AI alignment relies on annotator judgments, yet annotation pipelines often treat annotators as interchangeable, obscuring how their social position shapes annotation. We introduce reflexive annotating as a probe that invites crowd workers to reflect on how their positionality informs subjective annotation judgments in a language model alignment context. Through a qualitative study with crowd workers (N = 30), including follow-up interviews (N = 5), we examine how our probe shapes annotators' behaviour, experience, and the situated metadata it elicits. We find that reflexive annotating captures epistemic metadata beyond static demographics by eliciting intersectional reasoning, surfacing positional humility, and nudging viewpoint change. Crucially, we also denote tensions between reflexive engagement and affective demands such as emotional exposure. We discuss the implications of our work for richer value elicitation and alignment practices that treat annotator judgments as situated and selectively integrate positional metadata.

As AI systems become embedded in everyday practice, value misalignment has emerged as a pressing concern. Yet, dominant alignment approaches remain model-centric, treating users as passive recipients of pre-specified values rather than as epistemic agents who encounter and respond to misalignment during interactions. Drawing on situated perspectives, we frame alignment as an interactional practice co-constructed during human-AI interaction. We investigate how users understand and wish to contribute to this process through a participatory workshop that combines misalignment diaries with generative design activities. We surface how misalignments materialise in practice and how users envision acting on them, grounded in the context of researchers using Large Language Models as research assistants. Our findings show that misalignments are experienced less as abstract ethical violations than as unexpected responses, and task or social breakdowns. Participants articulated roles ranging from adjusting and interpreting model behaviour to deliberate non-engagement as an alignment strategy. We conclude with implications for system design that supports alignment as ongoing, situated, and shared practice.

As values shape the design and governance of technology, it becomes critical to move beyond universal framings to explore the nuanced, subjective understandings individuals hold about values. Traditional value elicitation methods often identify values at play but overlook how they are interpreted through individuals’ social identities and lived experiences. This paper introduces an AI-augmented value exploration method inspired by photo elicitation, which involves interviews supported by participant-taken photographs. Instead, we use AI-generated imagery to uncover hidden associations and insights around personal understandings of values. In an exploratory study with six participants, we focused on the value of well-being, examining how AI-generated visuals prompted diverse personal interpretations and facilitated deeper value reflections. Our findings show that this method uncovers implicit meanings and deepens discussions by translating abstract ideas into tangible interpretations to yield richer data on situated values.