Principals must cope with the pressures arising from accountability while enabling flexibility in teachers' work. How do principals manage these tensions when attempting to improve their schools? And where are these tensions most commonly centered? Both questions relate to "managerial ambidexterity," or how principals simultaneously advance coordination and flexibility to motivate teachers. The process of managerial ambidexterity is not well understood either conceptually or empirically in the school and management literature. To investigate the topic, I take an exploratory and qualitative approach. Through an investigation of 15 school principals, I find that their managerial ambidexterity strongly resides in resolving tensions located between performance-based accountability and the professional autonomy of the teacher. To resolve these tensions, principals use three methods, including affective appeals, cognitive interpretation, and the use of data. I link these methods to specific profiles of schools where principals engage in their managerial ambidexterity differently. Principals' perceptions of their context act to condition which methods are employed. I describe these school-levels contexts as layering in political schools, drops of control in low systems schools, matching in high systems schools, and masking in humanist schools. My findings show how some principals develop their organizations differently through various forms of ambidexterity enactment. [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.]