Plain Language Contracts & LEgalese

Sometimes you hear complaints that contracts are too complex or full of “legalese,” and that lawyers serve as some kind of translation service between legal language and “plain English.” That’s kind of a flimsy dichotomy though. Although I like the idea of plain language contracting, when you consider the ultimate pragmatic function of a contract some of the conventions of legal language can be perfectly sensible and useful. At best, the contract language will be appropriate to the business relationship the contract embodies.

Here's a little bit about how I work. My approach to contract drafting & negotiation has two levels: on the first, I am formalizing an arm’s-length business relationship as clearly and as crisply as I can, from the compositional level to the word choice level, and making sure that my client’s specific concerns are expressly addressed; on the second, I am probing the document for enforceability concerns – trying to make sure that the contract itself can handle reasonably foreseeable breakdowns and disputes.

When I take in a contract for review I ask my client how they do business and what kinds of problems they might have and then we go through thought experiments in doom and disaster (that’s the part I really like!), then I go back to the contract and try to set it up so that the worst-case scenarios are managed in a reasonable and clear-eyed manner. A lot of times those things go back to language that is only going to be legalese, e.g., definitions of performance and delivery, scope of indemnification, defining contingencies, delineating the exceptions and the exceptions to the exceptions. Plus, I’m often negotiating the contract with another lawyer, so we are shaping the relationship from opposite sides, trading priorities and concessions, all through the text of the document.

In the end I want my client to understand how the contract works in the context of their business, what they can expect from the other party to the agreement, and the business risks that my client inherently assumes by signing it.

UPDATE (9-15-2025)

A couple of clients have asked me to review language they developed with the help of on-line AI services. It looks like AI was able to provide general plain-language summaries of existing contracts and to generate loose contractual language that summarized kind of what that parties to a contract might agree. For instance, an indemnification provisions says, in toto, “Each party shall indemnify and hold harmless the other party from and against any claims, damages, or liabilities arising out of negligence or willful misconduct in connection with the performance of this Agreement.” That is an indemnification provision that would be enforceable on its face, but is it good or bad for their business? The program could probably generate better terms if the prompter understood the purpose of their contract language better, but in this case it just provided sample placeholder language. AI will be more powerful when it can ask for clarification about the parties’s industry and negotiating strength and tailors the terms from there. It’s really going to be weird when judges use AI! “Hey Chat, what is the subcontractor’s liability for delay damages under this construction agreement?

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