This qualitative exploratory single case study was completed to analyze the role of how middle managers evaluate coaching ability of front-line supervisors, address unsuccessful coaching, and learn how those determinants factor into the manager's employment decision respective to retaining or hiring a front-line supervisor. The investigation occurred at a regional company in the Midwest of the United States that had previously attempted to enact a coaching culture program. Focus was placed on senior leaders and hiring/middle manager viewpoints and interviews were conducted with nine middle managers and three senior leaders. Additional data points included document analysis, direct observation, and expert testimony from a consultant who had worked with over 100 companies to implement a coaching culture. Data were analyzed through an eclectic two-phase coding system with emphasis upon hypothesis coding, word frequency, and thematic coding reassembly. Identified themes were then investigated through a lens of assertion development, and decision modeling. Five critical conclusions emerged and those findings aligned to how companies evaluate coaching ability and use those assessments in hiring decisions. Each of the five findings have a direct effect on the success of implementing a coaching culture. (1) Leaders should fully align on organizational coaching expectations, behaviors, and definitions. (2) Organizations need a robust coaching supervision program to evaluate current front-line supervisors. (3) Companies need to develop a comprehensive interviewing process to ascertain the coaching ability of potential candidates for the front-line supervisor role. (4) Leaders should also mitigate factors that inhibit coaching activity particularly emphasizing the importance of the coaching dyad. (5) Companies need to ensure the quality and consistency of coaching throughout the organization.