Caleb Bowie discusses the importance of understanding the underlying needs behind metric requests from stakeholders, using a request for a "workspace freshness" metric as an example. He emphasizes that saying yes to requests without comprehending their true purpose can lead to building metrics that do not drive effective decisions, potentially eroding trust in data. Bowie outlines a process for translating stakeholder requests into actionable metrics by asking exploratory questions, gathering real-life examples, and looking for existing solutions. In the case of the workspace freshness metric, Bowie discovered that the product team already tracked engagement metrics that aligned with the stakeholder's goals, allowing for a more efficient and aligned approach. By focusing on translating requests into meaningful metrics, Bowie highlights the role of analysts as translators between business intuition and measurable reality, emphasizing that their job is to help organizations understand problems they are trying to solve rather than merely fulfilling requests.