Challenges such as overcrowded classrooms, poor administrative and parental support, loss of control in the classroom, and bureaucratic red tape are enough to make any teacher abandon the fight for educational excellence and run for the ridge. When teachers retreat, they cross a line between simple stress and serious burnout. In burnout, their relationships become increasingly depersonalized and they become chronically pessimistic. Teachers in or approaching burnout suffer depleted energy, lowered resistance to illness, increased absenteeism, and decreased effectiveness on the job. Consequently, everyone suffers when teachers are trapped in this cycle of stress, withdrawal, and burnout. But not all teachers are consumed in this cycle. Some cope well and remain resilient in the same environments that overwhelm others. This article discusses five crucial conversations that drive educational excellence while preventing teacher burnout. These crucial conversations can be tricky to navigate, and all require skill. Some approaches that will help reduce stress and increase the chance of a good outcome are presented.