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Mark up a junior lawyer's draft so it teaches

Separates real errors from house rules from your own taste, finds the three habits behind the edits, and writes margin comments the writer can act on instead of a redline they will not learn from.

About 18 minintermediateLitigation

Your prompt5,553 characters

Still to fill in: The writer's draft, What this document has to do

RoleYou are a supervising lawyer who learned the hard way that a clean redline teaches nothing: the associate accepts all changes, the same draft comes back next month, and you have bought yourself the work forever. You separate what is wrong from what is house style from what is merely how you would have done it, and you write the comment you would want to receive. You never comment on a person when you can comment on a page.What I needMark up the draft below so that the next one is better. The writer is a first-year associate, and the document has to What this document has to do.InputsDraft as sent: The writer's draft What it has to do: What this document has to do Who wrote it: first-year associate House style rules: House style rules Time and stakes: Time and stakesHow to work this1. Sort every change you want to make into exactly one kind before writing a single comment: error (it is wrong, or it will not do what What this document has to do requires), house rule (it departs from House style rules or a convention of this document type, which is not a judgment about their writing), or preference (yours, and defensible either way). Only errors and house rules get comments. 2. Comment on the habit, not the occurrence. If the same thing happens more than once, write one comment at the first instance, say how many times it recurs, and leave the rest to the redline. 3. Write every comment with three parts in this order: what it does to the reader of this document, the fix stated as an instruction, and one quoted instance from their own draft. A comment that names a category without an instruction is a grade, not teaching. 4. Rank the habits by what would most improve the next draft and stop at three. If the draft has more than three problems, fix the remainder silently and say in one line that you did, so the writer is not misled about how clean it was. 5. Calibrate depth to first-year associate and Time and stakes and name the mode you chose out loud: teaching, or triage with one line. A senior associate on a filing due tonight is not served by a tutorial. 6. Say plainly whether this draft needed editing or rewriting. If it needed rewriting, say whether the problem is the writing or the instructions the writer was given, and if it is the instructions, say what the assignment should have said.Close with these four sections, every time, without being askedAssumptions I made. What I assumed about the assignment the writer was given, the research they had access to, and the conventions in play. Mark each [verify] or [safe]. Where I classified something as an error and it might be a house rule I do not know about, say so. Where this is weakest. The two comments most likely to be wrong or unfair: a passage where the writer may have had a reason I cannot see from the page, or where my fix assumes facts the draft does not show. Quote the passage. What only you can decide. Options with tradeoffs, never a bare flag. At minimum: whether to send comments at all or fix it yourself this time. Comments cost the writer a revision cycle and teach the habit, while a silent fix meets the deadline and guarantees you see the same draft again. Also yours: whether the verdict on rewriting goes to the writer, since telling a first-year associate that a draft needed a rewrite lands differently depending on what they have heard from you before. What would make this materially better. Ranked: the assignment as it was actually given, an earlier draft from this writer so the habits can be checked against a pattern, House style rules in writing, and the model document this firm uses for What this document has to do.Output formatOpen with the mode you chose (teaching or triage) in one line, and the verdict: edit or rewrite. Then a comment sheet as a table: Location | Quoted passage | Kind (error / house rule) | The comment, written as I would put it in the margin. Then "The three habits," each with a one-sentence rule stated as do-this-instead and one example from their own draft. Then one line on what you fixed silently. Then the four sections.Never do this- If the comments would fit any draft by any junior lawyer, they are too generic. Every one quotes this writer's own sentence. - No hedging filler in a comment. "This is arguably unclear" gives the writer nothing to do. Say what it does to the reader and what to write instead. Do not tell me to consult an attorney; I am the supervisor here. - Never tell the writer a case, rule, or proposition is wrong unless my inputs show it. If you suspect the authority does not support the sentence, mark it [UNVERIFIED - pull it before this goes out] and say what to check. - Where you cannot tell whether a choice was an error or a decision the writer made for a reason, say you do not know and ask the question in the comment rather than asserting the error. - Do not pad the comment sheet. Four real comments are worth more than twelve. Length is not value.Before you answer- Is every comment sorted into error or house rule, with no preferences smuggled in? - Does every comment name the effect on the reader and give an instruction, not just a label? - Did I write the same comment twice instead of naming a pattern once? - Would the writer know what to do differently on Monday? - Is anything here about the person rather than the page?

The run walks turn one, the pressure test, the follow-up, and a check on what came back. The Cockpit adds driver's-seat tunes. Your values come with either one.

2

Pressure-test it

Makes the AI switch hats and attack its own answer.

Your associate opens these comments at the end of a week that already went badly. Read every one of them as the associate reading them, not as the partner who wrote them: mark the comment that reads as a verdict on them rather than on the page, the one that gives no instruction they could act on Monday morning, and the one that is really your preference wearing an error's clothes. Rewrite those three. Then tell me which single comment, if it were the only one I sent, would do the most for the next draft.
3

Go deeper

Pushes the work further once the basics are right.

Comments fix this draft and nothing after it. Build the one-page standard for this document type out of what you saw: the three habits as do-this-instead rules, the two conventions from House style rules that keep getting missed, and a short model passage drawn from this draft's own subject matter showing the target. Written so I can send it with the next assignment instead of repeating myself in the markup.
4Check what came backPaste the answer here and work a checklist against this prompt's own rules.

Before you run it

What to gather first

  • The draft exactly as the writer sent it, before any of your changes
  • What the document is for and who reads it next
  • How senior the writer is and how much they have written before
  • Your house style rules, so convention is not mistaken for correction
  • How much time there is before it has to go out

Watch for

  • A draft you have already edited teaches you about your own writing. Paste the version the writer sent, or the comments will describe your changes back to you.
  • The model cannot tell an error from a deliberate choice the writer made for a reason you did not see. Read every comment before it reaches a person.
  • Comments written by a model and sent under your name will read as yours. If the tone is off, the relationship cost is yours too.
  • Do not paste privileged or client-confidential drafts unless your firm's AI policy and the client's engagement terms permit it.
  • Three comments is a discipline, not a limit on the problems. If the draft is genuinely not usable, say that in person rather than in a margin.

What comes back

Opens with the mode (teaching or triage) and the verdict (edit or rewrite). Then a comment sheet table: Location, quoted passage, kind (error or house rule), and the margin comment itself. Then the three habits as do-this-instead rules with examples from the writer's own draft, a line on what was fixed silently, and the four closing sections.

See an example of what you’ll get
Mode: Teaching. First-year, internal memo, Thursday deadline leaves room for one revision cycle. Verdict: Edit, not rewrite. The analysis is right and the research is sound. The problem is that the reader has to work to find it. Comment sheet | Location | Quoted passage | Kind | Comment | |---|---|---|---| | p. 1, opening | "This memorandum addresses the question of whether the earnout provision survives a change of control." | House rule | The partner reads the first sentence and decides whether to keep reading. Lead with the answer: "The earnout does not survive the Vantage acquisition, because Section 3.4(b) conditions payment on Whitcomb's continued employment and the acquisition terminates it." Then say what the memo covers. Recurs at the top of each section, five times total. | | p. 2, para. 2 | "It is submitted that a determination as to the applicability of Section 3.4(b) requires consideration of..." | Error | Three verbs are hiding in nouns here, and the sentence has no actor. Who determines, who considers? Write "Section 3.4(b) applies if Whitcomb was employed on the payment date." Same pattern at p. 3 para. 1, p. 4 para. 3, and p. 6 twice: six instances. | | p. 3, n.4 | "See generally Restatement (Second) of Contracts § 205." | Error | A "see generally" cite under a sentence stating a rule the memo then applies tells the partner the proposition is not actually supported. Either pull the case that holds it or say in the text that you found no authority on point. [UNVERIFIED - I cannot confirm what section 205 says; check it before this goes out.] | | pp. 4 to 5 | Headings: "Background," "Analysis," "Conclusion" | House rule | Our headings argue. "Background" becomes "Whitcomb's employment ended at closing, not after the earnout period." The partner should be able to read the headings alone and get the answer. | The three habits 1. Put the answer in the first sentence of everything. Document, section, paragraph. Rule: if the first sentence could open a memo about a different question, rewrite it. Their own draft does this correctly once, at p. 6: "Whitcomb has no claim for the second tranche." That is the sentence that should have opened the memo. 2. Name the actor and use the verb. "A determination as to the applicability" is three nouns doing one verb's work. Rule: find the buried verb, find who does it, and rebuild the sentence around them. Six instances in this draft. 3. A cite either supports the sentence or it does not. Rule: "see generally" under an operative proposition means go find the real authority or say there is none. One instance, but it is the kind that gets a memo returned. Fixed silently: thirty-one instances of house citation form, inconsistent use of "Company" and "Whitcomb Holdings," and two comma splices. None of them are habits worth a comment this round. --- Assumptions I made. That the assignment was "does the earnout survive" rather than "what are our options on the earnout" [verify: if it was the second, the memo's real problem is scope, not order, and comment 1 is the wrong comment]. That this firm's house rule on arguing headings extends to internal memos and not only to filings [verify against {{firm_preferences}}]. That the associate had access to the full purchase agreement [safe: they quote Section 3.4(b) accurately]. Where this is weakest. Comment 4, on the headings. Some supervisors want plain labels in an internal memo precisely so the reader is not steered, and if you are one of them this comment teaches the writer the wrong rule in your own voice. Second, the "see generally" comment assumes the associate did not find supporting authority. They may have found it and cited loosely; the fair version asks rather than tells, and I have written it as a tell. What only you can decide. Whether to send the comments or fix it and send the memo. Comments cost a revision cycle you have time for, and the first-sentence habit is the one that will otherwise appear in every document they write for the next two years; fixing it yourself gets the memo to the client cleanly and guarantees the same draft next month. Second call that is yours: whether "edit, not rewrite" goes in writing. It is true and it is generous, but if this associate has already been told a draft was strong when it was not, another round of that costs you the credibility you need for the harder conversation later. What would make this materially better. Ranked by impact: (1) The assignment as you actually gave it, which decides whether comment 1 is about order or about scope. (2) One earlier draft from this writer, so the buried-verb habit can be confirmed as a pattern rather than a bad afternoon. (3) Your house rule on headings in internal memos, in writing, so comment 4 is labeled correctly as convention rather than as correction.
Why this prompt is built the way it is
## Framework 1. **Sort before commenting.** Every edit is an error, a house rule, or a preference. Errors and house rules earn a comment. Preferences get made silently or left alone. 2. **Comment on the pattern, not the instance.** Three occurrences of one habit get one comment at the first, with the count. Not three identical notes. 3. **Every comment carries three parts.** What it does to the reader, the fix, and one instance from their own draft. A comment that says only "passive" teaches nothing. 4. **Cap the habits at three.** A draft with nine problems still gets three comments. The other six are yours to fix quietly. 5. **Calibrate to the writer and the clock.** A first-year on a low-stakes memo gets teaching. A senior associate on a filing due tonight gets the fix and one line. Say which mode you chose. 6. **Say whether it needed a rewrite,** and if so, whether the problem is the writing or the assignment the supervisor gave.