Background: Most adolescents in the United States do not obtain sufficient sleep. Early school start times play a significant role in adolescent sleep deprivation. Most primary and secondary schools begin classes earlier than the 8:30 am. Perceived barriers to implementing a delayed school start time have been suggested in the literature but have not been quantified. This study explored perceived barriers and facilitating factors for implementing delayed high-school start times. Methods: A cross-sectional study. School administrators who had delayed their school start times were invited to complete an online questionnaire ranking the perceived barriers and facilitating factors for implementing the delayed start times. Results: Most commonly cited perceived barriers were lack of a tiered bus system, school athletes missing more afternoon classes, and less time after school for athletics. Most commonly cited facilitating factors were school-administrator involvement in the decision-making process and sleep education for family members and school administrators. Conclusions: Participants found that providing sleep education to fellow administrators, teachers, school staff members, families, and students and including them in the decision-making process positively facilitated the implementation of delayed school start times. Perceived barriers to implementation may be overcome with support from stakeholders and planning committees.