Proactive behaviors at work refer to behaviors that are self-starting, future-focused, and change oriented. These behaviors can benefit both the employee (e.g., job promotion) and organization (e.g., innovation). Proactive behaviors are generally thought of as positive and desired. However, they can also backfire (e.g., due to unintended consequences), reflecting what scholars have called the “proactivity paradox.” Through the perspectives of health care executives, we investigated how health care workers can be in more effective when engaging in proactive behaviors. We used the episodic narrative interview method, where health care executives narrated instances of proactive behaviors among health care workers that they considered to be effective or ineffective. We then performed an inductive, qualitative analysis of these episodes. We found that the effectiveness of proactive behaviors among health care workers is shaped by three dimensions: managerial expectation (in)congruence (e.g., going through chain of command); organizational priority (in)congruence (e.g., not overly motivated by individual benefits); and boundaries of action and change (e.g., financial budgets). Our results show that engaging in proactive behaviors is not a straightforward process; there is a considerable amount of navigation needed for health care workers to be effective. Further, health care workers should equip themselves with knowledge on relevant expectations, priorities, and boundaries when engaging in proactive behaviors at work. Among the dimensions, managerial expectations may be the most challenging for health care workers to access. Health care managers and leaders should thus aim to share these expectations so that workers can better use proactivity to generate benefits for themselves and the organization.