What was your most challenging experience with contract interpretation in litigation, and how did you approach it? What lesson did you learn that you now apply to drafting?

One of my most challenging contract interpretation cases involved a lease with an option to purchase. The contract provided the tenant with the ability to purchase the property but there was another clause in the lease that stated that if the tenant defaulted on any term of the lease, then the option to purchase was forfeited. While the tenant faithfully performed all the terms of the lease, he did have a check that bounced a year prior and despite immediately replacing the check, the landlord/seller used that opportunity to now permit the election to purchase. This turned into a 2 year litigation since the lease contained a "grace period" and it was argued that tenant was not technically late. From a litigation perspective, it became a battle over strict construction versus equitable interpretation. The landlord took the position that the option clause was to be strictly interpreted and a grace period still equated to a late payment. The tenant's position was that the payment was not late, rather it was paid and honored in the grace period and therefore not late. I approached the case on behalf of the tenant, by researching case law on grace periods and interpretations by different courts. But also using the pattern and equity and fairness arguments. I learned that courts and Judges are human, and generally dislike forfeitures, especially when a party has invested significant sums into the property. So we appealed to the humanity part of the deal and trier of fact. The case is still ongoing and set for trial but this was a huge learning lesson for me to not rely on contract headings. The heading labeled "Option to Purchase" would lead one to believe that no where else in the contract would there be mention of or change the terms of the option to purchase. However, this is completely false. One clause later in the contract, with a completely different heading, can completely cancel out this clause, despite a different heading. It is crucial to read the contract as a whole and see what other clauses in the contract affect the prior clause, despite a different heading.

One of the most challenging experiences I had with contract interpretation in litigation was around a notice period. The contract just said "X days' notice" without specifying whether those were calendar days or business days. Of course, that became a huge point of contention—one party argued it meant calendar days, the other insisted on business days, which made a big difference in timing. The lesson I took away—and now always apply when drafting—is to clearly specify which "calendar" or "business days" you mean for any notice period. It sounds simple, but it can prevent a lot of headaches later. Ambiguity in something as basic as timing can turn into costly disputes, so I'm really strict about spelling that out up front now.

One of the most difficult situations I faced involved a contract where key obligations were defined with vague language. Both parties believed the wording supported their position, leaving the court to resolve the ambiguity. I approached the case by breaking down the document clause by clause, highlighting inconsistencies, and supporting my client's interpretation with external evidence of intent. The lesson was clear: precision in drafting prevents costly disputes. Today, I avoid broad terms without concrete definitions. I use plain language, outline responsibilities in detail, and make sure all parties understand the implications before signing. Ambiguity is rarely accidental, and eliminating it reduces risk.

A difficult case with contract interpretation was an agreement that had vague wording, which could have restricted my client's stance. The language was open to several different interpretations, and I needed to thoroughly study every clause to determine its possible implications. I studied applicable legal concepts and consulted the potential interpretations with other professionals to make sure that I thought of all the possibilities. The procedure needed a careful, word-by-word analysis to understand the literal interpretation as well as the real implication. I also envisioned counterarguments of the opposing party, working out an orderly method of putting forth my arguments clearly before the court. Detail was important, as one small mistake could have influenced the decision. This experience reaffirmed the need for clarity and forward thinking when preparing contracts. I now pay close attention to writing clear language, thinking about how clauses might be read in two different ways, and adding contingencies to safeguard my clients. Careful drafting is as important as persuasive advocacy, and every clause must protect clients' interests while leaving little room for argument.