School heads in Zimbabwe face relentless changes in the environment in which they operate. Volatility, uncertainty, complexity and ambiguity (VUCA) created by the diversity, intensity and rapidity of these changes present challenges on ways to effectively lead as existing methods apparently prove inadequate. This study examines the major sources of volatility that affect school operations in Zimbabwe. It explores the challenges faced by school heads as they live through volatility in their operational environments. It further explores the strategies that have been put in place to ensure that schools counter these challenges. The study employs a mixed design methodology that involves the use of both qualitative and quantitative methods complementing each other. The study employed convenience sampling to select twenty school heads that formed the study sample. The theoretical framework guiding this study was the chaos theory. The study found the major sources of volatility and resultant challenges were economic crisis, political interference, globalization, poor technology and disasters (both natural and manmade). The study found that agility, that is, the ability to communicate across the organization and to move quickly to apply solutions, was the key strategy school leaders could employ to cope and win in volatile environments. Resource planning was also found to be an important strategy to win in volatile environments characterized by many changes that affect the normal operations of schools. Perhaps the major finding was that complex problems in schools could be resolved through deliberate coordination, interventions and creative effort. System oriented thinking was found to enhance such interaction and engagement. The key recommendation for this study was the need for school heads to employ readiness strategies in turbulent environments and organizational resilience principles in line with this study’s findings.