Varun Vemulapalli

Day 32 of 100 · Phase 4: Giving AI knowledge

Chunking and retrieval quality

2 min readBy Varun Vemulapalli

A member asks the health plan's assistant: "What's my deductible for an out-of-network specialist?"

The 80-page benefits booklet has the answer. The assistant still gets it wrong, because the table was cut in half before the AI ever saw it.

Video explainer · 1:58
Key takeaway

Good RAG starts with good chunks: split by structure, keep tables whole, add overlap and metadata, and test retrieval with real questions.

Day 32 visual: Chunking and retrieval quality
The visual from the original post.

The concept

RAG (Day 31) doesn't search whole documents. It searches chunks: smaller pieces the documents were split into ahead of time. Each chunk gets its own embedding (Day 11) and sits in the vector database (Day 30).

Chunking: how you cut documents into those pieces. It quietly decides whether retrieval finds the right passage.

Walkthrough: an 80-page benefits booklet

Too big: 1 chunk per 10 pages

  • A chunk covers deductibles, pharmacy, vision and appeals all at once. Its embedding is a blurry average of everything.
  • It matches lots of questions weakly, and fills the context window (Day 20) with noise.

Too small: 1 chunk per sentence

  • "The deductible is $3,000." Which deductible? In-network? Family? The context is gone.

The bad cut
Say the deductible table sits on page 14:

  • Column headers: In-network | Out-of-network
  • Individual: $1,500 | $3,000
  • Family: $3,000 | $6,000

A fixed 500-word splitter cuts right after the headers. Chunk A has the headers, chunk B has the numbers with no labels. Retrieval finds chunk B, and the model guesses which column "$3,000" belongs to.

Better chunking

  • Split by structure: headings and sections, not a fixed word count.
  • Keep tables whole, with their headers.
  • Add overlap: repeat a sentence or two between neighboring chunks so ideas aren't sliced mid-thought.
  • Attach metadata: section title, plan name, plan year, page number. Then you can filter ("2026 Gold plan only") and cite the page.
  • Aim for chunks that answer one question well, often a few paragraphs.

Measure it, don't guess
Write 20–30 real member questions with the correct page for each. Run them through retrieval and check: is the right chunk in the top 3? Say 17 of 25 are. Fix the chunking, rerun, compare. Now you know it improved.

Where you see it at work

  • Healthcare: benefits booklets, prior-authorization rules, clinical protocols.
  • Insurance: policy wordings where exclusions sit pages away from coverage.
  • Banking: fee schedules and rate tables that must never lose their headers.
  • Business analysis: writing the test questions is a perfect BA task. You know what users actually ask.

In one sentence

Good RAG starts with good chunks: split by structure, keep tables whole, add overlap and metadata, and test retrieval with real questions.

Your turn: which document at your work would be hardest to chunk well, and why? 👇

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