The success and satisfaction of students with online courses is significantly impacted by the sequencing of learning objectives and activities. Equally critical is designing online degree programs and structuring multiple courses to reduce learners' cognitive load and attain maximum learning success. In its current form, the evaluation of program design is complex and done primarily using stakeholders' perceptions and qualitative methods, which are subjective. Emerging technologies produce enormous amounts of educational data that have the potential to lead to evidence-based practice to reform the design of study programs. Although a few studies adopt such data-driven approaches to evaluate and enhance study programs, remarkably little is known about the sequencing of learning objectives and the influence of their mastery in one course on performance across subsequent courses. This study aims to assess the interdependency of learning objectives from multiple courses in a MOOC-based program by drawing on an interdisciplinary approach intersecting analytic techniques and measurement models. Situated in the context of professional leadership skill development, we ground our findings in leadership theory and how learners acquire skills over time and across varying contexts.