Orientation: Leaders who find it difficult to connect emotionally with colleagues are often seen as incompetent, the idea that they may suffer from alexithymia – an inability to feel – is not taken into account. This coaching model seemed to be not successful in changing this behaviour pattern. Research purpose: The purpose of the research was to describe the coaching experiences of leaders with symptoms of alexithymia and to formulate hypotheses around their leadership experiences. Motivation for the study: Effective leadership is strongly associated with emotional connections with colleagues. Leaders suffering from alexithymia, struggle with making these connections. It was thought that coaching might help them bridge the gap towards building effective relationships. Research design, approach and method: A qualitative research design using case studies was used. Three participants underwent 10 months of systems psychodynamic leadership coaching, including role analysis. Researcher’s field notes and participant essays were discourse analysed. The researcher’s unconscious experiences were included in the interpretations. Main findings: Five themes manifested themselves namely, leaders’ difficult experiences with coaching, the dynamics underlying their normative, experiential and phenomenal roles and the coach’s unconscious experiences affecting the relationship. The research hypothesis referred to the differences between the role parts and the resulting anxiety. Practical/managerial implications: This coaching model did not provide sufficient opportunities for the participating leaders with regard to emotional reactivity and regulation. Contribution/value-add: The research created awareness of how alexithymia amongst leaders manifests in organisations. Unfortunately the coaching was unsuccessful in addressing the emotional task. Other ways need to be explored.