This chapter explores the perceived impact of strategic learning plans on growth-focussed small service firms from the owner-manager’s (OM) perspective. Adopting a social learning lens, the study employs the action research method, involving three cycles performed over a 12-month period wherein the authors studied the co-created design and implementation of a strategic learning plan in each of the three participant firms. Findings present insights into the ways in which firms that wish to grow can be facilitated to learn strategically. A contextualised approach involving OMs in both design and implementation resulted in openness to the formal planning process. Notably, OMs may impede growth depending on their learning orientation, planning perspective, and their ability to delegate tasks. Over time, the OMs honed their reflective skills to the benefit of organic learning strategies. There was a distinct preference for social learning, and a perceived need for external monitoring to sustain plan momentum. The proposed framework offers a process for embedding a strategic learning approach in order to leverage strategic position. It also highlights the value of considering and evaluating OM perceptions of their own learning activities and the impact that these perceptions may have on the enactment of enabling policies to promote growth in their firms.