In this article we share our learning experiences on the organizational design barriers we perceived to have encountered with scenario planning in higher education for program development. Our perceived barriers discussed include misalignment of culture and change intervention; constructing organizational reality and meaning making; knowledge creation and transfer of knowledge; and short term versus long term outcomes. Our retrospective analysis contributes to the understanding of the complexity of change in higher education and adds to the knowledge base on using scenario planning in a bureaucratic, hierarchical context. Our experiences are incongruent with implicit assumptions that scenario planning can be used in any context (Balarezo et al., 2017), and illustrate some important constraints to consider before using this type of forward-thinking intervention. We provide recommendations for using scenario planning and for transformational change in higher education. These changes have implications for more creative, future-oriented educational planning processes for improving higher education teaching and learning experiences.