This article investigates the sales force socialization process, wherein newly hired salespeople often face failure-prone environments. Drawing from the learned helplessness paradigm, the authors hypothesize that cumulative periods of sales performance failure are associated with sales-oriented behavior intentions. In addition, the authors examine the influence of leadership, expecting core transformational leadership to have a diminishing effect as unmet sales goals accumulate. Study 1 finds support for these hypotheses using panel survey data from 221 new hires during six months of a furniture retailer's sales force socialization process. Then, aiming to uncover the underlying mechanism driving salesperson helplessness and a managerial approach that has a sustained impact, the authors conduct Study 2, a scenario-based experiment focused on the business-to-business insurance industry. The authors find that perceived task difficulty mediates the focal relationship and that error management enables core transformational leadership to have a lasting effect such that new hires have the lowest sales-oriented behavior intentions when transformational sales managers encourage them to make errors during their interactions with customers and to actively learn from their failures.