2. Fundamentals of Legal Prompt Engineering
The Three Golden Rules of Effective Prompting
Before diving into complex frameworks and techniques, you need to understand three foundational principles that separate effective prompts from ineffective ones. These golden rules apply to every prompt you'll ever write, from simple questions to complex multi-step legal analysis.
Rule 1: Clarity
Your prompt should be unambiguous and straightforward. AI models interpret your instructions literally—if there's room for multiple interpretations, you'll get unpredictable results.
Poor Example:
Tell me about summary judgment.Better Example:
Explain the legal standard for summary judgment in federal court under
Rule 56 of the Federal Rules of Civil Procedure, including the burden
of proof and the standard for viewing evidence.The second prompt removes ambiguity. Are you asking for a definition? A history? Application to a specific case? The clearer your request, the more useful the response.
Rule 2: Specificity
General prompts produce general responses. Specific prompts produce actionable work product. The more specific you are about what you need, the more the AI can tailor its response to your exact requirements.
Poor Example:
Draft a contract.Better Example:
Draft a commercial lease agreement for retail space in California,
including provisions for: (1) 5-year term with two 3-year renewal
options, (2) triple-net lease structure, (3) percentage rent clause
tied to gross sales, (4) tenant improvement allowance, and (5)
standard force majeure provisions.Specificity transforms AI from a generic tool into a precision instrument.
Rule 3: Context
Context helps the AI understand not just what you're asking, but why you're asking it and how the answer will be used. This shapes the tone, depth, and format of the response.
Poor Example:
What are the elements of negligence?Better Example:
I am preparing jury instructions for a premises liability case in Texas
state court. What are the elements of negligence that must be proven,
and how should they be explained to a jury in plain language?The context tells the AI this needs to be jury-appropriate language in a specific jurisdiction, not an academic treatise on tort law.
Common Pitfalls and How to Avoid Them
Understanding what doesn't work is just as important as knowing what does. Here are the most common mistakes legal professionals make when prompting AI.
Pitfall 1: Vague and Short Statements
Most people prompt AI the way they use search engines—short queries that lack detail.
Example of the Problem:
Draft an operating agreement for a private trust company domiciled in Georgia.This prompt seems clear, but it's missing critical information:
Member-managed or manager-managed?
Which Georgia (state, country, city)?
Who are the members/managers?
What is the trust company's purpose?
Is the trustee role bifurcated (administrative vs. distribution)?
Is there an investment committee?
The Solution: Add layers of specificity and context:
Draft a member-managed operating agreement for a private trust company
domiciled in the State of Georgia. The trust company has three members:
John Doe (50% interest), Jane Smith (30% interest), and ABC Family Trust
(20% interest). The company will serve as trustee for family trusts
holding both traditional securities and digital assets. Include provisions
for: (1) member voting rights proportional to ownership, (2) annual
distributions based on company profits, (3) fiduciary duties specific
to trust administration, and (4) procedures for adding/removing members.Pitfall 2: Lack of Contextual Information
Without context, AI makes assumptions that may not align with your needs.
Example of the Problem:
Draft an operating agreement for a private trust company domiciled in Georgia.This prompt fails to mention that the trust company will serve as trustee to specific types of trusts with specific assets.
The Solution: Provide the relevant contextual backdrop:
Draft an operating agreement for a private trust company domiciled in
Georgia. The trust company will serve as trustee to an Irrevocable
Self-Settled Spendthrift Trust which will hold title to equities and
digital assets (cryptocurrency). The trust will follow a HEMS (Healthcare,
Education, Maintenance, & Support) distribution model. The operating
agreement should address the unique considerations of serving as trustee
for trusts holding digital assets.Pitfall 3: Not Accounting for Hallucination
AI can fabricate information that sounds plausible but is entirely false. In legal work, this is particularly dangerous.
Example of the Problem:
Draft an operating agreement for a private trust company domiciled in Georgia.Here's the fundamental issue: Georgia does not have state legislation recognizing private trust companies. The AI will not alert you to this fact and will proceed to generate an operating agreement anyway.
The Solution: Build verification requirements into your prompts:
You are an estate planning attorney drafting trust agreements and legal
contracts. Your work is strictly based on state statutes and federal laws.
When asked to draft legal contracts that are state-specific, make sure to
reference the state's statutes for a regulatory framework specifically
designed for that type of legal contract.
If such state statutes do not exist, reply by saying "I cannot complete
this request due to regulatory uncertainty" and nothing else.
Now, draft an operating agreement for a private trust company in the
state of Georgia.With these instructions, the AI correctly responds: "I cannot complete this request due to regulatory uncertainty."
Pitfall 4: Lack of Structure
Unstructured prompts produce inconsistent results. Adding structure to your prompts dramatically improves output quality and reliability.
The C.A.S.E. Framework
The C.A.S.E. Framework is your systematic approach to crafting effective legal prompts. Every successful legal prompt contains these four crucial elements:
C - Context
Define the subject matter and provide background on the task, jurisdiction, court (if applicable), and area of law. Context shapes how the AI interprets and responds to your request.
Elements to Include:
Subject matter and background
Jurisdiction (federal, state, specific court)
Area of law
Input data references
Example:
I am preparing for a civil trial in the Southern District of New York
concerning a breach of commercial lease agreement. The lease was executed
in 2020 for retail space in Manhattan. The landlord is claiming $500,000
in damages for early termination.A - Audience & Action (Persona)
Assign the AI a specific role or persona. This shapes the tone, expertise level, and approach of the response. Then define the specific action you need performed.
Persona Examples:
"Act as a litigation paralegal preparing document summaries..."
"Assume the role of opposing counsel evaluating weaknesses in my case..."
"You are a senior partner specializing in tort law reviewing an associate's work..."
Action Verbs to Use:
Summarize
Draft
Compare and contrast
Generate objections
Outline
Analyze
Extract
Identify
Example:
Act as a litigation paralegal preparing for trial. Review the following
deposition transcript and generate a table with three columns: (1) Page/Line
number, (2) Key Statement, and (3) Inconsistency (compared to the witness's
prior statements).S - Structure & Style
Define exactly how you want the response organized and what tone it should adopt. This ensures the output matches your specific needs and professional standards.
Format Specifications:
"Provide the summary as a three-column table"
"Format the response as bullet points"
"Draft as a formal email"
"Use only IRAC structure (Issue, Rule, Analysis, Conclusion)"
"Present as a two-page executive summary followed by detailed appendices"
Tone Specifications:
"Highly persuasive and aggressive"
"Neutral and objective"
"Plain language suitable for a client with no legal background"
"Professional but empathetic"
"Academic and scholarly"
Example:
Format your response as a formal memorandum with the following sections:
1. Summary (3 sentences maximum)
2. Background (chronological narrative)
3. Legal Analysis (using IRAC format)
4. Recommendation (numbered list of next steps)
Use professional legal terminology but ensure clarity for a business client.E - Ethical and Verification Directives
Always include instructions that promote accuracy and identify limitations. This is your safeguard against hallucination and unreliable output.
Citation Requirements:
Where citing case law, provide the full Bluebook citation. For every
legal proposition, cite to the primary source (statute, case, regulation).Limitation Acknowledgment:
If you cannot find a relevant source, explicitly state "I could not locate
relevant authority on this issue" rather than fabricating information.
If a legal conclusion is speculative or uncertain, clearly indicate this
with phrases like "the law is unclear on this point" or "courts have
reached conflicting conclusions."Example of Complete Ethical Directive:
For all legal citations:
1. Provide full Bluebook citations
2. If you're uncertain whether a case exists, state "I recommend verifying
this citation in Westlaw or Lexis"
3. Do not cite cases you cannot verify
4. If the law is unsettled, acknowledge conflicting authorities
5. Clearly distinguish between majority and minority positionsThe "Prompt Sandwich" Structure
The "Prompt Sandwich" is a proven template that incorporates all elements of the C.A.S.E. Framework in a structured, repeatable format:
┌─────────────────────────────────┐
│ INSTRUCTIONS (Top Bun) │ ← Persona, ethical directives,
│ │ general guidelines
├─────────────────────────────────┤
│ CONTEXT (The Filling) │ ← Background, jurisdiction,
│ │ relevant facts
├─────────────────────────────────┤
│ INPUT (More Filling) │ ← The specific task, question,
│ │ or document to analyze
├─────────────────────────────────┤
│ OUTPUT (Bottom Bun) │ ← Format requirements, structure
│ │ specifications, what to exclude
└─────────────────────────────────┘Example: Complete Prompt Sandwich
**INSTRUCTIONS**
You are an estate planning attorney drafting complex trust agreements and
other legal contracts. Your work is strictly based on state statutes and
federal laws. When asked to draft legal contracts that are state-specific,
make sure to reference the state's statutes for a regulatory framework
specifically designed for the type of legal contract. If such state statutes
do not exist, reply by saying "I cannot complete this request due to
regulatory uncertainty" and nothing else.
Only include the resulting output in your response. Exclude legal disclaimers,
preamble, and any reasoning in your response.
**CONTEXT**
Client is John Doe of Atlanta, Georgia.
[Attach: Irrevocable Trust document]
**INPUT**
Draft an operating agreement for a private trust company in the state of Nevada
that will serve as trustee for the attached irrevocable trust. The trust company
will be manager-managed with two managers: John Doe and Jane Doe. The company
will have authority to hold and manage both traditional securities and digital
assets.
**OUTPUT**
Format as a professional operating agreement with:
- Article I: Organization and Purpose
- Article II: Management Structure
- Article III: Capital Contributions
- Article IV: Distributions
- Article V: Fiduciary Duties
- Article VI: Amendment Procedures
Use formal legal language appropriate for filing with the Nevada Secretary
of State.Preventing AI Hallucination in Legal Work
Hallucination—when AI fabricates information that sounds plausible but is false—poses the greatest risk to legal professionals. Here are strategies to minimize this risk:
Strategy 1: Explicit Uncertainty Instructions
If you do not know the answer or do not have sufficient information,
respond by saying "I do not have enough information to answer this
question reliably" instead of generating a response.Strategy 2: Request Source Attribution
For every factual statement, indicate the source of that information.
If the information comes from your training data, say "Based on general
legal principles" rather than citing to specific authority you cannot
verify.Strategy 3: Confidence Levels
For each conclusion you reach, indicate your confidence level:
- HIGH CONFIDENCE: Well-established legal principle with clear authority
- MEDIUM CONFIDENCE: Generally accepted principle but with some variation
- LOW CONFIDENCE: Uncertain or evolving area of law
- SPECULATIVE: No clear authority; this is an educated inferenceStrategy 4: Multiple Verification Steps
Don't rely on a single AI response. Use this multi-step verification approach:
Initial prompt with strong verification requirements
Second prompt asking the AI to identify weaknesses or uncertainties in its first response
Manual verification of all citations and key legal propositions in primary sources
Example Second-Step Prompt:
Review your previous response. Identify any statements that you are not
highly confident about. For each citation provided, indicate whether you
are certain this case exists and accurately supports the proposition cited.Putting It All Together: Before and After Examples
Example 1: Contract Review
Poor Prompt:
Review this contract and tell me if there are any issues.Improved Prompt Using C.A.S.E.:
**INSTRUCTIONS**
Act as a senior corporate attorney conducting due diligence review. Focus
on risk identification and business impact. For any issue identified, assess
the severity as Critical, High, Medium, or Low.
**CONTEXT**
I represent the buyer in an asset purchase transaction valued at $5 million.
We are acquiring a software-as-a-service business. This is a key supplier
agreement that will transfer to us post-closing.
**INPUT**
Review the attached Master Services Agreement between the target company
and their primary cloud infrastructure provider.
Identify and analyze:
1. Termination provisions and change of control implications
2. Liability limitations and indemnification
3. Data security and privacy obligations
4. Pricing and renewal terms
5. Any provisions that could create post-closing issues
**OUTPUT**
Provide response in this format:
EXECUTIVE SUMMARY (3-4 sentences)
CRITICAL ISSUES (if any)
- Issue description
- Business impact
- Recommended action
HIGH-PRIORITY ISSUES
[Same format as above]
MEDIUM/LOW-PRIORITY ISSUES
[Same format as above]
OVERALL RISK ASSESSMENT
[One paragraph summary]Example 2: Legal Research
Poor Prompt:
What's the law on non-compete agreements in California?Improved Prompt Using C.A.S.E.:
**INSTRUCTIONS**
You are a legal research specialist. Provide comprehensive analysis with
full citations. If any statement is based on interpretation rather than
explicit statutory or case law, clearly indicate this. If the law has
changed recently or is subject to pending legislation, note this.
**CONTEXT**
I represent an employer who is considering requiring new employees to sign
non-compete agreements. The company is headquartered in California but
has employees in several states. We need to understand California's
approach before rolling out any policies.
**INPUT**
Research and analyze California law regarding the enforceability of
employee non-compete agreements. Address:
1. The general rule in California regarding non-competes
2. Statutory basis (cite specific California statutes)
3. Key exceptions or narrow circumstances where non-competes may be
enforceable
4. Recent case law developments (last 5 years)
5. Practical alternatives employers can use to protect business interests
**OUTPUT**
Structure your response as:
OVERVIEW (one paragraph summary of California's position)
STATUTORY FRAMEWORK
- Cite relevant California Business & Professions Code sections
- Explain key statutory language
EXCEPTIONS AND SPECIAL CASES
- Business sale exception
- Trade secret protection
- Other recognized exceptions
CASE LAW ANALYSIS
- 2-3 key cases with full citations
- Brief summary of holdings
PRACTICAL ALTERNATIVES
- Non-solicitation agreements
- Confidentiality agreements
- Other protective measures
All case citations must include: Case name, citation, court, and year.
Example: Edwards v. Arthur Andersen LLP, 44 Cal. 4th 937 (2008)Practice Exercise
To reinforce these concepts, take this poorly constructed prompt and rebuild it using the C.A.S.E. Framework:
Poor Prompt:
Summarize this deposition.Your Task: Before looking at the answer below, try rewriting this prompt to include:
Clear context about the case and the deposition's significance
A specific persona for the AI
Detailed structure requirements
Ethical verification requirements
Example Improved Version:
**INSTRUCTIONS**
Act as a litigation paralegal preparing materials for trial counsel.
Focus on identifying admissions, inconsistencies with prior testimony,
and statements that support or undermine our case theory. Flag any
testimony that may require follow-up in future depositions.
**CONTEXT**
This is a products liability case involving an allegedly defective
medical device. The plaintiff claims the device malfunctioned during
surgery, causing permanent injury. This deposition is of the defendant's
engineering director who oversaw the device's design and testing.
Our case theory: The device had a known design flaw that the defendant
failed to disclose.
Defendant's position: The device functioned properly and any injury was
due to surgical error.
**INPUT**
Summarize the attached 200-page deposition transcript of Dr. Robert Chen,
Engineering Director.
Focus specifically on:
1. Testimony regarding the device's testing protocols
2. Any admissions about design modifications or safety concerns
3. What Dr. Chen knew about prior incidents with the device
4. Statements that contradict the company's public statements or
marketing materials
**OUTPUT**
Provide a summary in this format:
KEY ADMISSIONS (most important testimony supporting our case)
- Quote with page:line citation
- Significance for our case theory
INCONSISTENCIES (testimony that conflicts with other evidence)
- Statement from this deposition (page:line)
- Conflicting prior statement (source and citation)
- Potential impact
HELPFUL DEFENSE TESTIMONY (testimony that supports defendant's case)
- Quote with citation
- How this may be used against us
AREAS FOR FOLLOW-UP (topics needing clarification or further inquiry)
CREDIBILITY ASSESSMENT (witness's demeanor, evasiveness, areas of
uncertainty)
Maximum 5 pages. Use bullet points. Include specific page and line
citations for every quoted statement.Chapter Summary
Mastering legal prompt engineering begins with understanding and applying these fundamental principles:
Follow the Three Golden Rules: Every prompt must be clear, specific, and contextual
Avoid Common Pitfalls: Vague prompts, missing context, and unstructured requests produce poor results
Use the C.A.S.E. Framework: Context, Audience & Action, Structure & Style, and Ethical directives
Apply the Prompt Sandwich Structure: Organize your prompts systematically for consistent results
Prevent Hallucination: Build verification requirements into every prompt
These fundamentals will serve as the foundation for everything that follows. In the next chapter, we'll apply these principles to real-world legal tasks, providing you with ready-to-use prompt templates for discovery, research, drafting, and trial preparation.
In Chapter 3, we'll move from theory to practice with detailed examples of prompts for every stage of litigation—from early case assessment through trial preparation.
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