Reinventing Professionals

The 2025 Ari Kaplan Advisors Legal Tech GC/CLO Roundtable

I was honored to interview these remarkable leaders for the inaugural Ari Kaplan Advisors Legal Tech GC/CLO Roundtable, focusing on the key challenges, trends, and opportunities that are likely to affect strategic priorities in 2026:
Jason Barnwell, AgiloftMarla Crawford, CimplifiClint Crosier, iManageDennis Garcia, LiteraJenny Hamilton, ExterroBeth Kallet-Neuman, RelativityColin Levy, MalbekJohn Patzakis, X1JP Son, Verbit

*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.

The Advantages of Using an AI Agent in Contract Review

I spoke with Brian Powers, the Co-Founder & CEO of Markups.ai, a company that created an AI agent called Agent Marko to draft, revise, and analyze contracts from clients’ inboxes, with no new platform required, and Debbie Epstein Henry, the Founder of DEH Consulting, Speaking, and Writing, and the Chief Strategic Advisor to Markups.ai. We discussed the advantages of using an AI agent in contract review, where startups can distinguish themselves in a crowded market, the misconceptions about AI that leaders need to address before they can achieve broad adoption, and the skills legal professionals should enhance to fuel their success.

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.

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.

*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.

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.

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.

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

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.