WRITING

The Ultimate Guide to Leveraging AI in Your Legal Writing and Practice

Discover how to supercharge your legal writing with AI—smarter drafting, sharper editing, and streamlined workflows. This guide walks you through tools, prompts, and strategies to get it right.
  • Joe Regalia

Table of Contents

  • The WWWHR Framework
  • Empowering AI With Our Knowledge
  • Writing and Argumentation Skills
  • Thinking and Reasoning Skills
  • Client-Facing & Communication Skills
  • Administrative, Workflow, and Practice Improvement Skills
  • Litigation Practice Support Skills
  • Transactional Practice Support Skills
We’re not just writers anymore. Lawyers have always worn a dozen hats, but now, thanks to AI, we’re entering a new era. We’re becoming manufacturers—assemblers—of our own legal work product. Think less “drafting from scratch” and more “curating and refining.” With AI by your side, you’re still the expert. You just have more tools in your toolbox—and more control over how and when to use them.
AI isn’t here to replace your judgment. It’s here to scale it.
Instead of drafting a section heading from scratch, ask AI to generate five emotionally calibrated options—then choose the one that strikes the right chord for your judge or audience. Want to frame your case around the perfect theme? Feed your AI the facts and your target audience, and ask it to pitch three different themes. Then do what lawyers do best: pick the best one.
Instead of drafting a section heading from scratch, ask AI to generate five emotionally calibrated options—then choose the one that strikes the right chord for your judge or audience. Want to frame your case around the perfect theme? Feed your AI the facts and your target audience, and ask it to pitch three different themes. Then do what lawyers do best: pick the best one.
You’re still the decision-maker. You’re just wielding new power tools.

The WWWHR Framework

What tool should you use? Is it secure? Does it have the features most useful for your project? Does it have your information handy so that you don’t need to spend much time getting it primed for your work?
  • Generalized models might not be the right tool for highly technical, procedural tasks. Fine-tuned/domain-specific models have been shown to perform much better on technical tasks. There's been quite a bit of research on coding, for example—which often requires technical accuracy just like legal citations.
  • Based on other research out there, including some I am in the middle of, I would bet that popular foundation models like GPT would do better at spotting mistakes than they would at producing correct citations on their own (. I highlight this just because, to me, a lot of leveraging AI smartly is about using the right tools in the right ways.
  • Variability in outputs can be a feature instead of a bug. For many legal tasks, variability is a great thing—brainstorming, ideating, rewriting style—aren't about following if-then procedural rules. I think, again, work like this highlights that (at this stage at least) it's about using AI for the right things.
  • GenAI often works best when partnered up with other technology. A ton of tools out there stack on top of GenAI to achieve more technical, consistent results. I know dozens of startups using a slew of software—with GenAI powering up pieces in the right places—to achieve incredibly consistent results. So for citations, you could imagine a GenAI helping locate the relevant rule, understand mistakes or context in the user's input—but then a more rules-based algorithm producing the final citation. Like domain-specific models, this is just another plug for using general popular products like ChatGPT for the right things—other tools are often more effective for particular tasks.
When should you use AI during your project? A lot of the battle is know when to think about using AI, and when not to. At what steps in the writing or drafting process should you turn and ask AI for ideas or some work? Refer to the AI Tasks section for more insight here, and continue building your skills to get better at it. But here is an example here’s why this is an important step: A recent study suggested that even the top LLMs can’t format a legal citation consistently—scoring only an average of about 60-95% across different source types when asked to write out a citation from source material. But these same models are almost perfectly accurate in spotting a problem in those same citations. So it’s a great idea to turn to AI to have it do a second check for mistakes—but perhaps not the best tool when you’re first drafting a citation. (Although query how much time you’d save having the LLM do the first crack at the citations and just correcting the occasional slip up?)
  • LLMs often perform better as editors or evaluators of text than as creators of perfectly accurate text.
  • Free-form generation introduces more variability into LLM answers than pattern recognition and extraction. That is a good thing when you are ideating. Not so good if you are correcting a citation.
  • General models might not be the right tool for highly technical, procedural tasks. Domain-specific models have performed much better on technical tasks. There's been quite a bit of research on coding, for example, which often requires rule-based technical accuracy.
  • Evaluation may be more suited to general models than generation. Based on other research out there, including some I am in the middle of, I would bet that popular models like GPT would do better at spotting mistakes than they would at producing correct citations on their own (so you might get more consistent results asking an LLM to find the mistakes in your citations rather than having it generate citations from scratch).
  • Variability in outputs can be a feature instead of a bug. For many legal tasks, variability is a great thing—brainstorming, ideating, rewriting style—aren't about following if-then procedural rules. I think work like this highlights that (at this stage at least) it's about using AI for the right things in the right ways.
  • Keep accuracy in perspective. Let's say you needed to create a bunch of citations from source documents (a real-world use case of the research in this article). Would you save time having an AI do it all with 75% accuracy and then quickly correcting the 25% that has a small issue? On this one, I do think humans would be more accurate than what the study revealed—so I can't say humans would make as many mistakes. But maybe. If I had an associate quickly write out 800+ citations from source materials, maybe the rates would be similar?
Why are you using AI? A vision of the results you’re looking for will make it much easier to quickly identify useful results. If you keep your vision vague, then you can spend hours diving down AI rabbit holes. Take a moment to think about what the final version should look like.
How can you best leverage AI for this task? What prompting, saved prompts, context, documents, information, data can you give the AI to get the best results quickly?
Refine. Take stock of what works and what doesn’t. Start saving prompts, templates, examples, and any other information that has helped you get better AI results, so that you can easily reuse it later. Take stock of your writing and other practice processes so you can better decide the WWWH in the future for each of the major tasks you work on regularly. Revisit your processes (including using AI to help) so that you can benchmark your work and continuously improve. The age of AI is the age of process.

Empowering AI With Our Knowledge

You would never have an assistant go use Wikipedia as a reference when writing a brief. The same is true for AI. We want AI brains using the same quality information you work off of.
  • Understanding AI training in foundation models (technically you can train your own)
  • Software that automatically supplements AI with legal-specific data
  • Creating a prompt library
  • Custom instructions that can save
  • Memory features
  • A vector-based RAG

Creating Your Own RAG

Equip with:
  • Past firm memos, briefs, or other documents
  • Annotated templates
  • Key statutes + secondary sources
  • Strategy notes from you or others
Example:
“Show me how our firm typically argues against economic duress in the context of a contract renegotiation—especially when the client is a seller in a B2B dispute. Provide excerpts and identify any deviations in reasoning from recent cases. ”
Big AI companies offer some options: E.g., GPT
Emerging companies will now do it for you using the best tech: My favorite is CustomGPT.ai.

Step 1: Gather and Organize Your Content

  • Put all source documents into one Google Drive or Dropbox folder (or upload them directly)
  • Convert scans into OCR-processed PDFs or text for accuracy
  • Organize by use case (e. g., contracts, briefs, case law, memos)

Step 2: Create Your App

  • Go to https://customgpt. ai
  • Create a new project
  • Upload your files or connect to Google Drive or SharePoint

Step 3: Configure Retrieval Parameters

  • Adjust chunking (e. g., by paragraphs or sections)
  • Enable metadata tags (e. g., jurisdiction, document type)
  • Customize instructions (e. g., “Prioritize conservative tone in summaries”)

Step 4: Deploy + Test

  • Use the built-in chat interface or export to an embeddable widget (on your firm’s intranet)
  • Ask questions like:
“What arguments have we used in past motions to compel arbitration under Nevada law?”
“Summarize the differences between our 2022 and 2024 master service agreements. ”

Writing and Argumentation Skills

Summarizing
Condensing legal documents, cases, or fact records into clear, useful summaries tailored to different goals and audiences.
  • Tailor summaries by issue, audience, or task—internal, client-facing, or judicial
  • Use different lenses: timeline, doctrine, or persuasive framing
Sample prompt: 
 “Summarize this deposition transcript focusing only on gaps in the timeline and witness credibility.”
Drafting
Generating first drafts or alternative versions of legal documents—from contracts to emails—faster and with creative variation.
  • Start with bullet points, past templates, or messy notes
  • Ask for multiple takes to test different framings or tones
Sample prompt: 
“Draft a first-pass operating agreement from these notes, using plain language for a startup client.”
Styling
Adjusting tone, voice, and formality for different audiences and goals.
  • Shift from neutral to persuasive, from dense to digestible, from formal to informal
  • Ask AI to mimic the tone of a specific judge, partner, or past brief
Sample prompt: 
“Rewrite this letter in a warmer, more collaborative tone while keeping the legal ask firm.”
Brainstorming
Generating multiple ideas, framings, arguments, or structures to explore your best rhetorical approach.
  • Use it to kick off drafts or to get unstuck mid-writing
  • Request ideas targeted to specific goals: urgency, empathy, impact
Sample prompt: 
“Give me five different openings to this motion that emphasize urgency in different ways.”
Reframing
Reworking facts, arguments, or organization to shift emphasis or impact.
  • Try chronological, thematic, or issue-based ordering
  • Use it to test alternative framings of facts or counter-narratives
Sample prompt: 
“Reframe this section to emphasize institutional failure over individual negligence.”
Editing
Improving legal text at all levels: clarity, logic, and style.
  • Layer edits: grammar only, logic only, tone only
  • Ask for flags, explanations, and rewritten alternatives
Sample prompt: 
 “Edit this memo for clarity and flow—leave comments explaining any logic gaps. ”
Comparing
Analyzing multiple legal texts side by side—e.g., briefs, clauses, rulings—to evaluate and improve.
  • Use for strategic comparisons, e.g., your motion vs. theirs
  • Highlight tone, clarity, or logic differences
Sample prompt: 
“Compare these two versions of the clause and identify which is clearer and why.”
Synthesizing
Combining multiple legal sources into a coherent rule, theme, or analysis.
  • Ask the AI to extract common elements and unify them
  • Great for multi-case research or layered standards
Sample prompt: 
“Synthesize these five cases into a single articulation of the controlling test and its exceptions.”
Layering or Structuring
Helping you move between levels of abstraction—rule, application, policy, etc.
  • Ask the AI to bridge between layers or shift perspective
  • Use it to connect granular facts to overarching doctrine
Sample prompt: 
“Turn this rule and analysis into a big-picture summary that connects back to client goals.”
Narrative Structuring
Shaping legal writing into a persuasive, emotionally engaging story.
  • Ask for rising tension, character framing, or momentum building
  • Use it to highlight injustice, credibility, or cause-effect arcs
Sample prompt: 
“Turn this timeline into a compelling narrative that highlights bad faith by the opposing party.”
Calibration
Tuning tone, aggressiveness, or caution based on posture and audience.
  • Shift from aggressive to conciliatory, confident to cautious
  • Ask AI to calibrate tone to match the reader (judge, GC, regulator)
Sample prompt: 
“Revise this brief to sound more neutral and solution-oriented, assuming a skeptical judge.”
Consistency Checking
Ensuring coherent voice, structure, and terminology across complex or multi-author documents.
  • Flag inconsistencies in style, tone, argument, or formatting
  • Great for finalizing court filings or client-facing documents
Sample prompt: 
“Review this brief and highlight any inconsistent terminology or shifts in tone.”
Genre & Context Shifting
Transforming content across legal genres, formats, or contexts.
  • Ask the AI to convert a memo into a client alert, a checklist into a slide deck, or a contract into an argument outline
  • Use it when repurposing content for different audiences or uses
Sample prompt: 
“Turn this client FAQ into a training handout for new sales staff on legal dos and don’ts.”
Emulation
Mimicking the writing style or structure of a person, judge, firm, or institution.
  • Train AI on past writing to generate consistent tone, syntax, and formatting
  • Use it for ghostwriting, reply briefs, or firm-branded content
Sample prompt: 
“Rewrite this memo in the style of Judge X’s rulings from these two orders.”
Personas
Tailoring tone, content, and framing to a specific audience persona—e.g., GC, regulator, skeptical judge.
  • Ask the AI to prioritize information and adjust tone to match the recipient’s mindset and goals
  • Use for persuasive writing or strategic advice
Sample prompt: 
“Frame this analysis as if written for a cautious GC with little tolerance for legal uncertainty.”
Applying Rhetoric or Logic Structures
Using formal techniques to sharpen persuasion or clarity.
  • Ask the AI to apply structures like IRAC, Rule-Proof-Application, classical rhetorical moves, or analogical framing
  • Use to revise, test, or teach persuasive logic
Sample prompt: 
“Rewrite this argument using a Rule-Proof-Application structure, with a metaphor to reinforce the policy theme.”
Multilingual Support
Translating legal content and summarizing or clarifying it across languages.
  • Use the AI to translate and annotate foreign-language contracts, rulings, or correspondence
  • Especially useful in cross-border deals or international litigation
Sample prompt: 
“Translate this Spanish employment agreement into English and highlight any unusual severance provisions.”
Sanity Checks & Gut Checks
Asking AI for a second opinion on structure, logic, tone, or completeness.
  • Use it at the end of drafting or reviewing to check blind spots
  • Ask AI to rate strength, clarity, and risks
Sample prompt: 
“Gut check this letter—do I sound too aggressive and have I clearly stated the client’s ask?”
Extracting
Pulling key legal material from large or dense content sets.
  • Use to isolate precedent, patterns, red flags, or useful citations
  • Great for filings, rulings, contracts, or data-heavy records
Sample prompt: 
“Extract the governing law clauses and any termination triggers from these 30 contracts.”
Pattern Recognition & Trends
Identifying hidden themes, recurring issues, or strategic patterns across documents or matters.
  • Useful for surfacing market norms, repeated disputes, or overused arguments
  • Ask AI to detect what’s implicit, not just explicit
Sample prompt: 
“From these NDAs, what appears to be the market standard on termination and indemnity?”

Thinking and Reasoning Skills

Strategizing
Mapping out legal options, outcomes, and back-planned tactics aligned with case or client goals.
  • Use AI to generate pros/cons, likely responses, or settlement implications
  • Ideal for litigation, negotiation, or regulatory response planning
Sample prompt: 
“Outline three strategy options for handling this breach claim, each with risk and cost trade-offs.”
Pressure Testing
Challenging arguments by simulating scrutiny from judges, opposing counsel, or critical readers.
  • Use AI to find logical gaps, weak premises, or missing support
  • Ask for counterarguments and rhetorical vulnerabilities
Sample prompt: 
“Act as opposing counsel and critique this motion for any weak assumptions or unsupported conclusions.”
Risk Analysis & Forecasting
Modeling potential future legal outcomes or regulatory reactions.
  • Predict enforcement, litigation, discovery, or audit risks
  • Use to prepare clients for contingency planning
Sample prompt: 
“Given this fact pattern and recent SEC actions, what enforcement risks are most likely?”
Evaluation
Spot-checking logic, soundness, and sufficiency of legal reasoning.
  • Ask AI to flag unsupported assertions, overstatements, or misapplied rules
  • Use as a final gut-check or critique pass
Sample prompt: 
“Evaluate this memo and point out any places where the reasoning doesn’t follow from the facts.”
Statutory Comparison & Synthesis
Analyzing multiple statutes across jurisdictions and synthesizing differences.
  • Helpful for compliance, multi-state litigation, or transactional planning
Sample prompt: 
“Compare data breach notification statutes in California, Texas, and Florida for financial institutions.”
Negotiation Mapping
Planning negotiation strategy and anticipating positions, fallbacks, and options.
  • Use AI to simulate BATNAs, deal dynamics, and creative middle grounds
  • Tailor by party, leverage, and goals
Sample prompt: 
“Map out three likely negotiation paths with fallback terms for the indemnity clause.”
Fact & Evidence Mapping
Linking facts to legal issues and available evidence in a structured, visual or logical format.
  • Build issue trees, fact matrices, or burden-of-proof maps
  • Helps with discovery planning, motion support, or trial prep
Sample prompt: 
“Create an issue-to-fact matrix showing which facts support each element of the fraud claim.”
Reflective Lawyering
Analyzing your own work patterns, writing style, and practice habits for improvement.
  • Use AI to review past briefs, memos, or time logs and generate coaching suggestions
  • Great for identifying overused structures, tone issues, or recurring blind spots
Sample prompt: 
“Based on my last five motions, what clarity issues or style inconsistencies appear most often?”
Generating Hypotheticals & Analogies
Creating hypotheticals or real-world analogies to test legal logic or teach others.
  • Use to prepare for oral argument, explain issues to clients, or draft more vivid writing
  • Ask for analogies matched to tone or audience
Sample prompt: 
“Generate three hypotheticals that test the outer limits of this ADA compliance standard.”

Client-Facing & Communication Skills

Creating Client-Facing Materials
Drafting clear, tailored summaries, guidance, and explainers for client-facing use
  • Use AI to generate pros/cons, likely responses, or settlement implications.
  • Adapt tone, detail, and focus for the specific client relationship
Sample prompt: 
“Summarize this arbitration clause for a client unfamiliar with legal processes—include benefits and risks.”
Visual Creation
Using AI to generate timelines, issue maps, flowcharts, or tables that clarify complex facts or rules.
  • Great for litigation timelines, contract logic trees, or regulatory charts
  • Ask AI to draft diagrams based on narratives or checklists
Sample prompt: 
“Turn this set of events into a visual timeline that highlights causation and delay points.”
Follow-Up Communications
Drafting clear post-meeting emails, to-do lists, decision summaries, or progress reports.
  • Use AI to convert notes or recordings into polished follow-ups
  • Tailor format and tone to client expectations
Sample prompt: 
“Summarize this strategy meeting into a client-ready recap with next steps.”
Client Onboarding Packets
Creating comprehensive welcome and orientation materials tailored to the matter and client.
  • Include expected timelines, documents needed, contact info, and process overview
  • Ask AI to pull from precedent packets and customize per matter type
Sample prompt: 
“Build a new client onboarding packet for a data privacy compliance matter, modeled on this past example.”
Compliance Monitoring
Helping clients stay ahead of deadlines, updates, and jurisdictional obligations.
  • Generate compliance calendars, reminders, or policy summaries
  • Use to automate ongoing compliance alerts or notices
Sample prompt: 
“Create a compliance calendar for a biotech startup operating in California and New York.”
Plain-Language Explanation
Translating legal documents or concepts into client-accessible prose.
  • Eliminate jargon, explain terms, and connect issues to business impact
  • Ask for tone variation by client experience level
Sample prompt: 
“Rewrite this indemnity clause so a non-lawyer board member can understand the key risks.”
Client Q&A Assistance
Supporting fast, accurate responses to routine or predictable client questions.
  • Use AI to draft answers from internal precedent, handbooks, or firm knowledge bases
  • Can be integrated into chat-style help or live prep
Sample prompt: 
“Draft a response to a client asking what ‘reasonable efforts’ means in this clause.”
Educational Content Drafting
Creating CLE decks, client alerts, or internal training materials on legal topics
  • Ask AI to summarize statutes, provide examples, or build quiz questions
  • Tailor by audience sophistication and tone
Sample prompt: 
“Create a 5-slide training outline explaining the difference between employees and contractors under California law.”
Marketing & Thought Leadership Writing
Producing blog posts, newsletter content, or social media updates.
  • Translate legal substance into conversational, high-value insights
  • Ask for tone to match your brand, audience, or publication
Sample prompt: 
“Write a 500-word blog post summarizing the recent SEC crypto enforcement action and its implications for startups.”
Proposal & Pitch Drafting
Creating tailored materials for prospective clients or RFPs.
  • Summarize experience, customize value propositions, and draft team bios
  • Use AI to assemble pitches from firm bios, past matters, and client goals
Sample prompt: 
“Draft a pitch letter for a pharmaceutical client based on these sample bios and experience summaries.”

Administrative, Workflow, and Practice Improvement Skills

Organizing
Structuring large or messy content—e.g., discovery files, contract sets, or research notes—into usable formats.
  • Ask AI to group, sort, or label content based on topic, issue, or chronology
  • Use for clarity in long-term matters or complex documents
Sample prompt: 
“Organize these 300 emails into five categories based on relevance to the whistleblower claim.”
Legal Tech Tool Evaluation
Using AI to compare and assess potential software tools or vendor services.
  • Especially helpful for GCs, ops leads, or innovation teams
Sample prompt: 
“Compare Ironclad, SpotDraft, and LinkSquares based on features useful for a 5-person in-house team.”
Internal Policy & Manual Drafting
Drafting or updating internal firm policies, handbooks, or procedures.
  • Ask AI to align with best practices and local laws
Sample prompt: 
“Create a social media policy for a midsize law firm based on recent NLRB guidance.”
Admin Automation
Turning routine administrative tasks into automated workflows.
  • Generate checklists, auto-fill forms, clean up transcripts, or anonymize sensitive data
  • Especially useful for task follow-ups, scheduling, and compliance logs
Sample prompt: 
“Create a pre-deposition checklist from these case notes and prior templates.”
Process Design & Improvement
Creating or refining standard legal workflows for recurring work.
  • Map out steps, roles, and templates for better speed and quality
  • Ask AI to flag inefficiencies and suggest alternatives
Sample prompt: 
“Design a streamlined contract review process for a three-person in-house team.”
Information Hygiene
Checking for metadata, citation accuracy, formatting consistency, and document integrity.
  • Useful at final draft stage or when combining multi-author work
  • Ask AI to flag defined term mismatches, citation inconsistencies, or stray formatting
Sample prompt: 
“Review this memo for Bluebook accuracy, defined term consistency, and hanging headings.”
Learning & Tutoring
Turning legal content into teachable material or personalized lessons.
  • Ask AI to explain, quiz, or reframe concepts for trainees or clients
  • Excellent for new associates, clients, or lateral onboarding
Sample prompt: 
“Explain this patent claim construction order as if I’m a new associate seeing it for the first time.”
Work Improvement & Feedback Loops
Extracting lessons and upgrades from completed matters or documents.
  • Analyze past work product for clarity, timing, or success patterns
  • Use for institutional knowledge capture and future process refinement
Sample prompt: 
“From these past litigation memos, identify common gaps in early factual development.”
Staying Current
Tracking new legal developments and summarizing them by relevance.
  • Ask AI to monitor case law, regulations, or enforcement trends
  • Tailor updates by industry, jurisdiction, or client base
Sample prompt: 
“Give me a weekly update on new California privacy rulings affecting SaaS companies.”
Billing Narrative Drafting
Creating polished, compliant, and accurate billing entries.
  • Turn meetings, notes, or documents into clear time entries
  • Match formatting to client or system requirements
Sample prompt: 
“Draft billing entries from these notes for a tech client, following their narrative style guidelines.”
Matter Timeline Estimation
Forecasting key milestones and deadlines for legal matters.
  • Base predictions on similar past matters, templates, or known bottlenecks
  • Ask AI to create visual timelines or staffing plans
Sample prompt: 
“Estimate the timeline and team for closing this $15M Series A round, based on this checklist and client info.”
Knowledge Management Intake
Tagging and organizing documents for internal reference libraries.
  • Sort by clause, issue, jurisdiction, industry, or success outcome
  • Ask AI to identify duplicates or underused models
Sample prompt: 
“Auto-tag these agreements by jurisdiction, termination clause type, and dispute resolution method.”
Template & Clause Bank Maintenance
Improving and streamlining reusable language.
  • Identify outdated, redundant, or inconsistent clauses
  • Align templates with firm or client preferences and current market norms
Sample prompt: 
“Compare these service agreement templates and consolidate into a clean master version.”
Junior Lawyer Coaching
Simulating partner feedback, explaining edits, or offering writing support.
  • Ask AI to rewrite, critique, or annotate examples to teach better habits
  • Use to model professional tone, logic, and structure
Sample prompt: 
“Act as a partner reviewing this memo and leave comments on structure, tone, and clarity.”
Conflicts Checking Support
Summarizing and flagging potential client conflicts across past matters.
  • Use AI with structured data or unstructured matter descriptions
  • Ask for high-level summaries or specific red flags
Sample prompt: 
“Summarize any possible conflicts between this prospective biotech client and our past IP litigation work.”
Privilege & Work Product Review
Reviewing documents for privilege risk or business/legal content blending
  • Ask AI to highlight risky phrasing or recommend redactions
  • Use for decks, emails, and meeting summaries
Sample prompt: 
“Flag any content in this internal strategy deck that could jeopardize attorney-client privilege.”
Regulatory Risk Forecasting
Modeling enforcement likelihood, reputational exposure, or audit risk.
  • Ask AI to combine client facts with enforcement history and trends
  • Use to build early warning systems and response playbooks
Sample prompt: 
“Given this advertising model and FTC enforcement history, what compliance risks should we flag?”
Stress & Complexity Flagging
Having AI identify likely high-stress or complexity areas in documents or workflows.
  • Helpful for workload triage or support
Sample prompt: 
“Highlight areas in this trial calendar that may be unmanageable for a two-person team.”
Coaching & Mindset Reframing
Using AI as a mindset and communication coach to reframe difficult conversations or feedback.
  • Use when navigating challenging emails, team dynamics, or client pushback
Sample prompt: 
“Help me reframe this negative feedback email so it’s firm but constructive.
Wellness-Integrated Time Management
Helping lawyers balance billable tasks with breaks, wellness, and focused deep work.
  • Use AI to restructure task lists with built-in recovery time
Sample prompt: 
 “Break this to-do list into 90-minute sprints with short breaks and lower-cognitive-load tasks in the afternoon.”

Litigation Practice Support Skills

Deposition Preparation
Generating outlines, question sets, impeachment material, and prep packets for witnesses or attorneys.
  • Ask AI to simulate opposing answers or anticipate evasive responses
  • Build themes and key facts into the question flow
Sample prompt: 
“Create a deposition outline focused on the CFO’s knowledge of internal controls and inconsistencies in their past statements.”
Motion Practice Planning
Outlining motion strategy, argument structure, and local rule requirements.
  • Ask AI to prioritize motion types based on facts, timing, and judge profile
  • Use for early-stage planning or motion sequencing
Sample prompt: 
“Given this case and judge, suggest three likely-to-succeed pretrial motions and how to frame each one.”
Discovery Management
Summarizing responses, spotting inconsistencies, and generating follow-up tasks.
  • Use AI to find incomplete answers, evasions, or cross-document inconsistencies
  • Ask for targeted follow-up questions or sanction motion options
Sample prompt: 
“Summarize these RFP responses and flag which ones are incomplete, evasive, or raise privilege concerns.”
Pretrial Planning
Generating checklists, exhibit lists, trial themes, and logistical plans.
  • Ask AI to organize tasks across teams, prep timelines, or generate trial week workflows
  • Use for coordination across litigation support, witness teams, and filings
Sample prompt: 
“Draft a pretrial checklist for a two-week federal jury trial including deadlines, logistics, and witness prep.”
Drafting Jury Instructions
Customizing pattern instructions or proposing tailored language to match your theory of the case.
  • Ask AI to synthesize model instructions and suggest edits
  • Use to align language with your key themes and burdens
Sample prompt: 
“Draft a negligence instruction based on 9th Circuit pattern language, tailored to a product defect claim.”
Simulating Cross/Direct Examination
Using AI to simulate witnesses or attorneys to test question impact and story flow.
  • Ask AI to role-play evasive or hostile witnesses based on real deposition or trial testimony
  • Use AI to train junior litigators or rehearse key moments
Sample prompt: 
“Play the role of the plaintiff in this employment case and answer 10 direct questions. Then switch to hostile cross-mode.”
Brief Bank Mining
Extracting reusable arguments, rule language, or structure from a set of past filings.
  • Ask AI to find persuasive hooks, analogies, or citations used previously
  • Use to speed drafting or maintain firm tone consistency
Sample prompt: 
“Pull the strongest causation arguments from our last five MSJs in product liability cases.”

Transactional Practice Support Skills

Due Diligence Review
Summarizing, flagging, and organizing key clauses, deviations, and risks from documents.
  • Ask AI to compare terms to standards, prior deals, or firm templates
  • Generate summary tables, red flag memos, or client-ready summaries
Sample prompt: 
“Review these 20 commercial leases and identify any unusual assignment or subletting restrictions.”
Term Sheet Drafting & Translation
Turning bullet points into structured term sheets—or full agreements from term sheets.
  • Ask AI to identify missing standard terms or flag ambiguous phrasing
  • Use to align parties early and surface redline hotspots
Sample prompt: 
“Draft a convertible note term sheet from these negotiation notes and add standard terms where missing.”
Closing Checklist Creation
Generating comprehensive deal checklists and assigning tasks by role and timeline.
  • Tailor checklists to deal type, jurisdiction, or client
  • Ask AI to group documents by priority, party, or approval stage
Sample prompt: 
“Create a closing checklist for a private asset purchase involving IP, employment, and international compliance.”
Negotiation Simulation
Testing how proposed changes will impact leverage, position, or deal risk.
  • Ask AI to simulate counterparty responses or highlight concession paths
  • Use to explore fallback positions or escalation triggers
Sample prompt: 
“How might the other side respond if we insist on deleting the limitation of liability cap?”
Post-Deal Analysis
Extracting insights from what caused deal friction, delays, or concessions.
  • Use for firm knowledge capture, template improvements, or client reporting
  • Ask AI to identify repeat bottlenecks or decision inflection points
Sample prompt: 
“From these annotated agreements, summarize which clauses required the most negotiation and why.”
Drafting & Editing (Transactional)
Generating, polishing, or explaining contracts and commercial documents.
  • Ask AI to draft clauses, clean up dense language, or rewrite for plain English
  • Great for translating business needs into legal language (and vice versa)
Sample prompt: 
“Rewrite this indemnification section in plain English and explain the business impact of each subclause.”
As legal professionals, our toolkit is evolving fast—but our core strengths remain the same. AI is not about replacing what makes great lawyering possible. It’s about enhancing it: helping us write faster, think deeper, and communicate more effectively. With the right tools and smart strategies, you can unlock extraordinary value in your legal work—while staying grounded in the judgment and creativity that only you can bring. Now’s the time to explore, experiment, and lead the charge into the future of legal writing.
Joe Regalia
Write.law co-founder Joe Regalia combines his experience as both practitioner and professor to create exciting new ways to teach legal skills.  Learn more about Joe

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