We Asked ChatGPT, Claude, Gemini, and SimpleAI to Review the Same Contract
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Overview
AI tools like ChatGPT, Claude, and Gemini are rapidly finding their way into legal workflows. Teams are experimenting with them to summarize agreements, draft language, and increasingly, to review contracts.
But an important question remains: what actually happens when these systems are asked to analyze a contract in a meaningful way?
To explore that question, we ran a simple test. Using the same agreement and the same instructions, we asked ChatGPT, Claude, Gemini, and SimpleAI to review the contract.
The responses revealed some interesting patterns and raised broader questions about how different AI systems approach legal analysis.
In this session, Electra Japonas will walk through the comparison and discuss what legal teams should think about as AI becomes part of contract review workflows.
During the session, we’ll explore:
- How different AI systems approach the same contract review task
- What becomes visible when you compare the outputs side by side
- The role of legal context in AI-assisted contract review
- What legal teams should consider when evaluating AI tools
If your team is exploring how AI fits into contract review, this session offers a chance to see how several widely used systems behave when given the same task.
About the Host
Electra Japonas is the Chief Product Officer at SimpleDocs where she leads the product vision behind the company’s AI-powered contract tools. She works at the intersection of legal expertise and product design, helping shape how AI can be applied to real-world legal workflows like contract review, clause drafting, and playbook automation.
As the Founder of oneNDA, the global standard for NDAs, Electra brings a deep focus on standardization and usability to her work, pushing for tools that are not just smart, but genuinely adoptable.
Before joining the organization in 2024 following its acquisition of oneNDA, she was CEO and Founder of legal operations firm TLB, and held senior legal roles at the European Space Agency, Disney, BAT, and EY. She is a dual-qualified Solicitor (England & Wales) and Cyprus Attorney.
Preston Clark is the CEO and co-founder of SimpleDocs, an AI-powered contract automation platform that helps legal and business teams draft, review, and manage contracts more efficiently. He is also the co-founder of Law Insider, the world’s largest public contract and clause database, serving thousands of legal and business professionals worldwide.
With more than 15 years of experience at the intersection of legal operations, software, and AI, Preston has built and scaled products focused on modernizing how contracts are created, negotiated, and managed. Prior to becoming an entrepreneur, he held leadership roles at several venture-backed startups and served as Assistant General Counsel at the University of Miami.