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This chapter revisits and examines the experience of working with a new senior level administrator who failed to understand their role on the team. This was further compounded by the administrator’s inability to establish trust and rapport, assimilate into an established organizational culture, and empower staff. Additionally, this administrator’s style could best be described as managing instead of leading. This failure to assess and learn the group dynamics of the team resulted in a lack of buy-in and a visceral decrease in team morale. Change was swift and fast, but not transformational. Within 14 months of the hire of the new senior administrator, two office support staff assistants resigned and four of the six associate/assistant directors within the office resigned. Within two years, the senior administrator resigned. The authors will provide remedies that will assist future leaders in similar situations in making better decisions, as well as provide examples of ways to connect with staff and implement change together.