Issues of gender, leadership, and values have occupied the minds of researchers in educational administration and leadership for decades. Breakthroughs in neuroscience and neuroepigenetics have produced numerous insights into the complex operations and influences in the human brain between men and women. Taking into account some of these differences, in this chapter, I will revisit the literature on leadership, gender, and values with a two-fold purpose: one, to review understandings that have accumulated, and two, to add a new perspective for re-examining these understandings. At first, I review existing theories of gender, leadership, and values, paying attention to the different modes of operation between men and women to recapture the conclusions these lines of research have produced. Then, I turn my attention to recent findings from neuroscience and neuroepigenetics as a new lens through which these reported differences can be illuminated. My thesis in this conceptual paper is to raise awareness of this emerging line of research and its potential to shed more light into the neural dark of our conceptions about gender and women’s ways of leading in education with significant implications for educators and educational leaders.