This paper presents a dilemmatic approach to democratic school leadership and governance (DSL). Rather than viewing dilemmas and inner tensions as debilitating democratic governance, a dilemmatic approach views tensions between core values as a defining feature of DSL. A dilemmatic approach differs from central views in the field by regarding DSL as a variable mode of democratic governance, characterized by a dynamic movement across democratic models. After discussing prominent views in the DSL literature, the paper concludes with a discussion of the principles that assist in elaborating the mechanism activating the movement among different modes of DSL.