Conversations of head, heart, and hand require a very personal exploration and so we often refer to this work as a courageous conversation. Involvement of the affective domain as well as the cognitive domain ultimately determines what actions we might take for dismantling oppressions. Another dimension of this exploration must also include how each of us, regardless of our identity, is hurt by oppressions. Healing therefore is an element of this reform effort. Any reform effort designed to reduce the achievement gap that does not help whites and people of color heal from the hurts of racism will not likely succeed over time. Instead Margaret Wheatley emerges from the intentional design of social justice leaders that promotes reflection and provides direction. This chapter present five attributes of design that have proven to nurture engagement, participation, and continual reflections. They are Attribute of Design: Balance, Conditions for the Conversation, Definitions, Reflection as Pedagogy and Space.