The manager of a rapidly expanding tax and accounting services franchise had been impressed by the performance his right-hand man, but also worried about the pressure he put himself under. Possessing an unusual and valuable skillset, this employee was able to anticipate his manager's needs exceptionally well. Unfortunately, his manager found out he had hacked into his email to do so. The case is designed to surface students' instinctive decision-making tendencies. Thus it is short enough to be read and responded to in class. Students are assigned readings and assignments related to the case after class discussion in which they are encouraged to reflect on their initial responses. The case is quite flexible and would work in any course that deals with leadership, ethics, difficult conversations, decision-making, organizational behavior, human resources, or related topics. It is appropriate for a range of levels and audiences, including undergraduate, MBA, and executive education.