Advances in data science are transforming the research ecosystem at unprecedented rates. While universities are central in those advancements, their administrative systems may lag considerably, obviating even basic analytical approaches to strategic development. In some cases, necessary data do not exist− in other cases, it may exist across isolated systems that are not readily interoperable. We present case studies of institutional questions that guide senior administrators in strategic development (e.g. targeted communications; EDI initiatives; identifying competitive applicants/nominees; development of multi-level research metrics). We highlight technical challenges associated with each analytical exercise, share patchwork solutions we have employed, and describe some of the opportunities available to institutions that can rapidly link data across their systems. Our intent is to expose the HE IT community to the types of analytical exercises used in institutional strategic development and start conversations on how we can collaborate to tackle some of the technical challenges associated with these activities.