The purpose of this study was to explore the relationship between the attitude toward mathematics, including related mathematics anxiety, and the frequency of classroom observations of mathematics lessons by elementary school administrators. This study considered Approach-Avoidance Motivation as part of the conceptual framework guiding the research. Approach-avoidance motivation refers to a person's approach of tasks that are pleasant or enjoyable and avoidance of tasks that are disliked or not enjoyable. This research sought to answer the questions: 1. What is the academic background in mathematics of elementary school administrators? 2. What is the attitude toward mathematics of elementary school administrators? 3. What is the frequency of classroom observations of mathematics lessons by elementary school administrators? 4. What, if any, is the relationship between the attitude toward mathematics, including related mathematics anxiety, and the frequency of classroom observations of mathematics lessons by elementary school administrators? The participants in this study included elementary school principals and assistant principals in one school division in Virginia. Data were collected to investigate the mathematics background, attitude toward mathematics, and frequency of classroom observations of mathematics lessons by elementary school administrators. This study also examined the possible relationship between the attitude toward mathematics, including related mathematics anxiety, and the frequency of classroom observations of mathematics lessons. The attitude toward mathematics, including related mathematics anxiety, was found to have no relationship with the frequency of both formal and informal classroom observations of mathematics lessons conducted. The sample population data indicated positive attitudes toward mathematics and low levels of mathematics anxiety, which conflicts with some previous research (Dorward and Hadley, 2011; Hembree, 1990). The mathematics background of participants was found to be limited in the number of mathematics courses completed and teaching licensure endorsements specific to mathematics instruction. The findings provide educational leaders with relevant research related to attitude toward mathematics and the instructional leadership practice of observing mathematics classrooms. Central office and school leaders could benefit from explicit expectations relating to the observation of mathematics lessons in schools. / Ed. D.