Work product, AI, and represented parties, oh my!

When does the work product doctrine apply to generative artificial intelligence (AI) prompts and responses? Courts across the country have considered this question, with the answer depending on the status of the person using the tool and whether they were represented by counsel or appeared pro se. Even when the underlying factors are identical, the conclusions reached have varied.

In one recent case, handed down in June, the Superior Court of Massachusetts considered the doctrine’s applicability to a novel factual scenario not yet addressed by other courts. In Shealy v. Seaside Investments (No. 2684CV00799-BLS2), the plaintiffs were represented by counsel when the AI use in question occurred. (Online: https://masslawyersweekly.com/files/2026/07/09-070-26.pdf).

After receiving a Reservation of Rights letter, a promissory note, and a purchase agreement from the defendants, Shealy forwarded them to his romantic partner so that she could, at his request, upload them into ChatGPT. She then provided him with the chatbot’s response to the query that accompanied the documents. This activity occurred solely at the plaintiff’s request; his attorney was not involved in the interaction.

The defense sought access to the email communications between the plaintiff and his romantic partner, including the discussions and attachments related to the ChatGPT response. The plaintiffs asserted that the work product doctrine applied since the ChatGPT conversations occurred in preparation for litigation.

The court agreed with the defendants, declining to apply the attorney work product doctrine protections. In reaching its decision, the court explained that the doctrine “protects (1) documents and tangible things, [prepared] (2) by or for another party or by or for that other party’s representative (including his attorney, consultant, surety, indemnitor, insurer, or agent), and (3) in anticipation of litigation or for trial.”

The primary issue the court considered was whether the AI output was prepared by or for a “representative” of the plaintiffs. In other words, was Shealy’s romantic partner a party or a representative of the plaintiffs?

The court declined to extend the definition of “representative” to a romantic partner with no connection to the case, and thus answered that question in the negative: “Plaintiffs are represented by sophisticated, capable counsel. Plaintiffs’ counsel had nothing to do with Shealy’s decision to ask his romantic partner to upload documents to ChatGPT and generate information and documents.”

Therefore, because the AI inquiry did not occur at the direction of Shealy’s lawyer, “neither the queries of AI programs for legal assistance by a party’s romantic partner nor the AI output are protected from disclosure under the work product doctrine.”

Importantly, the court determined that ChatGPT was also not a representative. According to the court, AI “is a tool, not a person,” since its output does not disclose the “mental impressions, conclusions, opinions, or legal theories of an attorney or other representative of a party concerning the litigation.”

As far as I’m concerned, that’s the correct and only way to approach AI and other emerging tools. Expanding the concept of personhood to include AI simply because it is new and unfamiliar is unwise. Doing so would create confusion in the short term and unnecessary complexity in the long term, with courts struggling to reconcile misguided holdings as the technology evolves and becomes commonplace.

Any other conclusion would repeat the legal profession’s history of knee-jerk reactions to emerging technologies, most of which are reversed as adoption becomes widespread. AI may be far more advanced than the technologies that preceded it, but it remains a tool and should be treated as such.

Nicole Black is a Rochester, New York attorney, author, journalist, and Principal Legal Insight Strategist at 8am, the team behind MyCase, LawPay, CasePeer, and DocketWise.She is the nationally-recognized author of “Cloud Computing for Lawyers” (2012) and co-authors “Social Media for Lawyers: The Next Frontier” (2010), both published by the American Bar Association. She also co-authors “Criminal Law in New York,” a Thomson Reuters treatise. She writes regular columns for Above the Law, ABA Journal, and The Daily Record, has authored hundreds of articles for other publications, and regularly speaks at conferences regarding the intersection of law and emerging technologies. She is an ABA Legal Rebel, and is listed on the Fastcase 50 and ABA LTRC Women in Legal Tech. She can be contacted at [email protected].