The workshop “Case Studies: Challenges and Opportunities” at the TESOL convention focused on strategic planning for small and midsized organizations. The goal was to understand strategic planning as a strategy for assessing the organization’s performance, identifying any challenges, and seeking future opportunities. The presenter shared the process Maryland TESOL went through during the planning for the plan and forming the strategic planning committee. She then shared the support the committee received from the organization and the current board members. Finally, the presenter shared some of the findings from the strengths, weaknesses, opportunities, and threats analysis (SWOT). The participants in the workshop had the opportunity to reflect on their own affiliates’ needs during the SWOT analysis. The workshop was a great opportunity for affiliate leaders to showcase their own challenges and success stories from their affiliates.