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The technology they use is often not designed for their unique needs, and can feel burdensome on top of their already cognitively and emotionally taxing work. While existing literature focuses on data-driven technologies that automate or streamline frontline decision-making about vulnerable individuals, we discuss scenarios in which staff may resist such automation. We then suggest how data-driven technologies can better align with their human-centred decision-making processes. This paper presents findings from a qualitative fieldwork study conducted from 2022 to 2024 at a large emergency shelter in Canada. The goal of this fieldwork was to co-design, develop, and deploy an interactive data-navigation interface that supports frontline staff when making collaborative, high-stakes decisions about individuals experiencing homelessness. 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