Holistic educational development supports multiple, intersected facets of the faculty career to include teaching and learning, research and scholarship, leadership, career planning, wellness, and more. This constructivist qualitative study explores the landscape of 12 holistic educational development centers, with focus on how their leaders engage their centers and units in strategic and operational planning. The moniker "constantly in flux" enveloped the results, pointing to agile, leaderful processes that blurred the boundaries between short- and long-term planning efforts. Core themes were centering the faculty voice, "leveraging disciplinary identity," "trying methodologies on for size," and "adapting agilely." Disrupting commonly held stereotypes about strategic planning processes, directors illuminated the centrality of characteristics such as nimbleness, curiosity, transparency, experimentation, creativity, and collaboration. Study results point to opportunities for sharing, merging, and dissemination of planning frameworks across the holistic educational development network.