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Tutorial 02: Getting Started with OpenAI for Legal Work

Learn how to choose the right OpenAI plan, structure effective legal prompts, and complete your first contract analysis and research workflow.

Learning Objectives

By the end of this tutorial, you will:

  • Understand which OpenAI plan is right for your legal practice
  • Know how to structure legal prompts effectively
  • Complete your first contract analysis
  • Set up a basic legal research workflow

Choosing Your OpenAI Plan

Available Options

PlanPrice (Public List)Best ForKey Features
Free$0Testing/light useBasic ChatGPT access
Plus~$20/moSolo practitionersMore usage, GPT-4, file uploads, Custom GPTs
TeamFrom $25/user/moSmall firmsTeam admin controls and shared workflows
EnterpriseCustomLarge firmsSSO, dedicated support, compliance

If you need more than the free tier, ChatGPT Plus is the usual starting point. This gives you:

  • More usage than Free
  • GPT-4 access for document analysis
  • File uploads for contract review
  • Custom GPTs for matter-specific workflows
  • Better day-to-day workflow depth for active legal practice

Upgrade to Team or Enterprise when you:

  • Hit message limits regularly
  • Need to share workflows with colleagues
  • Require admin controls for compliance

Pricing references are vendor-published list prices for context only. Legalai.guide is free and independent. Always verify current pricing on OpenAI's official site.

Legal work requires precision. A well-structured prompt dramatically improves ChatGPT's output quality.

C - Context (Who are you? What's the situation?) R - Role (What expertise should ChatGPT assume?) I - Instructions (What specific task?) S - Specifics (Jurisdiction, format, constraints) P - Parameters (Length, tone, citations needed?)

Example: Generic vs. CRISP Prompt

Generic Prompt (Avoid)

Review this contract

CRISP Prompt (Use This)

CONTEXT: I am in-house counsel at a SaaS company. We are the vendor
negotiating with a Fortune 500 customer who sent back redlines to
our standard MSA.

ROLE: Act as a senior commercial contracts attorney with 15+ years
of enterprise software licensing experience.

INSTRUCTIONS:
1. Identify the 5 most significant changes they've proposed
2. For each change, assess risk level (HIGH/MEDIUM/LOW)
3. Recommend our response (ACCEPT/REJECT/COUNTER)
4. Draft counter-proposal language where appropriate

SPECIFICS:
- Governing law: Delaware
- Our standard position: 12-month liability cap equal to fees paid
- Customer is in healthcare (HIPAA considerations)

PARAMETERS:
- Format as a table for items 1-3
- Provide draft language in a separate section
- Be concise—this is for an internal strategy memo

Your First Contract Analysis

Exercise 1: Indemnification Clause Review

Time: 10 minutes

Scenario: A vendor has sent you their standard SaaS agreement. Your client is the customer. Analyze this indemnification clause.

Step 1: Copy this prompt to ChatGPT:

CONTEXT: I represent a mid-size healthcare company evaluating a SaaS
vendor's standard agreement. We will be the CUSTOMER.

ROLE: Senior healthcare regulatory and commercial attorney.

TASK: Analyze this indemnification clause and provide:
1. Summary of what each party is agreeing to indemnify
2. Risk assessment (with specific concerns for healthcare)
3. Missing protections we should request
4. Suggested redline language for our top 3 concerns

CLAUSE TO ANALYZE:
"Customer shall indemnify, defend, and hold harmless Vendor and its
affiliates, officers, directors, employees, and agents from and against
any and all claims, damages, losses, liabilities, costs, and expenses
(including reasonable attorneys' fees) arising out of or relating to:
(a) Customer's use of the Services in violation of this Agreement;
(b) Customer Data or any content provided by Customer;
(c) Customer's violation of any applicable law or regulation.

Vendor shall indemnify Customer against third-party claims alleging
that the Services, as provided by Vendor, infringe any valid US patent
or copyright, provided Customer promptly notifies Vendor and gives
Vendor sole control of the defense."

CONSTRAINTS:
- California law applies
- HIPAA/healthcare data considerations are critical
- Focus on practical, negotiable positions

Step 2: Review ChatGPT's response

Step 3: Ask these follow-up questions:

  • "What's the most important missing provision from Vendor's indemnity?"
  • "Draft a mutual indemnification provision that would be more balanced"
  • "How would you prioritize these asks if we can only get 2 changes?"

What to Look For in ChatGPT's Response

Good signs:

  • Identifies asymmetry (customer indemnifies more broadly)
  • Notes missing data breach/security indemnity
  • Recognizes HIPAA-specific risks
  • Provides practical, negotiable language

Always verify:

  • Specific legal citations
  • State-specific requirements
  • Recent case law references

Understanding ChatGPT's Research Capabilities

What ChatGPT Can Do Well:

  • Explain legal concepts and doctrines
  • Identify relevant areas of law to research
  • Synthesize information from documents you provide
  • Generate research outlines and issue checklists
  • Draft memoranda based on research you supply

What Requires Additional Tools:

  • Current case law citations (use a dedicated case law database)
  • Up-to-date statutory language (verify against official sources)
  • Local rules and procedures (always verify)

Case Law Source Options (Alternatives)

Use one primary source and one backup source for citation verification.

Paid platforms:

  • Westlaw / Lexis: Primary commercial research platforms
  • vLex (incl. Fastcase Library): Commercial alternative with broad case law coverage

Free/public options:

  • CourtListener (Free Law Project): Large free opinion database + RECAP archive
  • Google Scholar (Case law mode): Fast, free starting point for case lookup
  • Justia / Cornell LII: Helpful for quick checks and primary-law navigation

Exercise 2: Research Planning

Scenario: Your client wants to know if their non-compete agreement is enforceable.

Step 1: Use this research planning prompt:

TASK: Create a legal research plan for analyzing non-compete enforceability.

FACTS:
- Employee: Software engineer in California
- Employer: Delaware corporation with offices in TX and CA
- Non-compete: 2-year restriction, 50-mile radius, signed in Texas
- Employee now wants to join competitor in California

PROVIDE:
1. Key legal issues to research (prioritized)
2. Relevant jurisdictions and potential conflicts
3. Types of sources needed (statutes, cases, secondary)
4. Specific search queries I should run in Westlaw/Lexis
5. Potential arguments for both sides
6. Red flags or complications I should watch for

FORMAT: Research checklist I can use to guide my work

Step 2: Review ChatGPT's research plan

Step 3: Follow up with:

  • "What's the leading case on this conflict of laws issue?"
  • "If we were representing the employer, what's our best argument?"
  • "Draft an outline for a memo analyzing this issue"

Pro Tip: Using ChatGPT with Traditional Research

ChatGPT works best as a research accelerator, not a replacement:

  1. Start with ChatGPT: Get issue framework and search strategies
  2. Run searches in Westlaw/Lexis: Find actual citations
  3. Return to ChatGPT: Upload cases/statutes for synthesis
  4. Draft with ChatGPT: Create memo structure
  5. Review and verify: Always check citations yourself

Document Drafting Basics

The Three-Stage Drafting Process

Stage 1: Outline & Strategy

I need to draft a demand letter for [situation]. Before drafting:
1. What are the key elements this letter must contain?
2. What tone is most appropriate?
3. What should I avoid saying (privilege/litigation concerns)?
4. Suggest an outline structure.

Stage 2: First Draft

Based on our outline, draft the letter. Use these facts:
[Insert specific facts]

Tone: [Professional/firm/conciliatory]
Length: [Target length]
Key demands: [List specific demands]

Stage 3: Refinement

Review this draft for:
1. Any statements that could waive privilege
2. Tone consistency
3. Unclear or ambiguous language
4. Missing elements
5. Overly aggressive language that might backfire

Then provide a revised version.

Exercise 3: Draft a Client Communication

Scenario: You need to explain a complex settlement offer to a client.

CONTEXT: I'm a litigation attorney representing plaintiff in a
personal injury case. We received a settlement offer.

TASK: Draft an email to my client explaining the offer and my
recommendation. The client is not legally sophisticated.

OFFER DETAILS:
- Defendant offers $175,000
- Must sign full release of all claims
- Confidentiality clause included
- Must be accepted within 14 days

CASE BACKGROUND:
- Client injured in car accident, rear-ended
- $45,000 in medical bills
- Lost 3 months of work ($22,500)
- Case value estimated at $150,000-$250,000 if we win at trial
- Trial would be 6-8 months away
- Defendant has good insurance coverage

MY RECOMMENDATION: Accept with counter on confidentiality

REQUIREMENTS:
- Plain English, no legal jargon
- Explain pros and cons objectively
- Be clear about next steps
- Professional but warm tone
- Under 400 words

Organizing with ChatGPT Memory and Custom GPTs

ChatGPT memory and Custom GPTs let you create persistent workspaces for different matters or practice areas.

How to Set Up a Custom GPT for Contract Review:

  1. Go to ChatGPT and create a new Custom GPT
  2. Add a clear name (e.g., "Acme Corp - MSA Review")
  3. Write custom instructions (your playbook)
  4. Configure file upload capability for relevant documents

Example Custom Instructions for Contract Review:

PROJECT: Standard SaaS Agreement Reviews

CONTEXT:
- I review SaaS vendor agreements for [Company Name]
- We are always the CUSTOMER/licensee
- Industry: Healthcare (HIPAA applies)
- Risk tolerance: Moderate (we're a mid-size company)

STANDARD POSITIONS:
1. Liability cap: Prefer uncapped for data breach; minimum 2x annual fees
2. Indemnification: Must include vendor security breach indemnity
3. Data: We own all our data; vendor gets no rights to use it
4. Termination: Need termination for convenience with 30 days notice
5. SLAs: Require 99.9% uptime with service credits

REVIEW PROCESS:
When I share a contract:
1. First identify the contract type and our role
2. Summarize key commercial terms
3. Flag deviations from our standard positions using:
   - RED: Must negotiate (deal-breaker)
   - YELLOW: Should negotiate (significant risk)
   - GREEN: Acceptable (minor or standard)
4. Provide specific redline suggestions for RED and YELLOW items

TONE: Business-focused, not overly legalistic. I report to a non-lawyer.

Create these standard Custom GPTs:

  • [Client] - [Matter]: Matter-specific workspace
  • Contract Playbook - [Type]: Your firm's standard positions
  • Legal Research - [Practice Area]: Practice area knowledge base
  • Templates & Precedents: Standard documents for reference

Quality Control Checklist

Before relying on any ChatGPT output:

Citation Verification

  • Verify all case citations in Westlaw/Lexis
  • Check that cited statutes are current
  • Confirm procedural rules match your jurisdiction
  • Validate any regulatory references

Accuracy Check

  • Do the legal conclusions follow from the analysis?
  • Are there counterarguments not addressed?
  • Does the advice fit your specific facts?
  • Have you checked for recent developments?

Client-Ready Review

  • Remove any obvious "AI-generated" language
  • Verify tone is appropriate for audience
  • Check for any confidential information leakage
  • Ensure advice is actionable and specific

Homework Before Tutorial 03

  1. Complete all three exercises in this tutorial
  2. Create your first Custom GPT for a current matter
  3. Draft custom instructions for one type of work you do regularly
  4. Try 5 different legal tasks with ChatGPT and note what works/doesn't

Contract Review

Review this [contract type] from the perspective of [party].
Identify: (1) unusual terms, (2) missing protections, (3) risk
areas. For each issue, suggest specific redline language.
What are the key legal issues and relevant authority for
[situation] in [jurisdiction]? Provide a research roadmap
including specific search terms.

Document Drafting

Draft a [document type] for [situation]. Tone: [formal/plain
English]. Include: [required elements]. Avoid: [prohibited content].

Client Communication

Explain [legal concept/situation] to a client who is not legally
trained. Use plain English, avoid jargon, and focus on practical
implications and next steps.

Do This Now

  • Choose your OpenAI plan and complete Exercise 1 (indemnification clause review)
  • Run the research planning prompt (Exercise 2)
  • Draft a client communication (Exercise 3)

Continue to Document Analysis -> | Previous: Overview



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