Anthony M. DeSimone is a leading advocate for integrating generative AI into the legal profession, specializing in helping law firms harness AI to enhance efficiency, profitability, and client service. With more than 25 years of experience as a CPA and CMA, Anthony began his career at Deloitte before transitioning to focus on business optimization. Today, he operates "You're the Expert Now, LLC" and serves as a faculty member at the University at Buffalo Center for Entrepreneurial Leadership.
In addition to delivering keynote presentations at national conferences, Tony leads AI accelerator courses and shares insights through his YouTube channel and podcast, "AI Mastermind." His groundbreaking work, including publishing a book in under 24 hours and producing AI-generated illustrations, underscores his expertise at the intersection of AI, data, and legal practice.
WHAT’S COVERED IN THIS EPISODE ON AI STRATEGY FOR LAW FIRMS
Many law firms are intrigued by AI, but unsure how to move forward. Questions about confidentiality, security risks, and the reliability of AI tools leave many lawyers hesitant, and expose firms to risks they don’t fully understand.
But AI isn’t about replacing lawyers. It’s about amplifying their capabilities while safeguarding client trust. Firms that learn how to integrate AI strategically will not only protect sensitive data but also position themselves for greater efficiency, profitability, and resilience in a changing legal landscape.
In this episode of The Lawyer’s Edge Podcast, Elise Holtzman talks with Anthony DeSimone, a CPA, CMA, and AI strategist who advises law firms on safe and effective AI adoption. Tony shares practical insights on the risks lawyers can’t afford to ignore, how to train teams to use AI responsibly, and how the right AI strategy can streamline firm operations without sacrificing security or professionalism.
2:10 – How law firms are approaching AI today — early adopters versus laggards
4:20 – The hidden risks when lawyers use AI tools without firm oversight
6:00 – What AI hallucinations are and why they matter for law firms
8:42 – Practical ways lawyers are using AI now — drafting, research, and more
13:14 – How to safeguard client confidentiality when using AI
17:23 – The leadership role in encouraging smart AI experimentation
21:35 – Why large language models struggle with numbers and how that impacts legal work
24:50 – What’s next — how AI will reshape law firm operations in the next five years
MENTIONED IN ANTHONY DESIMONE | MAKING AI WORK FOR YOUR LAW FIRM WITHOUT COMPROMISING SECURITY OR EXCELLENCE
You're the Expert Now, LLC | LinkedIn
Get connected with the coaching team: hello@thelawyersedge.com
SPONSOR FOR THIS EPISODE…
Today’s episode is brought to you by the coaching team at The Lawyer’s Edge, a training and coaching firm that has been focused exclusively on lawyers and law firms since 2008. Each member of The Lawyer’s Edge coaching team is a trained, certified, and experienced professional coach—and either a former practicing attorney or a former law firm marketing and business development professional.
Whatever your professional objectives, our coaches can help you achieve your goals more quickly, more easily, and with significantly less stress.
To get connected with your coach, just email the team at hello@thelawyersedge.com.
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