This article describes the ways in which a 25-hour internship with families who have children with disabilities impacted four doctoral students in educational leadership. We discuss the lessons we learned as a result of our experiences and provide insight into the structural components of the internship experience that were critical to enhancing our professional development. Key lessons include: (1) the realization that disability is a socially-constructed term that does not describe the talents, feelings, and aspirations of individuals with disabilities; (2) increased knowledge and strategies about how school leaders can provide support to families by listening to their hopes, dreams, and challenges; and (3) the critical need to include families in decision-making processes to ensure that the family perspective is represented. Important structural components of the internship experience included spending time with families in their homes and communities for extended periods of time. Implications for the preparation of educational leaders are discussed.