This chapter examines how advising upwards often means being a courageous follower. It demonstrates appropriate intelligent disobedience in action, a scenario involving a challenging and time-constrained major programme of work. The degree of gain or loss is viewed from both a personal and an organisational standpoint. Extraordinary actions and the risks inherent in them should only be taken if the resulting gain or loss due to a lack of action is deemed worthwhile. Leaders have shared that taking a long overdue action is the most frequent driver for acts of intelligent disobedience. The presence or lack of other more traditional alternatives for achieving a valued business goal is the next significant catalyst for acts of intelligent disobedience. Leaders whose moral stance is challenged are compelled to ensure the appropriate business outcome is achieved, or to ensure that something they considered to be wrong was quickly corrected.