The primary objective of this thesis is to evolve a method for assessing and developing features of a learning organization . To fulfill this, I approached the thesis by examining several research questions and using multiple research methodologies. The research questions were not all established at the outset. Rather, they evolved as features of a journey down a road less traveled. With this journey came the decision to write the thesis in the first person. The first research question was Q1: What will bridge the divide between organizational learning and the learning organization? By reviewing the extant literature on organizational learning and the learning organization, I developed a theoretical framework that linked these two streams. The framework suggests that the extent of divide between the two streams is determined by the extent of learning transfer. The learning transfer is affected by the learning barriers operating at the levels of learning (i.e., individuals, groups, and organizational). This led me to my second research question Q2: What are these barriers to learning transfer and how do they impact the levels of learning in the organization? I cumulated the dispersed literature on learning barriers, and synthesized the learning barriers into five key dimensions: Intrapersonal, relational, cultural, structural, and societal. I then used the Delphi technique on 17 individuals to investigate the impact of the learning barriers on the levels of learning. This generated two additional research questions. The third research question was Q3: How do individuals initiate a double-loop change? This deals with the little researched area of initiation of double-loop change whilst engaging with the interfaces at the levels of learning. I used multiple case studies to examine this question and found that individuals transit through four distinct stages when initiating double-loop change: 'embedded', 'embedded discomfited', 'scripted', and 'unscripted'. Once double-loop learning has been initiated at the individual level, it is important that it is transferred across the organization. Therefore, my fourth research question was Q4: How does a new shared understanding for a double-loop change develop across the organization? I did an in-depth, single case based investigation of an organization. Using Identity and Complexity theory perspectives, I tracked the evolving new shared understanding through four phases: de-identification phase, situated re-identification phase, transition phase, and identification with core ideology phase. The key insights from examining these research questions, particularly insights from examining Q3 and Q4, enabled me to suggest nine key organizational interventions necessary to overcome the learning barriers and develop a learning organization: Identifying, developing, and dispersing double-loop mastery; Enabling constructive contradictions; Creating a superordinate organizational identity; Building emotional intelligence (in individuals and groups); Ambidextrous leadership; Strategic support for experimentation; Promoting 'systems doing'; Accessibility of valid information; Institutionalizing scanning across industry boundaries. When these nine organizational interventions are implemented, they produce five new learning organization orientations: genetic diversity, organizational ideology, organizational dualism, organizational coupling, and strategic play. These five new learning organizational orientations provide the archetypes of the learning organization. I then developed an instrument to assess these five new orientations, and did a preliminary testing of the instrument. While aspects of my work overlaid with previous knowledge, new advances in knowledge were established by: Postulating a link between the streams of organizational learning and learning organization Synthesizing learning barriers into the five key dimensions, and investigating their impact on the levels of learning Understanding the stages of double-loop learning initiation by an individual, whilst engaging with the interfaces at the levels of learning Understanding the process of a new shared understanding evolving Postulating five new orientations of the learning organization