The post-modern economy has altered the career landscape – career trajectories are now far more fluid and unpredictable, punctuated by multiple occupational changes, increased job mobility and more frequent and increasingly difficult job transitions. Leaders are frequently ill-prepared for the changing world of work that is progressively dominated by self-managed careers. Taking on a new role is fraught with complexity - for the “chosen one” and for organisations. The implications of successful, failed or derailed job transitions can have strategic and other ramifications for organisations and individuals alike. This study explores the career transition experiences of and the usefulness of career transition executive coaching for eleven individual leaders from various South African organisations. It is a descriptive, explanatory and exploratory qualitative study, employing the systems psychodynamic paradigm, chosen because it focuses on depth psychology and is a developmentally oriented, psycho-educational organisational theory. The study adopted an interpretive stance for understanding leaders’ systemic conscious and unconscious behaviour. The ACIBART model helped to interpret the experiences of leaders in transition. These transitions involve the taking and making of a role, implying the loss which attends leaving a previous role, and adjustment to and being authorised in a new, unfamiliar role, including a liminal period of being “in between”. This inevitably produces an inner drama in which internalised past figures, possibly related to the new role, are brought back to life, and perhaps even amplified in the present. These “unconscious echoes” explain the powerful emotions that frequently attend transitions, especially at the so-called mid-life, and which in turn activate various defence mechanisms. The systems psychodynamic approach to career transition coaching was particularly useful in helping the participants identify personal patterns and link these to their past and thereby develop personal awareness and insight. The “coaching space” thus became a containing, “transitional space” where the participants could safely do the work required to make the adjustment to their new roles. Finally, recommendations to various stakeholders regarding the provision of systems psychodynamic coaching for leaders in career transition are made. / Psychology / D. Phil. (Psychology)