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30 August 2023 ·

5 ways to boost productivity for legal contracts using generative AI



The use of artificial intelligence is all the buzz right now.  From Microsoft Bing’s use of OpenAI’s ChatGPT to Google’s Bard AI Chat Bot, the topic of responsible use of artificial intelligence continues to trend. To add to that, generative artificial intelligence (a useful AI technology feature that generates human-like content) is being reviewed extensively -- not only from a usability perspective, but from a legal work standpoint.

The realm of legal ops and contract management – traditionally viewed as time consuming and laborious – is ripe for automation and streamlining with the power of AI. Generative AI for contracts plays a pivotal role – enhancing accuracy and efficiency. Let’s explore five ways how.

But first…

How has Artificial Intelligence changed everything?

Over the past fifty years, our society has seen artificial intelligence being advanced and adopted in many areas -- from predictive analytics (such as weather forecasting) to technology that adjusts to changing surroundings (such as GPS navigation). Now, AI technology can construct what we previously saw as creative assets -- such as drawings and written pieces of content.

So how can legal teams get in on the action? The answer is generative AI for contracts – and here are five key ways it is helping transform contract management.

1 – Contract Clause Recommendations

With new natural language processing and deeper contextual understanding of linguistics, generative AI tools can provide clause recommendations that compare existing clauses to not only those in your organization’s playbook of legal clauses, but also those from a larger corpus of pre-training and generated clauses.

This contract intelligence1 process can not only minimize the risk of missing essential clauses, but can also save precious time – enhancing the efficiency of contract drafting2 and negotiation. Additionally, less experienced members of legal teams can glean valuable information for performing legal research and for understanding the intricacies of different clauses and how they fit into different types of business contracts.

2 – Generative Clauses

As a waterfall benefit to my clause recommendation above, I rank generative clauses next.   Generative contract AI3 can summarize or augment clauses automatically. With vast databases of categorized clauses and improvements with generative technologies, modern AI-powered tools can generate clauses in seconds. As a greater benefit, specific tools can set or select preferences for specific words or phrases in clauses with favorable (or less) terms.  This reduces the need for manual contract drafting and reduces the risk of human error to virtually ensure accuracy for every contract.

3 – Contract Automatic Redlining

Building upon items 1 and 2 above, generative AI can significantly streamline contract redlining. AI can automatically redline legal contract documents, such as MS Word documents, Google Docs, or documents stored within contract management software,4 and quickly change clause text for favorable contract language. This technology can not only review a draft, and redline a contract, it can also…

  • locate clauses;
  • match clause-based context to a clause category; and
  • compare certain clauses to clauses in a configured and optimized legal library.  Such library would be specific to a legal team’s needs and either pretrained to function as a legal team’s playbook; or autogenerated from a legal intelligence system.

Auto redlining can help ensure that each contract aligns with established legal parameters to enhance the accuracy and compliance of every agreement. When legal teams streamline contract review processes, they are free to perform more strategic tasks.


4 – Contract Pattern Recognition

Pattern recognition extracts many elements of document text and transforms such elements into useful contract data points -- then uses historical data and predictive analytics to provide corrective recommendations as an assistive tool for legal technology.  For example, a pattern recognition identifies a discrepancy in the scenario below:  

Although our payment terms are a net 60 days, the legal assistive AI recognizes that, for a specific contract, the terms are net 90 days. The system would then show assistive alerts to bring this discrepancy to the attention of a legal team.

5 – Contract Auto Drafting

Contract auto drafting combines many of the items listed above, but it uses specified rules to detect data and trigger entire contracts, amendments, and more.  By integrating clause recommendations, generative clauses, auto redlining, and pattern recognition, generative AI can draft comprehensive contracts that fulfill legal requirements, cater to the specificities of a business relationship, and minimize risk.

Contract auto-drafting not only improves CLM efficiency, but also enhances the quality of contracts – virtually ensuring that they are thorough, compliant, and optimized. As such, legal teams can shift their focus to contract analytics5 and future-minded insights.

Key Takeaway for Generative Contract AI

Of course, it’s impressive!   How legal technology is growing and becoming adaptive very quickly. The above points reflect assistive technologies that empower legal workers to do their best work, and still recognize how technology cannot replace the deep thought and human understanding that empowers legal operations’ success.

If your legal team and/or legal practice is interested in learning more about how you can leverage these and other legal artificial intelligence tools, book a free demo of CobbleStone Contract Insight® CLM software today.

Join CobbleStone on September 25th during World CC’s AI Contracting Week where Michael Gormley, Sales Manager, will show a sneak peak of CobbleStone Contract Insight. Register Today!

*Legal Disclaimer: This article is not legal advice.  The content of this article is for general informational and educational purposes only.  The information on this website may not present the most up-to-date legal information.  Readers should contact their attorneys for legal advice regarding any particular legal matter.


Mark Nastasi is the Executive VP and founder of CobbleStone Software with over 20 years of professional experience in the industry.  He launched the first commercial contract software in 1995 named CMTS (Contract Management Tracking System). He has worked extensively with general counsels, paralegals, lawyers, and legal professionals to help manage contracts better. 


  1. Cobblestone Software article titled Contract Intelligence: Embracing Smarter Contract Management
  2. Cobblestone Software article titled Contract Drafting Made Easy With Contract Software
  3. Cobblestone Software article titled, What is AI-Based Contract Management?
  4. Cobblestone Software article titled Contract Management Software, Fast Setup. User-Friendly. Highly Configurable. Seamlessly Integrated
  5. Cobblestone Software article titled Contract Management Analytics & Reporting
Mark Nastasi
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