Proactive behaviors at work refer to behaviors that are self-starting, future focused, and change oriented. Proactive behaviors are generally thought of as positive and desired and can benefit both the employee (e.g., job promotion) and organization (e.g., innovation). These behaviors can, however, backfire (e.g., due to unintended consequences), reflecting the "initiative paradox." The aim of this study was to investigate, through the perspectives of health care executives, how employees can be more effective when engaging in proactive behaviors. We used the episodic narrative interview method. Health care executives narrated instances of perceived effective and ineffective proactive behaviors among employees. We then performed an inductive qualitative analysis of these episodes to identify emerging themes and dimensions. The effectiveness of proactive behaviors among health care employees is shaped by three dimensions: managerial expectation (in)congruence (e.g., knowledge of expectations, engagement with chain of command), organizational priority (in)congruence (e.g., degree of alignment between individual and organizational benefits), and boundaries of action and change (e.g., nonadherence to regulatory or financial conditions). Among the dimensions, managerial expectations may be the most challenging for employees to navigate. Engaging in proactive behaviors is not a straightforward process. Navigating multiple dimensions is necessary for health care employees to be effective. Employees should be equipped with knowledge on relevant expectations, priorities, and boundaries when engaging in proactive behaviors at work. Health care leaders and managers should aim to clarify and periodically reassess these dimensions to facilitate effective proactive behaviors and to generate benefits for employees and the organization.