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The Challenges of Contract Review

The Challenges of Contract Review


Contract review is one of the most important things attorneys do. It’s also one of the most time-consuming. Millions of hours are logged by lawyers to ensure that every defined term and every cross-reference in a contract is correct. How can this work be streamlined?

Different kinds of contracts pose different kinds of problems. Reviewing a large number of similar short contracts (10 pages or less, say) is tedious, but short contracts are generally easier to digest than long ones. The real challenge is analyzing a long contact (100 pages or more, say), which can be like digesting one entire volume of an encyclopedia.

The easiest way to tackle a long contract, of course, is to use software that’s designed for the job. Good contract review software can analyze a contract with speed and accuracy that humans can never hope to match.

But whether or not you use contract review software, it’s worth figuring out what attributes make this kind of software helpful in order to apply them to manual contract review. These attributes are also important to keep in mind when you’re choosing a contract review application to use.


Limitations of Text

A major challenge of contract review is that, generally, you’re dealing with plain text. By “plain text” I don’t mean “unformatted text” (although you often are dealing with that too). I mean text that you can’t interact with – and, generally, the on-screen text you see in Microsoft Word or Adobe Reader isn’t any more interactive than print. Without text analysis software, you’re more or less stuck in the era of the typewriter. And while there have been a few steps toward a universal contract markup language, such a thing doesn’t seem imminent – so, at least for the foreseeable future, you’re left with the raw text of the contract that’s in front of you.

As a bare minimum, it’s essential to make your contract machine-readable if it isn’t already – even for scanned documents, OCR software ranges from modestly priced to free. Doing this will, at the very least, make the text of your contract searchable.



Perhaps the biggest challenge of reviewing contracts is their inherent interconnectedness. Whether you’re dealing with a single contract or a set of related contracts, there’s simply no way around connections – imagine trying to draft a contract without using cross-references, defined terms, exhibits, and so on. And this means that there’s no way around having to ensure that these connections are right.

The first step is finding all the connections, which is no small task in a typical contract. Next is making sure they’re right. For years, this has meant running countless text searches in Word – tedious, but better than just reading and hoping for the best.

Contract review applications use the same concept; they just do it faster and more elegantly, pulling together all instances of a connection almost instantly. The most familiar way to review connections is through an interface by which you can navigate between them by clicking or tapping – we’re accustomed to working this way from browsing the internet. Navigation history (Back and Forward buttons) is essential here, again owing to internet habits. When you review connections that are pre-organized with a familiar interface, you can focus entirely on substantive content.


Personnel Management

Contract review is further complicated by the fact that there are almost always multiple reviewers (you, your client, opposing counsel, their client, and so on). It might be appealing to think that more reviewers will yield a faster review, but the opposite tends to be true.

In the course of any team doing work, team members need to be brought up to speed, have meetings, follow up, and so on. In other words, adding team members increases the number of people who need to coordinate. While two heads are better than one and there’s nothing inherently wrong with delegating, adding reviewers often means adding personnel management overhead to an already laborious task. It’s best to limit the number of people on a review team and avoid adding people over time. (This is really just Fred Brooks’ famous mythical man-month applied to contract review.)

There’s no getting around the fact that reviewing a contract is one of the most time-consuming and complicated tasks lawyers handle. However, by employing a systematic approach and, if possible, using software designed to make your task easier, you can make the burdensome undertaking a bit more manageable.


Vicki LaBrosse
Vicki LaBrosse
Benjamin Whetsell on EmailBenjamin Whetsell on LinkedinBenjamin Whetsell on Twitter
Benjamin Whetsell
Benjamin Whetsell
Benjamin Whetsell is a co-founder of Paper Software, developer of Turner for working with contracts on Mac, and Contract Tools for working with contracts with Word on Windows PC. He is admitted to the bars of New York and Washington DC. Previously, he was an associate at Fried Frank in New York City, where he worked on financings, mergers, and fund structures for clients such as Bank of America and Goldman Sachs. He holds a BBA from the University of Michigan Business School and a JD from Columbia Law School.


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