For years, legal departments hired for expertise. They still do, of course. But expertise is no longer the differentiator it once was.
Today, AI can summarize a contract in seconds. It can draft a clause, compare agreements, identify missing provisions, and even explain the legal issues buried inside a complex commercial agreement. Every month, those capabilities get better.
So if AI is becoming increasingly competent at legal analysis, what becomes more valuable?
Judgment.
That was the central theme of my recent conversation with Matthew Thomas, senior corporate counsel at Elastic. We set out to talk about mistakes, but somewhere along the way the conversation became much more interesting. We ended up talking about what good judgment actually looks like, how it develops, and why it may become the defining skill of the next generation of in-house lawyers.
Matthew said something that every experienced lawyer immediately recognizes as true.
“Good judgment really does come from experience.”
That sounds almost cliché until you hear how he explains it.
“We learn the technical aspects in school,” he said. “But day-to-day practice looks very different. Experience teaches you which things are and are not the most important to worry about.”
That distinction matters more today than ever.
AI Can Analyze. Lawyers Still Decide.
When lawyers first leave law school, almost everything feels equally important. Every clause deserves attention. Every risk deserves escalation. Every issue feels capable of bringing down the company.
Experience changes that.
Matthew described how younger lawyers often approach every contract with the same intensity until they begin recognizing something more important than legal doctrine: proportionality.
“You think everything is critically important or the world’s going to explode,” he said. “After a while, you realize very seldom are you dealing with things where lives are on the line or the entire company is going to implode.”
That observation struck me because it captures something AI still struggles to do well.
AI is excellent at identifying issues. It is much less capable of deciding which issues deserve attention, which ones deserve negotiation, and which ones deserve letting go. Those decisions depend on business context, relationships, priorities, and experience. They depend on judgment.
As in-house lawyers, that is increasingly where our value lives.
The Best Lawyers Don’t Fight Every Battle
One part of our conversation made me laugh because it was painfully familiar.
Matthew talked about mentoring younger lawyers who would return from reviewing a contract with pages of comments, only to hear their manager say, “This is great. We need about 10% of this.”
Every legal department has lived some version of that conversation.
Good judgment isn’t finding more issues. Good judgment is recognizing which issues actually matter.
Matthew offered a practical example that every commercial lawyer has encountered. If the governing law ends up being Illinois instead of New York, is that really the hill worth dying on? Maybe sometimes. Most of the time, probably not.
He put it simply.
“I’m not killing a deal over that.”
That isn’t lowering standards. It’s understanding priorities.
The best in-house lawyers become trusted advisors because business leaders know they won’t create unnecessary friction. They know when to say no, but they also know when to say yes.
Relationships Outlast Contracts
Matthew shared an early-career mistake that had nothing to do with legal analysis.
He admitted being too aggressive with a vendor during negotiations. Then came an uncomfortable phone call from inside his own company after it turned out the other side had personal relationships with senior leadership.
His takeaway wasn’t simply to be nicer.
It was to remember that business operates through relationships.
“Anybody you’re talking to might know your general counsel, might know your CEO,” he said. “Be mindful of the fact that anyone you talk to might know someone that you care about.”
That’s increasingly true in today’s connected legal community.
People move between companies. Customers become vendors. Opposing counsel become future colleagues. LinkedIn makes the professional world feel surprisingly small.
Legal departments often spend enormous energy protecting contractual relationships while paying less attention to human relationships. The irony is that both affect outcomes.
Judgment Starts With Perspective
Another part of the conversation stayed with me long after we finished recording.
Last year, Matthew was diagnosed with leukemia. That experience fundamentally changed how he thinks about work, pressure, and risk.
He told me something I suspect many lawyers need to hear.
“We’re not saving lives.”
Coming from someone who spent significant time surrounded by medical professionals who actually were saving lives, those words carry unusual weight.
Matthew wasn’t minimizing legal work. He wasn’t suggesting contracts don’t matter or that companies shouldn’t care about risk.
He was reminding us to keep perspective.
“The worst mistake that I could possibly make in my company will cost money, but it won’t cost anybody their life.”
That perspective changes how you approach difficult negotiations. It changes how you recover from mistakes. It changes how you treat the people across the table.
It also makes it easier to remember that most disagreements are temporary. Most negotiations eventually finish. Most mistakes can be corrected.
Judgment Is Becoming The Competitive Advantage
Toward the end of our conversation, Matthew said something that perfectly summarized where the profession is heading.
“If it was just going by the absolute objective thing, AI would do it faster.”
Exactly.
The future of in-house law isn’t about competing with AI on speed. We will lose that race every time.
The future is about doing what technology still cannot reliably do. Understanding context. Knowing when a theoretical risk isn’t a practical risk. Balancing legal exposure against business opportunity. Reading the room before reading another clause. Helping people move forward instead of simply identifying everything that could go wrong.
Those are not technical skills. They are judgment skills.
Ironically, the better AI becomes, the more valuable those skills become.
Matthew opened our conversation by joking that good judgment comes from questionable judgment. There is more truth in that joke than many of us would like to admit.
Every experienced in-house lawyer has a story they wish they could rewrite. Every one of us has sent the email we shouldn’t have sent, negotiated too hard, missed something important, or worried far too much about something that ultimately didn’t matter.
The difference isn’t avoiding mistakes.
The difference is learning which lessons are worth carrying into the next decision.
That’s what builds judgment. And for the foreseeable future, it’s still something only humans can do.
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 Matthew Thomas Is Right: Good Legal Judgment Can’t Be Automated appeared first on Above the Law.