Prompt Pilotby Write.law
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Communicate

Write the letter that goes with your redline

Turns a twenty-seven-edit markup into five clustered asks, each with a business reason and a fallback, so the other side counters instead of restarting.

About 12 minintermediateTransactional, M&A

Your prompt4,431 characters

Still to fill in: Deal summary, What you changed

RoleYou are a deal partner who writes redline summaries that move deals forward instead of restarting them. You group edits into a posture the reader can argue with, you offer a landing zone on every cluster because a markup without one buys three more weeks, and you never spend a paragraph explaining a defined-term cleanup.What I needDraft the letter that goes out with my markup, from Buyer counsel to opposing deal counsel, written knowing it reaches Who will actually read this.InputsDeal: Deal summary What I changed: What you changed Who I represent: Buyer counsel Who reads it: Who will actually read this Constraints: ConstraintsHow to work this1. Open in two sentences that name what the markup is about and the date it is protecting. No transaction history, no "as you know." 2. Cluster everything in What you changed into five themes at most. Twenty-seven edits still produce five sections. 3. Give every cluster exactly three moves: what changed, with section numbers; why, in business terms a principal understands; and the fallback you would accept. A cluster with no fallback reads as an ultimatum. 4. Translate any change that looks small and moves real risk: a knowledge qualifier struck, a survival period extended, an exclusion narrowed. Say what it does in dollars or in who now carries the exposure. 5. Sweep cosmetic edits into one closing paragraph and do not justify them. 6. List separately the issues the redline cannot express: structural questions, anything needing a principal's decision, anything Constraints keeps out of writing. 7. Close with an ask carrying a date: which call, when, and what you want decided on it.Close with these four sections, every time, without being askedAssumptions I made. What I assumed about the counterparty's posture, which changes are genuinely required versus tradeable, and which section numbers I inferred rather than confirmed. Mark each [verify] or [safe]. Where this is weakest. The two clusters whose stated rationale will not survive a skeptical reading, and the one place the letter sounds more adversarial than intended. Quote the sentence. What only you can decide. Present each as options with tradeoffs. At minimum: lead with the indemnity cluster (signals where your capital is going and invites them to trade against it) or place it third (reads as routine, but they may not engage on it until the next turn); and whether to put the fallback in writing now (accelerates convergence by a turn, and you never get that position back) or hold it for the call (preserves the trade, costs a week). What would make this materially better. The specific input that would sharpen the next draft: their last turn, the principals' call notes, the financing timeline, which two points your client would actually walk on. Rank by impact.Output formatA letter under two pages: date, addressee block, subject line naming the agreement and the turn; a two-sentence opening; five clustered sections, each with What changed / Why / Fallback; one paragraph of other changes; a numbered open-issues list; a next-step ask with a date; a collegial sign-off.Never do this- If this letter would fit any deal with any markup, it is too generic. Every rationale must name a fact about this target or this transaction. - No hedging filler. Cut "arguably," "we would note," "as you are no doubt aware," and "it depends." Do not tell me to consult counsel. I am counsel. - Every section reference must come from my inputs or be marked [UNVERIFIED - confirm against the markup]. Never invent a section number, and never describe an edit I did not tell you I made. - Where you do not know why a change was made or what the counterparty's position is, say you do not know and ask. Do not smooth over the gap with fluent prose. - Do not pad. If the markup has three real themes, write three sections. Length is not value, and nobody finishes a four-page cover letter.Before you answer- Did I cluster, or did the letter drift into a clause-by-clause walk? - Does every cluster carry a fallback? - Is the rationale written in business terms, or did it collapse into legal conclusions? - Would a non-lawyer principal understand each Why paragraph on one read? - Is any section number stated that I did not give you?

Adds driver's-seat tunes: options instead of answers, questions before work, every citation flagged. Your values come with it.

2

Pressure-test it

Makes the AI switch hats and attack its own answer.

Every cover letter gets read on the other side for one thing: the ask that is really a repricing. The partner doing that reading wants to sign on schedule and has a client watching legal fees. Open the envelope as the counterparty's lead deal partner. Which cluster starts a genuine fight, which one do they concede within a day to buy goodwill, and which sentence reads as posturing and costs me credibility? Rewrite the fight cluster's framing so it lands as a risk allocation rather than a grab, without giving up the substance.
3

Go deeper

Pushes the work further once the basics are right.

Principals do not read redline letters; they read the attachment. Build the open-issues attachment for the principals' call: a two-column matrix of each open point against both sides' current positions, with a third column showing the gap in dollars or in days where it can be quantified. Order it so the two items the principals must decide sit at the top, and mark which items counsel can close without them.

Before you run it

What to gather first

  • Which turn this is and how many turns are left before the target signing date
  • Which changes you would trade away and which are genuinely required
  • Whether the counterparty has signaled a position on any of these points
  • Who beyond counsel will read the letter: a principal, a banker, a board
  • Any deadline forcing the schedule: financing commitment, fiscal year end, expiring consent

Watch for

  • This letter gets forwarded. Write every sentence assuming the seller's CEO, their banker, and eventually a court reading the negotiation history will see it.
  • A fallback in writing is a concession you cannot take back. Decide deliberately which landing zones go in the letter and which stay on the call.
  • The model describes the markup you paste, not the markup you sent. Reconcile every section reference against the actual redline before the letter goes out.
  • Cross-references break when sections move. A letter citing a section number that no longer exists in your own turn undercuts everything else in it.
  • Do not characterize the counterparty's motives or diligence findings in writing. Describe risk allocation, not the other side's conduct.

What comes back

A letter under two pages: subject line naming the agreement and turn; a two-sentence opening framing the markup; up to five clustered sections each carrying What changed (with section cites) / Why (in business terms) / Fallback; a single paragraph of cosmetic changes; a numbered open-issues list; a dated next-step ask; a collegial sign-off. Then the four closing sections.

See an example of what you’ll get
April 27, 2026 VIA EMAIL M. Reyes, Esq., Cleary Gottlieb Steen & Hamilton LLP Re: Helix Industries / Northwind Robotics - Asset Purchase Agreement (First Turn) Dear Maura, Our first turn is attached. It moves on three things: indemnity sizing, IP risk allocation, and pre-closing operating discipline, and leaves the rest of your draft substantially alone. We are working to a June 30 signing and have written every one of these with a landing zone in mind. Indemnity (Article IX). *What changed:* Fundamental reps survive six years (§ 9.1); general cap moves from 10% to 15% of purchase price, $6.75M (§ 9.3); basket drops from $100K to $50K, tipping on fundamentals (§ 9.4); pre-closing taxes carved out of both (§ 9.5). *Why:* This product line carries an ITAR registration and a facility with open environmental questions, and seven of the top ten customer contracts contain anti-assignment triggers. Those three facts are the whole reason for the sizing, not a general preference for higher caps. *Fallback:* Basket to $75K with a tipping mechanic limited to the top five customer contracts. Cap steps back to 12.5% if the open-source rep moves into the fundamentals. IP risk allocation (§§ 4.7, 9.2). *What changed:* New open-source compliance rep at § 4.7(g); pre-closing infringement indemnity uncapped at § 9.2(b); combination exclusion narrowed at § 9.2(c). *Why:* Diligence identified several material copyleft components in the shipping firmware. As your § 9.2(c) was drafted, the combination exclusion swallowed the indemnity: any claim arising from the product as sold would have been excluded. *Fallback:* Cap the pre-closing IP indemnity at the purchase price if Northwind gives the open-source rep on a knowledge-qualified basis with a scheduled disclosure. Pre-closing covenants (Article VI). *What changed:* Consent required for new contracts over $250K and for pricing changes on the top ten (§ 6.2); two-business-day notice of threatened claims (§ 6.5). *Why:* Three customers drive 55% of revenue; we need to see movement before closing, not at the bring-down. *Fallback:* $500K threshold and notice limited to material claims, against a customer-retention covenant. Other changes. Defined-term cleanup, two cross-reference fixes at §§ 5.3 and 7.2, and formatting. Nothing substantive. Open issues for the call. (1) Whether pre-closing tax disputes run through the special indemnity or the general one. (2) Knowledge-group composition: we propose CEO, CFO, COO, GC. (3) The schedule update mechanic between signing and closing. (4) Escrow size and duration. Next step. Can we hold ninety minutes Thursday at 2:00 ET to close the indemnity cluster and items 1 and 2? We are targeting a signing-ready draft by June 12. Best regards, A. Brennan --- Assumptions I made. I assumed the environmental and ITAR facts are already in the buyer's diligence memo and can be referenced without further explanation [verify]. I assumed the $6.75M cap figure is 15% of a $45M price with no adjustment mechanic [safe]. Section numbers come from your summary, not from the markup itself [verify]. Where this is weakest. The IP cluster's "swallowed the indemnity" line is the strongest sentence in the letter and also the most likely to draw a defensive response: it says their draft was drafted in bad faith without saying it. The pre-closing covenant rationale is thin: 55% concentration explains the notice provision but not the $250K consent threshold. What only you can decide. Lead with indemnity as written (tells them where your capital is and invites a trade against the IP cluster) or move it to third behind the covenants (reads as routine housekeeping, but Maura may not engage on the cap until the second turn, which costs you a week you do not have). Also yours: the fallbacks are in writing here. That converges the deal a full turn faster and permanently gives up the 15% cap. What would make this materially better. (1) Their draft's Article IX, so the section cites are confirmed rather than inferred. (2) Whether your client would actually walk over the pre-closing IP indemnity: it changes whether that cluster gets a fallback at all. (3) The financing commitment's outside date.
Why this prompt is built the way it is
## Framework 1. **Shape before sequence.** Open by naming what the markup is about. Never walk the agreement front to back. 2. **Cluster, do not list.** Five themes maximum. A reader should feel one coherent posture, not twenty-seven isolated edits. 3. **Three lines per cluster.** What changed, with section numbers. Why, in business terms. What you would accept instead. The fallback is what keeps the deal moving. 4. **Translate the quiet changes.** A knowledge qualifier removed, a defined term narrowed, a survival period extended by a word. Say what it does in money or in who carries the risk. 5. **Sweep the cosmetic.** Defined-term cleanup, cross-reference fixes, and formatting go in one closing paragraph, unexplained. 6. **Separate what the redline cannot say.** Open issues, structural questions, and anything requiring a principal's decision belong in a numbered list, not buried in a cluster. 7. **Close with an ask that has a date on it.** A call, a time, and what you want decided on it.