Organizations might benefit from maintaining relationships with former employees, who could be rehired later or encouraged to refer job applicants and customers. We integrate the management literature on voluntary resignations and the communication literature on relationship dissolution to explore how conversations between an exiting employee and his or her manager facilitate (or constrain) post‐exit relationships. Employees who had recently resigned from full‐time jobs described their exit experiences in semistructured interviews with the research team. The results suggest two dominant patterns. When employees exited for external reasons (e.g., to pursue a program of study), they engaged in very direct communication strategies, elicited positive responses from their managers, and left with high interest in a post‐exit relationship. But when employees exited for internal reasons (problems within the employment relationship), they engaged in multiple exit cycles and moved from indirect communication strategies toward increasingly direct ones. Managerial responses to these strategies failed to capitalize on opportunities to nurture post‐exit relationships and sometimes generated a “vendetta effect” among exiting employees. The results suggest that managers might benefit from training in how to conduct effective exit conversations, particularly with employees who are leaving for internal reasons. © 2014 Wiley Periodicals, Inc.