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This study investigates the relationships among literature, educational leadership and teaching. A review of professional literature suggests that literature, leadership and teaching share the characteristics of meaning making, dialogue, artistic/aesthetic experience, transformation, and empathy. The purpose of the study was to consider current educational leaders interpretations of their experiences as humanities instructors and its connection to leadership in their current positions. The author reflects on preparation paths for prospective leaders as well. Three life stories were collected from current educational leaders who previously served as English instructors. Narrative inquiry methodology was utilized, and texts were analyzed using selectivity, slippage, silence, and intertextuality (Casey, 1993; Casey, 1995-1996). Each leader was positioned within a leadership paradigm based on their language and interpretive experiences as leaders. While all felt explicitly that their experiences as English instructors impacted their style and beliefs as educational leaders, textual analysis suggested that family background and personal experiences most influence leadership style and philosophy