Change process research often discusses barriers that impede organizational change (e.g., Banta, 1997; Cavacuiti and Locke, 2013; Mutchler, 1990; Stewart et al., 2012); however, no empirical research has addressed how behaviors established in leadership models counteract these barriers. This study explored these two interconnected constructs of leadership and change in stories of secondary school department chair change attempts, and identified specific leadership behaviors described within their stories that aided the conversion of change barriers into conditions that enhanced the change process. Leadership behavior identification within department chair stories of change was guided by Blake and Mouton’s (1962) leadership theory, which has been further delineated by Yukl et al. (2002), and identification of change process barriers was guided by Ely’s (1990a) eight conditions for change. From the combined descriptions of six successful and four unsuccessful narratives of department chair-led change emerged essential conditions for change and commonly occurring change barriers. Specific leadership behaviors capable of overcoming these change barriers were also identified. Unexpectedly, this investigation also unearthed a change barrier seemingly unrelated to previously identified conditions of change: the contentious resistor. The contentious resistor was described as the most detrimental barrier to department chairs’ leadership of the change process.