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How would you use a user's booking history to personalize search: fine-tune embeddings or build a reranker?

A real interview question with a trap in its framing: it offers you two expensive options and hides the cheap one. The escalation ladder from feature-based reranking to two-tower fine-tuning, with the cold-start and position-bias answers ready.

Updated Aug 2026 · Grounded in real Forward Deployed Engineer interview loops and written to a senior-engineer editorial bar.

A real interview question with a trap in its framing: it offers you two expensive options and hides the cheap one. The escalation ladder from feature-based reranking to two-tower fine-tuning, with the cold-start and position-bias answers ready.

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