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The people of Taiwan are no strangers to natural disasters; the island sits astride the junction point of the Philippine and Eurasian tectonic plates, making it a frequent victim of sometimes calamitous earthquakes. The island also lies in the path of yearly typhoons that buffet the island, risking life and property damage. These natural disasters have become a fact of life for the Taiwanese people, and the population has long looked to the government for leadership in ensuring disaster preparation, relief, and recovery. This chapter is focused on the leadership qualities exhibited by public administrators in the field of emergency management in Taiwan, and how they navigate the uncharted waters of this new field in a traditional culture. Beginning with a general examination of the cultural and societal influences on the position of leader in Taiwan society and the qualities demanded of that position, the research narrows to the specific field of emergency management and how administration in this realm is accomplished given (a) the relative newness of the field itself and (b) the cultural barriers in Taiwan to the widespread embrace of such disaster mitigation initiatives. The struggle of Taiwan public administrators to adopt disaster preparedness programs in the nation presents itself as a unique opportunity to examine how leaders in such situations walk the razor’s edge between doing what is necessary to ensure that the population have access to the advantages of the modern world while respecting the cultural sensitivities that can often stand in the way of administrative progress.