Today’s law students are entering a profession being reshaped by AI, making technology literacy more important than ever. What does it mean to build a legal career and professional identity in this rapidly evolving landscape? Dennis Kennedy’s students have been exploring that very question in one of his most recent classes, and he joins Tom to share what they’ve learned. Together, they examine the realities facing today’s law students and new associates, discuss why technological fluency is becoming an essential legal skill, and highlight the opportunities young lawyers have to emerge as technology leaders within their firms and the broader profession.

As always, stay tuned for the parting shots—that one tip, website, or observation you can use the second the podcast ends.

Have a technology question for Dennis and Tom? Call their Tech Question Hotline at 720-441-6820 for answers to your most burning tech questions.

Show Notes:

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When lawyers understand the value technology brings to their lives, it becomes exponentially easier to help them adopt new tools, and the best leaders in legal will help their firms thrive with thoughtful, prudent technology on their side. Dennis Kennedy and Tom Mighell welcome Debbie Foster to discuss technology, leadership, and the future of the profession.

Debbie shares insights from her upcoming book, Be a Next Level Leader, a legal industry playbook for leadership in modern law firms. They discuss the most pressing needs in the profession, and Debbie explains how well-trained leaders are critical to the future success of the legal world, particularly with the rapid advances of AI technologies in mind.

Show Notes:

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Some of the lesser-known problems in our AI tools may actually pose the greatest dangers to legal professionals. Dennis and Tom take a hard look at AI shortcomings like semantic flattening, drift, marketing claims, and more to suss out the realities of these tools and the increasingly apparent need for greater human wisdom and oversight.

Later, are AI-written materials already polluting future AI source data? The guys discuss. 

As always, stay tuned for the parting shots, that one tip, website, or observation that you can use the second the podcast ends.

Have a technology question for Dennis and Tom? Call their Tech Question Hotline at 720-441-6820 for the answers to your most burning tech questions.

Show Notes: 

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As a longtime innovator in legal business ecosystems, Anastasia Boyko has deep insights on operations, technology, and helping law firms make smart decisions that drive growth. Dennis and Tom chat with Anastasia about her strategies for assessing law firm needs, selecting tech tool solutions that truly fit, and successfully deploying technology—even for tech-averse legal professionals.

In a world with thousands of legal tech options, Anastasia explains practical methods for gaining a broader understanding of technology in realistic doses. She later outlines her path from lawyer to legal innovator, discusses current AI evolutions, shares tips for law students, and much more! 

As always, stay tuned for the parting shots, that one tip, website, or observation you can use the second the podcast ends.

Have a technology question for Dennis and Tom? Call their Tech Question Hotline at 720-441-6820 for answers to your most burning tech questions.

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CLE sessions featuring “60 Tips in 60 Minutes” have long been a conference staple, but has this format outlived its usefulness? Sometimes they’re great fun, sometimes too-slow presenters cheat you out of the full 60, sometimes you get some info gems, and sometimes you get nebulous snippets. So, is there still enough value there? Well, as you lawyers love to say—it depends. Dennis and Tom debate the pros and cons of these rapid-fire presentations and talk through what could bring new and greater worth to these sessions. 

Later, the guys answer a listener question on agentic AI. They hash out the ethics, security, and risk factors associated with these AI tools to take a hard look at both their helpful and potentially harmful elements.

As always, stay tuned for the parting shots, that one tip, website, or observation that you can use the second the podcast ends.

Have a technology question for Dennis and Tom? Call their Tech Question Hotline at 720-441-6820 for the answers to your most burning tech questions.

Show Notes:

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Dennis and Tom compare notes on their current AI projects, discussing what has recently captured their attention and which discoveries have been worth further exploration. Dennis discusses his efforts for extracting greater value (and fun!) from AI processes while avoiding the phenomenon of “AI drift”. Tom explains his work toward partnering with AI to create usable products and tools to solve everyday problems. And, we even hear about Dennis’s quirky creation of an AI sleuth based on detectives in literature and TV. 

Later, Dennis shifts this AI-centric conversation to his latest methods for extracting essential data from AI sessions for greater refinement and usefulness.   

As always, stay tuned for the parting shots, that one tip, website, or observation that you can use the second the podcast ends.

Have a technology question for Dennis and Tom? Call their Tech Question Hotline at 720-441-6820 for the answers to your most burning tech questions.

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AI’s rapid development has resulted in some pretty frenetic responses from the populace–lawyers included! Some have dreaded its advance, fearing losses or misuse. Others are excited by its possibilities, seeing new avenues for problem solving and growth. No matter which camp you’re in, all lawyers need to have an understanding of how AI affects legal practice and those they serve. Dennis and Tom welcome Tom Martin to discuss the landscape of AI in law, learn about his legal tech journey, and much more

As always, stay tuned for the parting shots, that one tip, website, or observation that you can use the second the podcast ends.

Have a technology question for Dennis and Tom? Call their Tech Question Hotline at 720-441-6820 for the answers to your most burning tech questions

Tom Martin is the founder and CEO of LawDroid and an adjunct professor at the Suffolk University Law School. 

Show Notes:

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The constant growth and change in legal tech can be challenging, but learning about it in simple, relatable ways can help attorneys everywhere engage effectively. Dennis and Tom welcome Erika Pagano to discuss her perspectives on technology and innovation in the profession. Erika shares her passion for human-centric approaches to technology adoption and emphasizes the importance of developing relational and collaborative skills. Later, she shares her thoughts on AI in legal tech innovation and what the future may hold.

As always, stay tuned for the parting shots, that one tip, website, or observation that you can use the second the podcast ends.

Have a technology question for Dennis and Tom? Call their Tech Question Hotline at 720-441-6820 for the answers to your most burning tech questions.

Show Notes:

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The quality and foresight of a law firm's technology often reflect the tech competence of its leader, but that’s not how it should be! Proper tech use can and should be a part of every law firm. Dennis and Tom welcome Thomas Officer to discuss his insights on legal tech and AI for attorneys. As a former lawyer, Thomas understands legal practice needs firsthand. He discusses the landscape of modern tech for lawyers, casts a tech vision for lawyers to consider as they engage with up-and-coming tools, and offers countless tips for employing AI in the practice of law. 

As always, stay tuned for the parting shots, that one tip, website, or observation that you can use the second the podcast ends.

Have a technology question for Dennis and Tom? Call their Tech Question Hotline at 720-441-6820 for the answers to your most burning tech questions.

Show Notes:

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Being curious and adaptable is essential for legal professionals in today’s quickly changing technology landscape. For extra-fresh tech perspectives from young attorneys, the guys welcome two of Dennis’ former students to the podcast, data privacy analyst Megan Morrison and second-year associate Laith Quasem. Their discussion covers a wide range of topics, including technology competence, their budding careers, advancements in AI, concerns regarding tech safety and privacy, and practical advice for adopting new tools.

As always, stay tuned for the parting shots, that one tip, website, or observation that you can use the second the podcast ends.

Have a technology question for Dennis and Tom? Call their Tech Question Hotline at 720-441-6820 for the answers to your most burning tech questions.

Show Notes:

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