ABSTRACT This study examines how leaders of community sport organizations (CSOs) engage in a strategic planning process through the intersection of institutional work and the strategy-as-practice (SAP) approach. The SAP approach focuses on the micro-level social activities, processes, and practices that inform how organizational leaders engage in strategic planning. A multiple-case study of four CSOs with contrasting approaches to the practice of strategy provides insight into the role of strategy practitioners and their choice of strategy activities. The study also examines how these activities contribute to the procedural legitimacy of strategic planning. The findings highlight four roles that strategy practitioners hold within their clubs (i.e. consultant, board member, staff member, facilitator) and three general types of activities that indicate varying levels of stakeholder involvement in planning. The findings provide evidence of the need for a granular approach to the study of strategic planning and a focus on how organizational leaders’ roles and choice of activities shape strategic planning and its legitimacy.