The Technique to Develop: Learning to Identify Vagueness Early On

The greatest pitfalls in contract negotiation are buried in terms that sound straightforward until money changes hands or a deadline draws near. New practitioners swiftly read over sentences, assuming that terms like “reasonable” or “promptly” share a common-sense interpretation, only to realize later that the meanings differed between parties. The technique to cultivate now is the ability to recognize language that is potentially ambiguous and to slow down whenever you encounter words that describe time, amount, extent, or degree without a specific criterion for measurement. When you see these, immediately pause to consider what evidence would satisfy or violate the provision.

For example, consider the phrase “in a timely manner.” While seemingly innocuous, litigators and arbitrators have found enough ambiguity in this phrase to keep courts busy for decades, depending on the custom of the trade, course of dealing, and other contextual factors. A good practice when encountering any performance term is to take the ambiguous adverb or adjective and to insert in its place first the most unfavorable reasonable interpretation that the counterparty could apply, and then the most favorable reasonable interpretation that your party could apply. When written side by side, it should become clear whether further definition is needed before the document is executed. Many people overlook this practice because it takes some cognitive work to perform, but if vagueness is viewed as the enemy in every situation rather than something to be tolerated, most post-execution surprises can be avoided.

One of the most common missteps for new practitioners is the use of words such as “including” or “such as” in enumerated lists. Most novices read these words to mean examples rather than illustrations, whereas the former implies exclusion of items not on the list and the latter implies inclusion of similar items not on the list. By default, the law considers “including” to mean including but not limited to, unless the provision explicitly states otherwise. To adjust your instincts on this issue, mentally add the phrase “but not limited to” whenever you see this language. If doing so seems redundant or poses a risk, the provision is likely worthy of reevaluation or discussion before execution.

To hone this skill, dedicate a small amount of time each day to identifying qualifying words in sample documents. It is important to work in short intervals to maintain focus but avoid mental fatigue. Each day, obtain a sample commercial agreement (e.g., a form agreement for consulting services or a lease) and read through the document to identify qualifying words (reasonable, promptly, material, substantial, appropriate, sufficient). Underline each occurrence of these words, and then spend 10 minutes rewriting the sentence containing each qualifying word one time with a specific measure or deadline inserted and one time with the most ambiguous measure or deadline that the counterparty could reasonably insert. Read the modified sentences in the context of the original sentence to recognize how the presence of a specific measure eliminates potential ambiguities. The next day, use a different document to continue this exercise. Over time, patterns will emerge across types of agreements rather than merely a single agreement with which you become intimately familiar.

With time, this exercise will teach you to stop reading agreements as blocks of boilerplate text and to start reading them as minefields of potential ambiguities. Your objective should always be the same: recognize potential ambiguity before it becomes a dispute, a disagreement, or a lawsuit. Each time you practice rewriting ambiguous language, you are developing your judgment, which will become increasingly refined as you repeat the exercise. As you continue this practice, your reviews will become increasingly efficient and effective, and the likelihood of you signing something that may create an unexpectedly costly need for clarification will diminish.