Organizational approaches to knowledge management are unlikely to lead to organizational wisdom unless the organization increases its awareness of factors that contribute to epistemological myopia—a nearsightedness that limits what and how the organization knows and how it learns. Contributors to this myopia include organizational learning pathologies, an unquestioning acceptance of fundamental concepts, such as time, and measuring success as the absence of failure. In many instances, the vocabulary, language, and business methods used by an organization, society, or culture reify these pathological factors and thereby further hamper the potential for learning. By raising our awareness of these contributors and the factors that support their reification and continued acceptance, we seek either to avoid these limitations or to develop corrective lenses that can extend the organization’s vision and enable it to resolve issues with greater clarity. The conceptual frameworks used in this chapter are drawn from four distinct areas of study: systems theory, organizational knowledge and learning, the organization as a learning community and community of practice, and linguistic relativity. The underlying theme is the organization as an inquiring system—a system that seeks to learn and become more knowledgeable. Because learning processes are culturally biased, and the bias is reinforced by a culture’s values, language, and vocabulary, the premise is that these biases and values constrain the organization’s epistemological methods and processes. The potential solutions to epistemological myopia include deliberate nurturing of cultural diversity, the institutionalization of Singerian approaches to inquiry, and the fostering of managed risk in experiments that do not guarantee success. While few organizations exhibit all of these desirable characteristics, there are some examples from the literature and practice that provide confidence that organizations can avoid epistemological myopia.