When Congress passed the Affordable Care Act in 2010, it required all non-profit hospitals in the United States to routinely conduct a community health needs assessment. The purpose of a community health needs assessment is to first identify the community health needs and then create an implementation strategy to address the identified needs. Little guidance has been provided by the federal requirement on how to conduct this community research. Through conducting more than 25 community health needs assessments, I describe the mistakes encountered as an outsider trying to gather primary data at the community level, including administrative resistance and lack of participation. Specifically, the need to arrange for key informant interviews and focus groups, and distribute a survey, was hampered by lack of knowledge of the community and its events. This essay describes the strengths and weaknesses of working with administrators. The ability to outline the tasks associated with roles and responsibilities helps to identify the skill sets needed to ensure the right people come to the table. The creation of a steering committee is described as one way to help gain access to the community, foster cooperation, and increase engagement.