One of the biggest surprises of my in-house career is realizing how rarely people want “a legal answer.”
At least not in the way lawyers are trained to think about it.
Early in my career, I believe the best lawyers are those who can analyze the issue with the greatest precision, identify the hidden risk most quickly, or explain the doctrine with the greatest confidence. People who always seem intellectually closed off. People who walk into a room and immediately notice what everyone else is missing.
Law school rewards this instinct.
Law firms also reward him.
And to be clear, accuracy matters. A lot.
But over time, especially internally, I start to notice something uncomfortable. Many of the times when legal creates the most value have very little to do with providing a perfect legal explanation.
The company is usually trying to answer an entirely different question.
Not: “What does the law say?
But: “What should we do?
This distinction seems small until you sit in enough rooms where tough decisions are made.
Nobody really wants a conference
I still remember being in a product review meeting where every path forward carries some level of uncertainty.
Engineering wants to move quickly. Marketing has already started preparing the launch materials. Sales must manage customer expectations. Leadership wants momentum.
And the legal side has concerns.
No catastrophic worries. No obvious violations. This isn’t the kind of problem where everyone immediately agrees that the answer is “absolutely not.”
The problem is ambiguity.
The law is not perfectly clear.
The regulatory environment is evolving.
The reputational consequences are difficult to predict.
Operational compromises matter as much as the legal analysis itself.
And I suddenly realize that no one in the room really needs me to give an impeccable legal course.
What they need is help in making a decision.
Should we move forward?
Should we slow down?
Should we narrow the scope?
Should we add safeguards?
Should we accept the risk?
This is the real work.
Not just identifying problems.
Helping the business overcome uncertainty.
And honestly, I don’t think the profession historically trains lawyers particularly well for this role.
AI is quietly changing the values of the profession
This distinction is much more important today as AI is rapidly changing the legal work environment.
For years, legal expertise has depended heavily on access to information. Research takes time. Finding a precedent takes time. Comparing contracts takes time. Producing an analysis takes time.
AI compresses a lot of that.
Today, AI generates analyses, summarizes regulations, compares documents, identifies clauses, surfaces risks and writes language in seconds.
Some of them are truly impressive.
Some of them are mediocre.
Some of them are certainly false.
But whatever the quality, one thing is becoming increasingly clear:
The answers themselves become abundant.
And when the answers become abundant, the profession begins to shift its value elsewhere.
More and more, I think that “elsewhere” is a judgment.
Accuracy is entered.
Judgment is deciding what to do.
This distinction is quietly becoming one of the most important framing shifts in my own thinking about the future of legal work.
Because judgment isn’t really about memorizing doctrine.
It’s about prioritizing.
Compromises.
Timing.
Consequences.
Context.
It’s about understanding which risks are most important, which risks are acceptable, and which path forward fits with the company’s broader goals.
Two lawyers can examine the same legal question and recommend completely different approaches. The difference is often not legal knowledge.
It’s a judgment.
The strange way lawyers learn to judge
What fascinates me is how most lawyers develop this skill informally.
Historically, judgment is absorbed rather than explicitly taught.
You learn by watching seasoned lawyers handle difficult situations. You learn by participating in tense meetings. We learn by making mistakes. You learn by living the consequences.
Some people grow quickly because they benefit from amazing mentors and exposure early in their careers.
Others don’t.
A surprising amount depends on environment, access, and luck.
This learning model works reasonably well when the legal knowledge itself is difficult to scale.
But AI changes this equation.
Because many of the tasks historically performed by young lawyers are not just productive work. These are also development works. This repetition helps people develop their instincts slowly over time.
And if professionals outsource too much reasoning too soon, there is a real danger that they will stop developing their judgment altogether.
I already see signs of it.
People accept exits too quickly.
People fail to question assumptions.
People stop at the first plausible answer instead of exploring alternatives.
The risk is not just in poor legal outcomes.
The deepest risk is intellectual passivity.
The part about AI that really fascinates me
At the same time, I think there is another possible outcome here that receives much less attention.
AI could actually help accelerate the development of judgment.
This possibility interests me far more than the endless debate over whether AI will replace lawyers.
Because if used thoughtfully, AI can expose reasoning in ways that are historically difficult to scale.
He can create simulations.
This may bring up competing considerations.
This can force prioritization.
This may expose second-order consequences.
It can create comparison loops between scenarios.
More importantly, it can make invisible reasoning more visible.
This is important because experienced professionals often have difficulty explaining how they arrive at a conclusion. After enough years, judgment begins to become instinctive.
But instinct is usually a compressed experience.
Once you start to unpack this experience, patterns emerge.
The same questions come up repeatedly under difficult decisions:
What matters most?
What are we optimizing for?
How much risk are we really willing to tolerate?
What happens if we are wrong?
What happens if we wait?
This is where the legal judgment really lies.
Not in abstract doctrine.
In decisions under duress.
What companies are starting to value more
I increasingly believe that the lawyers who thrive in the next decade will not necessarily be the fastest researchers or the most effective writers.
AI is increasingly handling this work.
The lawyers who will stand out are those who know how to navigate ambiguity without getting stuck. Those who know how to balance legal analysis with operational reality. Those who can translate uncertainty into action.
Because companies rarely pay lawyers just to identify problems.
They pay lawyers to help them make decisions.
And in an AI-driven world, this distinction becomes much more important.
If you are interested in learning how legal judgment can be developed more intentionally for product consulting, the Frankie Early Access the list is open.
Olga V. Mack is the CEO of TermScout, where she builds legal systems that make contracts faster to understand, easier to use, and more reliable in real-world business conditions. His work focuses on how legal rules distribute power, manage risk, and shape decisions in the face of uncertainty. A serial CEO and former general counsel, Olga previously led a legal technology company when it was acquired by LexisNexis. She teaches at Berkeley Law and is a member of CodeX, the Stanford Center for Legal Informatics. She is the author of several books on legal innovation and technology, has given six TEDx talks, and her insights appear regularly in Forbes, Bloomberg Law, VentureBeat, TechCrunch, and Above the Law. His work treats law as essential infrastructure, designed for the actual functioning of organizations.
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