Over the years, I’ve noticed something interesting.
The compliance conversations that drag on for weeks rarely end because lawyers finally found the right legal argument.
They end because someone finally explained the problem in a way the business understood.
I learned that lesson early in my career. I remember walking into a meeting convinced I had the stronger legal position. I had the statutes, the cases, the policy, and all the reasons why we couldn’t move forward. Then someone asked a simple question: “What actually happens to our customer if we do this?”
The entire conversation changed.
We weren’t debating the law anymore. We were debating the outcome.
I’ve thought about that moment many times over the years because it captures what I believe is one of the biggest shifts happening inside legal departments. The modern in-house lawyer isn’t valuable because they know more law than everyone else. They’re valuable because they can translate between legal requirements, business objectives, technology, and human behavior.
That idea came up repeatedly during my recent conversation with Angela Madathil, corporate counsel at Werner Enterprises.
We started by talking about compliance, AI, and technology.
We ended up talking about something much more important: the future of the in-house lawyer.
Angela never described herself as a compliance enforcer.
She described herself as someone who helps people find common ground.
That distinction matters.
Legal Advice Isn’t Enough If Nobody Understands Why It Matters
One of the things I appreciated most about Angela’s perspective is how practical it is.
When I asked how she approaches compliance, she didn’t begin with regulations or legal frameworks.
She began with people.
“I think it’s really helpful to understand how AI is going to impact the end user.”
That sounds obvious.
It isn’t.
Many compliance discussions happen entirely inside conference rooms. The people making decisions often never meet the people who will actually live with those decisions.
Angela has made that part of her job.
Working for one of the country’s largest transportation companies, she intentionally builds relationships with truck drivers who use the technology she helps govern. She follows them on LinkedIn. She asks about their day-to-day experiences. She listens to what’s frustrating and what’s working.
“I think when you have that opportunity to engage with people and become friends, that’s when we provide the most value.”
That’s a remarkable observation.
Notice what she didn’t say.
She didn’t say lawyers create value by citing another regulation.
She said lawyers create value by understanding people.
I think she’s right.
Stories Move People In Ways Legal Arguments Often Can’t
One example from our conversation has stayed with me.
Like many companies, Werner is introducing more AI into its operations. One discussion centered on AI voice interactions.
Should users immediately be told they’re speaking with AI?
Legally, there are evolving disclosure requirements.
Operationally, there are questions about efficiency, adoption, and customer experience.
Angela didn’t frame the discussion around legal risk.
She framed it around the driver’s experience.
She explained that many drivers spend long hours alone on the road. Imagine believing you’re talking with another person, only to discover halfway through the conversation that it was AI.
“They’ll feel even more apart and not supported.”
That sentence probably changed more minds than another memo ever could.
It transformed compliance from an abstract legal requirement into a human experience.
Stories do that.
They help people see consequences instead of obligations.
That’s often the difference between resistance and alignment.
Great Compliance Scales Because Trust Scales
One of the biggest misconceptions about compliance is that every meaningful decision has to flow through legal.
That model doesn’t work anymore.
It certainly won’t work in an AI-powered organization where hundreds or thousands of small decisions happen every day.
Angela described a very different approach.
Her goal isn’t to approve every decision.
It’s to help the business develop principles it can confidently apply without her.
“I think it’s really great when you can kind of work on these guidelines and then the business kind of handles it. They don’t have to come over to me to sign off on every decision.”
That’s exactly where I think the profession is headed.
The best legal departments won’t measure success by how many decisions legal made.
They’ll measure success by how many good decisions the business made without needing legal in the room.
That’s what legal maturity looks like.
Product Lawyers Need Empathy As Much As Legal Expertise
Angela’s career has gradually expanded from commercial contracts into technology, privacy, AI, compliance, and product counseling.
That mirrors what’s happening across the profession.
Today’s in-house lawyers influence products long before customers ever see them.
That requires more than legal knowledge.
It requires curiosity.
It requires empathy.
It requires understanding how technology actually affects the people using it.
When I asked Angela what qualities matter most in leaders today, she didn’t mention technical expertise first.
“I think the ability to listen, to understand people’s challenges, having compassion for the pain points that they’re dealing with all the time.”
That’s product thinking.
It’s also good lawyering.
The lawyers who create the most value aren’t always the ones who know the most law.
They’re often the ones who understand people the best.
Translation May Become Legal’s Most Valuable Skill
AI is changing how legal work gets done.
Research is faster.
Drafting is faster.
Negotiations are becoming more informed.
Information itself is becoming abundant.
That doesn’t make lawyers less valuable.
It changes where our value lives.
The scarce resource is no longer information.
It’s judgment.
It’s context.
It’s helping organizations understand not only what the law requires, but why a particular path makes sense for the business, the customer, and the people using the product.
Near the end of our conversation, Angela summarized it better than I could.
“The laws are what they are, but coming to people with that lens of how it’s affecting their business and the people that use their products really helps give them the perspective they need to make the best decisions.”
I think that’s exactly right.
The future of in-house law isn’t about becoming better at saying no.
It isn’t about becoming faster at saying yes.
It’s about becoming better translators.
The best in-house lawyers don’t simply explain the law.
They explain the people behind the law.
And in a profession increasingly shaped by AI, that may become our most valuable skill.
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.