Work-integrated learning (WIL) is vital for preparing health-work students for practice. WIL activities have multiple stakeholders, each with their own set of expectations and requirements, both explicit and implicit. Negotiations to provide these learning experiences for students happen at many levels and those at the coalface are often unaware of the different expectations of the various stakeholders. By developing their ability to consider multiple stakeholder perspectives, health students and their clinical educators are in a strong position to maximize the benefits, limit the disadvantages, and increase the satisfaction of the multiple stakeholders. Social awareness, communication skills and relationship development and maintenance hold the key to building capacity to manage the WIL experiences more skillfully, leading to better outcomes for all. This discussion paper examines an example from the field that drew attention to the need for a better understanding of the needs of all stakeholders.