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This contribution focuses on the connection between Scharmer's Theory U and individual coaching. How can Theory U be used in coaching for supporting transformational learning in coachees? First, the authors present an approach called Core Reflection. In this approach, Theory U is linked to specific levels of reflection and awareness, described by the so-called “onion model.” Through the use of Core Reflection, the personal and professional aspects of both inner processes and performance become connected. Two research studies on the use of coaching based on Core Reflection with teachers show its strong impact on practitioners, clarifying how it can promote deep learning and strengths-based performance, even in situations experienced by the coachee as problematic. The authors conclude that the Core Reflection approach is a practical and effective method for helping people move through Scharmer’s …