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Probate & Property

Jul/Aug 2023

If You’re a Good Legal Writer, You Don’t Write Good: Better Contract Writing for Transactional Lawyers

Michael H Rubin


  • The client wants clarity and the ability to enforce the document precisely as intended.
  • It can be tough and demanding to rethink how to write contracts clearly and succinctly and then produce a result that accomplishes these goals.
  • We should keep in mind not only the reading level of the average juror, but also the fact that even judges, arbitrators, and mediators.
If You’re a Good Legal Writer, You Don’t Write Good: Better Contract Writing for Transactional Lawyers
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The minute you read something you can’t understand, you can almost be sure it was drawn up by lawyers.

—Will Rogers

Transactional lawyers write contracts every day. Leases. Purchase agreements. Easements. Finance documents.

We’ve become so skilled at this that we frequently use terms of art and legal phrases that are clear to other experienced transactional lawyers. We’re adept at deciphering long paragraphs comprising only one or two sentences, at parsing through complex provisions with parentheticals galore, and at relishing the opportunity to add to our next document some useful phrase, clause, or provision that we have found in another contract.

Yet, although we understand documents others send us and know that they’ll understand ours and can negotiate complex provisions with knowledgeable counsel on the other side of the table, in our often-closed world of transactional practice we tend to lose sight of the most important purpose of contracts.

Of course, contracts exist to memorialize the intent of the parties, delineate how the relationships should work, define events of default, set forth remedies, and make sure that all the deal points are covered. But, even with all these bases covered, one underlying issue remains—enforcing the contract’s provisions in court.

Whether the issue is to be tried by a judge or a jury, someone who is not an expert in transactions will have to read the document, interpret it, and decide how to enforce it. And if a jury is involved, the task becomes difficult, and not only because jurors are not trained transactional lawyers. According to The Literacy Project, the average American reading level is that of a seventh- or eighth-grader—someone 12-to-13 years old. Another study suggests that half of US adults cannot read and comprehend materials written at or above the eighth-grade reading level. Thus, it is likely that as many as half of the jurors serving in any case may be functioning at or below the eighth-grade level of reading comprehension.

Litigators enforcing a contract in a jury setting are at a disadvantage if they have to explain what a provision means, “translate” unfamiliar legal terminology, or clarify the parties’ intent when the jurors cannot ascertain it on their own because of the document’s complexity of language, verbiage, or prolixity. Indeed, the average juror may not easily comprehend the previous sentence.

The best contracts are the ones that can be easily understood by the average juror, and our contract drafting should be driven by this fact.

The Cut-and-Paste Contract

Each of us is always trying to make documents and contracts more precise and cover more areas of concern. One “easy” way to do this is to cut and paste sentences, clauses, or entire sections from other contracts that we encounter. But doing so often results in contracts containing inadvertent internal inconsistencies—often in style, and sometimes even in substance. The way drafters usually deal with potential discrepancies is not to do the difficult work of reworking the entire contract from scratch but rather by using the phrase, “notwithstanding anything to the contrary.” This formulation, however, does not make contracts clearer; rather, it is an indication that the contract contains provisions that may be ambiguous or incompatible. As difficult and as time-consuming as it may be, the solution is to rethink contracts and phrase them in such a way that a juror with an eighth-grade reading level can understand the meaning of each sentence.

The price of clarity, of course, is that the clearer the document, the more obvious its substantive deficiencies. For the lazy or dull, the price may be too high.

Professor F. Reed Dickerson, Indiana University Law School

Think Hemingway, Not Faulkner

When I started law school many years ago, I asked a 3L how to get good grades. She said, “Write lots, use big words, and spell them all correctly.” Although that was sound advice for the situation, it is the wrong advice for drafters of contracts. Even when there are bench trials and no juries involved, judges complain about having to decipher a contract with “confusing and complex language and unclear construction, ” a provision that is “poorly worded and confusing,” or a document with “paragraphs as long as seven pages and lengthy, confusing sentences.”

Writing clearly and succinctly can be arduous. Mark Twain is reputed to have said, “I didn’t have time to write a short letter, so I wrote you a long one instead.” Writing short sentences in tightly-crafted paragraphs that easily convey to the reader precisely what you mean is not a simple task. The premier book on effective written communication, one that every lawyer should have, is The Elements of Style by Strunk and White, which states: “Vigorous writing is concise. A sentence should contain no unnecessary words, a paragraph no unnecessary sentences.”

One of the problems lawyers have is that, in law school, we were not only trained to decipher poor writing, but also we were rewarded for it. We read cases written in legalese, most often by judges who employed Latin phrases, formalisms, and convoluted syntax. Our grades often correlated to how well we wrote in this style. We began to think that all lawyers should write this way, forgetting that judges were writing for other lawyers and judges, not for the lay public, and certainly not for a juror with an eighth-grade reading level.

Ernest Hemingway was known for his succinct and powerful writing. Once, when asked for the shortest story possible, he wrote: “For sale. Baby shoes. Never worn.” On the other hand, William Faulkner won kudos for his novels, though he could wax eloquent at length. In Absalom, Absalom!, there is one sentence containing 1,287 words.

In drafting contracts, we should seek to follow Strunk and White’s advice and emulate Hemingway rather than Faulkner.

Short Takes

As drafters of contracts and documents, we should keep in mind not only the reading level of the average juror, but also the fact that even judges, arbitrators, and mediators may not have been trained as transactional lawyers who are unfazed by a Faulknerian sentence.

Most legal writing is atrocious.

—Judge Mark P. Painter (Ohio)

There are many articles and references for better contract drafting, and from these, I have culled a few helpful suggestions:

  • No multiple definitions. Not: The parties to this agreement are Conglomerate Inc. (“Conglomerate” or “Contractor”). Multiple definitions are confusing and a sign of a cut-and-paste contract. Use a single definition for each party or concept.
  • All definitions in one place. Don’t scatter definitions throughout the contract. Not: For the purposes of this Section, “Utilities” shall mean . . . . Put all the defined terms in a single definition section, and then make it easy for the reader to understand by always putting the defined term in bold or italics or with the Initial Letter capitalized. But don’t use all caps; that’s hard for anyone to read, and it looks like shouting. For example, “Utilities” instead of “UTILITIES.”
  • Define “shall” and “may.” Some courts have held that “shall” does not necessarily indicate something that must be done. Make the contract clear. Define “shall” as mandatory and “may” as discretionary,” and then don’t confuse things either by using “will” and “must” elsewhere in the contract or by writing that a party “shall, in its discretion, . . .”
  • No legalese. Avoid all of the following: whereas, heretofore, hereinafter, hereinabove, and pursuant to. Never use “said” to modify any noun, such as, “said contract” (that’s as opposed to the unsaid contract?).
  • No “and/or.” And/or has rightly been called “a Janus-faced verbal monstrosity” and “senseless jargon.” It can lead to ambiguity. For example, one court held that the following sentence was ambiguous: There must be approval from all appropriate divisions and/or groups. Did it require, if there were both divisions and groups that were “appropriate,” that all had to concur? Did it mean that the approval of “all appropriate groups” was sufficient even if a division did not approve? Clarity was impaired, not improved, through the use of and/or.
  • No Latinisms. “Later,” not “subsequently.” “Before,” not “prior to.”
  • Use the Oxford comma. When there are three or more items with either an “or” or “and” before the last item, put a comma between each item as well as before the “or” or “and.” That way one avoids confusing formulations such as “A panda eats, shoots and leaves,” or “She finds inspiration in cooking her family and her dog.”
  • Give examples of calculations. Many contracts use words to describe formulas, percentages, or other mathematical calculations. To help clarify the formula or calculation for the judge or jury, give an example in the document using numbers so that there is no question about how the calculation should be made.


It’s easy to pull a form contract up on the computer, rework a previous contract, or plug in clauses from other contracts. Making the drafting process easy for a lawyer, however, is not in the client’s primary, secondary, or even tertiary interest. The client wants clarity and the ability to enforce the document precisely as intended. When litigation occurs, if a contract is hard to read or understand, the opposing party will likely assert that the document is ambiguous, which means that summary judgment cannot be obtained.

It can be tough and demanding to rethink how to write contracts clearly and succinctly and then produce a result that accomplishes these goals. That hard task, however, pays off when the contract has to be enforced.