Teacher Leadership is an effective way to support positive school change (Lai and Cheung 2015; Mangin and Stoelinga in Effective teacher leadership, Teachers College Press, New York, pp 1-9, 2008). To accelerate success, professional development programs aimed at building teacher leadership have proliferated across the globe. And yet, teacher leaders attending such programs often report difficulty in transferring their new knowledge and skills to their schools in meaningful ways (Snoek and Volman in Teach Teach Educ 37:91-100, 2014). In this study, we propose these results may stem from a failure of such programs to support double loop learning. To test this idea, we apply Argyris and Schön's (Theory in practice: increasing professional effectiveness, Jossey-Bass, San Francisco, 1996) theory of action framework as a tool to examine teachers' (n = 13) and administrators' (n = 6) experiences with a teacher leadership development program and specifically whether there were gaps in their espoused theories and theories-in-use. We find double loop learning occurred regarding informal teacher leadership and the cultural norms of autonomy, egalitarianism, and seniority. However, such learning did not extend to principals' orientation towards shared decision making and authority. While administrators (re)-created structures for teacher leaders to participate in such decision-making (e.g., instructional leadership teams) (i.e., single loop learning), they failed to shift power and authority regarding decision-making in these venues. As a result, teacher leaders' efficacy was diminished as was the school's ability to fully engage in change.