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Interview: Dennis Kennedy: Bridging the Gap Between Law and Technology

Dennis Kennedy took a career test in high school that said his personality and skills were best suited for being a judge. Following this recommendation, he spent several years clerking for judges after graduating law school.

However, as the Internet age dawned, Kennedy discovered his real love - technology. In 1995, as a partner at his firm, Kennedy established his own web site on estate planning law, making him one of first lawyers to have a presence on the Web. In 1997, he wrote his first article on a computer technology topic – the first of what are now more than 300 written print and Web pieces on law and technology that have appeared locally, nationally and internationally.

Kennedy now operates his own consulting and law practice combining legal advice with law technology consulting. His website offers a wide selection of articles, products and upcoming events relating to law and technology, while his blog is widely read for its insights on legal technology trends.

Kennedy credits Pat Bush - a career coach and counselor - with having helped him decide what he really wanted to do and develop a strategy for doing it. Kennedy acknowledges that it is a very difficult step for any lawyer to leave a firm, but still advises that if you're so unhappy at what you're doing that, for example, it negatively affects your health, it’s time to leave and seek help from a coach or counselor in charting a new career path.

JD Bliss (JDB):  Since you got your J.D. degree 20 years ago, your career path has taken you from estates and trusts lawyer to “TechnoLawyer of the Year” with your own technology law and legal technology practices.  What was the starting point of your interest in the law?

Kennedy:  Although I never had a driving ambition to be a lawyer, I took a career test in high school that said my personality and skills were best suited for being a judge.  So I entered Georgetown Law School with the general idea of becoming a lawyer.  But it was at Georgetown that I had my first exposure to what became my real love, when I took and thoroughly enjoyed one of the first seminars in “Computers and the Law” offered anywhere in the country.  After graduation I clerked for several years with the judges of the Twenty-Second Judicial Circuit of Missouri in St. Louis, then in 1988 entered a trusts and estates practice at a St. Louis firm.  Even there I maintained my interest in technology, serving as a member of the firm’s Technology Committee and helping with the implementation of everything from document assembly systems to the firm’s use of the World Wide Web.  By the mid-1990s, when the Internet really began to take off, I realized that – and not tax law – was my true calling.

JDB:  The mid-90s really were the dawn of the Internet Age.  Did you have any sense of how big the on-line revolution was to become?

Kennedy:  I truly felt that the growth of the Internet was just as momentous as the invention of the printing press.  I had a feeling that this was a historic change, and I wanted to say in later years that I was a part of it.  In 1995, when I was a partner in my firm, I established my own web site on estate planning law, which made me one of the first lawyers to have a presence on the Web.  I began reading as much as I could, and talking with as many people as I could find, to increase my understanding of this new technology, and gained confidence in my ability to understand and apply it.  In 1996 I wrote my initial article on a computer technology topic – the first of what are now more than 300 written print and Web pieces that have appeared locally, nationally and internationally.  I gradually realized that people were treating me as an expert in this new area of law and technology, and I decided to focus on it. 

JDB:  It must have been a difficult decision to pursue this new path after practicing in a firm for 10 years.  Did you leave the practice of law entirely to pursue technology?

Kennedy:  I would emphasize that I’ve never left the practice of law. I'm proud that over the course of my legal career I've developed a good reputation for my work in two completely different practice areas.  After leaving my first firm I’ve maintained my AV Martindale-Hubble rating, practiced in the IP and Information Technology Department of another St. Louis firm, and taught classes in IP and E-Commerce law at Washington University School of Law. My familiarity with technology law helps me differentiate my current consulting practice, and my counsel to clients combines legal and technology expertise with a practical business focus.  So I’ve developed a niche as a technology lawyer who’s equally adept at understanding and applying the technology I deal with.

JDB:  How did you establish the technology consulting part of your practice?  Did you do it all at once in 1998, or has it been a gradual process?

Kennedy:  It has definitely been step-by-step process.  I thought about making a move for several years, especially after I got involved with the Bar Association of Metropolitan St. Louis's Internet Committee, which became a focal point for lawyers in St. Louis who were interested in technology. Lawyers who really "got" the implications of technology for the practice of law - Bob Babione, Art Smith, Alan Steinberg, John Davidson, Diane Camerlo, Christine Gilsinan, to name a few – gathered on a regular basis to share experiences and ideas. This group helped me make my decision and encouraged me when I left my firm in 1998 to found, LLC, a legal technology and Internet consulting firm. I also founded and began editing a monthly legal technology email newsletter, Legal Technology Strategies, to which Bob and other colleagues in the tech field contributed. 

The next step came in 1999 I joined NetTech, a legal technology firm founded by a consultant who I met when he made an unsuccessful bid to upgrade the technology at my old firm.  He and I had a radical idea:  that law firms would take advantage of the Y2K problem to upgrade their technology across the board and consider innovative approaches to technology. We, and others, misjudged the market, but I found that people increasingly thought of me as an Internet lawyer. I had the opportunity to join a St. Louis firm that was starting an Intellectual Property and Information Technology Department and stayed there for the next three years or so.  I continued to speak and write on technology topics and found an audience and a growing reputation in the field, Through my colleague, Chip Fendell, I also got the chance to teach a law school class at Washington University Law School. I reached a point where I wanted to diversify my work and split my time between a focused technology law practice, legal technology consulting and speaking and writing. I'd been working with a great career counselor named Pat Bush for several years and, with her help, I felt that I was ready to go out on my own.

JDB:  How important was that career counseling to you in starting the practice you have now?

Kennedy:  The counselor took me through a process of analysis that, in the end, confirmed for me that my idea of combining law and technology in a consulting practice of my own was a good one. It also helped me understand what I do best, what is important to me, and how vital it is to honor those things.  Career counseling also emphasized that establishing my own business wasn’t going to be easy.  I learned the “Rule of Three” about starting a new business:  no matter what you attempt, it’s going to be three times tougher, longer and more expensive than you expected in order for you to become successful.   Finally I learned that when you change fields – as I was in the process of doing for several years – you really have to create a distinct new impression in the minds of potential clients to define yourself as unique.  So I really emphasized writing and speaking on innovative, but practical technology applications in a wide range of forums, and got intensively involved in the TechShow and Webzine Boards of the ABA’s Law Practice Management Section.  My selection as “TechnoLawyer of the Year” by in 2001 was both a recognition of my efforts from my peers, and a confirmation that I was conveying the right message to the right people.

JDB:  Has your consulting practice, involving as it does the roles of both lawyer and technology advisor, evolved as you expected it to?

Kennedy:  I made the conscious decision at the start that my best focus was on practicing technology law.  I knew that the local clients were there and they already thought of me as one of the few information technology and Internet lawyers, I had the contacts to reach them, and I understood both their business and legal problems.  Many lawyers do not understand the underlying technologies or the business needs in the way that I think I do.

From the start my practice had three components:  legal practice, paid writing and speaking, and technology consulting.  For a while, the legal practice was the bulk of what I did.  The three elements have now come more into balance, and it has led me to develop the most satisfying aspect of what I do:  bridging the gap between people and technology and helping clients and others understand and make good decisions about the technology decisions they face. On the consulting side, I bring the point of view of a lawyer, which many technology consultants simply do not have, and in my law practice, I bring the point of view of someone who understands, uses and advocates the underlying technologies, something that most lawyers do not have.  There is a nice symmetry, I believe, to that approach.

JDB:  How would you define your role at bridging that gap – who are you working with, and what do you do to make technology more useful to them?

Kennedy:  I’m working with all parties in the law firm technology equation and corporate legal departments as well. My main area of interest lately has been something I call "client-driven technologies," ways clients and lawyers can work together to meet client needs through technology. I'm also trying to focus more Internet technologies, where my enthusiasm has remained consistent over the years. Don't get me started on RSS feeds or "web services" unless you have some time to spare.  For lawyers, who are often so crushed by the weight of billable hour expectations that they can’t find technology mentoring on non-billable time, my approach is simple.  I help partners and associates, solos and small firms, managing partners and technology partners all develop and apply technology strategies and tactics to their practice, and in the process expand and improve the quality of their legal careers. I truly enjoy getting the chance to work with lawyers who want to do innovative things, but I'll also help a firm figure out where it is wasting money on technology and make better use of its technology budget.

For technology experts, from CIOs to webmasters, I help them understand lawyer expectations and needs in the use of technology as it applies to the law.  Most technology people feel lawyers talk past them, and I take the time to help them see just what lawyers need from them.  To me, technology's best use is to connect people. Not too long ago an IT director of a law firm said to me after the question-and-answer session for one of my presentations, “This is the first conversation I’ve had with a lawyer that was helpful.”  Perhaps that was a bit of an exaggeration, but the process of diagnosing communications as well as technology problems so that lawyers and IT people work better together is one I really enjoy. My blog is a new example of the way you can use the Internet to connect with people from all over the world and create communities of interest.

JDB:  What suggestions would you make to other lawyers who lack similar satisfaction in what they do, but aren’t sure how to find it?

Kennedy:  Based on my own experience, I’m a strong advocate of seeking guidance from a knowledgeable third party – a career coach, or someone similar, perhaps even a group of trusted advisors – who can help you decide what you really want to do and develop a strategy for doing it.  I acknowledge that it is a very difficult step for any lawyer to leave a firm, but I've met too many unhappy lawyers who feel they are trapped and "can't leave" their firms. I've also learned that if you’re so unhappy at what you’re doing that it negatively affects your health, it’s time to leave. However, it's far better to recognize that you need to make a change before you see health or other consequences. When you decide to make a change, you have to ask for help.

Lawyers are used to helping people and not asking for help for themselves. It's a surprisingly difficult barrier. I had never  even would have considered using a career coach before making the decision to move away from trusts and estates law, and the work and people I really enjoyed. Making the first phone call was pretty difficult, but I knew that I wanted to do it right and not later look back with any second thoughts or regrets. I was fortunate to work with someone insightful and effective, who helped me look at what I wanted in a systematic and helpful way.  I learned that a person should move toward the next stage in their career, not away from the last one.  Lawyers, I believe, tend to think that they can’t do anything other than practice law.  A trained third party can help you move toward a new career goal by getting back to basics, deciding what you like, and creating a strategy to pursue it. I now recommend that everyone I meet considering a major career change seek out a career counselor or coach. If you made me choose one message I have for people, it would be to try to ask for help when you need it, especially when there are people trained to give you the help you need. Asking for help is not an easy thing to do, especially for me. But, I'm learning and if my example can help someone, I'll be quite pleased.

Dennis Kennedy can be reached at

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