A District Magistrate (DM) is a civil servant who occupies an important position in the Indian public administration. A DM is to a district what a Chief Executive Officer is to a multinational company. His or her efficient leadership ensures a smooth functioning of all administrative functions in the district and thereby greatly affects the daily life of the citizens. This case describes experiences of the DM of East Singhbhum, a district in the mining and industrial belt of Eastern India. Four varied episodes are described to demonstrate distinct processes of responding to the state of affairs, to facilitate an understanding of how a leader makes sense differently in diverse circumstances – namely, simple, complicated, complex, and chaotic – and take decisions accordingly. The DM’s approach to these different circumstances offers insights into a leader’s sense-making process through the Cynefin framework.