AI In High-Stakes Litigation: The Critical Role of Experienced Attorneys

I was late to the AI party. In 2019 a legal journal editor asked me a question about AI. I replied “I’m 67 years old and have developed a little expertise in a few areas. At this point in my life it’s too late for me to try to learn about something new and as complicated as AI. I don’t have the time. I’ll leave that for younger, more ambitious lawyers.”

That was then. This is now.

ChatGPT 3.5 was released in November 2022. It and other AI apps are changing the world. I realized I could no longer ignore AI. Since then, learning to use AI has been my top professional priority. It’s just that important. This article is intended to help other experienced lawyers, especially those involved in high stakes matters, to understand the situation and decide whether they should follow the same path.

Skepticism about AI is not only justified—it’s evidence of good judgment. There are indeed pitfalls to AI use. Inept use of AI won’t help you, but my experience has been that in the hands of skilled lawyers with good judgment, AI is essential to obtaining the best results, for one simple reason:

AI is only as good as the question it’s given. This is where senior lawyers excel. Knowing what issue to frame, what clause to focus on, what fact might tip the case—this is precisely what you’ve spent your career developing.

AI can assist. But it still needs someone to think.

The “Centaur” Approach is the Optimal Model (For Now)

Today’s chess-playing computers can crush the best human players without breaking a sweat. This wasn’t always true. Twenty years ago teams of the strongest humans and the most powerful computers were stronger than either humans or computers alone. These teams were sometimes called “centaurs.” They combined the strength of a mighty beast with human judgment.

For at least the next few years, legal centaur teams combining the experience of the best lawyers and top AI apps will always win over either human lawyers or AI apps working alone.

Today’s best legal AI experts (including Richard Susskind) believe that this may not always be true. They speculate that eventually computers will reach a stage of “hyperintelligence” in which AI systems become unfathomably more capable than humans. We are not there yet, and we may never get there. For the foreseeable future, experienced lawyers who know how to use AI will dominate.

Today I have no problem asking an AI app a simple question about licensing of speech therapists. I would verify any its analysis before relying on it for anything important, but AI is now my first choice for a relatively simple question where the stakes are low.

I would never dream of relying on an unassisted AI app for an important issue in $40 million litigation. Neither should you.

At the same time, today I no longer fully trust my un-assisted human judgment on a high stakes matter.

The rules of thumb I explained in a January LLRX.com article describe the best approach:

  • Never rely on anything AI tells you about crucial issues.
  • Always ask AI for advice on crucial issues.

Keeping AI In Its Place

AI in the legal world is not a sentient being. It doesn’t argue cases, it doesn’t replace lawyers, and it certainly doesn’t understand the law in the way the best lawyers can.

What it can do is process large amounts of text quickly and find patterns in ways that mimic certain kinds of legal work—especially the repetitive and time-consuming parts. It can:

  • Summarize documents.
  • Draft emails or memos in plain English.
  • Spot irregularities in contracts.
  • Retrieve relevant case law.

Think of it as a very fast, very literal junior associate who never sleeps and has no billing rate.

And just as important: you don’t need to understand how it works to use it. If you can use Google, you can use most AI tools. You—or better yet, a competent assistant–ask questions in plain English, and the machine gives you a draft response or suggested research. You review it, improve it, and decide what’s worth keeping—just like you always have.

You’ve practiced through more than one technology cycle, and you’ve seen the promises outrun the performance. “User-friendly” systems that required hours of training. “Seamless” integrations that never quite integrated. “Efficiency tools” that created new inefficiencies.

You also didn’t enter this profession to become your own IT department. You chose law because you valued reasoning, advocacy, and judgment—not because you wanted to troubleshoot email servers.

But here’s the thing: you’ve adapted before. You didn’t retreat when research moved from books to databases. You didn’t leave the field when filings went digital. You adjusted, selectively and thoughtfully. That’s exactly the same approach to use with AI.

Delegation Is Still a Superpower

You’ve built your practice by knowing what to delegate and to whom. The same principle applies here.

AI doesn’t have to be your project. It can be a shared one—implemented by a younger partner, a paralegal, or even a tech-savvy law clerk. Your role is to direct, review, and refine.

The key point to remember is that AI’s usefulness depends entirely on the questions it’s asked. That’s where senior lawyers excel. Knowing what issue to frame, what clause to focus on, what fact might tip the case—this is precisely what you’ve spent your career developing.

At the same time, you can’t delegate effectively without having a least a general grasp of what needs to be done and how to evaluate the work done at your direction.

Putting Your Toe in the Water: The Limits of Delegation

In Richard Susskind’s excellent new book How to Think About AI he explains the danger of what he calls “irrational objectionism”:

Too often I hear people speaking unfavorably about [artificial intelligence], and I am amazed to learn, after a little probing—OK, cross-examination—that they haven’t actually used the system themselves.

How much time do you need to invest to develop a basic understanding of AI? Ethan Mollick, a business professor at Wharton and a leading expert on practical uses of AI, has suggested that “10 or so hours with AI are required to really understand what it does.” Dr. Mollick’s suggestion reminds me of the common recommendation that people should strive to walk 10,000 steps a day. There is no scientific basis for the 10,000 step rule, but both it and the 10-hour suggestion are pretty good rules of thumb.

Once you’ve decided to invested 10 hours—or 100—the next question is: Where to begin?

Fortunately, the answer isn’t “in the deep end.” Much of my experience with artificial intelligence has come from tools like ChatGPT, Gemini, Copilot and the AI-powered Perplexity search engine. None of these are specifically legal platforms—but they’re incredibly helpful for legal professionals.

Pro Tip: Whatever platform you decide to use, pay for the premium version. $20 a month is a trivial investment compared to the quality gains you’ll see.

They can:

  • Draft letters or summarize legal documents.
  • Generate a list of arguments for or against a motion.
  • Explain complex topics in plain English (or help you explain them to clients).
  • Even assist with CLE preparation, speech drafting, or brainstorming memos.

In other words, they function like thoughtful assistants with good general instincts—and they’re available around the clock.

You don’t have to abandon caution. But dipping a toe into AI through these tools can build comfort and familiarity—without any risk to client confidentiality or case integrity. (Just be careful not to share confidential information unless you’re using secure, enterprise-grade tools.) The always-reliable Dennis Kennedy and Tom Mighell provide some excellent advice for lawyers seeking to select the right AI tools for them.

Legal-Specific Tools Can Add Even More Value

Once you’re comfortable with the idea, specialized tools tailored to law practice can extend that value further. Here are some examples:

  • CoCounsel helps generate briefs, memos, and conduct legal research.
  • Lexis+ AI can assist with detailed contract analysis and discovery review.
  • Clearbrief helps align legal arguments with the record, citing support you may have missed (general knowledge, no direct search result).

Here’s one possible starting point: You’re preparing a letter to opposing counsel. Draft the key points, then ask Copilot or ChatGPT to rephrase it with a firmer (or gentler) tone. You keep full control—but the process is faster, smoother, and less taxing. I’ve found that if I ask the right questions (referred to as “prompts” in this context), AI apps nearly always suggest a few angles that had not occurred to me.

The key takeaway is this: start small, and start where you’re comfortable. Use the tools to help with admin work, summaries, or writing clean-up. You don’t need to master a platform overnight—or at all. What matters is that you begin to see how these tools can support your work rather than complicate it.

And if you like what you see, there’s a deeper bench of legal-specific platforms waiting. You might just find one that becomes as indispensable as email once did.

Getting Down to Business

Once you have become comfortable with AI basics, the next step is identifying ways AI can help lawyers. Catherine Brock provides a good list of starting points:

  • Creating, editing, and summarizing legal documents. With a detailed prompt or series of prompts, the application can quickly draft, edit, or summarize documents. Any output should be carefully reviewed prior to use.
  • Performing legal research and discovery. ChatGPT legal research can summarize cases, laws, deposition transcripts, or pleadings filed with the court.
  • Transcribing voice and video recordings. With add-on tools and access to GPT-4, you can upload audio and video files and have them transcribed.
  • Assisting with client communications. ChatGPT can produce quick drafts of client emails.
  • Analyzing case details and predicting outcomes. AI-powered predictions of case outcomes can inform case strategy.
  • Drafting marketing content. Small firms that don’t have a marketing copywriter on staff can tap ChatGPT to draft content for marketing collateral.

Once you have a general feeling for what is possible, a good next step is to use a suggested prompt created by Eric Porris. Just cut and paste it in the general AI app you prefer:

l’d like to consult you as an Al expert. I would like your help to identify ways to leverage Al in my day-to-day work. Would you please interview me asking only one question at a time until you have enough context about my work responsibilities and daily tasks and workflows and KPls such that you could make what you consider to be two obvious recommendations and two or three non-obvious recommendations for how to leverage generative Al.

Conclusion

AI does not replace experience. It reveals its value.

Legal reasoning isn’t formulaic. It involves judgment, ethics, and insight—things machines still can’t simulate. AI can help organize information, test arguments, and highlight gaps. But it doesn’t know what matters. You do.

And as we’ve emphasized: your ability to ask the right question is more essential than ever. The usefulness of AI begins and ends with human direction. And senior lawyers are often best at setting that direction.

So use the tool. Train the next generation. Keep doing what you do best.

And if the robot offers to carry the briefcase, let it. Just make sure you’re the one walking into court.

 

Posted in: AI, Communications, E-Discovery, Law Firm Marketing, Legal Marketing, Legal Profession, Legal Research