The increasing accuracy and falling costs of AI have stimulated the increased use of AI technologies in mainstream user-facing applications and services. However, there is a disconnect between mathematically rigorous AI approaches and the human stakeholders’ needs, motivations, and values, as well as organizational and institutional realities, contexts, and constraints; this disconnect is likely to undermine practical initiatives and may sometimes lead to negative societal impacts. In this presentation, I will discuss my research on incorporating human stakeholders’ tacit values and explicit feedback into the creation process of AItechnologies. I will describe a specific project — designing and evaluating intelligent recruitment tools for WikiProjects on Wikipedia — to illustrate my approach. I hope this presentation will contribute to the rich ongoing conversation concerning bridging HCI and AI and using HCI methods to address AI challenges.