Wisdom is not an abstraction. It isn’t a static state of peace, beauty, or justice. Although a wealth of philosophical treatises and literary reflections have articulated visions of existence lived wisely, finally, wisdom is about making choices in the concrete circumstances of life. In the process of decision-making, persons are conscious and intentional about living their values and priorities. In the heat of discernment, one faces the embodiment of one’s character and identity. This process of discernment is equally important for organizations of all kinds, from families to unions, from NGOs to multinational corporations. The quest for wisdom requires two key dimensions: a process for wise decision-making and a set of criteria upon which to base judgments. This paper will propose one such process and set of criteria based on core themes found across the Jewish wisdom tradition, the Christian scriptures, and the Rule of Saint Benedict. The creation of a set of operating principles for decision-making will be informed by the contemporary theory and practice of dialogue and by the reflection and formation processes used so effectively by Parker Palmer in his programs and writings on the courage to teach and lead. Admittedly, this process and set of criteria will be grounded in the Western philosophical and theological tradition. However, the process will be open to and will intentionally invite the perspectives of other traditions, so that a self-transforming process for discernment is envisioned. The following core themes that permeate the Jewish wisdom tradition, the Christian scriptures and the Rule of Saint Benedict will be explored: 1. valuation of the diversity of voices, especially the perspectives of the marginalized and disenfranchised; 2. integration of the whole person—body, mind, soul and spirit; 3. realization that truth is embedded in common human experience; and 4. the necessity for preservation and transformation. Drawing out the implications of each of these core themes, operating principles for the decision-making and criteria for judgment will be identified.