The Kennedy-Mighell Report

46:23

How Your Personal Prompting Style Affects Your AI...

The Kennedy-Mighell Report ·

2026/10/02

Philosophies and approaches to AI use differ vastly amongst its users, and Dennis and Tom are no exception. While Dennis imagines “panning for gold” with a high-level thought partner, Tom treats AI as a well-managed, prudent employee. The guys give detailed insights into their prompting styles and discuss both the goals and results of their differing modes of use.Later, they experiment with AI to analyze the podcast and make inferences about who their audience is and what they want out of the

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43:56

Fresh Voices on Legal Tech with Ariana Paulino

The Kennedy-Mighell Report ·

2026/09/18

For a unique perspective on legal technology, Dennis Kennedy and Tom Mighell welcome law librarian Ariana Paulino. Ariana shares her insights on engaging with today’s leading technologies and AI tools, as well as helping law students learn to use them effectively in legal practice. They explore how building relationships with technology vendors can help lawyers stay current on essential tools for their firms and discuss the importance of balancing AI’s capabilities with strong foundational legal

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46:34

Should You Be Wearing AI?

The Kennedy-Mighell Report ·

2026/09/04

New, wearable AI technology products are entering the market in a steady stream, but should any of us be rushing to get these new, shiny tech toys? Dennis Kennedy and Tom Mighell dig into the world of wearable AI, from rings to pendants to glasses and more, to explore their intent and discuss the controversies that have inevitably followed in their wake. Do these gadgets deliver unique value? Is your privacy at risk? Are you violating others’ rights to privacy if you wear them? The guys unpack these

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45:51

AI’s Role at Your Law Firm: Ethical Delegation to AI...

The Kennedy-Mighell Report ·

2026/08/21

AI assistants can be incredibly helpful to attorneys, but what exactly can and should these tools be doing for your law firm? Dennis Kennedy and Tom Mighell welcome Maddy Martin of Smith.ai for a roundtable discussion on the current landscape of AI assistant tools and their value for lawyers. They examine these tools through the scope of jobs to be done, looking at real-life attorney pain points and explaining ways to identify which tasks can effectively and ethically be handed off to AI assistants

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42:11

Fresh Voices on Legal Tech with Adriana Linares

The Kennedy-Mighell Report ·

2026/08/07

Adriana has trained lawyers through legal tech developments for decades, so she’s pretty much seen it all! Dennis and Tom pick her brain on the trajectory of AI tools, technology competence, collaboration, and much more. Adriana offers deep insights into lawyers’ commonly underutilized tools in Microsoft and Adobe, pointing out that they may already be paying for the solutions they need.Later, they also discuss Adriana’s career path and dig into the advantages of using practice management

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51:39

Fresh Voices on Legal Tech with Julia Montgomery

The Kennedy-Mighell Report ·

2026/07/24

Lawyers are a unique group often characterized as being hyper-resistant to change, but is that really true? As technology changes, lawyers must adapt, but it is important to appreciate their tendency toward skepticism and caution to be able to effectively help them adopt new tools. To discuss this topic, Dennis and Tom welcome Julia Montgomery to learn about her processes for change management in law firms. Julia talks about the unique traits of attorneys, what real change management should look

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45:46

Fresh Voices on Legal Tech with Christian Puzder

The Kennedy-Mighell Report ·

2026/07/10

Good lawyers are good delegators—and those lawyers shouldn’t be afraid to start delegating to their AI tools! This time on the Kennedy-Mighell Report, Dennis and Tom welcome Christian Puzder to talk about AI and good governance. Christian explains the importance of proper and effective AI use in the practice of law, emphasizing the ethical need to embrace new technology, train your firm well, and serve your clients better.Later, Chris discusses his career journey from attorney to legal

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42:16

Legal Technology Literacy and Leadership

The Kennedy-Mighell Report ·

2026/06/26

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

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49:59

Fresh Voices on Legal Tech with Debbie Foster

The Kennedy-Mighell Report ·

2026/06/12

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

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45:16

The Expanding Minefield of Legal AI

The Kennedy-Mighell Report ·

2026/05/29

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

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47:51

Fresh Voices on Legal Tech with Anastasia Boyko

The Kennedy-Mighell Report ·

2026/05/15

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

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47:41

“60 Tips” Rapid-Fire CLEs – Slow Death or New Potential?

The Kennedy-Mighell Report ·

2026/05/04

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

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45:29

Adventures in AI: Design, Detectives, & Drift with...

The Kennedy-Mighell Report ·

2026/04/17

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

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43:22

Fresh Voices on Legal Tech with Tom Martin

The Kennedy-Mighell Report ·

2026/04/03

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

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52:25

Fresh Voices on Legal Tech with Erika Pagano

The Kennedy-Mighell Report ·

2026/03/20

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

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47:28

Fresh Voices on Legal Tech with Thomas Officer

The Kennedy-Mighell Report ·

2026/03/06

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,

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58:57

Fresh Voices on Legal Tech with Megan Morrison and...

The Kennedy-Mighell Report ·

2026/02/20

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

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43:21

Fresh Voices on Legal Tech with Chantal McNaught

The Kennedy-Mighell Report ·

2026/02/06

The tensions between the practice and business of law have long been a touchy subject, but lawyers must wrestle with these challenges to thrive in the profession. Dennis and Tom welcome Chantal McNaught to discuss her work at the intersection of law, business, and technology. Chantal delves into how ethics command technology use in legal practice and offers grounded, thoughtful insights on how to develop a sense of community and support in technological pursuits. As always, stay tuned for the

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44:23

This is Your Second Brain on AI | Rebroadcast

The Kennedy-Mighell Report ·

2026/01/23

Are the guys on the verge of a major Second Brain breakthrough, hand in hand with AI? Dennis and Tom reexamine their ongoing Second Brain projects, discussing nagging questions about the efficacy of their current systems and how they plan to move forward with their personal knowledge management.Later, a listener and long-time iPhone user wonders—are Android devices actually far superior? Tom has some major thoughts on the issue. As always, stay tuned for the parting shots, that one tip, website,

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41:05

Dennis & Tom’s 2026 Tech Resolutions

The Kennedy-Mighell Report ·

2026/01/09

Dennis and Tom continue their proud tradition of pondering the panorama of timely tech happenings and sharing personal resolutions for learning and development. But first, they both take a look at last year’s goals to gauge their progress (or, ahem, lack thereof). As for new resolutions—from investigative AI problem solving to streamlined tech tool usage to open-sourced writing to content creation, there’s lots to do in 2026! Later, the guys are loath to make predictions in an unpredictable world,

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