Employees desire performance feedback which helps them understand what they are doing well, what they are doing wrong, and how to develop so that they can advance in their careers. Yet, many comment that they do not receive enough performance feedback to help them understand if they are being successful in their work or where they can improve. In this qualitative study, I pursued the question of what might prevent supervisors from providing performance feedback to their direct reports by interviewing a group of front-line supervisors and their wardens in two Midwest Prisons. My goal was to identify what the supervisor participants believed performance feedback was, how they understood and explained their personal feedback delivery practices, and how they learned to deliver feedback. My research methodology involved three stages of data collection, including collecting a range of documents from the prison system, one-on-one interviews with the two wardens who led the two prisons involved in the study, and one-on-one interviews with 16 Sergeants. I leveraged Kolb’s Experiential Learning Cycle (ELC) as the theoretical lens of this study. As Kolb (2014) explains, every time an individual has an experience, they have the opportunity to learn from that experience. I was curious to understand if a group of supervisors in a correctional work environment learned how to deliver and improve upon their performance feedback practices through the on-going delivery of feedback. Through the data analysis process, I found that both Warden participants deeply valued performance feedback as a teaching method and see it as an important method supervisors can utilize to enhance Correction Officer (CO) growth and development. Additionally, I found that the majority of supervisor participants (15/16) believed and understood delivery of performance feedback to COs to be a function of their rank, while a slightly smaller majority (10/16) explained it as a responsibility of their rank. Further, I found that the supervisor participants naturally employed a comprehensive range of performance feedback best practices including being positive and supportive (14/16), providing praise for work done well (13/16), correcting poor performance or incorrect understanding of policy or procedure (12/16), and conducting the feedback exchange as a conversation (10/16). Finally, I found that the supervisors’ beliefs and understandings of how they learned to provide performance feedback align with Kolb’s ELC. A majority (13/16) of the supervisor participants explained that they learned to deliver performance feedback through experience (having an experience, ELC first mode) in the supervisory role, while half of the supervisor participants (8/16) described how they learned to deliver performance feedback to Correction Officers (COs) through reflecting on prior experience (reflecting on experience, ELC second mode). Several of the supervisor participants (5/16) explained how they thought through and planned (Abstract Conceptualization, ELC third mode) their feedback conversations with COs, while a small minority (2/16) of the participants spoke to their practice of experimenting with new approaches when delivering performance feedback (Active Experimentation, ELC fourth mode) to COs. I close my study by offering recommendations based on the findings to front-line supervisors, wardens, and to trainers and educators working within correctional organizations.