Although making mistakes is a part of human nature, they are still tabooed, covered up, or kept secret. This behavior probably has its origin in our socialization. Research has shown that errors made by people are perceived as a competence deficit. Causing of errors leads to a negative self-assessment, and also to rising perception of penalty as a necessity (März, 2007, Dimensions analytische Untersuchung zur Fehlerfreundlichkeit, Universität Duisburg-Essen, Essen). Since organizations can learn from both good and bad actions, a rethinking of these adopted settings is required (Argyris & Schön, 2006, Die lernende organisation: Grundlagen, methode, praxis. Stuttgart: Klett-Cotta). This article provides a concept for understanding and examining critical factors which support or inhibit the development of an encouraged “learning from failure culture” in an organization.