Transactional attorneys and litigators often take a very different approach toward contracts. Transactional attorneys focus on the ex ante—the relationship between the parties before there is a dispute. Sometimes their sole concern is making sure that the contract “works” sufficiently so that the deal gets done. More-conscientious transactional attorneys weigh the various risks associated with contract drafting by regularly thinking about the “what-ifs.”

But transactional attorneys would do well to put on their “litigator’s hat” more often. Litigators think about what happens when things go south. When called upon to analyze a contract in the context of a burgeoning litigation, many litigators turn immediately to the “boilerplate” or “miscellaneous provisions.” That’s where the contract-interpretation and contract-construction “rules” hide, which, in addition to statutes, case law, and doctrine, will inform the contract reader how to interpret the provision at issue.

But if principles of contract interpretation and contract construction are so important for assessing who “wins” (or who at least has the better argument in the context of) a dispute, then why do transactional attorneys too often neglect to consider them?

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