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All’s Fair in Love and AI
AI is not your bestie. It’s a language model, a tool, and at least from what we’ve seen, not exactly your second brain. Not unless you spend the big bucks to create your own tailored, centralized and proprietary system. Even then, it’s not perfect. AI’s extreme notions of fairness undermine the practicality that underlies contract negotiations. And just to get this out of the way: your favorite AI bot is definitely not your romantic partner.
We’ve seen some things in a relatively short period of time. One recent pattern we keep seeing? “Agreement comments” that are really copy/paste jobs from AI replete with lines like: “If they disagree, you could also offer to agree to XYZ term—let me know if you want me to draft proposed language.” (RIP to the em dash).
We may think that AI is in our heads, but it’s really not…yet. What you’re really doing is outsourcing business judgment. The reality is that we need to get in AI’s head because frankly, the “bug” in the code is often the human being deploying it. So what does this look like in practice? Let’s walk through some real-world pitfalls, because unlike the movie WarGames, the winning move here is to play smart vs. not play at all.
AI Can Be a Deal-Killer
Once the parties start speaking through bots, the bots start negotiating with each other, resulting in hallucinations, circular reasoning, and seemingly endless revisions. Some models simply won’t settle. You can send it the same provision ten times and it will find an issue every time (sometimes inventing issues out of thin air). Why? Because these models are built to respond. They have to answer your question. If you ask it, “What’s wrong with this?” it will struggle to say, “Nothing, you’re good.”
Worst-case scenario? The parties reach an impasse and the deal stalls completely. It’s really a bizarre phenomenon: Humans implicitly trusting a machine so much that they ultimately get in their own way. Here’s the deal (pun intended): your standard LLM is not trained to have the same business sense as you or address your individualized legal risks and risk tolerance. They’ll tell you what is theoretically “risky”, but they won’t tell you if it’s a risk worth taking. That’s still up to you.
AI is a People Pleaser
Most language models that folks use nowadays are optimized for fairness between parties. So how does that play out? Let’s say you have proprietary information that you want to ensure is protected indefinitely, and you include a confidentiality clause in your agreement protecting your trade secrets. AI will suggest that you limit those protections to 2-5 years because that’s “standard”. Standard according to whom? And if it’s your agreement, why would you start by limiting your own protections?
Another example: mutuality. You hire a vendor and won’t meaningfully use their confidential information, but AI insists the confidentiality clause in your standard template should be mutual. Why create obligations where none are needed? Or let’s talk about indemnity. You hire a vendor to handle some high-stakes work, maybe involving sensitive client data or regulated information. You want them to indemnify you for their mistakes. AI, optimized for symmetry, suggests that your standard template indemnifies them too. For what, exactly? Paying their invoices on time? “Fair” does not always mean practical.
Is This Play About Us?
As we’ve said before, we are not anti-AI. We are, however, pro-getting the deal to the finish line through mindful and practical negotiations. Used correctly, it’s a powerful tool that can accelerate drafting, surface issues, and sharpen thinking. It’s okay to ask AI for its insights, but read them, digest them, and disagree where necessary. That’s where AI becomes a competitive advantage vs. a limitation.
So if you’re reading this and wondering how you can best leverage technology like this, you should know by now that: as always, if you’ve got questions, you know we’ve got answers!
~ The W + K Team
ABOUT WEINSTEIN + KLEIN P.C.
Founded in 2019, Weinstein + Klein is a modern boutique law firm that serves as outside general counsel to businesses across industries. Weinstein + Klein provides strategic, day-to-day legal support with a focus on labor and employment law, corporate and transactional matters, and business litigation. Weinstein + Klein works closely with business owners, executives, and entrepreneurs to proactively manage risk, navigate complex employment issues, and handle key transactions – from formation to funding to exit.