Justice in the Margins

FOR YOUR PRACTICE | CONTRACT LAW

Justice in the Margins: Contract Redlining as Collaborative Advocacy and Client Education

BY NATASHA NAZARETH, ESQ.

Justice in the margins may sound like a grand aspiration for a small space. But in any law practice that involves contract negotiation, access to justice often begins in the narrow white column beside a clause.

A comment can calm a client who is trying to understand what is really at stake. A precise edit can turn a vague promise into a concrete obligation with clear timing, triggers, and remedies— something each side can realistically deliver and enforce.

A thoughtful fallback can keep a difficult conversation moving when everyone is tired, protective, or unsure how far they can go.

Redlining and margin comments—the written annotations in the margin of the document—are the bread-and-butter skill of legal work. In our digital-first, asynchronous world, they are, perhaps counterintuitively, where the most human part of the work shows up.

Contract redlining shows up in commercial, employment, real estate, estate planning, settlement negotiations, and other legal matters. Across contexts, the redline is where broad goals become real choices: lawyers translate what the client wants into language the parties can rely on, make risk visible, and move the negotiation

toward a workable agreement. Done well, that work is a quiet form of access to justice—helping clients understand and own high-stakes decisions before they sign.

For Maryland lawyers, redlining is also grounded in the Maryland Rules of Professional Conduct (rules), which address competence, client decision-making, candid advice, communication, and truthfulness in dealings with others.

These rules give support to something good negotiators already know: the redline should help the client decide, help the other side understand, and help the agreement become more honest and workable. This article offers practical guidance on contract redlining, from principled advocacy and document craftsmanship to client education and writing for multiple readers, grounded in the ethical rules that shape how lawyers negotiate on the page.

Principled Advocacy in the Margins The best redlines begin before the lawyer touches the document.

They begin with a simple question: what problem are we trying to solve?

Clients often speak first in positions. That is natural. “I want full custody.” “We need unlimited indemnity.” “We cannot accept autorenewal.” “They have to sign our release.” Each position carries an interest, a risk, and a decision that the client may not understand.

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FOR YOUR PRACTICE | CONTRACT LAW

Justice in the Margins: Contract Redlining as Collaborative Advocacy and Client Education

BY NATASHA NAZARETH, ESQ.

Justice in the margins may sound like a grand aspiration for a small space. But in any law practice that involves contract negotiation, access to justice often begins in the narrow white column beside a clause.

A comment can calm a client who is trying to understand what is really at stake. A precise edit can turn a vague promise into a concrete obligation with clear timing, triggers, and remedies— something each side can realistically deliver and enforce.

A thoughtful fallback can keep a difficult conversation moving when everyone is tired, protective, or unsure how far they can go.

Redlining and margin comments—the written annotations in the margin of the document—are the bread-and-butter skill of legal work. In our digital-first, asynchronous world, they are, perhaps counterintuitively, where the most human part of the work shows up.

Contract redlining shows up in commercial, employment, real estate, estate planning, settlement negotiations, and other legal matters. Across contexts, the redline is where broad goals become real choices: lawyers translate what the client wants into language the parties can rely on, make risk visible, and move the negotiation 106

MSBA.ORG | VOLUME 8 ISSUE 1

toward a workable agreement. Done well, that work is a quiet form of access to justice—helping clients understand and own high-stakes decisions before they sign.

For Maryland lawyers, redlining is also grounded in the Maryland Rules of Professional Conduct (rules), which address competence, client decision-making, candid advice, communication, and truthfulness in dealings with others.

These rules give support to something good negotiators already know: the redline should help the client decide, help the other side understand, and help the agreement become more honest and workable. This article offers practical guidance on contract redlining, from principled advocacy and document craftsmanship to client education and writing for multiple readers, grounded in the ethical rules that shape how lawyers negotiate on the page.

Principled Advocacy in the Margins The best redlines begin before the lawyer touches the document.

They begin with a simple question: what problem are we trying to solve?

Clients often speak first in positions. That is natural. “I want full custody.” “We need unlimited indemnity.” “We cannot accept autorenewal.” “They have to sign our release.” Each position carries an interest, a risk, and a decision that the client may not understand.

This article offers practical guidance on contract redlining, from principled advocacy and document craftsmanship to client education and writing for multiple readers, grounded in the ethical rules that shape how lawyers negotiate on the page.

Our work is to listen for the interest underlying the position, then design workable frameworks, language, and solutions that the client can understand, choose, and later enforce.

A parent who insists on full custody may really be asking for a consistent home and school environment for the child. A client who demands unlimited indemnity may need a meaningful remedy if a vendor’s security failure exposes customer data. Rejecting autorenewal may come down to budget control. Insisting on a release may be about closure and certainty. Each interest calls for judgment, proportionality, and a record clear enough to guide conduct before anyone seeks a remedy in court.

As counsel, shifting from position to interest changes the redline. It also changes the conversation with your client and opposing counsel.

The ethical framework reinforces this. Md. Rule 19-301.2 keeps the roles clear: the lawyer supplies judgment, and the client owns the objective. Md. Rule 19-302.1 also gives a useful footing. Candid advice may include economic and practical considerations, as well as a legal answer. In redlining, that may sound like: “This point is legally cleaner, but may not be worth delaying settlement,” or “This vendor position is common, but the risk is meaningful because the data involved is sensitive.” That is transactional access in practice: the client receives a legal answer in a form that supports a real decision.

While a positional redline may simply delete the other side’s clause and insert our preferred language, a principled redline does more. It explains why the change matters and gives the other side a way to respond, moving the negotiation forward.

That distinction has roots in negotiation theory. Roger Fisher, William Ury, and Bruce Patton’s Getting to Yes (1981) remains useful because it provides lawyers with a disciplined way to separate people from problems, focus on interests rather than positions, generate options for mutual gain, and use objective criteria. In contract practice, those principles show up in the words we propose and in the comments we leave.1 By shifting towards comments that name the concern and give the other lawyer something useful to evaluate, we can

work towards a shared goal—a workable agreement that both parties can accept. Most lawyers on the other side are trying to solve a problem too. They may have different instructions, different pressure, or a different view of the risk.

For example, in a vendor services agreement, rather than using a comment such as “Company won’t agree to this payment method,” try “Revised to tie payment to completion of implementation milestones. This gives both parties a clear trigger for invoicing and avoids disagreement if launch is delayed.”

Objective criteria can help lower the temperature. Deal size, insurance limits, operational control, market practice, statutory requirements, and the economics of the matter can turn a contest of wills into a discussion about fit. “We never agree to this” may sometimes be true. Often, a more useful comment is: “For a contract of this size, a 12-month fees-paid cap is more consistent with the risk allocation our client can support.”2 That is one form of justice in the margins: helping the parties talk about the real issue, rather than reacting to the shadow cast by an unexplained position.

Craftsmanship in the Margin There is a technical side to this work, and it deserves care.

Microsoft Word remains the working standard for legal redlines, and Md. Rule 19-301.1 gives that practical skill an ethical grounding: legal competence includes enough technical command of the document to know what changed, what was accepted, what remains open, and what the client is being asked to sign.

That does not require every lawyer to love the software. But it likely does require them to understand how to control the file: save a clean version, use visible track changes, confirm insertions, deletions, and comments are showing, compare versions when files have moved between parties or PDFs have been converted, accept and reject changes deliberately, and inspect any final clean copy before signature to ensure it is the correct version.

One of the most considerate technical habits is editing at the smallest useful unit. Change the words that need changing.

Leave the rest alone. A narrow edit respects the reader’s

1 Roger Fisher, William Ury & Bruce Patton, Getting to Yes: Negotiating Agreement Without Giving In (3d ed. 2011).

2 A practical bridge between principled negotiation and good redlining for further reading is Nada Alnajafi’s Contract Redlining Etiquette (Contract Nerds method2method022).

The book shows how to operationalize negotiation strategy on the page—use explanatory margin comments, avoid “silent redlines,” and make your edits easy to follow so the other side has the opportunity to evaluate the reason, not just the markup

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time and helps everyone see what matters. It also does not cause unnecessary positioning or aggressiveness that can unnecessarily derail the negotiations. Laura Frederick’s “Practical Contract Drafting” advises writing what you mean in plain language, spending drafting energy where the risk is real, and resisting drowning a deal in low-stakes “lawyerly” cleanup.3 Even if you do not like the formatting or the font choice, there is no reason to change it unless it makes it difficult to understand the provisions and could cause ambiguity. If a full rewrite is needed, keep the negotiation moving by saying why, such as “Rewritten for clarity; risk allocation unchanged.”

In a settlement agreement, changing “all claims” to “all claims arising out of or relating to the dispute” may be more useful than rewriting the entire release. In a licensing agreement, changing “use” to “use internally for customer support purposes” can clarify the grant without reopening the whole license structure. In a services agreement, adding “to the extent caused by contractor’s negligence or willful misconduct” may calibrate indemnity more cleanly than replacing the clause.

When countering another party’s language, it is also helpful to preserve the negotiation history. Leave the other side’s proposal visible, insert your counter with track changes on, and explain the reason in a comment. The document itself should help tell the story of how the language evolved.

This technical proficiency is practical justice for clients: when the markup is accurate and the version history is clean, everyone can see the bargain, the client can consent with informed clarity, and the signed document becomes a reliable record.

Client Education in the Margin A margin comment offers an economy of words with outsized potential. It can educate a client, signal materiality, and keep a negotiation moving.

Md. Rule 19-301.4 requires a lawyer to keep the client reasonably informed and to inform the client of facts and communications from another party that may significantly affect settlement or resolution of the matter.

In negotiation, the margin can help fulfill that duty in a practical way by explaining what the clause does, why it matters, who decides, and how difficult the point may be to obtain.

It is also important to note that while margin comments are a valuable tool, they are not the only way that attorneys should advise clients. A client rarely needs a treatise in the margin. (If so, the client needs a phone call or more formal communication).

Examples: “Client: This clause shifts all delay costs to us, even if the delay is caused by the vendor.”

“Client: Legally acceptable, but this is a business decision.

From a risk perspective, I recommend pushing back.”

The form changes with the agreement, but the purpose is the same: explain the risk, state the ask, and leave the client or counterparty with a clear path to respond.

A client who understands the choice can be confident in making the choice. That may be one of the most practical forms of justice a lawyer provides.

Keep in mind that internal notes to clients should be separated from external redlines, particularly where they reveal advice, strategy, or authority. Before sending an external version, inspect the document for internal comments, hidden text, metadata, and personal information. This reflects confidentiality practice, client service, and professional care.

Once the client understands the risk and the options, the next question is how to write on the page for the people who will actually negotiate, approve, and live with the language.

3 Laura Frederick, Practical Contract Drafting: Clarity, Not Florid Language, Is Key to Managing Risk Through Contracts, www.legaldive.com/news/contracts-drafting-negotiating-redliningrisk-management-legal/690278/ (last visited May 4, 2026).

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Writing for the Reader in the Margin

When we say, “Rewritten for clarity; allocation unchanged,” the allocation should be unchanged.

Every redline has more than one reader. The same comment may be skimmed by business stakeholders for bottom-line impact, reviewed by in-house counsel for triage, and scrutinized by outside counsel for leverage, drafting precision, and enforcement risk.

Staying within those bounds is easier when comments follow a consistent structure. One useful paradigm is: reason, ask, fallback. For example:

Before you type, ask two questions: who is the primary reader on the other end of this draft, and what decision—or next move—should this comment enable?

“Reason: This indemnity is broader than the risks within our client’s control. Ask: Limit indemnity to third-party claims arising from breach, negligence, willful misconduct, and IP infringement.

Fallback: We can discuss separate treatment for confidentiality and data security claims.”

That structure works across many kinds of agreements.

Once the client understands the risk and the options, the next question is how to write on the page for the people who will actually negotiate, approve, and live with the language.

For sophisticated counsel, calibrate tone and comment density to the deal context—and make it easy to see what is truly material. A heavily negotiated acquisition agreement may justify more explanation than a routine services agreement. A separation agreement may call for plainer drafting and fewer rhetorical flourishes. A settlement agreement may require special precision around dismissal mechanics, payment triggers, confidentiality, and tax treatment. Where a nonlawyer reader is likely to touch the document, favor concrete language over shorthand and avoid “inside baseball” that obscures meaning.

It is also important to remember Md. Rule 19-304.1: In representing a client, a lawyer may not knowingly make a false statement of material fact or law to a third person, and may not fail to disclose a material fact when disclosure is necessary to avoid assisting a client’s criminal or fraudulent act. Put practically, negotiation pressure has to stay within the bounds of truthful statements, accurate framing, and sound professional judgment.

A redline comment should not imply agreement where none exists. It should not describe a preference as a legal impossibility.

It should not bury a material change in a cosmetic cleanup. When we say, “This is a priority issue for our client,” that should be true.

In a settlement agreement: “Reason: The confidentiality provision should allow ordinary compliance activity. Ask: Add carveouts for tax advisors, insurers, auditors, courts, and government agencies.

Fallback: We can require those recipients to be informed of the confidentiality obligation where practical.”

These comments are practical and relational. They say to the other side, “Here is what we are trying to solve. Here is one way to solve it. We are open to discussing the path.”

Good redlining respects the practical clock ticking without letting urgency drive sloppy language. We need to know when to press, when to explain, when to package issues, and when to accept a workable, if not ideal, answer.

In a settlement agreement: “If your client can agree to mutual non-disparagement, we can accept the confidentiality language with the revised legal-process carveout.”

This kind of packaging enhances civility and moves the deal forward by acknowledging both sides’ interests. It also helps the parties move from isolated clause-by-clause friction to a more complete agreement.

From Redline to Record The last stretch of a negotiation can be deceptively difficult. People are tired. The hard points may be resolved. Everyone wants a signature. That is when the process deserves a steady hand.

Md. Rule 19-308.4 explicitly prohibits dishonesty, fraud, deceit, and misrepresentation. It is professional misconduct. Redlining habits should be built with that value in mind. Hidden edits, misleading redlines, or implying agreement where none exists can create both professional and enforceability problems.

Before signing, review the final document or document package in both No Markup and All Markup, inspect it for any unresolved changes or internal comments, and export it only after approval. The signed agreement should be clean, usable, and faithful to the bargain.

A contract is a working document that lives on after the lawyers finish the negotiation. The clearer the record, the less often the parties need a court to reconstruct what they meant.

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Putting Justice in the Margins Into Practice Before sending your next redline, pause over four questions.

Does the redline make the issue visible?

The edit should show what risk, obligation, ambiguity, or practical concern is being addressed.

Does the comment help the reader decide?

A useful comment explains the reason, the ask, and, where helpful, the fallback.

Does the process preserve trust?

Track Changes should be visible. Counters should preserve negotiation history. Internal strategy should stay internal.

Does the final document serve the parties’ actual needs?

The agreement should be clean, readable, operational, and faithful to the bargain.

Those questions elevate redlining from habit into ethical craft. The red ink is only the visible part. Beneath it are preparation, restraint, technical skill, practical judgment, and care. That is the discipline of contract redlining. That is advocacy, ethics, and access to justice hidden in plain sight.

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The red ink is only the visible part. Beneath it are preparation, restraint, technical skill, practical judgment, and care. That is the discipline of contract redlining.

____________ Natasha Nazareth is co-founder and partner at Nazareth Bonifacino Law, Maryland’s first Certified B Corp law firm, where she provides outside general counsel services to purpose-driven businesses, schools, nonprofits, and underserved entrepreneurs. Nazareth currently serves as Treasurer to the Maryland State Bar Association and received a lifetime achievement award from the GP Solo Division of the American Bar Association in 2024.