Little is known about the factors that shape the employment-related decisions of individuals with Intellectual and/or Developmental Disabilities (ID/DD). This article presents findings from qualitative interviews with individuals with ID/DD, their family members and employment-support professionals from four Community Rehabilitation Providers (CRPs) throughout Massachusetts. Recognizing the value of participatory action research, this study also included a co-researcher with ID/DD who participated in all facets of the research process. Findings revealed a collection of people and factors considered influential in employment-related decision-making. The family in the formative years, school-based staff and early employment experiences, the culture of the CRP, the job developer, and personal preferences all played a role in the decisions participants made. Through an understanding of these persuasive elements, and the parts of the employment process at which they occur, critical intervention points surfaced. Recommendations are offered to those in the ID/DD field to optimize employment choices and outcomes.