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Learn how small firm lawyers are using AI to redline contracts faster and more accurately, without giving up control. This practical guide covers legal AI tools, real-world prompts, and workflows for corporate and real estate transactions using Gavel Exec.
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I’ll never forget one particular night early in my legal career as a summer associate. It was past midnight, and I was hunched over a hefty contract, manually comparing it to an earlier term sheet. The office was silent except for the rustling of paper and my muttering every time I spotted a subtle change. I wanted to be a litigator, but here I was negotiating a settlement agreement line by line, eyes burning from toggling between documents. I remember thinking: there has to be a better way. Years later, as the CEO of Gavel, I often hear similar stories from small firm lawyers. Whether it’s a 50-page commercial lease or a startup’s financing agreement, the grunt work of redlining – spotting changes, enforcing your playbook, and revising language – can consume hours.
What if an AI could handle the busywork, and hand you a nearly-finished markup by the time you finish your coffee? In this whitepaper, I’ll share how that’s not just wishful thinking, but an everyday reality with tools like Gavel Exec. I’ll walk through the basics of legal AI in plain English, give you ten ready-to-use prompts for contract review, and even recount a realistic deal scenario showing how an AI “associate” works in practice. The goal is to help you redline contracts faster and more effectively – with less risk and zero loss of control. Let’s dive into the new AI-assisted playbook for contract review.
Before we get to the fun stuff, let’s cover a few key terms and concepts. This isn’t a theoretical tech lecture – it’s a human-centered primer on how AI actually fits into our contract review workflow:
That’s it – the ABCs of AI for contract review: LLMs that generate text, prompts that you control, the risk of hallucinations (managed by careful context injection and verification), playbooks to encode your expert knowledge, and token limits to keep in mind for document size. Now, let’s get practical and look at how you can put this to use today.
One of the best ways to “level up” your AI use in day-to-day work is to start with a library of proven prompts. Below are ten real examples tailored to corporate and real estate contract redlining. I’ve focused on scenarios that small firm lawyers encounter regularly – and each prompt is written in plain language as you might input it into Gavel Exec’s chat sidebar in Word:
Each of these prompts is like a power tool in your toolbox. They’re not pie-in-the-sky ideas; they’re things you can literally copy-paste into Gavel Exec (or a similar LLM-powered assistant) and get results today. The more you practice crafting prompts, the more you’ll develop your own playbook of go-to AI moves. Remember, you can always refine the prompt and run it again if the output isn’t spot on. It’s an iterative conversation. Next, let’s see how this actually plays out in a real-life scenario – from receiving a contract to sending out a revised draft – with AI as part of the team.
To illustrate the workflow, let’s follow a small firm lawyer, “Alice,” through a realistic transaction. Alice represents a startup tenant, and they’re negotiating a commercial office lease. They signed a Letter of Intent a few weeks ago, and now the landlord’s attorney has sent over a 40-page lease draft. Alice could manually redline it, but instead she fires up Gavel Exec in Word to help. Here’s how the process unfolds:
1. Opening the Document with AI at Hand: Alice opens the landlord’s lease in Microsoft Word. She has the Gavel Exec add-in installed (it lives in Word’s sidebar). With one click, she pulls up the Gavel Exec panel next to her document. She’s essentially got a smart co-pilot ready to go on the same screen. The interface looks like a chat window where she can ask questions or give instructions, and a menu for running her playbooks. (If you’ve seen modern Word plugins, you can picture it – a clean sidebar with a prompt box at the bottom, and options for uploading reference docs or selecting playbooks.)
2. Context Injection – Uploading the LOI: Before asking the AI anything, Alice provides context. She uses the “Reference Document” feature to upload the signed LOI that outlined the key deal terms. In the chat, it now shows that an LOI.pdf is attached as context. By doing this, Alice ensures the AI knows the “deal” and can catch any discrepancies. This is a crucial step – rather than trusting the AI’s general training, she’s feeding it the exact term sheet both parties already agreed on.
3. “Find What’s Missing” – Prompting a Comparison: Alice types: “Redline this lease based on the attached LOI. List any terms that don’t match the LOI or are missing, and suggest edits.” She hits send. Under the hood, Gavel Exec’s AI quickly reads both the LOI and the lease. Within about 30 seconds, the chat populates with a response. It’s a rundown of differences, essentially an issues list:
And so on. Alice is impressed – in one go, the AI spotted four or five substantive inconsistencies. It also suggested language for adding the missing renewal option, pulling phrasing from common practice. Essentially, it gave her a redline markup: inserted a new section with the renewal terms from the LOI and highlighted the rent and term for correction. Alice clicks “Apply All,” and Gavel Exec inserts those changes into the Word document (with Track Changes on). Just like that, major LOI alignment issues are handled. Alice, of course, double-checks each against the LOI – and they all align perfectly. She’s still in control, but saved a ton of time.
4. Running a Built-In Market Playbook: Next, Alice wants to ensure the lease is reasonable by market standards, not just matching the LOI. She switches to the Playbook tab in the Gavel Exec sidebar. There, she selects the “Tenant-Favorable Commercial Lease” playbook – one of the built-in options Gavel provides, developed with experienced real estate attorneys. (This playbook knows common tenant asks and typical market clauses for office leases.) She clicks “Run Playbook.”
In moments, the AI produces a set of redlines and comments throughout the lease, all following the playbook’s rules. For example:
Alice reviews these playbook-driven changes in the redline. It’s like having a senior real estate lawyer whispering in her ear about what to fix. She doesn’t accept all of them blindly – for instance, she knows this particular landlord never agrees to a CAM cap above 3%, so she tweaks the AI’s inserted 5% to 3%. But the heavy lifting is done. In a few minutes, Alice has advanced the lease to a much more tenant-friendly state and documented the rationale behind each change with comments. Importantly, she’s in control: she reviews each suggestion. The AI’s suggestions were based on standard positions, but Alice applies her client’s specific goals on top.
5. Clause-by-Clause Refinement via Chat: With the broad strokes done, Alice now zeroes in on a few tricky clauses for fine-tuning. One is the “Default and Remedies” section, which is three pages long and full of legalese. Alice highlights a particularly dense paragraph (about five default scenarios) and in the Gavel Exec chat types: “Summarize this default clause in plain English, and suggest if any part of it poses unusual risks to the tenant.” The AI quickly outputs a summary: “If the tenant fails to do X, landlord can do Y... etc.” and notes that one provision is a bit harsh (the landlord can accelerate the entire rent for minor breaches, which is not common). This jibes with Alice’s own impression. She asks a follow-up in chat: “What changes would make it more tenant-favorable without likely rejection?” The AI suggests a softer remedy (no acceleration for non-monetary defaults until 30 days opportunity to cure, for example). Alice likes that and manually incorporates a version of it into her redline, using the AI’s suggestion as a template.
She then scrolls to the insurance clause. It’s full of jargon and specific limits. Alice isn’t an insurance law expert, so she asks the AI: “Is the insurance coverage specified here typical for an office lease of this size? Anything missing or excessive?” The AI responds: “The required liability coverage ($1M per occurrence, $3M aggregate) is typical. Requiring the tenant to waive subrogation is standard. However, the lease lacks mutual waiver of subrogation by the landlord – consider adding that so landlord also waives claims covered by insurance.” Great point – a mutual waiver of subrogation benefits her client. Alice adds a comment in the document to request that change from the landlord. (She could have the AI insert the exact clause, but she decides a comment is sufficient for this point.)
Finally, Alice tackles the rent escalation clause. It’s a bit confusing in wording. She types: “Rewrite the rent escalation clause in clearer language, keeping the 3% annual increase, and add a cap that it never exceeds 3% even if CPI is higher.” In a flash, the AI revises the clause, simplifying some convoluted formula and explicitly stating the 3% cap. She inserts that as a redline. It reads much cleaner and her client will appreciate the predictable cap.
6. Quality Check and AI Double-Check: Now the lease is heavily marked up with changes (in Track Changes) and sprinkled with comments explaining them. Before sending it out, Alice does a final review. She uses one more AI prompt as a safety net: “Scan the document and list any places where the tenant might still be over-exposed or any clause that a tenant-side attorney would typically push back on that we haven’t addressed.” Essentially, “did I miss anything?” Even after all that, the AI flags one item: “The guarantee clause makes the startup founder personally liable. Tenant attorneys often try to limit or remove personal guarantees. Consider if this aligns with your client’s risk tolerance.” Alice had indeed overlooked the personal guarantee section because she was focusing on the main lease. Now, she discusses with her client and they decide to propose a limited guarantee (maybe just for the first year’s rent). She adds that to her markups as well. It’s a prime example of how the AI, with its wide lens, can act as a backstop so nothing important is missed. The AI essentially acted like a diligent associate doing a second review of her work.
7. Delivering the Marked Draft – With Confidence: Within a couple of hours, Alice has taken a landlord-friendly lease to a balanced document ready to send back. She’s used the AI to compare against the deal memo, enforce her client’s playbook preferences, translate and refine complex clauses, and ensure consistency. All the while, she has exercised her own judgment on which suggestions to keep. The final product is her work product – just accelerated and augmented by AI. When she emails it out, she includes a note to the opposing counsel highlighting a couple of major changes (the AI even helped draft those explanations).
From the outside, what the landlord’s lawyer sees is a thorough, well-reasoned redline that looks like Alice spent days crafting. In reality, it was one afternoon, and Alice was able to make a soccer game with her kids that evening instead of pulling another late night.
This story shows AI in a supporting role. The AI didn’t magically produce a perfect lease on its own – it needed Alice’s prompts and guidance at each step. But it dramatically reduced the manual effort and enhanced the quality of the review. It’s like she had a tireless junior attorney plus a market research guru plus an editor all in one. The result: a faster turnaround for the client, a stronger negotiating position, and a less stressed lawyer.
(As a side note, imagine the competitive advantage here: a solo or small firm lawyer can go toe-to-toe with BigLaw speed when they leverage these tools. The AI helps “level the playing field, especially when a small firm is negotiating against a larger team” by handling the rote work and surfacing issues. And because Gavel Exec is built into Word, you’re not having to export documents to some external system – you stay in the zone where you’re comfortable, with Track Changes and Word comments like you’ve always used.)
Using AI to draft and redline is powerful, but don’t let the novelty distract you from the fundamentals of good lawyering. Here’s a practical checklist to make sure you, the lawyer, remain in the driver’s seat:
By following this checklist, you ensure that AI remains a tool, not an actor, in your practice. You maintain control over the substance and quality of the work. The end result should always be something you’re proud to put your name on, with the AI having been the helpful assistant that made it easier.
When I talk to fellow attorneys about AI, I often get asked, “Is this thing going to replace lawyers?” Let me be clear: No. What it’s going to do – and is already doing – is replace certain tedious aspects of lawyering. And thank goodness for that! I don’t know any small firm lawyer who woke up excited to compare PDFs line-by-line or re-type the same clause for the 100th time. AI automates those tasks, so you can focus on the higher-value work: advising clients, negotiating business points, crafting deal strategy, exercising judgment.
Think of AI as a force multiplier for lawyers. It’s like having an army of capable (albeit imperfect) interns who work at superhuman speed. You’re still the partner supervising them. With AI, a solo practitioner can review as many contracts in a day as a whole team might have done before. You can take on more deals or close them faster, effectively scaling your impact without needing to sacrifice sleep or hire an army of associates you can’t budget for. For a small firm, that means staying competitive – you can go up against BigLaw in an M&A negotiation and not be the bottleneck on turnarounds. It’s a confidence booster for you and your clients.
Importantly, using AI doesn’t mean ceding control or quality. As we’ve emphasized, you remain the final decision-maker. In our story, Alice used Gavel Exec to augment her work, but every change was ultimately her call. The AI didn’t invent client strategy or cut corners – it followed her lead. In my experience, when lawyers integrate AI thoughtfully, the end product is actually better than it would have been purely by human effort, because the AI catches minutiae we might miss and provides suggestions we might not have thought of. It’s like having a safety net and a springboard at once.
I’ll also note the obvious: AI doesn’t have legal ethics or a practicing license. It won’t appear in court for you, it won’t sign off on a deal, and it won’t shoulder malpractice liability. Those are squarely on us as lawyers. Which is to say – our role isn’t going away. If anything, it’s elevated: we get to apply our human creativity, empathy, and advocacy with fewer distractions. We get to spend more time thinking about how to win for our clients and less time proof-reading schedules or compiling diligence lists.
At the end of the day, “Redlining with AI” means you have a new playbook – one where man and machine collaborate. It’s not sci-fi; it’s here now, and it’s remarkably easy to slot into your existing practice. If you’ve dabbled with ChatGPT, consider Gavel Exec your upgraded, lawyerly version of that experience – one that understands our documents and sits right inside Word, where you already work. My advice is simple: give it a try on your next deal. Even if you start with just one or two prompts from the list above, you’ll get a taste of how much time and sanity it can save you.
As someone who left the grind of big-firm life to build legal tech, I genuinely believe this technology can make practicing law more enjoyable. It automates the rote, reduces risk (through consistency and comprehensive checks), and helps you deliver results faster. And happy clients who get quick, thorough service are a boon to your business.
So, the next time you open a contract and sigh at the thought of redlining it, remember: you’ve got an AI assistant in your corner now. Embrace it. You’re not giving up control – you’re gaining an edge. This is the new playbook for contract review, and you as the lawyer are still the quarterback calling the shots. The AI is just your MVP teammate, ready to execute your game plan and help carry you across the finish line.
— Dorna Moini, CEO of Gavel (and former sleepy contract-reviewing attorney who is very glad AI is here!)
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