Using AI to draft contracts without legal expertise is a lot like someone with zero cultivation experience using ChatGPT to start a cannabis grow.

Everything might look good at first. The SOPs look right. The facility is built. The plants are hopefully growing. But when harvest comes, all the things you didn't know to look for inevitably pop up.

The same thing happens with contracts.

AI can produce documents that look professional. The problem is that if you don't know which risks to address, you probably won't recognize what's missing. And by the time you find out, you're already in a dispute, dealing with regulators, or paying someone to fix the problem.

To be clear, I'm not anti-AI. I use AI to draft and review contracts every day.
But there's a big difference between using an out-of-the-box LLM and using AI that's guided by custom skills, MCPs, legal playbooks, and subject-matter expertise.

Will this change in the future? Probably. But today, expertise is still what allows you to spot the problems AI consistently misses.

What are your thoughts on using AI to draft contracts? Let me know in the comments.

DISCLAIMER: Attorney advertising. This post and any comments are not legal advice.

Draft smarter, right where you already work.

Clio for Word is now in beta, bringing legal AI drafting, analysis, and review directly into Microsoft Word so you can stay in the environment where you already do your best work.

Drawing on the world's largest legal database, it generates first drafts, surfaces revision suggestions through track changes, and analyzes documents for legal and structural risks, all without switching applications.

Learn more at the link in comments.

Docusign agents triage, review, and move agreements forward across its Intelligent Agreement Management platform, solving business problems in the way point products cannot

SAN FRANCISCO, May 11, 2026 /PRNewswire/ -- Docusign (NASDAQ: DOCU) today announced a new set of AI-powered capabilities and strategic partnerships designed to help in-house legal teams drive progress for their companies while enjoying cutting edge AI-based legal tools. With the introduction of a contract assistant and agents, Docusign is expanding its Intelligent Agreement Management (IAM) platform — the only platform with total context of your agreement history and relationships — to serve as the system of action for legal professionals and the teams they support.

Microsoft just dropped something big for the legal world & we need to talk about it. Yesterday, April 30 2026, Microsoft launched the Legal Agent in Word, a purpose-built AI tool for legal workflows like contract review, clause-by-clause analysis, automated redlining and negotiation support. This is not a generic chatbot repurposed for law. It was built with legal engineers and lives inside Word, where most legal work already happens. Now as a lawyer in Kenya and across Africa, here’s my take: THE UPSIDE & IT'S REAL: For legal professionals in Kenya, East Africa and beyond, AI contract review could genuinely level the playing field. A junior associate in Nairobi can now access clause-by-clause analysis that once required senior counsel time. Small firms and solo practitioners across Africa’s legal ecosystem can punch above their weight. Turnaround on contracts, NDAs and due diligence could drop from days to hours. That’s not just efficiency; that’s access to justice. THE RISKS & WE MUST NOT LOOK AWAY: Here it gets serious. While AI should improve efficiency, it must NEVER replace human judgment in law. And we have evidence... Just days ago, South Africa’s Communications Minister Solly Malatsi withdrew the country’s draft National AI Policy after journalists found at least 6 of 67 academic citations were AI hallucinations. The papers did not exist, authors were invented. A national AI governance document undone by the very thing it sought to regulate. This is not isolated. Courts globally, including in US cases, have sanctioned lawyers for submitting AI-generated briefs citing non-existent cases. Over 1,000 incidents have been tracked worldwide. In Kenya and Africa, where precedent matters deeply, courts are stretched, and one bad citation can affect access to justice, the stakes are even higher. HUMAN IN THE LOOP, ALWAYS: Lawyers take oaths for a reason. Our work touches livelihoods, liberty, families, futures. The ripple effects of legal error are profound and often irreversible. AI should be a sharp pencil, not the hand. Human oversight is not optional. Microsoft itself says: "The Legal Agent does not provide legal advice or professional determinations and is not a substitute for a qualified legal professional." We must not let machines dictate critical decisions more so because, when we remove the human from the loop, we don’t enter the future, we enter dangerous times! As our African wisdom says: "Umuntu ngumuntu ngabantu." A person is a person through other people. No machine can carry that moral weight. AI should be adopted with discipline, not blind trust, especially in high-stakes legal environments across Africa. Human verification remains essential. always!!! #LegalTech #AIInLaw #MicrosoftLegalAgent #HumanInTheLoop #AIHallucinations #CyberSecurityLawyer #ResponsibleAI #LegalEthics #FutureOfLaw #AfricanLawyers https://lnkd.in/dJb85MDt

Microsoft launches Legal Agent inside Word: Microsoft has introduced a new **Legal Agent** inside **Word** that automates contract review, redlining, and negotiation workflows, according to reporting from The Verge and Artificial Lawyer. Per a Microsoft blog post quoted by Artificial Lawyer, the agent "follows structured workflows shaped by real legal practice" and applies edits via a purpose-built insertion algorithm that preserves Word formatting and tracked changes. The Verge reports Microsoft is releasing the feature to members of its Frontier program in the US, and multiple outlets say engineers who joined Microsoft from legal AI startup Robin contributed to the product. Editorial analysis: Companies embedding specialized agents into dominant authoring tools often create adoption friction for third-party vendors and shift where legal teams run document workflows. http://dlvr.it/TSK8zR #Microsoft #LegalTech #AI #ContractReview #Word

I have 4-year-old twins, a full legal department of one, and approximately zero time to read 50 think pieces about "the future of AI in law."

So let me save you some time.

The biggest shift happening right now isn't which AI tool you're using. It's what you're asking it to do.

We've moved from "summarize this contract" to "review this contract, flag the deviations from my standard positions, draft a redline, and explain your reasoning." That's not a search engine anymore. That's a junior associate that doesn't sleep, doesn't bill by the hour, and never once has asked me to "circle back."

Here's what I've actually changed in my workflow in the last few months:
✅ I stopped treating AI as a search tool and started treating it like a first-year I have to supervise — capable, but not unsupervised 🔍 I built a short internal playbook for how I prompt contract reviews — same prompts, every time, so results are consistent and auditable ⚠️ I added a standing question to every AI-assisted review: "What did you not find, and why?" — it forces the tool to surface its own gaps

Is it perfect? No. Do I still review everything myself? Yes. But I'm doing it in a fraction of the time, and I'm better rested for it. (Marginally. The twins are still four.)

The lawyers who are going to thrive aren't the ones waiting for someone else — their GC, their ops team, their outside counsel — to hand them a playbook. They're building one.

What's one thing you've changed in your AI workflow lately? I'm genuinely collecting ideas. 👇 #InHouseLife #LegalOps #AIinLaw #LegalTech #WomenInLaw #GC #ContractManagement

I built a legal research agent that writes structured memos in 3 minutes.

I built a contract review tool that flags 23 risk categories across any commercial agreement.

I built a client intake system that cut my admin work from 3 hours a week to 20 minutes.

None of this required a developer. None of it required coding knowledge. I built all of it using AI tools that are available to every lawyer and law student right now.

And most of you have no idea these tools exist.

That is the problem I am solving on April 18th.

I am running a free 2-hour live workshop where I will show you exactly how AI can transform the way you practice law, study law, and build a legal career.

This is not a webinar where someone reads slides about "the future of legal tech." I am going to open my laptop, share my screen, and build things in front of you. Live.

Here is what I will cover:

- How to build AI agents that handle legal research, drafting, and document review in minutes instead of hours. Not in theory. I will build one live during the workshop.

- How to automate the repetitive parts of legal practice: client intake, memo generation, contract checklists, compliance tracking — so you can focus on the work that actually requires a lawyer's judgment.

- The exact AI tools I use in my own practice every day. What works. What does not. What is worth paying for and what is a waste of money.

- How law students can use AI right now to prepare better research, write better memos, and walk into their first job with skills most senior associates do not have yet.

- Prompt engineering for legal work, the difference between getting generic output and getting something you can actually send to a client.


The details:

Date: April 18, 2026
Time: 8:00 PM IST

I am keeping registrations limited because I want this to be interactive, not a broadcast. If you have questions during the session, I will answer them live.

Register here: https://lnkd.in/gnzEcQ4s

Who should attend:

- Law students who want to graduate with skills their peers will not have.
- Junior associates drowning in research and drafting work.
- Solo practitioners and freelance lawyers who want to take on more clients without burning out.
- Senior lawyers who keep hearing about AI but have not seen it actually work on legal tasks.
- Anyone who has tried ChatGPT for legal work and thought "this is not useful", because you were using the wrong tool the wrong way.

I have spent hundreds of hours testing AI tools on real legal work. Contracts, memos, research, compliance, client communication. I know what works and I know what fails. This workshop is everything I have learned, compressed into 2 hours, demonstrated live.

See you there.

#AIforLawyers #LegalTech #LawStudents #LawyersofLinkedIn #LegalAI #FreeLegalWorkshop #AIWorkshop #LegalInnovation #FutureLawyer #AIAgents

You see your colleagues using AI in their in-house legal work and want to do the same.

Exactly how to do that, though? That part can feel insurmountable, especially if you put high pressure or high stakes on the result of what you hope to use it for.

Join Kevin Keller and me, along with the Sandstone team, next week to talk about how we're using AI in our legal departments.

I'll focus on what has and hasn't worked in my own journey to using AI for my in-house legal work. My use cases are simple, but the impact is significant. I'll take these steps farther one day, but the value I've seen to date is worth all the time and energy to get to where we are.

On my end, I'll discuss:
- Where dedicated legal tech didn't work for us
- Building an NDA review agent to act like a fellow teammate (but still encourage human review)
- Trying, failing, and learning on what successful legal matter tracking looks like for us

See you April 9th! Register in the link in comments.

𝗔𝗜 𝗦𝗼𝘂𝗻𝗱𝘀 𝗟𝗶𝗸𝗲 𝗮 𝗟𝗮𝘄𝘆𝗲𝗿. 𝗧𝗵𝗮𝘁'𝘀 𝘁𝗵𝗲 𝗣𝗿𝗼𝗯𝗹𝗲𝗺.

I was a Prodigy kid.

Not the musical kind. The dial-up, message-board, pre-AOL kind.

My fascination with tech never waned. It took me to the White House, where I helped shape early federal cloud policy, launch the U.S. Digital Service, and advance the government's first bug bounty program. I saw what it looks like when transformative technologies move from experimentation to adoption at scale.

So when generative AI arrived, I wasn't skeptical. I was excited. I still am. But I'm also a lawyer. And that's where it gets complicated.

𝗧𝗵𝗲 𝗣𝗿𝗼𝗺𝗶𝘀𝗲 𝗜𝘀 𝗥𝗲𝗮𝗹

AI has real utility in legal work. My team uses it for the first redline of routine documents. NDAs, vendor agreements, standard commercial terms. It saves time and catches obvious stuff. As a starting point, it's useful. Key emphasis on "starting point."

𝗧𝗵𝗲 𝗣𝗿𝗼𝗯𝗹𝗲𝗺 𝗜𝘀𝗻'𝘁 𝗧𝗵𝗮𝘁 𝗔𝗜 𝗜𝘀 𝗪𝗿𝗼𝗻𝗴. 𝗜𝘁'𝘀 𝗧𝗵𝗮𝘁 𝗜𝘁 𝗦𝗼𝘂𝗻𝗱𝘀 𝗦𝗼 𝗥𝗶𝗴𝗵𝘁.

AI has mastered the aesthetic of legal analysis without mastering the substance. The output looks like a memo from a senior associate. Confident, structured, occasionally citing cases that don't exist or don't support what the model claims.

I've seen AI-generated redlines come back and I can tell immediately. Provisions that look like standard market terms but don't carry settled legal meaning. Indemnities that shift liability in ways the drafter didn't intend.

"𝗕𝘂𝘁 𝗖𝗵𝗮𝘁𝗚𝗣𝗧 𝗚𝗮𝘃𝗲 𝗠𝗲 𝗮 𝗗𝗶𝗳𝗳𝗲𝗿𝗲𝗻𝘁 𝗔𝗻𝘀𝘄𝗲𝗿"

I hear this more and more. I don't take it personally. Efficiency is a legitimate goal. But there is a real difference between information and legal judgment.

AI cannot know your company's litigation history, your board's sensitivities, or the regulatory posture you've taken in past filings. Law is not a lookup table. It is applied judgment under uncertainty, shaped by facts specific to you.

𝗧𝗵𝗲 𝗤𝘂𝗲𝘀𝘁𝗶𝗼𝗻 𝗖𝗼𝘂𝗿𝘁𝘀 𝗛𝗮𝘃𝗲𝗻'𝘁 𝗔𝗻𝘀𝘄𝗲𝗿𝗲𝗱 𝗬𝗲𝘁

Courts know how to interpret contracts, but they have not yet confronted AI-drafted clauses at scale.

What happens when a court is asked to interpret language optimized for fluency rather than precision? Will litigants discover the clause they're fighting over does not carry the meaning they assumed?

That moment is coming. Tech moves fast; contract disputes do not. AI-generated clauses will spread long before courts are asked what they actually mean.

𝗪𝗵𝗲𝗿𝗲 𝗗𝗼𝗲𝘀 𝗧𝗵𝗮𝘁 𝗟𝗲𝗮𝘃𝗲 𝗨𝘀?

Use AI as a starting point. Train it on your playbooks. Let it handle the first pass. But have a real lawyer review it. Someone who knows your company, your risk appetite, and the enforceability questions that don't show up in a training dataset.

AI produces information. Lawyers provide judgment. Right now, you need both.

𝗜'𝗱 𝗹𝗼𝘃𝗲 𝘁𝗼 𝗵𝗲𝗮𝗿 𝘆𝗼𝘂𝗿 𝗽𝗲𝗿𝘀𝗽𝗲𝗰𝘁𝗶𝘃𝗲.

A year ago, I shared on LinkedIn that contract drafting was becoming obsolete. The post sparked plenty of disagreement, including from Ken Adams (I always appreciate good debates).

My next prediction: contract negotiation, as lawyers know it today, is about to change too.

Contract negotiation never took too long because lawyers typed too slowly.
It took time because legal judgment depends on context.

When I was in-house counsel, it was completely normal to revert on contract redlines in a week. Sometimes longer. This was because, before you could take a sensible position, you often needed to understand what the business actually cared about, what had been agreed before, where the fallback positions were, and which precedent was actually relevant.

The first wave of legal AI helped lawyers generate and edit text faster.

What is changing now is that AI systems are starting to surface the context that sits behind legal judgment and negotiation strategy.

➡️ In this new episode of the Legal Intelligence Platform (LIP) deep dive, I explore how I would use an AI contract assistant, SimpleAI by SimpleDocs, to review redlines and negotiate a contract as in-house counsel today, and share my pov on where I think the real upside and limits still are.

✴️ Watch here: https://lnkd.in/gQ8P96Zt
---
📌 Stay tuned for part two (dropping tomorrow), where I ask Preston Clark, CEO of SimpleDocs, some tough questions about:
- Why he thinks SimpleDocs can win in contract AI, the most crowded category in legal AI, and
- How legal teams should evaluate products in a market full of "lookalikes".

Note: This video was made in partnership with SimpleDocs. SimpleDocs provided product access and reviewed the video for factual accuracy. Editorial opinions and conclusions remain mine.