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This qualitative study is a two-part inquiry into the issues of superintendents from mid-western and western states. Part one of the study focused on gathering the issues of superintendents from open-ended questions and part two of the study focused on digging deeper into the issues by capturing the voice of superintendents through semi-structured interviews. Data was thematical coded and findings were distilled through the feedback gathered through the Research on the Superintendency Fireside Chats held during 2022-24 as a method of centering the data. Emergent Themes from part one of the study centered on teacher shortages, funding concerns, building relationships with internal stakeholders and concerns with external ones, and assistance from researchers on adequacy models and foundations of basic education.