This case explores Crabapple Middle, a struggling urban school in the midst of a transition that seeks new leadership that can overcome the challenges of two sub-cultures that divide the school and community. In an effort to address issues of low academic performance and negative community perception, an International Baccalaureate magnet program was introduced as a proactive solution. However, the failure to engage in problem posing to identify underlying problems lead school leaders to seek solutions too quickly and to overlook the deeper systemic issues. Teaching notes are provided that outline the concept of problem posing as a means of overcoming the rush to problem solving. Teaching notes advocate for actively prompting discourse that challenges the theory/practice binary and facilitates discursive assessment and critical reflectivity.