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

B Segment: We Answer a Question from our ChatGPT Audience

Parting Shots:

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:

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:

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:

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:

Debbie Foster hosts this edition of the Kennedy-Mighel Report to talk with Dennis and Tom about their 19 years and 400 episodes of podcasting! They talk through the past, present, and future of the podcast, discussing how they’ve remained in the space for so long, cringy and favorite moments from podcasts past, and what they’ve learned over many years together. They also talk about their future plans for the show and how new technology trends are influencing both the podcast and the broader 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:

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

B Segment: Should iPhone Users be Jealous of Android’s Obvious Superiority?

Parting Shots:

Is AI the technology that will finally force lawyer tech competence? With rapid advances and the ability to address numerous problems and pain points in our legal systems, AI simply can’t be ignored. Dennis & Tom welcome Bridget McCormack to discuss her perspectives on current AI trends and other exciting new tech applications in legal spaces. Bridget also talks us through her fascinating career path and current projects. 

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:

What we do as lawyers and judges is deeply human and deeply connected to our communities—so how does technology fit into that perspective? Dennis and Tom welcome Bridgette Carr to share her insights on technology training, AI, and the use of modern tools to solve legal problems and bolster the communities we serve. Drawing from her work with law students and clinical research, Bridgette explores the exciting ways AI and tech can advance the practice of law and improve access to justice.

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.

Bridgette Carr is a clinical professor at Michigan Law and co-directs its Human Trafficking and Immigration Clinic.

Show Notes:

Subscription and flat fee legal services have endless potential for modern law practice, and with legal tech by your side, you can scale with this fresh billing model. Dennis and Tom talk with Kimberly Bennett of Fidu about her experience developing subscription legal services and her current perspectives on the state of legal tech in the profession. They discuss Kimberly’s career path, how Fidu got its start, and her thoughts on the transformative potential of AI in legal practice. 

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.

Kimberly is Co-Founder and CEO of Fidu, a client experience platform to help you sell, deliver, and scale your flat-fee & subscription legal services.

Show Notes: