High school students feel pressure to excel in their school subjects and participate in after-school activities. However, with scheduled hours in the school day, students must find a way to balance their academics and their after-school activities while finding time to sleep. Some research suggests that later start times may increase students' attention span, thereby allowing students to excel in their studies. Other studies show that despite the suggestion that start times should be later, high school start times have remained the same. To examine how district administrators view high school start times, this study asks a primary research question: What do Wisconsin superintendents report when considering high school start times? For this study, data were collected in a survey which was sent by email to all Wisconsin superintendents with at least one brick and mortar high school in their district. The response rate for this survey was 29.49%. The data analysis techniques were descriptive and inferential statistics and Exploratory Data Analysis (EDA), away to determine outliers and examine patterns in the data. From the analysis, the findings were that: (a) Superintendents reported they were informed about the comprehensive list of school district and community factors they had to consider in the process of changing a high school's start time; (b) Superintendents rejected alternative programming options that allowed for a later high school start time; (c) Superintendents rejected the idea that a later high school start time would improve students' health concerns; and (d) Superintendents reported that they feared negative consequences associated with delaying after-school activities would happen to families such as a loss of income. Three recommendations to superintendents and policymakers are as follows: (1) continue to evaluate evolving educational technology to examine alternative programming options for schools; (2) continue to examine potential costs and benefits of a later high-school-start time; and (3) engage with legislators in the discussion about start times. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]