The purpose of this study was to determine if the teacher’s leadership style in the middle school classroom is related to students’ willingness to engage in challenging cognitive tasks. Seventh and eighth grade students (N = 689) from an affluent suburban middle school were surveyed using an online survey of combined questions from the Multifactor Leadership Questionnaire (MLQ Form 5X-short) and the Patterns of Adaptive Learning Scales (PALS). The outcome factors on the MLQ (5X-short) were not included, and the PALS survey was shortened to use only the student questions that were applicable to cognitive engagement factors. Students rated their teacher’s leadership style based on transformational, transactional, and passive-avoidant behaviors from the MLQ (5X-short). Students also rated their own personal goal orientations, classroom goal structures, academic efficacy, academic press, and avoidance of novel work using the adapted PALS instrument. A bivariate correlational analysis was run using SPSS, Version 19, software. Additional correlational analyses were run for each subject area. The highest statistically significant positive correlations were found between transformational leadership and mastery goal orientation (r = .343, p < .001), mastery goal structures (r = .563, p < .001), academic efficacy (r = .490, p < .001), and academic press (r = .736, p < .001). Statistically significant positive relationships were also found between transactional leadership and these desired student factors, but the relationships were not as high. Statistically significant negative correlations were found between passive-avoidant leadership and mastery goal orientation ( r = -.214, p < .001), mastery goal structures (r = -.451, p < .001), academic efficacy (r = -.381, p < .001) and academic press (r = -.473, p < .001). The highest statistically significant correlation was between transformational classroom leadership and academic press in art/drama (r = .832, p < .001).