This chapter argues for an emphasis on process as a way of addressing big questions of art history, especially those involving art's relationship to society. With the example of a dataset from the Weimar Republic of the German construction firm of Dyckerhoff & Widmann, an evaluation of the structuring and querying of the data leads to specific analytical points that challenge the established narrative for the architectural development of Weimar Germany. At the same time, grappling with large bodies of data necessarily opens up the scale of the research itself in a manner that demands further—and collaborative—work if big questions of art history are to be addressed. Thus, while the evidence and its digital visualization help point to a different narrative of architecture and the building industry in Weimar, understanding the political economic goals of the period demands more data and further complexity. That is to say, embracing the critical concept of the art historical process is a way of demanding attention for a wider field of evidence as well as calling for a more collective and exploratory approach to answering disciplinary questions at scale. This approach is exactly what a critical digital art history can provide.