This mixed-methods study examined the relationship between leadership behaviors and successful second-order change, in the case of a once traditional elementary school in the midwestern United States that transformed beyond the industrial-age design into a learning model that fosters the skills essential to success in the 21st century. This descriptive case study was anchored in the theoretical constructs of transformational leadership (Burns, 1978; Bass, 1985), transformational educational leadership (Leithwood & Jantzi, 2000; Leithwood, Jantzi, & Fernandez, 1994), and second-order change (Watzlawick, Weakland, & Fisch, 1974). Nine faculty members from Webster Elementary School completed Leithwood's Educational Leadership Survey; descriptive statistical methods were used to analyze survey data. Three survey respondents also participated in a follow-up focus group discussion based on survey results. Two school administrators participated in semistructured interviews; interview questions were guided by data collected during the focus group discussion and grounded in the results of the teacher survey.