The purpose of the study is to analyze the challenges of coaching leadership in practice, by examining middle managers’ perceptions of their leadership. The study analyzes the challenges based on Habermas’ (1995) communication theory, Krams’ (1983) theory of mentor relationships, but also Sobel and Holms’ (2019) description of coaching as leadership. Coaching as leadership results from the transformative leadership, specifically from the content "inspirational motivation" where the leader and the manager are in focus when it comes to being a good role model. The study is a qualitative survey based on semi-structured interviews where the respondents are managers closest to the employees, often referred to as supervisors. The respondents were selected on the basis of a goal-directed sample where these came to be relevant for the research questions that were developed and for the implementation of the study. Six interviews were conducted and then analyzed with a thematic analysis according to Braun and Clarke (2006). When transcribing all the interviews, both main and sub-themes emerged, which were then analyzed and discussed between both of us authors. The choice of analysis method was based on the transcriptions contribution to creating a clear structure and thus facilitating the analysis of the material. The results showed that coaching leadership as it is theoretically described did not always correspond with the respondents' perceptions of their leadership. During the interviews, it was discovered that much of the leadership in the various organizations was situational with challenges that mainly revolved around communication, time and contextual factors. / <p>Godkänt 2022-06-15.</p>