

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

Oct 13, 2025 • 10min
The Most Exciting Opportunities AI is Creating for Lawyers
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 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.

Oct 10, 2025 • 10min
Mixtape: Relativity Fest 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.
Freya Zhou, Co-Founder & COO, Fileread.

Oct 3, 2025 • 11min
How the Value of CLM Has Changed Since the Emergence of Generative AI
I spoke with Matt Patel, Founder and Chief Operating Officer at Malbek, an enterprise CLM company providing comprehensive contract management solutions for procurement, legal, sales, and other functions. We discussed who gains the most value from CLM, how its value has changed since the emergence of generative AI, and how it is evolving.

Sep 24, 2025 • 8min
How AI-driven Data Mapping and Labeling Tools are Changing the Way Companies Manage Their Data Risk
I spoke with Brandon Hollinder, the Vice President of eDiscovery and Cyber Solutions at Epiq, a provider of legal and business services. We discussed the proactive steps companies should take to strengthen their information governance, how AI-driven data mapping and labeling tools are changing the way companies understand and manage their data risk, and ways that AI is affecting cybersecurity.

Sep 22, 2025 • 22min
*Special Episode* Featuring Caroline Hill, Editor-in-Chief of Legal IT Insider, on Charting Change in Legal Ep 47
In this 47th episode of Charting Change in Legal, Caroline Hill, Editor and Publisher of Legal IT Insider, and I discussed Legal IT Insider's 30th anniversary, reimagining billable work, anticipating disruption, and providing value.

Sep 19, 2025 • 11min
How AI Transparency, Speed, and Cost-Efficiency Have Transformed Client Expectations
I spoke with John Lee, the General Counsel and Head of Strategy for Ruli, a legal AI platform for corporate law departments. We discussed how legal teams should calculate the ROI or value of a legal technology investment, the qualities buyers should consider when selecting a legal AI vendor, and ways that client expectations have changed due to advanced AI transparency, speed, and cost-efficiency.

Sep 17, 2025 • 15min
Leveraging Technology to Prepare Witnesses to Testify
I spoke with Karl Schieneman, a Co-Founder of TestMyWitness, which empowers witness preparation using AI. We discussed how legal teams can leverage technology to prepare witnesses to testify, and how that process is evolving.

Sep 15, 2025 • 10min
How Law Department Leaders Should Approach Technology Adoption to Maximize Impact and Efficiency
I spoke with Anne Post, CEO of Xakia, North America, a provider of legal matter and contract management solutions. We discussed how law department leaders should approach technology adoption to maximize impact and efficiency, the biggest challenges in-house legal teams face in demonstrating value, and the most compelling opportunities for legal departments to become true strategic partners within their organizations.

Sep 12, 2025 • 24min
*Special Episode* Featuring Caroline Hill, Editor-in-Chief of Legal IT Insider, on Charting Change in Legal Ep 46
Caroline Hill discusses the power of community in the legal industry, highlighting collaboration and shared experiences for collective growth. The importance of strategic idea-sharing emerges as a competitive advantage. As 2023 wraps up, the emphasis on budgeting for emerging technologies shifts the conversation about tech adoption. Insights on measuring ROI reveal the implications of generative AI on law practices. The episode also showcases a successful partnership in navigating change, underscoring the legal tech sector's role in community initiatives.

Sep 10, 2025 • 15min
How In-House Counsel Can Use the RAILS Risk Framework to Better Approach AI Risk Assessment and Governance
I spoke with Diane Homolak, the VP of Technology Solutions for Integreon, Sylvain Magdinier, an independent consultant specializing in legal transformation and innovation, and Gayle Gorvett, the CEO and Managing Director of GGorvett Consulting. They are all part of a workstream within RAILS that helped further the deployment and development of AI in the legal profession. We discussed how in-house counsel can use the RAILS Risk Framework to better approach AI risk assessment and governance, and ways that legal teams are managing AI risk, along with privacy and cybersecurity.