Beyond the Personal Assistant: How Expectations for Enterprise AI in Teamwork Diverged as Generative AI Took Shape, 2023-2025

HCI often draws on users' articulated needs and expectations to explore design opportunities for emerging technologies. Yet, these accounts are shaped by how technologies take form over time. We examine this dynamic through a two-phase interview study of enterprise AI in a project-based software development organization. We interviewed 15 practitioners in 2023 and re-interviewed 10 in 2025. In 2023, participants expected enterprise AI built around teams: systems integrating signals across workplace tools, detecting coordination problems, and intervening in team processes. By 2025, no such team-focused systems had entered their work, while personal AI assistants were prevalent. These expectations diverged from one another: some expectations were deferred, some rejected as undesirable or infeasible, and some no longer articulated as expectations they had held. These trajectories show how design possibilities can remain open-ended, narrow, or disappear as technologies take shape, with implications for designing enterprise AI and interpreting present-day user accounts.