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This paper describes an innovative cognitive-coaching program for mid-career principals. Coaching, as opposed to mentoring, pinpoints leadership development as goal-oriented instead resembling sponsorship for career-building. Socratic questioning remains a preferred coaching strategy in multiple-fields; rarely used in principal development. This report describes how a group of coaches used questioning with practicing principals in guiding their capacity for school improvement. With solution-focused questioning, coaches helped principals serve as powerful social support for improved teaching and learning. An emergent finding associated with this program unveiled the emotional work of leadership and supports multiple calls for revamping professional learning to address emotions in teaching, learning, and leading.