For the past two years, the legal industry has been obsessed with one question: Will AI replace lawyers?
I think we’re asking the wrong question.
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 “Notes to My (Legal) Self.” What emerged wasn’t 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.
Cherryn has a simple phrase that captures the shift: “Automate the 80%, own the 20%.” At first, it sounds like another catchy AI slogan. The longer we talked, the more I realized it’s actually a blueprint for the future of in-house legal.
AI Isn’t The Decision Maker
Legal teams often describe AI as a way to work faster. That’s true, but speed alone isn’t the destination. Speed only matters if it creates space for better decisions.
As Cherryn explained, “There is a large portion that the AI can just blanketly apply our positions to. What it can’t do is … 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.” That distinction is easy to overlook, yet it changes everything.
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’s the ability to decide what actually matters.
The Future Belongs To Lawyers Who Understand The Business
One idea kept surfacing throughout our conversation. Great commercial lawyers don’t begin with the contract. They begin with the business.
Cherryn repeatedly returned to balancing legal, operational, and commercial considerations. Those aren’t separate conversations. They’re 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’s risk tolerance.
As she put it, “You have to understand what your business needs are and what your business risk appetite is.” 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.
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.
Stop Negotiating Noise
One phrase from Cherryn deserves to enter every legal department’s vocabulary: “contract noise.”
She described how AI can remove the repetitive work by identifying what deserves attention instead of encouraging lawyers to rewrite every sentence. “It cuts through the contract noise,” she said. “It identifies the areas that you actually need to focus on.”
That observation struck me because I see a similar pattern through TermScout’s benchmarking work. Contracts often accumulate rounds of revisions that create activity without meaningfully changing business outcomes. Lawyers negotiate wording because it’s there to negotiate, not because it materially changes the allocation of risk.
We’ve 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.
The future isn’t about redlining faster. It’s about recognizing which redlines actually matter.
Judgment Is Becoming The Premium Skill
One of my favorite moments came when we discussed limitation of liability provisions. AI can apply your preferred position every time. That isn’t difficult.
The difficult part begins when the other side pushes back.
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’s not a drafting exercise. That’s judgment.
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. “If it’s possible but not probable, then it’s something that I will most likely let go. If it’s something that’s actually a real possibility, then it’s something that I’m going to take more seriously.”
That’s exactly the type of thinking AI cannot automate. It requires context, experience, and understanding of how the business actually operates.
Better Systems Create Better Lawyers
One part of our conversation that particularly resonated with me wasn’t about AI at all. It was about systems.
Cherryn shared an example of creating a simple contract primer explaining how LegalSifter’s product works, how customer data flows through the platform, and who owns which intellectual property. The goal wasn’t to write better contract language. The goal was to eliminate unnecessary negotiations before they even started.
That idea reflects a broader shift happening across legal departments. Increasingly, the competitive advantage won’t come from having smarter lawyers. It will come from building smarter legal systems.
Playbooks. Standard positions. Better communication. AI-assisted review. Internal education. Benchmarking. Operational discipline.
Individually, none of those ideas are revolutionary. Together, they transform how legal supports the business.
AI Doesn’t Replace Lawyers. It Changes What Makes Them Valuable.
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.
The lawyers who thrive won’t 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.
Cherryn put it well when she encouraged lawyers not to fear AI. Instead, she urged them to “implement the small steps one step at a time” so they can spend their time “focusing on the strategic outcomes of a deal … as opposed to simply focusing on the sentence structure of a particular clause.”
I couldn’t agree more.
The future of in-house legal won’t be defined by who writes the best contracts. AI will continue narrowing that gap.
It will be defined by who makes the best decisions.
And that is work worth owning.
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. 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. 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.
The post Cherryn-Paige Bissett Says AI Didn’t Replace Lawyers. It Repriced Judgment. appeared first on Above the Law.
For the past two years, the legal industry has been obsessed with one question: Will AI replace lawyers?
I think we’re asking the wrong question.
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 “Notes to My (Legal) Self.” What emerged wasn’t 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.
Cherryn has a simple phrase that captures the shift: “Automate the 80%, own the 20%.” At first, it sounds like another catchy AI slogan. The longer we talked, the more I realized it’s actually a blueprint for the future of in-house legal.
AI Isn’t The Decision Maker
Legal teams often describe AI as a way to work faster. That’s true, but speed alone isn’t the destination. Speed only matters if it creates space for better decisions.
As Cherryn explained, “There is a large portion that the AI can just blanketly apply our positions to. What it can’t do is … 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.” That distinction is easy to overlook, yet it changes everything.
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’s the ability to decide what actually matters.
The Future Belongs To Lawyers Who Understand The Business
One idea kept surfacing throughout our conversation. Great commercial lawyers don’t begin with the contract. They begin with the business.
Cherryn repeatedly returned to balancing legal, operational, and commercial considerations. Those aren’t separate conversations. They’re 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’s risk tolerance.
As she put it, “You have to understand what your business needs are and what your business risk appetite is.” 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.
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.
Stop Negotiating Noise
One phrase from Cherryn deserves to enter every legal department’s vocabulary: “contract noise.”
She described how AI can remove the repetitive work by identifying what deserves attention instead of encouraging lawyers to rewrite every sentence. “It cuts through the contract noise,” she said. “It identifies the areas that you actually need to focus on.”
That observation struck me because I see a similar pattern through TermScout’s benchmarking work. Contracts often accumulate rounds of revisions that create activity without meaningfully changing business outcomes. Lawyers negotiate wording because it’s there to negotiate, not because it materially changes the allocation of risk.
We’ve 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.
The future isn’t about redlining faster. It’s about recognizing which redlines actually matter.
Judgment Is Becoming The Premium Skill
One of my favorite moments came when we discussed limitation of liability provisions. AI can apply your preferred position every time. That isn’t difficult.
The difficult part begins when the other side pushes back.
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’s not a drafting exercise. That’s judgment.
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. “If it’s possible but not probable, then it’s something that I will most likely let go. If it’s something that’s actually a real possibility, then it’s something that I’m going to take more seriously.”
That’s exactly the type of thinking AI cannot automate. It requires context, experience, and understanding of how the business actually operates.
Better Systems Create Better Lawyers
One part of our conversation that particularly resonated with me wasn’t about AI at all. It was about systems.
Cherryn shared an example of creating a simple contract primer explaining how LegalSifter’s product works, how customer data flows through the platform, and who owns which intellectual property. The goal wasn’t to write better contract language. The goal was to eliminate unnecessary negotiations before they even started.
That idea reflects a broader shift happening across legal departments. Increasingly, the competitive advantage won’t come from having smarter lawyers. It will come from building smarter legal systems.
Playbooks. Standard positions. Better communication. AI-assisted review. Internal education. Benchmarking. Operational discipline.
Individually, none of those ideas are revolutionary. Together, they transform how legal supports the business.
AI Doesn’t Replace Lawyers. It Changes What Makes Them Valuable.
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.
The lawyers who thrive won’t 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.
Cherryn put it well when she encouraged lawyers not to fear AI. Instead, she urged them to “implement the small steps one step at a time” so they can spend their time “focusing on the strategic outcomes of a deal … as opposed to simply focusing on the sentence structure of a particular clause.”
I couldn’t agree more.
The future of in-house legal won’t be defined by who writes the best contracts. AI will continue narrowing that gap.
It will be defined by who makes the best decisions.
And that is work worth owning.
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. 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. 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.
