Objectives:Until now, rather limited empirical research has been conducted as regards managers who coach their employees (Crabb, 2011). The aim of this research was to investigate the managers’ challenging and successful experience when coaching their employees and how these coaching sessions were assessed by their employees.Design:The overall study investigated 15 middle managers – from a major Danish nationwide company who were trained to coach by two coaching psychologists through theoretical presentations, individual coaching and peer coaching sessions with direct supervision (learning-by-doing: Spaten, 2011b) – when they were coaching their 75 employees through an online survey and semi-structured interviews.Methods:Four middle managers and employees were interviewed after the intervention. Thematic analysis was chosen and elicited three main themes: (1) coaching skills; (2) professional and personal development; and (3) the coaching relationship and power relation.Results:The study found that the manager as coach should be highly sensitive and empathetic in building the coaching relationship, should be aware of the power relation, and should draw clear boundaries between their role as leader and their role as coach. The middle managers’ coaching skills were assessed very positively by employees.