This dissertation is a study of policy stakeholders (N = 24) in four countries within the regional Caribbean Community and Common Market (CARICOM) policy environment. The scope was to identify how they navigated and interpreted conceptualizations of TVET and general education, which have been explicitly tied to national and regional sustainability, development, poverty abatement and skilled labor migration initiatives. Despite variable levels of codified TVET policy, academic centric institutional frameworks, and political will, education policy stakeholders recognized the substantive impact of TVET on their nations and the region. Supported by networked regional knowledge exchanges that are informed by shared tenets central to the Ideal Caribbean Person, they strategically implemented nationally adapted blended TVET and academic education policy. As such, this policy environment has operationalized a rarely seen collaborative governance institutional design and learning system, quadruple-loop learning. At the national level, quadruple-learning principals conditioned calculated risk-taking and innovation, which productively informed regional knowledge exchanges and policy. As an effective tool to recognize, identify, and manage wicked problems, the outcome of this research is a new quadruple-loop learning policy model useful across different regions, national contexts, and connected institutional systems. Data was collected from interviews, policy documents, environmental scans, and public records. Analysis methods employed triangulating coded data, and network and policy analyses to produce modified comparative multi-site case studies and a comparative analysis of case study findings. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]