{"id":159976,"date":"2026-08-10T11:35:04","date_gmt":"2026-08-10T19:35:04","guid":{"rendered":"https:\/\/xira.com\/p\/2026\/08\/10\/cherryn-paige-bissett-says-ai-didnt-replace-lawyers-it-repriced-judgment\/"},"modified":"2026-08-10T11:35:04","modified_gmt":"2026-08-10T19:35:04","slug":"cherryn-paige-bissett-says-ai-didnt-replace-lawyers-it-repriced-judgment","status":"publish","type":"post","link":"https:\/\/xira.com\/p\/2026\/08\/10\/cherryn-paige-bissett-says-ai-didnt-replace-lawyers-it-repriced-judgment\/","title":{"rendered":"Cherryn-Paige Bissett Says AI Didn\u2019t Replace Lawyers. It Repriced Judgment."},"content":{"rendered":"
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(Image via Getty)<\/figcaption><\/figure>\n

For the past two years, the legal industry has been obsessed with one question: Will AI replace lawyers?<\/p>\n

I think we\u2019re asking the wrong question.<\/p>\n

The better question is this: If AI takes over routine legal work, what becomes more valuable? That was the theme of my recent conversation with Cherryn-Paige Bissett, commercial counsel at LegalSifter, on \u201cNotes to My (Legal) Self.\u201d What emerged wasn\u2019t another discussion about prompts, copilots, or whether AI can draft a better indemnity clause. It was a conversation about judgment. More specifically, why judgment may become the most valuable skill an in-house lawyer can bring to the business.<\/p>\n

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Cherryn has a simple phrase that captures the shift: \u201cAutomate the 80%, own the 20%.\u201d At first, it sounds like another catchy AI slogan. The longer we talked, the more I realized it\u2019s actually a blueprint for the future of in-house legal.<\/p>\n

AI Isn\u2019t The Decision Maker<\/strong><\/p>\n

Legal teams often describe AI as a way to work faster. That\u2019s true, but speed alone isn\u2019t the destination. Speed only matters if it creates space for better decisions.<\/p>\n

As Cherryn explained, \u201cThere is a large portion that the AI can just blanketly apply our positions to. What it can\u2019t do is \u2026 look at what are the actual parameters of the deal, what are the nuances of the deal, and why is it important to the business to get it done.\u201d That distinction is easy to overlook, yet it changes everything.<\/p>\n

For years, lawyers built value by knowing the language of contracts. AI is increasingly capable of reading that language, comparing it against playbooks, identifying deviations, and suggesting revisions. Those tasks are becoming operational. The scarce resource is no longer the ability to process legal language. It\u2019s the ability to decide what actually matters.<\/p>\n

The Future Belongs To Lawyers Who Understand The Business<\/strong><\/p>\n

One idea kept surfacing throughout our conversation. Great commercial lawyers don\u2019t begin with the contract. They begin with the business.<\/p>\n

Cherryn repeatedly returned to balancing legal, operational, and commercial considerations. Those aren\u2019t separate conversations. They\u2019re the same conversation viewed through different lenses. A clause that looks risky in isolation may be perfectly acceptable once you understand the customer, the strategic value of the deal, the competitive landscape, or the company\u2019s risk tolerance.<\/p>\n

As she put it, \u201cYou have to understand what your business needs are and what your business risk appetite is.\u201d That sounds obvious, but many legal teams still spend disproportionate energy refining language while spending too little time understanding why the business is pursuing the deal in the first place.<\/p>\n

The best in-house lawyers have always acted as business advisors. AI raises the bar. It pushes lawyers further away from document editing and closer to business decision-making.<\/p>\n

Stop Negotiating Noise<\/strong><\/p>\n

One phrase from Cherryn deserves to enter every legal department\u2019s vocabulary: \u201ccontract noise.\u201d<\/p>\n

She described how AI can remove the repetitive work by identifying what deserves attention instead of encouraging lawyers to rewrite every sentence. \u201cIt cuts through the contract noise,\u201d she said. \u201cIt identifies the areas that you actually need to focus on.\u201d<\/p>\n

That observation struck me because I see a similar pattern through TermScout\u2019s benchmarking work. Contracts often accumulate rounds of revisions that create activity without meaningfully changing business outcomes. Lawyers negotiate wording because it\u2019s there to negotiate, not because it materially changes the allocation of risk.<\/p>\n

We\u2019ve all seen deals delayed over changes that make almost no practical difference. Those discussions consume time, frustrate customers, and reinforce the stereotype that legal slows everything down.<\/p>\n

The future isn\u2019t about redlining faster. It\u2019s about recognizing which redlines actually matter.<\/p>\n

Judgment Is Becoming The Premium Skill<\/strong><\/p>\n

One of my favorite moments came when we discussed limitation of liability provisions. AI can apply your preferred position every time. That isn\u2019t difficult.<\/p>\n

The difficult part begins when the other side pushes back.<\/p>\n

Now someone has to decide whether the deal should move forward anyway. Someone has to weigh the strategic value of the customer, the likelihood of the risk, the commercial implications, and the alternatives available. That\u2019s not a drafting exercise. That\u2019s judgment.<\/p>\n

Cherryn offered a practical framework that I suspect many experienced commercial lawyers already use instinctively. She said she distinguishes between what is merely possible and what is actually probable. \u201cIf it\u2019s possible but not probable, then it\u2019s something that I will most likely let go. If it\u2019s something that\u2019s actually a real possibility, then it\u2019s something that I\u2019m going to take more seriously.\u201d<\/p>\n

That\u2019s exactly the type of thinking AI cannot automate. It requires context, experience, and understanding of how the business actually operates.<\/p>\n

Better Systems Create Better Lawyers<\/strong><\/p>\n

One part of our conversation that particularly resonated with me wasn\u2019t about AI at all. It was about systems.<\/p>\n

Cherryn shared an example of creating a simple contract primer explaining how LegalSifter\u2019s product works, how customer data flows through the platform, and who owns which intellectual property. The goal wasn\u2019t to write better contract language. The goal was to eliminate unnecessary negotiations before they even started.<\/p>\n

That idea reflects a broader shift happening across legal departments. Increasingly, the competitive advantage won\u2019t come from having smarter lawyers. It will come from building smarter legal systems.<\/p>\n

Playbooks. Standard positions. Better communication. AI-assisted review. Internal education. Benchmarking. Operational discipline.<\/p>\n

Individually, none of those ideas are revolutionary. Together, they transform how legal supports the business.<\/p>\n

AI Doesn\u2019t Replace Lawyers. It Changes What Makes Them Valuable.<\/strong><\/p>\n

The legal profession has always evolved alongside technology. Email replaced fax machines. Electronic signatures replaced overnight courier packages. Contract lifecycle management replaced shared drives. AI is another step in that progression, although a much bigger one.<\/p>\n

The lawyers who thrive won\u2019t be the ones who resist automation. They will be the ones who automate everything that should be automated so they can invest more of their energy where it creates the greatest value.<\/p>\n

Cherryn put it well when she encouraged lawyers not to fear AI. Instead, she urged them to \u201cimplement the small steps one step at a time\u201d so they can spend their time \u201cfocusing on the strategic outcomes of a deal \u2026 as opposed to simply focusing on the sentence structure of a particular clause.\u201d<\/p>\n

I couldn\u2019t agree more.<\/p>\n

The future of in-house legal won\u2019t be defined by who writes the best contracts. AI will continue narrowing that gap.<\/p>\n

It will be defined by who makes the best decisions.<\/p>\n

And that is work worth owning.<\/p>\n

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Olga V. Mack is the CEO of TermScout, where she builds legal systems that make contracts faster to understand, easier to operate, and more trustworthy in real business conditions. Her work focuses on how legal rules allocate power, manage risk, and shape decisions under uncertainty.<\/em><\/strong> A serial CEO and former General Counsel, Olga previously led a legal technology company through acquisition by LexisNexis. She teaches at Berkeley Law and is a Fellow at CodeX, the Stanford Center for Legal Informatics.<\/em><\/strong> She has authored several books on legal innovation and technology, delivered six TEDx talks, and her insights regularly appear in Forbes, Bloomberg Law, VentureBeat, TechCrunch, and Above the Law. Her work treats law as essential infrastructure, designed for how organizations actually operate.<\/em><\/strong><\/p>\n

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The post Cherryn-Paige Bissett Says AI Didn\u2019t Replace Lawyers. It Repriced Judgment.<\/a> appeared first on Above the Law<\/a>.<\/p>\n

\"\"
(Image via Getty)<\/figcaption><\/figure>\n

For the past two years, the legal industry has been obsessed with one question: Will AI replace lawyers?<\/p>\n

I think we\u2019re asking the wrong question.<\/p>\n

The better question is this: If AI takes over routine legal work, what becomes more valuable? That was the theme of my recent conversation with Cherryn-Paige Bissett, commercial counsel at LegalSifter, on \u201cNotes to My (Legal) Self.\u201d What emerged wasn\u2019t another discussion about prompts, copilots, or whether AI can draft a better indemnity clause. It was a conversation about judgment. More specifically, why judgment may become the most valuable skill an in-house lawyer can bring to the business.<\/p>\n