reflections, theories, and future research paths. Using open-ended questions, we ask the experts to think of one failed and one successful digital transformation. We ask them to describe the projects, and to provide their own explanations for the success or failure in each case. We analyze the qualitative data using cutting-edge language technology, network analysis, and machine learning. The findings reveal that small number of factors dictates the outcome for a large majority of cases, and a couple of those factors predict success or failure with a high degree of confidence. We theorize a mechanism for organizational behavior. We suggest that the findings can have important theoretical and practical implications for how organizational change is understood, and, ultimately, managed. We discuss whether the findings may provide new research questions on the essence of management and its impact on performance of business organizations, both during transformational change and under normal conditions.