AI Meets Estate Planning: How to Keep the Human Touch in a Digital Legal World

Trust Issues—Only the Kind that Make You Richer.

Episode Summary
In this follow-up episode of Trust Issues, Ruma Mazumdar welcomes back executive coach and AI expert Jesse Frye to discuss how AI is reshaping estate planning and what legal professionals need to know. From DIY will platforms to agentic AI tools that mimic human workflows, Ruma and Jesse dig into the promises, pitfalls, and personal hesitations around using AI in people-centered legal practices. They explore how to identify friction points, personalize client experiences, and scale law firms—without sacrificing trust. This is an essential conversation for anyone navigating the evolving balance between automation and empathy in law.

Key Timestamps
00:01 – Welcome Back: AI + Estate Planning Round 2
01:14 – The Rise of DIY Estate Planning Platforms
03:35 – Ruma’s Concerns: Where AI Helps vs. Where It Feels Cold
05:02 – Why Clients Still Need Human Advisors
07:10 – Could an AI Avatar Guide Clients Through Your Process?
09:45 – Mindset Shift: Delegating Without Abdicating
12:20 – Can Video Replace Face Time? How to Know What Clients Want
14:18 – The DMV Example: When AI Actually Improves the Experience
17:10 – Agentic AI for Legal Marketing & Admin Tasks
20:00 – Personalization vs. Automation: Where AI Shines
23:05 – The Admin Time Trap: Using AI for Time Tracking & Cost Control
25:30 – Better Research, Faster Results: Ruma’s AI Research Tips
28:00 – How to Start with AI Without Getting Overwhelmed
30:45 – Why You Shouldn’t Sign Long-Term Contracts with AI Vendors
33:00 – The VC Landscape: What’s Growing, What’s Getting Acquired
35:14 – Final Thoughts: How to Vet AI Tools in Your Legal Practice
36:50 – Where to Find Jesse Frye Online
38:10 – A Bit of Nostalgia: Coaching Memories & First-Year Doubts

About the Show

Trust Issues is hosted by estate planning attorney Ruma Mazumdar, who tackles the evolving challenges and innovations in law, leadership, and entrepreneurship. Through candid conversations with experts and disruptors, the show helps legal professionals build smarter, more resilient, and more human-centered practices in a digital-first world.