Managerial discretion is generally seen as a leadership capacity that affects organizations’ ability to adapt to new and changing demands and circumstances. The aim of this article is to examine this traditional view. Based on a review of the literature, I will argue: Both too little and too much managerial discretion might be disadvantageous to appropriate organizational adaptiveness. Based on findings from a pilot study of top leaders as "change agents," I will make the argument: It is difficult for top leaders as change agents to have both discretion and power.