#10: Why Law Firm Tech Feels Broken (And How to Fix It) with Jay McCalister

Law firm tech isn’t broken by accident - it’s broken by imitation, poor strategy, and bolting tools together without intention. In this episode, Chelsea Williams sits down with Jay McAllister to unpack the hard truths about law firm technology, AI adoption, and why more tools don’t automatically mean better results.

This is a deep, practical conversation about systems, constraints, and how law firm owners can stop creating “Frankenstein” businesses that drain time, money, and energy.

What You’ll Learn

1. Why law firms struggle with tech even after “upgrading”
2. The biggest mistakes firms make when adopting AI
3. Why copying other firms’ tech stacks backfires
4. How to identify the real constraint in your law firm systems
5. The difference between efficiency and complexity
6. Where AI actually delivers ROI in law firms
7. Why billing models matter more in an AI-driven world
8. How poor systems quietly destroy realization and profit
9. When automation helps — and when it hurts
10. How intentional tech strategy supports sustainable growth

As someone who has always had an unconventional interest in studying technology and business, approaching both with the healthy skepticism of someone who demands real results, Jay found his tribe within the legal profession. Whether he’s racing on the track or soaring through the skies, that same affinity for high performance fuels his work. He continuously explores new ways law firms can leverage technology and AI, sharing his learnings in real-time at legal tech conferences across the U.S., including Clio Con and through a growing content library of over 1,000 videos on LinkedIn and YouTube. As founder of Paragon Tech, Jay empowers law firm owners to harness technology that delivers greater value to their clients with less effort.

GUEST'S LINKS:

Website – https://paragontechit.com/law-firm-tools/

LinkedIn – https://www.linkedin.com/in/legaltechexpert/

YouTube – https://www.youtube.com/channel/UCo7-PTYl-HY2ZGrMCQ-C3gQ,

LAW FIRM MONEY MATTERS LINKS:

Video Podcast
Socials
Core Solutions Group, Inc. Website