Every lawyer says they know their client.
I’m increasingly convinced that many of us don’t.
Not because we don’t care. Not because we aren’t paying attention. Because we rarely stop long enough to understand how clients actually experience legal.
That became the central theme of my recent conversation with Marco Imperiale, founder of Better Ipsum and author of “Practicing Legal Design.” We started by talking about legal design. We ended somewhere much more interesting: customer obsession.
Marco said something that stayed with me long after we finished recording.
“You think that, yeah, I really know my client. No, you don’t really know your client.”
It’s a simple statement. It’s also an uncomfortable one.
Most lawyers measure client relationships by responsiveness. We answer emails quickly. We negotiate hard. We know the business. We solve difficult problems.
None of those things necessarily mean we understand what it’s actually like to work with us.
When Was The Last Time You Simply Listened?
Marco posed a series of questions that every legal department should ask itself.
“When was the last time you structured your feedback? When was the last time you spoke with your marketing department and looked at the feedback? When was the last time you reflected with your client about the way this person receives the communication? When was the last time that you spent a listening dinner with your client without selling services, just listening?”
I love that phrase: a listening dinner.
No presentation.
No legal update.
No quarterly review.
No discussion about outside counsel budgets.
Just listening.
As lawyers, we’re trained to diagnose problems and provide answers. That’s our profession. We often enter conversations already thinking about the solution before we’ve fully understood the experience.
That’s a dangerous habit.
The best product companies don’t start by building features. They start by understanding users. Amazon, Netflix, Uber, and Apple invest enormous effort into understanding how customers experience their products before deciding what to build next.
Legal should be no different.
Legal Design Isn’t Really About Design
Many people hear “legal design” and immediately think colorful contracts, icons, or prettier documents.
Marco argues that’s missing the point.
“It’s a new way of conceiving the legal practice and the law as we know it.”
I think he’s right.
The visuals matter. Clear language matters. Better typography matters. They all improve comprehension.
But those are outputs.
The real work happens much earlier.
It begins with questioning assumptions.
Why are definitions always at the beginning of a contract?
Why can’t contracts include timelines?
Why can’t clauses contain examples?
Why can’t legal documents reflect how people actually consume information today?
Those questions aren’t really about design.
They’re about curiosity.
Lawyers Optimize. Designers Experiment.
One of my favorite moments came when Marco contrasted how lawyers and designers approach problems.
“Lawyers tend to spend too much time thinking and not enough time doing.”
His answer wasn’t to think less.
It was to prototype more.
“Legal design is a matter of testing and validating.”
That mindset feels increasingly important in the AI era.
Artificial intelligence can help us draft faster.
It can summarize documents.
It can rewrite clauses.
It cannot tell us whether we’re solving the right problem.
Too often we automate processes we never questioned in the first place.
Making a bad process faster doesn’t make it better.
The legal departments creating the most value over the next decade won’t simply adopt AI. They’ll rethink how legal work gets delivered before deciding where AI belongs.
Expertise Is No Longer Enough
Toward the end of our conversation, Marco made another observation that resonated with me.
For years we told lawyers to specialize more deeply.
Then AI arrived.
“The more you’re relying on your knowledge, the more you may be substituted. The more you’re relying on curiosity, the better is the outcome for you.”
I don’t interpret that as dismissing expertise.
Expertise remains essential.
But expertise without curiosity becomes brittle.
Curiosity keeps expertise alive.
The best in-house lawyers I’ve worked with aren’t the ones who always have the fastest answer.
They’re the ones asking better questions.
They want to understand why the business works the way it does. They ask how sales actually sells. They spend time with procurement. They shadow customer support. They join product meetings. They learn how finance thinks.
That’s what makes their legal advice valuable.
Not because they know more law.
Because they understand more context.
Humility Creates Better Lawyers
I asked Marco for one final takeaway to leave with the audience.
His answer surprised me.
“I think that lawyers lack humbleness. A little bit less ego.”
He wasn’t criticizing lawyers.
He was describing a leadership opportunity.
The best legal advisors don’t pretend they already know everything.
They admit when something can improve.
They invite criticism.
They ask clients how legal could become easier to work with.
They understand that vulnerability isn’t weakness. It’s how trust develops.
That idea aligns closely with something I’ve believed for years.
Legal exists to help the business succeed.
If our clients struggle to understand our contracts, our policies, or our advice, the answer isn’t to explain why they’re wrong.
The answer is to ask why our communication failed.
That’s a much harder question.
It’s also a much more valuable one.
The future of legal won’t be defined only by AI, automation, or faster drafting.
It will be defined by lawyers who understand the people they serve better than anyone else.
That future starts with a surprisingly simple skill.
Listening.
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 Marco Imperiale Is Right: Lawyers Don’t Know Their Clients Nearly As Well As They Think appeared first on Above the Law.
Every lawyer says they know their client.
I’m increasingly convinced that many of us don’t.
Not because we don’t care. Not because we aren’t paying attention. Because we rarely stop long enough to understand how clients actually experience legal.
That became the central theme of my recent conversation with Marco Imperiale, founder of Better Ipsum and author of “Practicing Legal Design.” We started by talking about legal design. We ended somewhere much more interesting: customer obsession.
Marco said something that stayed with me long after we finished recording.
“You think that, yeah, I really know my client. No, you don’t really know your client.”
It’s a simple statement. It’s also an uncomfortable one.
Most lawyers measure client relationships by responsiveness. We answer emails quickly. We negotiate hard. We know the business. We solve difficult problems.
None of those things necessarily mean we understand what it’s actually like to work with us.
When Was The Last Time You Simply Listened?
Marco posed a series of questions that every legal department should ask itself.
“When was the last time you structured your feedback? When was the last time you spoke with your marketing department and looked at the feedback? When was the last time you reflected with your client about the way this person receives the communication? When was the last time that you spent a listening dinner with your client without selling services, just listening?”
I love that phrase: a listening dinner.
No presentation.
No legal update.
No quarterly review.
No discussion about outside counsel budgets.
Just listening.
As lawyers, we’re trained to diagnose problems and provide answers. That’s our profession. We often enter conversations already thinking about the solution before we’ve fully understood the experience.
That’s a dangerous habit.
The best product companies don’t start by building features. They start by understanding users. Amazon, Netflix, Uber, and Apple invest enormous effort into understanding how customers experience their products before deciding what to build next.
Legal should be no different.
Legal Design Isn’t Really About Design
Many people hear “legal design” and immediately think colorful contracts, icons, or prettier documents.
Marco argues that’s missing the point.
“It’s a new way of conceiving the legal practice and the law as we know it.”
I think he’s right.
The visuals matter. Clear language matters. Better typography matters. They all improve comprehension.
But those are outputs.
The real work happens much earlier.
It begins with questioning assumptions.
Why are definitions always at the beginning of a contract?
Why can’t contracts include timelines?
Why can’t clauses contain examples?
Why can’t legal documents reflect how people actually consume information today?
Those questions aren’t really about design.
They’re about curiosity.
Lawyers Optimize. Designers Experiment.
One of my favorite moments came when Marco contrasted how lawyers and designers approach problems.
“Lawyers tend to spend too much time thinking and not enough time doing.”
His answer wasn’t to think less.
It was to prototype more.
“Legal design is a matter of testing and validating.”
That mindset feels increasingly important in the AI era.
Artificial intelligence can help us draft faster.
It can summarize documents.
It can rewrite clauses.
It cannot tell us whether we’re solving the right problem.
Too often we automate processes we never questioned in the first place.
Making a bad process faster doesn’t make it better.
The legal departments creating the most value over the next decade won’t simply adopt AI. They’ll rethink how legal work gets delivered before deciding where AI belongs.
Expertise Is No Longer Enough
Toward the end of our conversation, Marco made another observation that resonated with me.
For years we told lawyers to specialize more deeply.
Then AI arrived.
“The more you’re relying on your knowledge, the more you may be substituted. The more you’re relying on curiosity, the better is the outcome for you.”
I don’t interpret that as dismissing expertise.
Expertise remains essential.
But expertise without curiosity becomes brittle.
Curiosity keeps expertise alive.
The best in-house lawyers I’ve worked with aren’t the ones who always have the fastest answer.
They’re the ones asking better questions.
They want to understand why the business works the way it does. They ask how sales actually sells. They spend time with procurement. They shadow customer support. They join product meetings. They learn how finance thinks.
That’s what makes their legal advice valuable.
Not because they know more law.
Because they understand more context.
Humility Creates Better Lawyers
I asked Marco for one final takeaway to leave with the audience.
His answer surprised me.
“I think that lawyers lack humbleness. A little bit less ego.”
He wasn’t criticizing lawyers.
He was describing a leadership opportunity.
The best legal advisors don’t pretend they already know everything.
They admit when something can improve.
They invite criticism.
They ask clients how legal could become easier to work with.
They understand that vulnerability isn’t weakness. It’s how trust develops.
That idea aligns closely with something I’ve believed for years.
Legal exists to help the business succeed.
If our clients struggle to understand our contracts, our policies, or our advice, the answer isn’t to explain why they’re wrong.
The answer is to ask why our communication failed.
That’s a much harder question.
It’s also a much more valuable one.
The future of legal won’t be defined only by AI, automation, or faster drafting.
It will be defined by lawyers who understand the people they serve better than anyone else.
That future starts with a surprisingly simple skill.
Listening.
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.
