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Design a Grounded LLM Assistant for Case Preparation

Last updated: Jul 28, 2026

Quick Overview

Design a grounded LLM assistant that organizes legal-dispute documents and drafts case-preparation material for human review. Address matter isolation, passage provenance, citations, contradictory evidence, document prompt injection, evaluation, privacy, retention, auditability, and strict limits on advice and external actions.

  • hard
  • Distyl
  • ML System Design
  • Software Engineer

Design a Grounded LLM Assistant for Case Preparation

Company: Distyl

Role: Software Engineer

Category: ML System Design

Difficulty: hard

Interview Round: Technical Screen

# Design a Grounded LLM Assistant for Case Preparation Design an LLM-based assistant that helps a user prepare a draft response from documents related to a legal dispute. The system may summarize documents, identify claims and supporting passages, organize a timeline, and draft text for review. It must not present itself as a lawyer or treat generated text as authoritative legal advice. Cover notebook-style interaction, ingestion, retrieval, grounding, prompt and tool boundaries, evaluation, privacy, and human review. The assistant can answer questions but must not autonomously file, send, or submit a response. ### Clarifying Questions to Ask - Which document types and jurisdictions are in scope? - Who is authorized to upload and view each matter? - Must every factual statement cite a source passage? - What retention, deletion, and audit requirements apply? - Which actions always require a qualified human reviewer? ### What a Strong Answer Covers - Matter-level access isolation and encrypted document storage - Parsing with provenance down to page or passage - Retrieval scoped to the current matter and resistant to prompt injection in documents - Draft generation that separates sourced facts, user assertions, and uncertainty - Citations that are mechanically checked against retrieved passages - Human approval, version history, and no autonomous external action - Evaluation for faithfulness, omission, citation quality, privacy, and unsafe overclaiming - Redaction, retention, deletion, incident response, and audit controls - Clear product warnings without relying on warnings as the only safeguard ### Follow-up Questions - How would you detect a citation that does not support the sentence? - What if two uploaded documents contradict each other? - How would you defend against malicious instructions embedded in evidence? - Which data should never be used for model training?

Quick Answer: Design a grounded LLM assistant that organizes legal-dispute documents and drafts case-preparation material for human review. Address matter isolation, passage provenance, citations, contradictory evidence, document prompt injection, evaluation, privacy, retention, auditability, and strict limits on advice and external actions.

|Home/ML System Design/Distyl

Design a Grounded LLM Assistant for Case Preparation

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Distyl
Jul 23, 2026, 12:00 AM
hardSoftware EngineerTechnical ScreenML System Design
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Design a Grounded LLM Assistant for Case Preparation

Design an LLM-based assistant that helps a user prepare a draft response from documents related to a legal dispute. The system may summarize documents, identify claims and supporting passages, organize a timeline, and draft text for review. It must not present itself as a lawyer or treat generated text as authoritative legal advice.

Cover notebook-style interaction, ingestion, retrieval, grounding, prompt and tool boundaries, evaluation, privacy, and human review. The assistant can answer questions but must not autonomously file, send, or submit a response.

Clarifying Questions to Ask Guidance

  • Which document types and jurisdictions are in scope?
  • Who is authorized to upload and view each matter?
  • Must every factual statement cite a source passage?
  • What retention, deletion, and audit requirements apply?
  • Which actions always require a qualified human reviewer?

What a Strong Answer Covers Guidance

  • Matter-level access isolation and encrypted document storage
  • Parsing with provenance down to page or passage
  • Retrieval scoped to the current matter and resistant to prompt injection in documents
  • Draft generation that separates sourced facts, user assertions, and uncertainty
  • Citations that are mechanically checked against retrieved passages
  • Human approval, version history, and no autonomous external action
  • Evaluation for faithfulness, omission, citation quality, privacy, and unsafe overclaiming
  • Redaction, retention, deletion, incident response, and audit controls
  • Clear product warnings without relying on warnings as the only safeguard

Follow-up Questions Guidance

  • How would you detect a citation that does not support the sentence?
  • What if two uploaded documents contradict each other?
  • How would you defend against malicious instructions embedded in evidence?
  • Which data should never be used for model training?

Submit Your Answer to Earn 20XP

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