Organizations increasingly engage executive coaches to help leaders develop capabilities necessary to achieve strategic change outcomes. A review of the strategic change, strategic leadership, and executive coaching literature reveals the relationship between coaching and strategic change leader development remains unexplored in academic research. On the one hand, researchers of strategic change have not explored how organizations develop those charged with leading strategic change. On the other, researchers of strategic leadership and executive coaching have not examined the relationship between executive coaching and the development and outcomes of strategic change leaders. This study investigates the relationship between executive coaching and strategic change leader development of transformational leadership capabilities (TLC), as measured by an adapted version of the Transformational Leadership Questionnaire (TLQ), and readiness for change, as measured by the Holt Readiness for Change Scale. It also explores the effect of executive coaching on an important proximate strategic change outcome: readiness for change of strategic change leaders’ direct reports (subordinates). With repeated measures MANCOVA, I analyzed multi-rater data collected before and after 18 strategic change leaders received seven months of executive coaching. Those leaders were chosen to manage the enterprise-wide digital transformation of a 24 billion dollars revenue, 100,000+ employee company. A comparison group of 22 executives participated in pretest-posttest data collection. The results suggest executive coaching positively affects both strategic change leaders’ development of TLC, as assessed by their 360-degree stakeholders, and their readiness for change. Moreover, biweekly coaching sessions, as opposed to more frequent ones, and supplemental leadership development activities, such as participation on change acceleration teams, appear to amplify these outcomes. Executive coaching, however, did not have a statistically significant effect on strategic change leaders’ self-ratings of their development of TLC. It also appears to have had an adverse effect on the readiness for change of their direct reports.