Many school leadership programs are set and delivered in specific modules or workshops in order to achieve a pre-determined set of competencies, knowledge, and skills. In addition, these programs are driven by the faculty member and the prescribed content. As Singapore schools become more complex in the roles and responsibilities to educate the future of the nation, new ways to develop school leaders is needed. This study investigates the effects on leadership learning based on a complexity theory-based design leadership program. The learning outcome emerged as practical leadership knowledge that participants generated as they actively participate in the leadership program. A serious implication of complexity-based design would mean shifting from an “objective and course-driven” learning to “learning that emerged and process-driven.”