Many start-ups fail, or are abandoned, due to flawed reasoning underpinning their products, business models, and engines of growth. Similarly, many strategic initiatives in large enterprises fail, or are decommissioned, because they are predicated on faulty assumptions that do not comport with reality. The lean start-up and lean enterprise approaches encourage decision makers to test their fundamental hypotheses and effect strategic pivots to identify new and superior fundamental hypotheses. This paper presents a model-based approach to support reasoning about strategic pivoting. It outlines key constructs from the i* modeling language that can be used to model various pivot types. Experience with a real-life application provided a preliminary validation about the benefits of modeling to support pivoting. The case study demonstrated how this approach can be used to compare alternatives for pivoting as well as to generate further ideas for alternative pivots.