The transition from an individual contributor to a managerial role is a common aspiration for many early-career workers. According to this article, about two-thirds of those starting out in their careers hope to move into management. Interestingly, one in five managers eventually come to regret their choice of pursuing a managerial position. Given the evolving and increasingly demanding nature of managerial responsibilities, organizations may encounter a rising number of both aspiring and current managers realizing that the manager role might not suit them well. To tackle these challenges, this article suggests that organizations should help potential managers assess their suitability for the role. This involves evaluating their skill set, relevant experience, and genuine interest in managerial tasks. For instance, WPS Health Solutions offers a case study, presenting a six-month trial self-discovery management program that enables potential managers to explore their fit for the role. The program aims to cultivate a competent pipeline of managers and equip them for the demanding facets of the position. After completing the program, participants have the opportunity for introspection and the choice to step away from the managerial track if they feel it’s not the right path for them. The article discusses other ideas for building a pipeline of effective managers.