If you follow the legal industry, you’ve probably seen the headlines: AI “attorneys” like Harvey and Legora are raising eye‑popping rounds and racing to “reinvent” how law gets done. Big Law is spinning up AI academies for associates, in‑house teams are testing tools as fast as they can get them through compliance, and investors are betting billions that software will finally crack a $1 trillion market.
As someone who makes a living helping dealers and business owners navigate complex, high‑stakes transactions, I’m less interested in who wins the startup race and more interested in what this means for the quality of legal advice my clients will get over the next decade.
Smarter Machines, Not Necessarily Better Lawyers
Veteran partners are starting to say the quiet part out loud: “Smarter machines don’t necessarily make better lawyers.” That line jumped out at me. For decades, the training model in big firms has been simple, if imperfect: young lawyers pay their dues in the trenches—reviewing mountains of documents, drafting and redrafting clauses, researching obscure points of law—and, in the process, they develop judgment.
Now, tools like Harvey and Legora can review contracts, compare data rooms, and draft solid first versions of briefs in minutes. That’s impressive. But if AI ends up doing most of the early‑career grunt work, where will the next generation of deal lawyers, litigators, and counselors get the repetitions they need to build that judgment? The risk isn’t that AI gets something wrong; it’s that the humans supervising it never learned how to tell the difference.
The Billable Hour Meets the Efficiency Machine
There’s also a basic business tension here. In‑house lawyers and corporate clients love anything that speeds up workflows. Big Law, on the other hand, still runs on billable hours. When a tool promises to cut review time by 30–50%, that sounds great to a CFO—and a lot less great to a partner staring at a realization report.
So firms face a choice. They can embrace AI as an opportunity to reprice, repackage, and genuinely improve service—or they can quietly use it to do the same work faster while trying to keep bills roughly where they’ve always been. One path builds trust; the other invites uncomfortable questions from clients who will eventually realize that their “hours” are being done by a server rack.
Training the Next Generation Is a Client Issue
Some leading firms are taking this seriously. Latham & Watkins, for example, has pulled hundreds of associates into an internal AI “academy,” explicitly telling them that AI isn’t optional—it’s part of how the firm will operate going forward. That’s the right direction: teach young lawyers how to oversee, question, and improve the machine’s output, not just how to click “run.”
But the bigger point, from where I sit, is that training isn’t an internal HR problem—it’s a client problem. If law firms let AI hollow out the apprenticeship phase, my clients aren’t just getting cheaper work; they’re getting less seasoned judgment in the room ten years from now. As in any complex business transaction, the risk usually doesn’t show up in the first closing. It shows up in the second downturn, the first regulatory surprise, or the one dispute that actually goes the distance.
What I’ll Be Asking Lawyers Going Forward
I don’t think AI will replace lawyers, and I don’t think it should. What it will do is force every serious client to ask better questions. When I have spoken recently with “seasoned” lawyers who have spent decades on dealership M & A transactions, who I have known for decades, I ask these questions and the “best” ones, ones who care about their clients, answer to the affirmative. Here are the questions I care about now:
- How are you using AI on my matters—specifically?
- Who is reviewing and challenging the AI’s output, and how experienced are they?
- Are your associates being trained to understand the underlying issues, or just to operate tools?
- Have you adjusted your pricing to reflect the efficiency gains you’re getting?
If a firm can give confident, transparent answers to those questions, AI becomes a competitive advantage. If they can’t, then from a client’s perspective, “AI‑enabled” may just mean “less training, same bill.”
The Bottom Line for Business Owners
For owners, dealers, and executives, the takeaway is simple: don’t be dazzled by the buzzwords. Ask how AI is actually being used on your deals, and how your lawyers are investing in the next generation of talent. The legal industry will figure out who wins the Harvey‑versus‑Legora race; what matters to you is whether the person across the table, ten years from now, has the scars and experience to see around the corner.
AI can and should make legal work faster, more consistent, and in some cases more affordable. But if we’re not careful, it could also produce a generation of lawyers who are great at prompting machines and weak at spotting the one issue the model didn’t think to look for. That’s not a future I’m interested in for my clients—or for the businesses they’ve spent a lifetime building.
Ready to Talk About Your Next Deal?
If you’re wondering what AI, shifting legal models, and market volatility really mean for your next dealership or business transaction, let’s talk it through before you’re sitting at the closing table. I’ve spent decades helping owners navigate complex deals, choose the right advisors, and avoid costly surprises—insights I’m happy to put to work for you. Call me, Gordon Wisbach, directly at 508-395-2500 or email gordon@gwmarketingservices.com to start a confidential, no‑obligation conversation about your options.