Digital transformation is a nebulous concept that transcends mere business model tweaks and process shifts. True digital transformation requires leaders to take a step back and profoundly rethink how their people, processes, and technology translate to business success. We as cybersecurity leaders must understand how to lead through transformational projects and deliver outcomes without destroying the trust of the business, impacting culture or creating burnout among employees. This session explores a humanistic angle of digital transformation and the importance of leadership, understanding, and grace through change.