Leading Questions: How to Prompt AI for Legal Work

I want a prompt I can reuse across matters for this task: [two or three sentences on the task, who handles it, and what they start with]. The result should come back as [a table, an outline, a one-page memo]. Require a source document and page for each factual statement, rule out any fact or authority I have not supplied, and require a plain statement whenever the material does not support a conclusion. Use bracketed placeholders for anything that changes from matter to matter. After the prompt, list three things someone should check before relying on what it produces.

I’m getting up to speed on a [type] case. The attached documents are [party]’s production. We represent [client], and the dispute comes down to [one sentence]. Give me four things: a one-page overview of what the production covers; the key people and the role each plays; a chronology of significant events, each tied to the document it comes from; and the five documents I should read first, with a reason for each. Cite the document by filename and date for every factual statement. Where a document is unclear or the set looks incomplete, tell me so and leave the gap open.

Working only from the attached transcript and interrogatory answers in this [type] matter, write a summary for the lead attorney organized by issue: admissions bearing on [the issue]; testimony that may conflict with the interrogatory answers; topics that need follow-up; and any other significant testimony. Give the page and line for every point. If the record does not support a conclusion, say that. Before calling anything an inconsistency, identify both statements.

Take the role of opposing counsel answering our attached motion for summary judgment. Tell me the three arguments in our motion most likely to fail, and why; the strongest authorities against us among the attached cases, with pinpoint cites; any statement of fact a court might read as misleading, quoting the record passage behind it; and the three hardest questions a skeptical judge would ask at argument. Don’t soften it. Use only authority found in the attached materials.

Prepare first-draft requests for production to [party] in the attached case. Each request should trace to a claim or defense in the attached complaint and answer. Borrow the style, structure, and definitions from our attached prior set. Since the case is in [court], apply [applicable rules] to scope and format. Give me [n] requests grouped by topic, each followed by a one-line note naming the allegation or defense it supports. Mark any request with thin support in the pleadings, and leave out anything unconnected to the pleaded claims.

I’m preparing a motion to [relief]. The only sources of fact are the attached pleadings and record excerpts, and our attached prior motion on the same issue is the model. Before any drafting, lay out the argument as a matrix with one row per proposition and columns for the supporting record cite, the governing authority (taken from the prior motion only), the counterargument to expect, and anything unresolved. Follow the matrix with a proposed outline. No prose yet, and no authority that isn’t in what I attached.

From the attached scheduling order in [court], pull every deadline and every provision that triggers a date. For each one, list the event; the date, or the rule for calculating it when it runs from another event (for example, responses due 14 days after service); the order’s exact language, quoted; and a short title I could use for a calendar entry. Put it in a table in date order. Where a deadline depends on a local rule and not on the order itself, mark it “VERIFY: local rule” and do not guess.

Before I file the attached draft, help me plan my cite check. Make a list of every authority cited. Next to each, note what the draft uses it for and quote the draft sentence that depends on it. Mark any citation where the quotation or the way the source is described needs a side-by-side comparison with the original. Your job is to point me to what needs checking; whether each citation holds up is my call.

Turn the attached call notes into three pieces: a dated matter note, in plain language, of what was discussed and decided; an action list giving each item an owner and a due date, marking any owner or date you had to infer; and a recap for the client of no more than 150 words in [describe your firm’s tone], which I will review before it goes out. Use nothing that is not in the notes.

Compare the attached draft billing entries against the client’s attached outside counsel guidelines. Flag each entry that may run afoul of the guidelines, such as block billing, vague descriptions, non-reimbursable expenses, or the wrong task code, and propose compliant wording for each one. Leave every hour and dollar amount untouched. Return a table with four columns: entry, issue, guideline provision, and suggested fix.

Below are eight samples of my professional writing. Describe how I write in concrete terms: sentence length, level of formality, how I open and close, phrases I use often, and things I never do. Make the description specific enough that I can paste it into future prompts and get drafts that sound like me.