In its desire to build a bridge between self-awareness and morally responsible leadership, this chapter seeks to contribute to the theory of authentic leadership. The central thesis of this chapter is that Ignatian spiritual discernment is a valuable resource for making this connection. Ignatian Spirituality is directed at the world, the world beyond the self and the world beyond our primary experiences. It is inherently aimed at the common good and is therefore an interesting source when contemplating moral leadership. We will discuss the Spiritual Exercises of humility, silence, and detachment, the prevalence of emotions and imagination, ethical evaluation, and journaling and mentoring as means for increasing self-awareness. We will do this in dialogue with the new Theory-U. This, too, is an approach where societal meaning is fundamental and seeks to increase awareness and genuine openness to the future by letting go of the self. This makes for an interesting dialogue, leading to a deeper understanding of spiritual discernment.