From Brief to Business

How mastering brief writing techniques is essential for successfully drafting transactional documents

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BY MIREILLE BUTLER

Transactional documents—contracts, wills, prenuptial agreements, residential real estate leases, merger agreements—are prospective documents that establish a binding agreement between two or more parties.¹1 Tina L. Stark, Drafting Contracts: How and Why Lawyers Do What They Do (2007); Kenneth A. Adams, A Manual of Style for Contract Drafting (2004). The goal of those transactional documents is to ensure the smooth operation of any business; as a result, they are different from briefs that typically look back at past actions.  

Most lawyers, therefore, only think of persuasive writing when thinking about litigation-related writing. Yet, like briefs, transactional documents must be drafted in a persuasive manner to ensure that they are effective in (1) securing a legally binding agreement that cannot be second-guessed and (2) communicating the parties’ intent. Persuasive writing techniques will help achieve these two goals. First, using persuasive language when drafting transactional documents is helpful to the  parties: persuasive drafting choices can convince the counterparty to perform according to the agreement.²2 Susan M. Chesler & Karen J. Sneddon, “Humanizing Transactional Documents: Why and How Transactional Drafters Should Use Narrative Techniques,” 23 Transactions: Tenn. J. of Bus. Law 222, 224 (2022). Second, while “the transactional drafter’s aim is to minimize the likelihood of third-party intervention,”³3 Id. at 225. if third-party intervention does occur, persuasive writing techniques can help ensure that the agreement will be interpreted in the way your client intended.  

The ultimate role of lawyers is to advocate for their clients,⁴4 Lori D. Jonson, “The Ethics of Non-Traditional Contract Drafting,” 84 U. Cin. L. Rev. 595, 605-06 (2016). mostly in writing. Rather than merely cutting and pasting clauses, the same techniques litigators use to convince a court to decide in favor of their clients should be used when drafting transactional documents.  

Develop a Theory of the Case

The first step in drafting a persuasive document is to know your audience. The litigator’s theory of the case (the short answer to the question: “Why should my client win?”) is interwoven throughout a brief with the goal of making the reader want to find for the client.⁵5 Kristen Tiscione, Legal Writing: From Advice to Advocacy, A Contemporary Approach, at 349 (2021). Similarly,  before drafting transactional documents, you need to understand who will be reading the document and carefully weigh what their interests and concerns are. This helps tailor your language and tone to communicate effectively with that audience. For example, providing in the recitals of a contract descriptive information about the parties, their identity, and their motives might ultimately facilitate the execution of the contract as intended. A court might view with suspicion a bland provision waiving a fundamental right of one of the parties. Infusing the clause instead with your “theory of the case,” i.e., your understanding of the specific motivations of the parties, might help a court find the provision enforceable.⁶6 Susan M. Chesler & Karen J.Sneddon, “Once Upon A Transaction: Narrative Techniques and Drafting,” 68 Okla. L. Rev. 263, 282-83 (2016) (discussing how a standard jury-waiver provision stating “the parties waive all right to a jury trial on all issues in any action or proceedings relating to this lease agreement” might be viewed with suspicion, while the same clause describing how “Theresa Taylor makes a voluntary, intentional, and knowing waiver of a right to a trial by jury [and] acknowledges that neither Logan Lucas nor any agent acting on Logan Lucas’s behalf has induced her waiver” would likely strengthen the enforceability of the provision).  

Think About Language  

Use Plain Language and Be Concise

As important as the use of plain, concise language is in a brief, it is even more important in transactional documents.7 To implement the true intent of the parties, the drafter must ensure that the document is easy to read and understand, without any ambiguity or confusion. This can be achieved by using all the precepts applicable to persuasive writing: Avoid technical jargon and legal terms that may be difficult for the average person to understand; avoid lawyerisms (e.g., herein, witnesseth, know all men by these presents); avoid legalese doublets and triplets (e.g., null and void; convey, transfer, and assign); be clear about “shall” (obligation) versus “may” (discretionary); avoid the use of passive voice (it is of paramount importance in a contract to know who must perform); and use correct punctuation.⁷8 O’Connor v. Oakhurst, 851 F.3d 69 (1st Cir. 2017), a case centered around the lack of an Oxford comma, settled for $5 million. The court stated, “For want of a comma, we have this case.”

Use Strong and Positive Language

Using strong and positive language can help a transactional document reflect more appropriately the parties’ intent. The Bill & Melinda Gates Foundation uses the following language to describe the vision of the foundation:⁸9 www.gatesfoundation.org/about/foundation-fact-sheet.

Guided by the belief that every life has equal value, the Bill & Melinda Gates Foundation works to help all people lead healthy, productive lives. In developing countries, it focuses on improving people’s health and giving them the chance to lift themselves out of hunger and extreme poverty. In the United States, it seeks to ensure that all people—especially those with the fewest resources—have access to the opportunities they need to succeed in school and life. Based in Seattle, Washington, the foundation is led by CEO Mark Suzman, under the direction of co-chairs Bill Gates and Melinda French Gates and the board of trustees.  

Because the interpretation of the terms of a charitable trust or of a foundation should be consistent with the founder’s or settlor’s intent, using vivid, strong language is important to assist trustees in performing more effectively.⁹10 Chesler & Sneddon, supra note 6, at 293; see also Joel Fleishman, The Foundation: A Great American Secret; How Private Wealth is Changing the World (2009).  

Maximize Presentation

Visual aids, such as tables, graphs, and charts, can be used to make a transactional document more persuasive. Many legal scholars have explored the use of visual writing strategies and techniques in a litigation context.¹⁰11 For numerous examples on how to use visual aids in briefs and pleadings to become a more effective advocate, see William S. Bailey, Show The Brief: Visual Writing Strategies & Techniques (Trial Guides, 2022). Visual aids can help illustrate complex information in a clear and concise manner, making it easier for the reader to understand. This is particularly true in a transactional setting, where an understanding of the complex relationship between various parties and assets, or the structures of a deal, might greatly benefit from the use of diagrams and similar visual tools. While visual aids are not typically associated with transactional work, they can in fact be used there effectively.¹¹12 Jay A. Mitchell, “Whiteboard and Black-Letter: Visual Communication in Commercial Contracts,” 20 J. Bus. L. 805, 833 (2018). Using visual aids in a transactional context to make the document more easily understandable will help increase its persuasiveness.¹²13 Mitchell, supra note 12, at 831-32, citing various surveys that have tested the use of visuals in varied contract settings and found that using contract visualization promotes comprehension and also helps shape the relationship between the parties (contract readers perceive visuals as trustworthy, collaborative, honest, and clear). And, of course, a basic way to maximize presentation that is equally applicable to contracts as to briefs is to proofread carefully, as a polished document free from errors will always tip the scales in the drafter’s favor.  

Organize to Emphasize Benefits and Address Counterarguments

When drafting a brief, a drafter will often persuade through organization, by prioritizing the strongest points before addressing counterarguments. In a transactional setting, the drafter should strive to do the same. First, the drafter should emphasize the benefits of the transaction. This means highlighting the advantages that the reader will gain by signing the document. For example, when drafting a contract for a business partnership, the recitals should emphasize the benefits of the partnership, such as increased profits, expanded customer base, and shared resources.¹³14 For an interesting use of recitals in a settlement agreement, using a variety of persuasive techniques to describe the claims of each party and their reasons to enter into the agreement, see the Confidential Settlement Agreement and Mutual Release; Assignment of Copyright and Non Disparagement Agreement between Donald Trump and Stephanie Clifford aka Stormy Daniels dated October 28, 2016, which used only pseudonyms to identify the parties. The NDA can be found as an attachment to the later complaint claiming the NDA was unenforceable. www.documentcloud.org/documents/4403880-Stormy-Daniels-complaint.html.

The transactional document drafter should also address potential concerns the reader may have. This means acknowledging potential risks or drawbacks associated with the transaction and explaining how they will be addressed. By addressing these concerns up front, the drafter will alleviate any anxiety or hesitation that the readers may have, making them more likely to sign the document. For example, a non-compete clause might include a section entitled “Reasonableness of Covenants” acknowledging that although the non-compete clause will preclude the employee from accepting other highly attractive offers for a limited period of time after the employment ends, the clause is necessary in light of the employee’s high-level position within the company and the type of business in which the company engages.¹⁴15 See Exhibit B to Declaration of Adam Selipsky in Support of Motion for Temporary Restraining Order, and Plaintiff’s Motion for Preliminary Injunction, 2012 WL 6210298 (W.D. Wash Nov. 6, 2012.) in Amazon.com Inc. v. Powers, 2012 WL 6726538, No. 12CV01911 (W.D. Wash. Dec. 27, 2012) (noting how Amazon had purposefully drafted the non-competition agreement to describe to Powers how his employment would be seriously limited, yet the restriction was reasonable). Despite those precautions, however, the court ultimately found the non-compete would likely be found overly broad and Amazon would not succeed on the merits of its efforts to enforce the clause.  

Use Examples

Finally, just as in persuasive drafting and oral advocacy, personal, concrete examples help make a transactional document more persuasive by illustrating abstract points in a concrete and relatable manner. Contract drafters have indicated how valuable it can be to use “for example” clauses when drafting.¹⁵16 Paul Comeaux 10/1/2008 comment to Adams on Contract Drafting blog, www.adamsdrafting.com/for-example/#:~:text=What%20bearing%20does%20this%20have,oranges%2C%20lemons%2C%20and%20grapefruit.

First, they can be used to show how a formula or process is to be applied: “For example, if Operating Costs during the year in which the Term commences were $100,000, the cap on Operating Costs for the fourth full year would be $122,504 ($100,000 times 1.07 times 1.07 times 1.07).”  

Second, they can also describe the most common or expected application of a more general statement: “If Tenant desires water to serve the Premises (for example, to serve a private lavatory or kitchen approved by Landlord),” or “If a third party breaches this restriction (for example, if another tenant begins to operate in violation of the restrictions above without Landlord’s permission”).  

In conclusion, transactional lawyers benefit from employing the same persuasive skills litigators use in three significant ways: First, persuasive abilities enhance the negotiation process, enabling lawyers to secure favorable terms and protect their clients’ interests. Second, effective persuasion fosters stronger contractual relationships, minimizing the potential for future disputes. Finally, leveraging persuasive techniques ensures that transactional lawyers can advocate convincingly for their clients’ positions, thereby increasing the likelihood of successful transactions and overall client satisfaction.    

NOTES

1.    Tina L. Stark, Drafting Contracts: How and Why Lawyers Do What They Do (2007); Kenneth A. Adams, A Manual of Style for Contract Drafting (2004).

2.    Susan M. Chesler & Karen J. Sneddon, “Humanizing Transactional Documents: Why and How Transactional Drafters Should Use Narrative Techniques,” 23 Transactions: Tenn. J. of Bus. Law 222, 224 (2022).

3. Id. at 225.

4.    Lori D. Jonson, “The Ethics of Non-Traditional Contract Drafting,” 84 U. Cin. L. Rev. 595, 605-06 (2016).

5.    Kristen Tiscione, Legal Writing: From Advice to Advocacy, A Contemporary Approach, at 349 (2021).

6.    Susan M. Chesler & Karen J.Sneddon, “Once Upon A Transaction: Narrative Techniques and Drafting,” 68 Okla. L. Rev. 263, 282-83 (2016) (discussing how a standard jury-waiver provision stating “the parties waive all right to a jury trial on all issues in any action or proceedings relating to this lease agreement” might be viewed with suspicion, while the same clause describing how “Theresa Taylor makes a voluntary, intentional, and knowing waiver of a right to a trial by jury [and] acknowledges that neither Logan Lucas nor any agent acting on Logan Lucas’s behalf has induced her waiver” would likely strengthen the enforceability of the provision).

7.    In 1998, the SEC published a guide, A Plain English Handbook: How to Create Clear SEC Disclosure Documents, available at www.sec.gov/pdf/handbook.pdf, showing securities lawyers and companies ways to reduce legalese. Also in 1998, the SEC adopted a rule requiring the use of plain English in certain sections of prospectuses. In 2008, the SEC adopted a rule providing for mutual fund summary prospectuses to be written in plain English.

8.    O’Connor v. Oakhurst, 851 F.3d 69 (1st Cir. 2017), a case centered around the lack of an Oxford comma, settled for $5 million. The court stated, “For want of a comma, we have this case.”

9.    www.gatesfoundation.org/about/foundation-fact-sheet.

10.  Chesler & Sneddon, supra note 6, at 293; see also Joel Fleishman, The Foundation: A Great American Secret; How Private Wealth is Changing the World (2009).

11.  For numerous examples on how to use visual aids in briefs and pleadings to become a more effective advocate, see William S. Bailey, Show The Brief: Visual Writing Strategies & Techniques (Trial Guides, 2022).

12.  Jay A. Mitchell, “Whiteboard and Black-Letter: Visual Communication in Commercial Contracts,” 20 J. Bus. L. 805, 833 (2018).

13.  Mitchell, supra note 12, at 831-32, citing various surveys that have tested the use of visuals in varied contract settings and found that using contract visualization promotes comprehension and also helps shape the relationship between the parties (contract readers perceive visuals as trustworthy, collaborative, honest, and clear).

14.  For an interesting use of recitals in a settlement agreement, using a variety of persuasive techniques to describe the claims of each party and their reasons to enter into the agreement, see the Confidential Settlement Agreement and Mutual Release; Assignment of Copyright and Non Disparagement Agreement between Donald Trump and Stephanie Clifford aka Stormy Daniels dated October 28, 2016, which used only pseudonyms to identify the parties. The NDA can be found as an attachment to the later complaint claiming the NDA was unenforceable. www.documentcloud.org/documents/4403880-Stormy-Daniels-complaint.html.

15.  See Exhibit B to Declaration of Adam Selipsky in Support of Motion for Temporary Restraining Order, and Plaintiff’s Motion for Preliminary Injunction, 2012 WL 6210298 (W.D. Wash Nov. 6, 2012.) in Amazon.com Inc. v. Powers, 2012 WL 6726538, No. 12CV01911 (W.D. Wash. Dec. 27, 2012) (noting how Amazon had purposefully drafted the non-competition agreement to describe to Powers how his employment would be seriously limited, yet the restriction was reasonable). Despite those precautions, however, the court ultimately found the non-compete would likely be found overly broad and Amazon would not succeed on the merits of its efforts to enforce the clause.

16.  Paul Comeaux 10/1/2008 comment to Adams on Contract Drafting blog, www.adamsdrafting.com/for-example/#:~:text=What%20bearing%20does%20this%20have,oranges%2C%20lemons%2C%20and%20grapefruit.