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The Kennedy-Mighell Report

Legal Talk Network

Hear how technology can help attorneys, legally speaking, with two of the top legal technology experts. Authors and lawyers, Dennis Kennedy and Tom Mighell host this Legal Talk Network show.

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  • 20 episodes
  • fortnightly
  • Avg 46 min
  • English

Episodes 20

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  • S1 · E427
    October 2 · 46 min

    How Your Personal Prompting Style Affects Your AI Experience

    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 show. Did AI get it right? Dennis and Tom 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: Google Weather Lab Optimize your workspace with AI

  • S1 · E426
    September 18 · 43 min

    Fresh Voices on Legal Tech with Ariana Paulino

    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 skills. 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: Data Camp getbrick.com

  • S1 · E425
    September 4 · 46 min

    Should You Be Wearing AI?

    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 weighty considerations and much more. Later, Tom’s got a new Second Brain! After a major overhaul, Tom’s pretty pleased with his new system, so the guys talk through his current approach and uses for this technology tool. 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: Spotify’s AI playlists

  • S1 · E424
    August 21 · 45 min

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

    This episode is sponsored by Smith.ai. 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 to improve both attorney and client experience. 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: Copilot for task tracking. Wispr Flow for easy voice dictation.

  • S1 · E423
    August 7 · 42 min

    Fresh Voices on Legal Tech with Adriana Linares

    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 platforms in today’s midsize and small firms. 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: UPS Devices

  • S1 · E422
    July 24 · 51 min

    Fresh Voices on Legal Tech with Julia Montgomery

    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 like in legal businesses, and how her love for legal led her to a career helping lawyers organize their work with effective, measurable strategies powered by technology and good practices. 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.

  • S1 · E420
    July 10 · 45 min

    Fresh Voices on Legal Tech with Christian Puzder

    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 technologist and offers his take on how to acquire trustworthy technology for your law firm that truly serves your needs. 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 answers to your most burning tech questions.

  • S1 · E420
    June 26 · 42 min

    Legal Technology Literacy and Leadership

    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: AI Ethics Rules are hitting the books. Florida: Rule of General Practice and Administration 2.515, New York: Part 161 Red Team Prompts – Using AI as an adversary to check your legal work.

  • S1 · E419
    June 12 · 49 min

    Fresh Voices on Legal Tech with Debbie Foster

    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: Debbie's Post on Conflict and Kindness Claude A Cautionary Tale for AI Memory Saving

  • S1 · E418
    May 29 · 45 min

    The Expanding Minefield of Legal AI

    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: Claude Cowork Edge Workspaces in Microsoft Edge

  • S1 · E417
    May 15 · 47 min

    Fresh Voices on Legal Tech with Anastasia Boyko

    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.

  • S1 · E416
    May 4 · 47 min

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

    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: Orb - Speed Test Logitech Lift Mouse

  • S1 · E415
    April 17 · 45 min

    Adventures in AI: Design, Detectives, & Drift with Dennis & Tom

    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.

  • S1 · E414
    April 3 · 43 min

    Fresh Voices on Legal Tech with Tom Martin

    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: lawdroid.com CC - Google Labs

  • S1 · E413
    March 20 · 52 min

    Fresh Voices on Legal Tech with Erika Pagano

    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: raindrop.io

  • S1 · E412
    March 6 · 47 min

    Fresh Voices on Legal Tech with Thomas Officer

    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: Every Legal Tech Coach - Thomas Officer Monologue - voice notes by Every Autobrowse Moltbook

  • S1 · E411
    February 20 · 58 min

    Fresh Voices on Legal Tech with Megan Morrison and Laith Quasem

    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: RemixAI

  • S1 · E410
    February 6 · 43 min

    Fresh Voices on Legal Tech with Chantal McNaught

    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 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: AI Fluency for Lawyers | 43 Degrees Below People in Legal Podcast Connect Gemini to Multiple LM Notebooks! Personal Strategy Compass | DennisKennedy.Blog

  • S1 · E409
    January 23 · 44 min

    This is Your Second Brain on AI | Rebroadcast

    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, 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 – This is Your Second Brain on AI A Segment: This is Your Second Brain on AI Notebook LM – https://notebooklm.google.com B Segment: Should iPhone Users be Jealous of Android’s Obvious Superiority? Google Pixel 10 https://store.google.com/category/phones?hl=en-US Parting Shots: Kortex – https://chromewebstore.google.com/detail/kortex/hdapplggdhndkblofffknpmnnnnbncbn?pli=1 Personal Strategy Compass – by Dennis Kennedy

  • S1 · E408
    January 9 · 41 min

    Dennis & Tom’s 2026 Tech Resolutions

    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, but decided to take a stab at it anyway! Listen in for their thoughts on the possible future and what technologies may become increasingly essential for lawyers. 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: Wispr Flow Speechify

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