Latest Episodes

October 29, 2025

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.

October 27, 2025
I spoke with Olivia Mockel, the Chief Brand and Market Strategy Officer at SurePoint Technologies, Debbie Foster, the CEO of Affinity Consulting Group, and Laura Wenzel, the Global Marketing & Insights Director at iManage. The three companies are part of a consortium that supported a new market research report featuring the perspectives of midsize law firm leaders called “Midsize Law Firms Are Balancing Potential and Pitfalls in Charting an Unpredictable Path Forward.” We discussed how chief financial officers, chief operating officers, chief information officers, and executive directors are approaching generative AI, data and financial intelligence, technology adoption, and training to help drive their firms into a new era of legal services. Download a copy of the executive summary here: http://bit.ly/4oAO3PV.
October 22, 2025

In this 48th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed the value of practical conversations about AI pricing, promoting wellness at conferences, and empowering change.

October 17, 2025
I spoke with Capri Miller and Matt Mahon, the Customer Partner and Vice President of Customer Experience, respectively, at Level Legal, a provider of managed services, about the Association of Corporate Counsel’s 2025 Annual Meeting in Philadelphia and how corporate legal departments are evolving.
October 15, 2025

I spoke with Kevin Klein, Co-Founder of LegalTech Connect and Head of Content & Programming at the KM&I for Legal Conference, and Patrick DiDomenico, who founded InspireKM Consulting and KM&I, and is now Co-Founder at LegalTech Connect. We discussed the convergence of KM&I and LegalTech Connect, the evolution of law firm knowledge management and innovation, and how conversations about KM and AI will drive the legal profession forward.

October 13, 2025

I spoke with Tom Martin, the founder and CEO of LawDroid, an Adjunct Professor teaching Generative AI and the Delivery of Legal Services at Suffolk University Law School, and a co-founder of the American Legal Technology Awards. We discussed the most exciting opportunities AI is creating for lawyers, best practices for persuading AI skeptics, the ethical and practical guardrails lawyers should consider, and the objective of the American Legal Technology Awards.

October 10, 2025
It was a privilege to speak with these leaders for this Relativity Fest 2025 mixtape:  Brett Chalmers, Website and Product Marketing Director, Opus 2, Mathew Corfield, Surveillance Product Owner, Theta Lake, Blake Ferger, Senior Consultant, Complete Discovery Source, Shawn Gaines, Chief Marketing Officer, OnDean, Frank Perrone, Founder and CEO, ReVia, Matt Rosenthal, Senior Vice President of Sales, Cimplifi, Alex Sappington, Co-CEO, Page Vault, Ben Sexton, Senior Vice President, Innovation and Strategy, JND Legal Administration, Marcin Święty, Chief Security Officer, Relativity, Alston Walker, Senior Discovery Consultant and Executive Client Services Liaison, HaystackID, and Freya Zhou, Co-Founder & COO, Fileread.
October 8, 2025
I spoke with Binit Agrawal, the Chief of Staff at Lucio, an India-based AI-native workspace for lawyers. We discussed the pitfalls of using AI in a legal practice, the mindset and skill set that junior lawyers should adopt, and how AI in the legal profession is evolving.
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