This chapter examines what constitutes a trust-conducive state of affairs and suggests a way forward that will facilitate strengthening trust in organizations that have a strong chaordic nature, at least in terms of their informal underlying cultures. One kind of trust is associated with the confidence that an individual will keep plugging away, continually trying new things or alternative paths to their destination. Issues surrounding interpersonal trust are better understood in situations where individuals have relatively frequent face-to-face contact. The chapter discusses trust among individuals, or within and between groups and organizations. Suppressing the acknowledgment of people’s feelings can be counterproductive to the long-term effectiveness of an organization. The Harvard Business School has surveyed executives to establish a database from which to evaluate the relative degree to which any organization that completes the survey can be considered to be a learning organization.