

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

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 10, 2025 • 6min
Mixtape: 2025 LegalTech Connect
Thanks to these industry leaders for speaking with me for my 2025 LegalTech Connect conference mixtape: James Lee, CEO, LegalMation; John DiMenna, Sales Director, Dealcloser; Moiz Shirazi, Co-Founder and CEO, SCOREalytics, Inc; Nicole Bradick, Global Head of Innovation, Factor; and, Scott Mozarsky, CEO and Managing Director, JEGI LEONIS.

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.

Oct 27, 2025 • 17min
Midsize Law Firms are Balancing Potential and Pitfalls in Charting an Unpredictable Path Forward
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.

Oct 24, 2025 • 9min
The Most Common Financial Challenges Law Firms Face and How Leaders are Using Technology to Address Them
I spoke with Rick Hellers, the CEO of Scan Logic, the provider of BillSync and APSync, designed to simplify law firm finances. We discussed the most common financial challenges law firms face, how leaders are using technology to address them, best practices for ensuring prompt and full payment of legal invoices, and how the economy is affecting the financial health of law firms.


