This chapter offers best practices, methods, planning options, and comparison information for two distinct scenarios for the implementation and utilization of retention and student success coaching services. The first implementation scenario is for institutions that want to consider outside coaching professionals to support their campus or program through an outsourced vendor contract. The second scenario is for institutions that are considering designing and developing a coaching department within their institution or organization. The chapter provides evaluation and selection criteria for selecting an outsourced coaching service, discusses a set of key implementation considerations, and outlines the operational steps to implementation of outsourced coaching services. The chapter recommends that institutions conduct an open RFP process for the selection of an outsourced coaching vendor. A sample timeline with a sample RFP are provided, along with a proposed implementation process. For institutions interested in designing and developing their own internal coaching operations, the chapter offers six key considerations and core principles to guide the project in order to ensure a focus on the most important coaching concepts and elements.