Recent MBA graduates, typically millennials, may be at odds with their baby boomer superiors’ vision of workplace expectations and values. This case presents a fictionalized annual review discussion at an investment bank between a high achieving African American male millennial on the verge of burning out, and a self-made woman who struggled for decades to achieve power in an “old boys’ network” culture—asking students to consider how the generational divide between these two individuals might begin to close.