Why a Business Attorney—Not ChatGPT—Should Handle Your Virginia Contract Dispute

A Massachusetts trial court has ruled that documents a party’s romantic partner drafted using ChatGPT, in anticipation of litigation, are not protected by the work product doctrine. The party’s own lawyer had nothing to do with the drafting. The decision, Shealy, et al. v. Seaside Investments, et al., is part of a small but growing body of case law holding that AI-assisted drafting earns work product protection only when directed by an attorney. Virginia has no reported decision on this exact question yet. However, the framework Virginia courts apply is the same one the Massachusetts court just interpreted. Therefore, Virginia courts are likely to reach the same conclusion.

• AI drafts created outside counsel’s direction get no work product protection.
• A represented party’s own use of AI—personally or through a family member—does not create the protections of attorney-client privilege.
• Pro se litigants may get more latitude than represented parties in the same courthouse.
• AI prompts and outputs can become discoverable.
• You may be damaged by the admissions found in prompts and outputs.
• Virginia’s work product rule tracks the same “prepared for a party’s representative” standard at issue in Shealy.
• Business owners in a dispute should route every document, including AI drafts, through their attorney.

Setting that rule with your team after litigation starts is too late.

The work product doctrine exists to let a party and her lawyer prepare for litigation without handing the other side a preview of their strategy. Virginia Supreme Court Rule 4:1(b)(3) protects documents and tangible things “prepared in anticipation of litigation or for trial by or for another party or that party’s representative.” Federal Rule of Civil Procedure 26(b)(3) uses nearly identical language and governs business disputes filed in Virginia’s federal courts.

Business owners often assume that anything created “because of the lawsuit” is automatically off-limits to opposing counsel. That assumption is not automatic. It depends on who created the material, and why. Shealy is a useful test case because it isolates that exact question: what happens when a party skips his own lawyer and uses AI—through a third party—to prepare for a fight he knows is coming.

The plaintiff was in a dispute over whether he had defaulted on a $2 million promissory note tied to a business transaction. After receiving a letter claiming default, he emailed the loan documents and the default letter to his girlfriend and asked her to run them through ChatGPT. She emailed back a draft response letter and other documents ChatGPT had generated. His own lawyer was not involved in any of it.

Once litigation started, the defendants moved to compel production of the email exchange between the plaintiff and his girlfriend, including the AI-generated documents. The plaintiff argued the material qualified for work product protection because it was prepared in anticipation of litigation. Judge Debra A. Squires-Lee disagreed and ordered the documents produced.

The lesson travels well beyond promissory notes. Any business owner anticipating a contract fight, a partnership breakup, or a dispute over who controls a company faces the same choice the plaintiff faced: loop in counsel, or improvise with whatever tool and whoever is nearby.

Judge Squires-Lee distinguished the case from Morgan v. V2X, Inc., a 2026 decision in which the U.S. District Court in Colorado held that materials a pro se plaintiff prepared using AI could qualify for work product protection. The plaintiff in Shealy was represented by sophisticated counsel who had nothing to do with his decision to have his girlfriend upload the loan documents to ChatGPT.

Instead, the judge found the case “more akin to” United States v. Heppner, a 2026 decision from the U.S. District Court for the Southern District of New York and subject of our blog here. In Heppner, the court held that AI documents a represented defendant generated on his own “volition” did not merit work product protection, because they were not prepared by or at the “behest” of counsel and did not reflect “counsel’s strategy.”

Judge Squires-Lee’s holding was direct: “I conclude, as a matter of first impression, that 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 unless performed at the direction of counsel.” Counsel’s involvement is not a formality. It is the entire basis for the protection.

We see the tension between Heppner and Morgan—one shields AI-assisted work, the other does not. Judge Squires-Lee squared the two decisions by drawing a line between a pro se litigant, who may genuinely need AI to help develop the legal theory of her case, and a party represented by counsel, who does not have the same need.

That distinction matters for business owners specifically because most of them are represented once a dispute turns serious. A founder fighting over a promissory note, a shareholder agreement, or control of a company almost never qualifies for the pro se latitude Morgan describes. The takeaway for represented clients is blunt: lawyers should keep warning clients not to use AI to develop legal strategy on their own. Consider this blog our warning!

As of the publication date for this post, we are not aware of a Virginia court ruling on whether a party’s own use of AI—personally or through a friend or family member—can qualify for work product protection. But the analytical framework already exists. Virginia Supreme Court Rule 4:1(b)(3) protects material “prepared in anticipation of litigation or for trial by or for another party or that party’s representative,” and defines “representative” to include the party’s attorney, consultant, surety, indemnitor, insurer, or agent. A girlfriend running documents through ChatGPT on her own initiative does not fit any of those categories.

Virginia’s federal courts apply the near-identical standard under Federal Rule of Civil Procedure 26(b)(3) in business disputes that land in the U.S. District Court for the Eastern District of Virginia or the Western District of Virginia. Under either rule, the question a Virginia judge would ask tracks the one Judge Squires-Lee already answered: was this material prepared by, or at the direction of, counsel? If the honest answer is no, the reasoning in Shealy and Heppner would very plausibly guide the result here, too.

Losing work product protection is not the only exposure. The warning goes further: The prompts you use could constitute a damning admission and are most likely not protected from discovery. A business owner describing the dispute to a chatbot, in his own words, before we have advised you, can hand the other side a written account of the weakest parts of your argument.

The principle is this: Work product protection exists to shield attorney work and protect the integrity of the legal process. When you act outside the shield we provide as your attorneys, the rationale for protection does not exist.  Unsupervised AI use is a right you may regret. Counsel-directed AI use is a defensible right.

Set these rules with your team before a dispute ripens, not after a default letter arrives:

• Route every document related to a dispute—drafts, research, correspondence—through your business attorney first
• Do not ask a spouse, partner, or family member to research or draft anything using AI on your behalf
• Do not type the facts of your dispute into a public AI tool to “see what it says” before calling counsel
• Treat any AI output already in your possession as presumptively discoverable, not privileged
• Ask your Dunlap Law attorney to set a written AI-use protocol as soon as a dispute becomes likely
• Preserve, do not delete, anything you or a family member already generated with AI

If you or someone helping you has already run dispute-related facts through ChatGPT or a similar tool, tell your attorney immediately. Do not delete the emails, chat logs, or drafts. Deleting discoverable material after a dispute is reasonably anticipated may create liability exposure, on top of the privilege problem Shealy already illustrates.

Your Dunlap Law attorney can assess what was disclosed, what remains protected, and how to adjust strategy around material that is now likely to reach the other side. Early disclosure to counsel narrows the damage. Silence compounds it.

Shealy is a first-impression ruling in Massachusetts, and not binding on Virginia courts. But the reasoning rests on rule language Virginia shares, and the stakes are the same for any Virginia business owner heading into a contract fight, a partnership breakup, or a dispute over company control: work product protection follows counsel’s involvement, not good intentions.

This material is for informational purposes only. It is not intended as legal advice and does not create an attorney-client relationship between its readers and Dunlap Law. Consult an attorney before taking action on issues outlined here. This is attorney ADVERTISING MATERIAL.

Image by Mohamed Hassan from Pixabay