The case focuses on the multifaceted challenges faced by Dr Vinayak Sahukar, a newly promoted chief district medical officer at the Baranpur District Hospital, including navigating organisational politics, managing under-resourced operations, building a cohesive team and transitioning from a clinical to an administrative leadership role. Sahukar was a passionate surgeon; however, he had little experience as a leader. With almost no training to lead a hospital, he made many errors in the first 10 months of his tenure. He alienated key team members, had a debacle in the media and an important project that he had started was left languishing. His experiences highlight the struggles of new leaders in adapting to complex, ambiguous situations and balancing operational priorities with strategic leadership. The case sheds light on the pitfalls of inconsistent decision-making, leadership biases and misaligned priorities while offering a lens to explore actionable solutions through adaptive leadership principles.