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Purpose This study examines situational challenges encountered by transformational leaders that hinder team performance in Brazilian companies, providing insights into the factors affecting optimal team functioning. Design/methodology/approach In total, 27 decision-makers assessed transformational leadership challenges in various team management scenarios outlined in the literature. The study employed a grey approach as a multi-criteria decision-making model to evaluate the readiness and identification of transformational leadership strategies. The study focused on five challenging situations as decision criteria, leading to a comparative ranking. Findings Preparation emerged as the most critical criterion for addressing transformational leadership challenges in team environments. Unequal workload distribution, which causes overload for certain team members, was identified as the most pressing issue, making it the most suitable scenario for applying transformational leadership strategies. Research limitations/implications The study’s reliance on expert opinions introduces subjectivity, and the focus on Brazilian companies may limit the generalizability of the findings. Future research should explore these challenges in broader contexts, integrating cross-cultural perspectives and objective criteria. Additionally, combining qualitative methods with the grey approach could provide deeper insights into the complex dynamics of transformational leadership and team performance. Originality/value This research contributes to the knowledge base by identifying barriers that impact team performance in Brazilian corporate settings. It offers context-specific strategies to enhance teamwork effectiveness and organizational outcomes, supporting leadership development in Brazil.