This research aims to find out the leadership strategy in Muhammadiyah College Student Association (IMM) Rosyad Sholeh Universitas 'Aisyiyah Yogyakarta. Beside aiming to find out the existing leadership strategy, this research also aims to find out the obstacles and the solutions in the leadership strategy mentioned. This research used a case study approach applying qualitative research type. The data collection technique used interviews, documentation, and observation. Meanwhile, in qualitative data analysis, it used Miles and Huberman model with 4 stages consisting of data collection, data reduction, data presentation, conclusion drawing, and verification. The research results show that the leadership strategy in Muhammadiyah College Student Association (IMM) Rosyad Sholeh are as follows: First, the leadership strategy in Muhammadiyah College Student Association (IMM) Rosyad Sholeh has already performed the elements of strategy formation covering strategy formulation, implementation, and evaluation. Second, if traced, the obstacles faced by Muhammadiyah College Student Association (IMM) Rosyad Sholeh in leadership strategy are found in the area of humanity. The obstacles are the lack of knowledge on organizational values, contradictory thoughts, and minimum level of initiation and innovation. Third, similar to the obstacles, the solutions offered in facing the obstacles are around the humanity solutions such as re-strengthening the organizational values and the understanding of the importance of evaluation.