Choropleth maps are a common and effective way to visualize geographic thematic data. Although cartographers have established many principles about map design, data binning and color usage, less is known about how mapmakers make individual decisions in practice. We interview 16 cartographers and geographic information systems (GIS) experts from 13 government organizations, NGOs, and federal agencies about their choropleth mapmaking decisions and workflows. We categorize our findings and report on how mapmakers follow cartographic guidelines and personal rules of thumb, collaborate with other stakeholders within and outside their organization, and how organizational structures and norms are tied to decision-making during data preparation, data analysis, data binning, map styling, and map post-processing. We find several points of variation as well as regularity across mapmakers and organizations and present takeaways to inform cartographic education and practice, including broader implications and opportunities for CSCW, HCI, and information visualization researchers and practitioners.