What if you had an AI that not only assisted you, but acted as a highly trained source of strategic support in your day-to-day work? Dennis and Tom explore the idea of creating an AI Chief of Staff that could function in an organizational or advisory role. They share their experimental approach, walk through their methods for developing and training the AI to work for them, and discuss the challenges they’ve encountered along the way.
Later, they shift to a common pitfall: buying technology to solve law firm pain points, only to discover it isn’t the right fit. The guys break down what you need to know before investing in that next shiny tech solution.
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 - Kennedy-Mighell Report #405
A Segment: Building an AI Chief of Staff
Claude
ChatGPT
Gemini
NotebookLM
B Segment: We Answer a Question from our ChatGPT Audience
Parting Shots:
Android and iPhone users can now share files, starting with the Pixel 10 family.
The VergeCast Extreme Smart Home Makeover: Extreme smart home makeover - Gadgets
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42:07
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42:07
Fresh Voices on Legal Tech with Mary Mack
AI, GenAI, agentic AI—what’s the difference between these forms of artificial intelligence? Dennis and Tom welcome Mary Mack of EDRM to talk through the latest in AI developments and how they are impacting legal in multitudinous ways. Mary also shares how her unique career blend of IT and law came about and offers her unique perspective on the opportunities in today’s market for technology careers adjacent to the legal profession.
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:
EDRM
The Operational Protocol Method: Systematic LLM Specialization Through Collaborative Persona Engineering and Agent Coordination – LLRX
Breath: The New Science of a Lost Art, by James Nestor
Range: Why Generalists Triumph in a Specialized World, by David Epstein
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46:56
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46:56
Fresh Voices on Legal Tech with Michael Kraft
When teaching technology, empathy and patience are key to helping the learner engage and understand tech’s necessary role in legal practice. Dennis and Tom talk with Michael Kraft about his many years in IT service to legal professionals. They discuss practical methods for encouraging tech competence, favorite tools for collaboration, recent legal tech trends, AI, and much more. Michael also shares insights into his fascinating career path in legal technology, with an early start founding Kraft Kennedy in 1988—a business that has grown into a trusted IT solutions provider in the legal industry and beyond.
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:
Kraft Kennedy
Perplexity Browser
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42:46
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42:46
Fresh Voices on Legal Tech with April Dawson
AI is disrupting every facet of the law, and understanding how to engage with AI technologies is essential for all attorneys and law students. Dennis and Tom talk with April Dawson about her experience researching and teaching about ethical, effective AI uses in the legal world while preserving vital learning skills for law students. They discuss AI challenges in law schools, AI governance considerations, new applications for AI in access to justice, 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.
Show Notes:
NCCU’s 4th Annual Law and Technology Summit on October 17, 2025.
April Dawson on LinkedIn
Voice Memos organized by ChatGPT!
Trello (explained by ChatGPT!)
AI prompt – “What am I missing?”
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50:55
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50:55
Fresh Voices on Legal Tech with Marc Lauritsen
Is true technology competence possible? The speed at which technology advances is now impossible to stay completely ahead of, but as lawyers, a commitment to lifelong learning and a focus on the humanistic side of law can help us engage effectively. Dennis and Tom talk with Marc Lauristen about his work with legal technology, lawyers, and law students. They talk through the challenges and opportunities surrounding AI, ways to manage technology education and implementation in the profession, and why being a good human is essential in our efforts to blend legal practice and services with helpful technologies.
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.
Marc Lauritsen is a Massachusetts lawyer and educator who helps people work more effectively through knowledge systems.
Show Notes:
Law Help Interactive
Capstone Practice Systems
Choiceboxer.com
Gary Marcus
The Return by Hisham Matar
Partiful
BenQ ScreenBar Pro LED Monitor Light Bar
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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.
Netherlands