Pioneers and Pathfinders

Looking back over the past two years of guests, we see a diversity of backgrounds and perspectives: different generations, different paths, and different areas of focus—legal ops, legal tech, law education, working in the A2J space, and attorney well-being, among others. We've covered a lot of ground. Obviously, we cannot recap everything we have discussed, but as we think about change in the profession, certain themes seem to emerge from the conversations. For these purposes though, let's focus on the corporate legal landscape. The thesis of today’s episode is simple: That landscape has become more complex over the past few years—complexity only fueled by the pandemic. We tend to extol the virtues of simplicity, and rightly so, but complexity has its own virtue, opening both organizational and individual opportunities. Managing complexity is its own challenge, but in speaking with our pathfinders, we find certain markers of success.

To celebrate the two-year anniversary of Pioneers and Pathfinders, we welcome a very special guest—Professor Richard Susskind OBE. For those who have been engaged in the discussions around legal tech for the past few decades, Richard needs no introduction. He is one of the most advanced thinkers on the impact of technology on the profession, and has been challenging our notions about what it will mean to be a lawyer for a long time. Richard is an adviser, speaker, and author who was focused on legal tech and the future of the profession long before these subjects were top of mind in the industry. In the 1980s, he wrote his doctorate at Oxford University on artificial intelligence, and today, his main area of expertise continues to be the impact of AI and other technologies on the legal profession. Among other roles, Richard is President of the Society for Computers and Law, and Technology Adviser to the Lord Chief Justice of England and Wales. He is also an adviser to leading professional firms, in-house legal departments, and governments and judiciaries around the world. He is a frequent speaker at conferences, seminars, retreats, and other events, having been invited to lecture in more than 60 countries. Richard has written 10 books and has contributed more than 150 articles to The Times of London. His most recent publication is the third edition of Tomorrow’s Lawyers, which guides legal professionals through the imminent future of law, and calls upon the next generation of lawyers to embrace technology in order to improve current legal and court services. In our conversation, Richard discusses the ways we should all be thinking about legal innovation, the challenges of training lawyers for the future, and the qualifications of those likely to develop breakthrough technologies in law, as well as his own journey and how he became interested in AI as an undergraduate student.

Our guest today is a true legal tech expert—Dennis Kennedy, director of the Center for Law, Technology and Innovation at Michigan State University College of Law. Dennis first saw the potential that technology had for advancing the legal industry when he started using computer tools in his estate and tax practice. He went on to work in house at MasterCard, where he focused on information technology and supported the company’s mobile wallet, API, and Labs business groups. For more than 20 years, Dennis has been an advisor and consultant on innovation, legal technology, and productization. Since 2015, he has been a law professor, helping his students explore nontraditional career paths in legal tech. Additionally, Dennis has written hundreds of articles on topics such as legal technology, innovation, and law practice management, as well as co-authored four books. He is also a frequent speaker and has co-hosted The Kennedy-Mighell Report podcast with attorney Tom Mighell for over a decade. Today, Dennis talks to us about his journey from an estate and tax practice to legal tech, being one of the first attorneys with a professional website, how he creates a sense of value around technology in law school, and his thoughts on recent advancements in artificial intelligence.

Today we speak with John Alber—retired lawyer, businessperson, and legal futurist. Like many of our guests, John’s career path has taken some fascinating turns. He was a partner at Bryan Cave LLP when he was given the opportunity to buy a company, which ultimately became Alber Leland, Inc., a database and software publisher in the transportation sector. John would later return to Bryan Cave as Strategic Innovation Partner—one of the first in the industry—applying his business skills and experience to find innovative ways for the firm to deliver legal services through new technology. Over time, he developed what we now might consider one of the first captive ALSPs. Additionally, John was a futurist for the International Legal Technology Association, where he served as a consultant on different programs and helped the organization focus on business strategies. Today, John dedicates himself to conservation in Florida, particularly the Apalachicola River, which has been called America's most endangered wild river. In our conversation, John tells us about his experience innovating at Bryan Cave, the ways he convinced lawyers to adopt technology, the advice he would give to legal professionals on tech and innovation, and his recent conservation efforts.

As the current discussion around the hot topic of ChatGPT evidences, legal technology is constantly evolving and developing. This results in a level of complexity and confusion for both legal organizations and tech companies as they try to stay competitive. One of the people helping them navigate these waters is Zach Abramowitz, founder of Killer Whale Strategies. A former M&A attorney, Zach founded the company in 2019, with the goals of facilitating connections between law firms and tech companies, and assisting with their strategic decisions and investments. Zach’s interest in legal tech goes beyond his work at Killer Whale Strategies. He is an advisory board member at LegalMation, and he frequently blogs about the impact of technology on the legal industry. In our conversation, Zach talks about maintaining professional relationships through virtual meetings, what he looks for in clients and investment opportunities, and his thoughts on the potential impact of generative AI on the legal industry.

Today’s guest is Paula Davis, founder and CEO of the Stress & Resilience Institute, which helps legal professionals and teams manage stress and avoid burnout. Paula entered the legal profession as a real estate attorney, but facing burnout herself, she ultimately left her practice to pursue a master’s degree in Applied Positive Psychology at the University of Pennsylvania. There she began working in a program for the US Army, helping teach senior NCOs, officers, and other Army leaders and their families techniques to build resiliency. In 2013, she founded the Stress & Resilience Institute, where she has taught thousands of legal professionals and legal leaders tools associated with building individual, team, and organizational resilience by drawing on scientific studies and data. Additionally, Paula is a writer on topics such as stress management, burnout prevention, and hybrid teaming, frequently appearing in publications around the globe. She has also authored and co-authored a number of books and e-books. In today’s discussion, Paula tells us about being a self-described “recovering perfectionist,” how she defines resilience and burnout, and how legal organizations can maintain a sense of belonging in hybrid working environments, which both helps to build resilience and prevent burnout in law. In light of the growing complexity of the legal industry—and the stress associated with it, this is a timely and informative conversation.

Today we are joined by David Cunningham, chief innovation officer at Reed Smith and founder of Legal Metrics. David began driving change in the legal industry many years ago—first working with legal professionals as a tech strategy consultant for law firms, drawing on his business background to help clients improve their practices. David went on to become chief information officer at Winston & Strawn, where he created the firm’s strategies and oversaw its innovation efforts. He also founded Legal Metrics, a company that helps legal departments and law firms calculate and benchmark legal operations metrics to ensure excellence in diversity, as well as other business metrics important to legal departments. Today, David is chief innovation officer at Reed Smith, the first person to ever hold this position at the firm. There he has led initiatives such as the Innovation Lab, a program that identifies new ways of delivering legal services—and helps attorneys adopt those practices. In our discussion, David tells us about the lessons he learned as a consultant and how he applies them to his current position, the value of hiring an anthropologist at a law firm, and what excites him about the future of legal tech.

Today's episode takes a break from our usual format. Last week, Steve Poor participated in a webinar hosted by the Association of Corporate Counsel (ACC) Law Department Management Network (LDMN) about the implications of ChatGPT with Khurram Gore of Verizon, and Amy Yeung of Sallie Mae. Khurram has a deep background in technology and innovation, focusing on the intersection of law, technology, and business. At Verizon, he leads legal for their chief product development officer and the technology development organization, including Verizon’s 5G Labs, innovation partnerships, augmented reality and virtual reality business, and emerging tech groups. In addition to other outside activities, Khurram is also the entrepreneur in residence at the Stevens Venture Center for the Stevens Institute of Technology. Amy, who moderated the conversation, is a technology executive and thought leader with extensive experience in disruptive technology, digital innovation, and other strategic initiatives across all company life cycles. She has a track record of success in transformation, technology products counseling and B2B and B2C settings, leading significant operational initiatives strategy, data governance, and data architecture, among other things. In this conversation, we focus on the basics of ChatGPT and its potential impact on the legal industry, as well as the shortcomings of the program. The speakers’ insights give a valuable perspective on the implications of generative AI broadly, as well as ChatGPT in particular. We have edited the conversation for clarity.

Today we speak with Alma Asay, senior director of Practice Innovation and Client Value at Crowell & Moring. Alma’s interest in innovation began while she was a litigator at Gibson, Dunn & Crutcher, using technology to improve efficiency for the firm’s clients. Without any experience in the technology industry or as an entrepreneur, she founded Allegory, a cloud-based litigation management platform that delivers services and insights across the entire litigation spectrum. The story of her journey with Allegory is a fascinating one of challenges, successes, and enormous perseverance. In 2017, Integreon bought the company, making Alma the first female founder to have a legal technology business acquired. At Crowell & Moring, Alma has built the firm’s innovation department, where she and her team address technology and legal operations needs. In today’s discussion, Alma talks to us about the lessons she learned in starting a company, the advice she shares with women entrepreneurs, and the impact her traveling experiences have had on her professional life.

Today we are joined by Catherine Alman MacDonagh, a lawyer, entrepreneur, and CEO and founder of the Legal Lean Sigma Institute. Catherine started her legal career as director of corporate marketing for Counsel Connect, a first-of-its-kind social network platform for attorneys. After several roles in marketing and business development at law firms, she founded the Legal Sales and Service Organization, where she developed the Legal Lean Sigma Institute. The Institute was formed out of Catherine’s interest in “harnessing the power of teams.” She believes that change management can help address matters such as DEI, the war for talent, and improving employee and client experiences. Catherine has also founded the Coalition of Professional Services Providers and co-founded Legal Sustainability and Social Impact. Additionally, she is the chief enthusiasm officer and co-founder of The Legal Mocktail, a program that teaches legal professionals the skills of networking through fun simulation exercises. In our discussion, Catherine tells us about how she was introduced to Lean and Six Sigma, how she confronts attorney skepticism toward change management, and what being a chief enthusiasm officer means to her.