Checking and refining legal reasoning, arguments, gaps, and document consistency

AI definitely has a place in legal services. I use it to review voluminous files, prepare preliminary drafts, and double check certain work for any additional suggestions. Given my legal training and three decades of experience, I know how to prompt it, I know how to review it, and I know when it’s right and when it’s wrong. It is still very often wrong.

I continue to see very bad AI created documents coming from clients and potential clients. Please understand that while these documents might have the right label, they lack the content necessary to solve problems and avoid litigation. I am deeply concerned that when problems arise, business owners and executives will lack the tools in their contracts and governance documents necessary to resolve them.

Please do not fuel the litigation pipeline. Consult with counsel about your legal needs and find counsel who can use AI appropriately as a tool to reduce legal fees, expedite services, and provide the best outcome.

The more I use AI as a lawyer, the more convinced I am of two things:

• It's going to fundamentally change the practice of law.
• And human judgment is going to become more valuable, not less.

I'm not naive enough to believe the legal profession is somehow sheltered from the reach of AI. I've experienced firsthand just how capable it can be, and I can say without hesitation that it has made me a better lawyer. I use it to challenge my thinking. Pressure-test arguments. Find the weakness in my reasoning. Sometimes it confirms my thinking. And sometimes, it changes it. Both are incredibly valuable.

But the better I get at using AI, the more aware I am of where my value lies.
I can give AI the contract. The transaction structure. The financing considerations. The business objective. I can explain the personalities involved and give it a very, very good prompt.

But I can't give it everything. Because I don't actually know everything I'm relying on when I make a judgment call.

Judgment is accumulated experience. It's the deal that went sideways ten years ago. The provision that looked harmless until someone used it against me. The negotiation where I pushed too hard. The one where I didn't push hard enough. The financing issue that taught me that the technically safest legal answer can be a terrible business answer. It's reading body language. Hearing the inflection in someone's voice. Understanding personalities. And a billion other little pieces of information acquired over a lifetime.

Eventually, those experiences stop feeling like individual pieces of information that can be identified and plugged into a prompt and become something more.

They become instinct. Intuition. And because no two lawyers have accumulated exactly the same experiences, each of us brings something different to the judgment we exercise.

That's why I don't think the most interesting question is whether AI will replace lawyers. It WILL replace some legal work. And I suspect it will change what clients and businesses are willing to pay lawyers to do.

But the more interesting question is: What becomes more valuable when information, analysis and drafting become increasingly accessible?

I think the answer is JUDGMENT.

Will technology one day find a way to fully externalize human judgment when we can't even identify everything that produced it? I don't know.
And oddly enough, that realization doesn't make me less enthusiastic about AI. It makes me more enthusiastic about using it for what I think it does extraordinarily well. And perhaps unexpectedly, it has given me a much clearer understanding of what I bring to the table.

AI can help me get to a decision. It can challenge my assumptions, reasoning and arguments.

And that's important because intuition isn't infallible. Experience can create blind spots just as easily as it creates insight—which is one reason I value having AI challenge mine.

But actually making the decision—and owning it?

That's still my job.

This final article is about something much bigger than insurance. Artificial intelligence identified an insurance coverage issue the human researchers initially missed. This result should interest every lawyer and academic because it offers a glimpse of how AI may improve the quality of professional work rather than simply make it faster.

This is how I use AI. I do not need a machine constantly agreeing with me. I want it to point out what I missed, what provision cuts against my conclusion, what opposing counsel will argue, whether I followed every cross-reference, and whether another reasonable interpretation exists. The AI does not become the authority. It becomes another reader—an extraordinarily fast one that can be instructed specifically to attack my preliminary conclusion.

Since launching its Clio Work AI product in October 2025, Clio says it has been the fastest-adopted product in the company’s 18-year history. But there was one place where Clio Work was not available — Canada, the country where Clio was founded and is headquartered.

Now Clio has brought home the bacon, so to speak, launching Clio Work in Canada — and doing it roughly six weeks after acquiring the Canadian legal data company that made the launch possible.

Clio Work went live in Canada on July 23, enabled by a corpus of more than 470,000 Canadian cases drawn from Jurisage, the Toronto-based legal AI and data company Clio acquired in June.

I use AI almost daily, yet I'm still amazed by it's capabilities, particularly in law.

At my recent law school reunion, I listened to how attorneys are using AI to strengthen credibility, cite sources, and refine arguments. It all opened my eyes to what's possible when we move beyond speed and start using AI for depth and precision.

AI won’t replace lawyers, but lawyers who are competent with it will replace those who aren't.

Technology quietly influences how work gets done. Part of AI's ripple effect is that often happens in unexpected ways. The decisions leaders make today about how to apply AI, thoughtfully and strategically, will impact how teams work for years to come.

Full insights here: https://lnkd.in/eR-XmHzV

A lot of professionals still look at AI like it’s some kind of boogeyman — especially in law and media.

I recently took part in a research study where we had to evaluate a court order — basically looking at how clear it was and how well the reasoning held up.

What stood out to me was this:

AI is getting pretty good at spotting problems.

It can flag things like:
• missing analysis
• unclear conclusions
• weak structure

But judgment is a different animal.

In the real world, legal reasoning isn’t just about logic. It’s:
• context
• discretion
• reading between the lines
• understanding what actually matters

And honestly — the order I reviewed wasn’t anything special. You see that kind of thing more often than people think.

Which gets to the bigger point:

There’s a difference between recognizing weak reasoning… and actually producing strong reasoning.

AI is getting better at the first.
The second is a lot harder.

That gap is where experience still matters.

Curious how others are seeing this play out.

What happened is closer to this: I spent hundreds of hours reading federal civil procedure. I read the statutes I was suing under. I read the case law on pleading standards. I went on PACER and just started buying and reading dockets. I used that to have AI help me understand of what a complaint needs to say, and why, and in what order.

Then I used AI the way a lawyer uses a team of associates.

Draft this section. Cross-reference these defined terms. Check whether this allegation satisfies this element of this cause of action. Flag internal inconsistencies across these six documents. Hold the entire case in memory while I think about what comes next.

The AI didn't practice law. I practiced law, badly at first and then less badly, using AI to do the production work that would have otherwise required a team I could not afford.

As a “tech-savvy” lawyer, this is how I use AI — and where I refuse to rely on it.

It’s important for us, as lawyers, to understand that AI is not intelligence, it is prediction.

It does not understand law. It recognizes patterns in how law has been written, argued, and interpreted before. This distinction matters more than most people realize.

In my practice, AI has become an instrument of acceleration — but never a substitute for judgment.

- I use AI to interrogate large volumes of information quickly.
- To identify structural patterns across agreements.
- To compare regulatory approaches across jurisdictions.
- To test the internal consistency of legal reasoning.

It compresses hours of mechanical effort into minutes. But as lawyers, it’s important for us to understand that law is not a mechanical profession, it is a profession of consequence.

AI can tell you what is typical. It cannot tell you what is safe.

It can identify what has been done before. It cannot evaluate what should never be done.

It does not bear liability.
It does not exercise fiduciary responsibility.
It does not understand risk in the way a human advisor must.

The greatest risk of AI in law is not that it will be wrong. It is that it will sound right. Create a nice attractive graphic also for this list

Which is why the real shift is not technological. It is cognitive.