

Reinventing Professionals
Ari Kaplan
The business of providing professional advice is changing. Today, anyone can go online and access a wealth of information about any topic, from legal and medical advice to financial planning and accounting suggestions. This blog is designed to offer ideas, guidance, and perspectives on how to effectively navigate a perpetually shifting professional landscape, with a unique focus on the legal industry and the technology that is driving its evolution.
Episodes
Mentioned books

Dec 23, 2025 • 24min
The 2025 Ari Kaplan Advisors Legal Tech GC/CLO Roundtable
In this insightful discussion, Beth Kallet-Neuman, General Counsel at Relativity, emphasizes the importance of product storytelling to highlight customer value. Marla Crawford from Cimplifi shares her experience with rapid onboarding in legal tech. Dennis Garcia, VP at Litera, talks about his role as a power user of internal products. John Patzakis, Chief Legal Officer at X1, highlights the unique challenges faced by legal tech companies regarding discovery standards, especially with the rise of AI and its impact on legal processes.

Dec 5, 2025 • 26min
*Special Episode* Featuring Caroline Hill, Editor-in-Chief of Legal IT Insider, on Charting Change in Legal Ep 50
In this 50th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the prospect of an AI bubble, innovation and client service, and proactively driving change.

Nov 20, 2025 • 13min
The Advantages of Using an AI Agent in Contract Review
Brian Powers, Co-founder and CEO of Markups.ai, develops AI agents for contract review. Debbie Epstein Henry, Founder of DEH Consulting, brings her legal innovation expertise to the discussion. They explore how AI can streamline contract processes, debunk common misconceptions about AI capabilities, and advise on startup differentiation through personalized services. Both emphasize the importance of legal professionals enhancing their skills, particularly in communication and strategic thinking, to thrive alongside AI advancements.

Nov 14, 2025 • 10min
How the Intersection of Design, Strategy, and Technology is Shaping the Future of Legal Practice
I spoke with Brandie Knox, the Principal & Creative Director of Knox Design Strategy, a consultancy that partners with law firms on branding, user experience, and user interface design. She is also the Founder & CEO of Moxx, a digital case notebook that helps litigators streamline case preparation and collaboration. We discussed best practices in legal to leverage design to stand out, and how the intersection of design, strategy, and technology is shaping the future of legal practice.

Nov 12, 2025 • 14min
How Legal Professionals Can Prevent Hallucinations and Build Trust in Legal AI
I spoke with Mark Doble, the Founder and CEO of Alexi, an AI-driven legal workflow platform. We discussed how legal professionals can prevent hallucinations and build trust in legal AI, the top privacy and compliance risks that law firms need to consider, and how generative AI will transform legal workflows.

Nov 7, 2025 • 32min
*Special Episode* Featuring Caroline Hill, Editor-in-Chief of Legal IT Insider, on Charting Change in Legal Ep 49
In this 49th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed Legal IT Insider’s 30th anniversary, the first Orange Rag, the potential for an AI bubble, and emerging AI leadership.

Nov 5, 2025 • 10min
Best Practices for Building a Strong Team of Lawyers and Legal Professionals to Enhance Law Firm Growth
I spoke with Howard Ankin, the Founder of Ankin Law, a personal injury and workers’ compensation law firm based in Chicago. We discussed the best practices for building a strong team of lawyers and legal professionals to enhance law firm growth, how technology can enhance client service, and how trial work will change in an AI-centric future.

Nov 3, 2025 • 7min
Mixtape: 2025 Knowledge Management & Innovation for Legal Conference
Thanks to these industry leaders for speaking with me for my 2025 Knowledge Management & Innovation for Legal (KM&I) conference mixtape:
Michelle Gleason, Regional Sales Manager at LexisNexis, Conan Hines, Director of Practice Innovation at Fried Frank, Kevin Klein, Co-Founder at Legal Tech Connect, Katya Linossi, Co-Founder and CEO at Atlas by ClearPeople, Kyle Poe, VP of Legal Innovation and Strategy at Legora Daniel Porus, Chief Commercial Officer at Legatics, Maureen Schlade, Director of Key Accounts at LexisNexis, Ryan Steadman, Global Commercial Leader at Epiq Law Advisory, and Ben Wightwick, Chief Commercial Officer at Autologix.

Oct 31, 2025 • 11min
Mixtape: 2025 Association of Corporate Counsel Annual Meeting
It was a privilege to interview these leaders for this mixtape from the 2025 Association of Corporate Counsel Annual Meeting:
Ashley Miller, General Counsel, Financial Services, North America, and Head of Legal Operations, Americas, Capgemini
Anthony Bégon, Vice President, Legal, Trellix
Daniel Bonner, Director of Client Solutions, Level Legal
Gabe Gross, Head of eDiscovery, DiliTrust
Janice Ryan, Partner, Venable
Jeni Turner, Director, Go-to-Market Strategy and Client Engagement, Corporate Legal, LexisNexis
Jim McGrew, Chief Client Services Officer, Ogletree Deakins
Joshua Maley, CEO and Co-Founder, Theorem Legal
Kyle Konz, Shareholder, Brooks Kushman
Mark Nastasi, Founder and CEO, CobbleStone Software
Michael Babitsky, Head of Strategy and Operations, Corporate Legal, LexisNexis
Monica Harris, Senior Product Manager, American Arbitration Association

Oct 29, 2025 • 12min
How KM and Legal Innovation are Shifting with the Emergence of Generative AI
I spoke with Oz Benamram, a leader in law firm knowledge management and innovation, and the Founder of SKILLS.law. We discussed the advisory services most in demand for law firms, how KM and legal innovation are shifting with the emergence of generative AI, the evolution of SKILLS.law, the likely impact of AI on legal, and the Michael Mills Memorial LegalTech Scholarship at Cornell Tech.


