The article aims to provide a standpoint from which to critically address two broad concerns. The first concern surrounds a naive view of mindfulness, which takes it as a given that it is a good thing to cultivate mindfulness and attendant qualities like compassion because these virtues are key to improving the quality of life and bettering effective decisionmaking within business. Yet the virtue of mindfulness has roots in religious and spiritual traditions, and the virtue of compassion is complex and contextual; neither of these virtues operate in a vacuum. Nor do they function independently from other virtues and values. Reasonable people of goodwill possessing the virtues of mindfulness and compassion in good measure, may nevertheless strongly disagree about what the compassionate, mindful thing to do is, particularly in a business setting. It is, moreover, conceivable that intensively cultivating mindfulness and compassion could lead one to reject altogether the “dog-eat dog” culture of competitive business that draws upon selective features of mindfulness meditation that lie in the corporate comfort zone yet which are not especially countercultural from a religious or spiritual vantage point. The second concern is that Western virtue-based business ethics is largely confined to academic philosophical theories. As such, virtue-driven business ethics is often more centered around developing theoretical wisdom than developing “hard core” practical wisdom earned through yoga asanas, meditation, chanting, and breathing, whereas for contemplative practices the reverse is the case, with practical wisdom (“knowing how-to”) emphasized over theoretical wisdom (“knowing that”). Accordingly, the article examines prospects for cross-fertilization between, on the one hand, mindfulness and compassion interpreted as virtues in Eastern contemplative practices, and on the other hand, mindfulness and compassion as interpreted within Western virtue-oriented business ethics. Illuminating a pathway for such interpretative cross-pollination calls for an appropriate conceptual frame of reference that the article organizes around a set of interconnected themes. The first theme is that mindfulness and compassion represent key virtues within contemplative practices. This indicates a promising touchpoint between Eastern and Western traditions: their respective focus upon character, inner states, intrinsic motivation, and self-improvement toward ethicality in the world. The second theme is that such virtues in Eastern contemplative practices, as well as character traits integral to Western virtue-oriented approaches, denote contested “normative-interpretive” concepts that engage philosophical debate rather than indisputable empirical-criterial concepts that can be taken at face-value. The third theme advocates moving beyond behaviorist and neuropsychological accounts of virtue, approaching character traits of Eastern contemplative practice and Western virtue ethics through nonscientific inquiry into normative interpretive questions concerning such virtues (questions about meaning, responsibility, the nature of the self, reasons for acting). This supports debate over competing views of the nature, purpose, cultivation, and cultural context of mindfulness, compassion, and other virtues – issues arising as mindfulness enters the business management sphere -- to be conducted on normative grounds. With the background conceptual framework established, the article presents key points about the prospects for cross-fertilization between virtue ethics and contemplative practice, and why it matters, with reference to business ethics.