Tell us a bit about yourself and how you came to be in (or a customer of) the legal business?

I didn’t have much of a choice.  My parents met as law students at NYU law school shortly after World War II.  My father attended on the GI bill and worked during the day.  My mother, one of less than a handful of women in her class, also worked full time and attended in the evenings.  Not surprisingly, two of their three children became lawyers.  The legal business appears to be somewhat genetic.

What do you do for a living right now?

I am the CEO of a legal technology company, Legal Outsourcing 2.0 (LO2).  We create and use technology to provide high-quality, lower cost solutions that address common needs in the legal service sector.

What has been your greatest triumph and your greatest success in the legal services field and what did you learn from each?

I have had some triumphs and successes, but those tend to just reinforce what I already knew or believed to be true. I have found that I have learned much more from my failures and the failures of those around me.  Success is fleeting.  Failure stings and stays with you.

Perhaps the most important lesson I learned from failure is one I continue to see duplicated in the legal outsourcing space by others who do not appear to have learned the lesson.  Law is about culture and history, not science or math.  Many in the legal outsourcing space do not appropriately account for that difference.  They structure their delivery model as if they were in the coding business.  It is a critical design flaw that creates repeated failure.

Do you think the legal industry is headed in the right direction, the wrong direction – or which direction?

I am not sure there is just one legal industry and I am not sure that it is headed anywhere in particular.  It seems to me that technology has enabled some sectors to modernize, in spite of many fighting the inevitable, but has made little inroad in others.

Who – or what – inspires you – and why?

I am a very competitive person. Later in life I learned to channel my competitive instincts to be competitive with myself and not as to others.  It tends to be healthier.  Success is not a zero-sum game.  I am satisfied if I am more effective and a better person today than I was yesterday.

What advice would you give to the younger generation contemplating law as a career?

I would ask them, are you sure?  Actually, I would down play the significance of the decision because the new generation will likely have several careers throughout their lifetimes. I would ask they why they thought they wanted to be lawyers and trouble-shoot their thinking with my experience. About half of the people who go to law school these days end up doing something other than the traditional practice of law. In some ways, law school is the new finishing school.

How ready for change do you think the legal industry is?

From an outsider’s perspective, it is ready for change.  From an insider’s perspective, it is not.  Lawyers don’t do change very well.

Is more – or different – leadership required? In what ways?

I don’t think it is necessarily a leadership issue.  It is a cultural one.  Most business problems are systems problems, not people problems.  Lawyers are trained to look backwards for answers.  They tend to be comfortable in a milieu of writing and history.  Technology tends to be about math and science.  Lawyers tend to find inspiration in leaders like Lincoln.  They should also learn to find it in leaders like Deming.

How deep do you think will be the inroads of technology in the industry?

No deeper than it is today. I remember when the technology big deal was the introduction of a Wang word processor to a law firm, back when I started practicing in 1980.  It was a big deal.  I can’t imagine writing an appellate brief before the word processor, but they managed to get by.  I expect 20 years from now there will be a few similar changes that lawyers will look back on and wonder how it was possible to practice law before the change.  While there will be some changes, increased use of AI for example, the essence of the practice of law will still be the same.

In ten years, do you see an industry much as it is – or do you see new players, new technology and an altered state?

I expect there will be a blurring around the edges a bit with what were once accounting firms providing cross-over services and continued development of AI tools which will essentially allow senior lawyers to leverage their craft using fewer junior lawyers.

What do you consider is the greatest challenge facing the industry?

The cost and availability of services to clients.  Most people cannot afford to hire a lawyer.  Probably the greatest innovation in the availability of services in the legal practice has nothing to do with technology.  It was the introduction of the contingency fee.

What do you see as the greatest opportunity for the sector looking forward?

AI enabled tools have the possibility to drive down the cost of lower level legal services, the type that most people need.  It will not replace lawyers, but it can make their services available to a wider swath of society

If a law firm was a startup pitching for investors, would you be an investor?

No.  Not if the business model was the current US law firm business model.