Optifit, an international brand of fitness equipment, had entered the Indian market in 2010 and had rapidly opened 45 stores in 8 years in the four metros (NCR region, Mumbai, Chennai and Kolkata). Jaiveer Roy was identified by Pravin Gupta (South Zone head) and Raghav Mehta (HR head) to join as Optifit’s Store Manager for its Alwarpet branch, Chennai, a store that had leadership difficulties from the day it started in May 2018. Roy joined the store in May 2018 and did very well soon after his appointment to the store. However, in less than three months, both Roy’s and his store’s performance began to suffer and his relationship with Gupta began to crumble. This case highlights issues in people management, especially support for people selected for leadership positions and examines the performance indicators of an individual’s performance at a broader level. The case also points towards the mistakes or errors leaders may commit vis-a-vis their own role as a leader and mentor.