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Little is known about what happens in a coaching conversation when an executive is at risk of derailing. Consequently, the coach might be unsure how to manage such challenging engagements. This phenomenological study takes the coach’s perspective in focusing on this gap in the evidence base. Findings highlight the importance of quickly tuning into the client’s unconscious scripts and schemas manifesting the maladaptive behaviour and high emotion. Readiness for change is identified before applying appropriate strategies and interventions. The coach is however required to apply their skills in complex environments where the vagaries of organisational systems become exposed.