Many theorists, corporations, and employers have struggled to foster an employee identity that benefits both the company and those working for it. Corporations have looked at ways to align its corporate identity and organizational identity in hopes that its employees will discern values similar to their own and identify with the organization. Companies hope this in turn will cause employees to support their organization, allow them to experience a stronger sense of loyalty to their company, and as a result, be retained for longer by their employers. As more millennials continue to enter the workforce, this need for retention through aligned identification with a company is even more significant. In this article we will strive to explain why corporations have had such difficulty retaining millennials, and why this generation is viewed as so hard to manage. We will do this by examining different forms of identity in a company, and isolating key millennial traits that may affect how they view their own employee identity. We will introduce the idea that millennials are stuck in a phase of neutral organizational identification, and that this is caused by a lack of alignment between what they, and the company, view as valuable. We will explore the need for companies to redefine their organizational identity to better match this new generation's needs, and discern whether an alignment between the two can be met. The concept of a generationally lower sense of self-categorization, affecting their ability to identify with their organization, will also be explored. In addition, we will discuss the idea that the largest struggle for millennial retention is caused by an inconsistency with their current job and their job expectations based on a lack of balance between their current degree of employee identification, and their idealized expectations. With these hypotheses, we will then discuss management suggestions, as well as possible further research.