Legal Talk Network - Law News and Legal Topics

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:

In episode 590 of Lawyerist Podcast, learn how practical, everyday AI can help lawyers work smarter—not harder. Zack Glaser sits down with Graydon Trusler, a practical AI specialist and longtime law-firm operations pro, to explore how attorneys can use “productive laziness” to eliminate repetitive tasks, streamline case management, and reclaim valuable time. Graydon shares real examples from his family law firm, including how custom AI assistants help review discovery, prep hearings, analyze documents, and even support lawyers in the courtroom. Together, they break down privacy concerns, adoption hurdles, and simple ways to start using AI without getting overwhelmed.

Discover why AI isn’t a distant future—it’s a powerful tool lawyers can start using today to improve workflows, reduce stress, and deliver better results for clients. 

 Links from the episode:  

LexpertAI 

 Listen to our previous episodes about Practical AI & Law Firm Efficiency:  

Have thoughts about today’s episode? Join the conversation on LinkedIn, Facebook, Instagram, and X! 

If today's podcast resonates with you and you haven't read The Small Firm Roadmap Revisited yet, get the first chapter right now for free! Looking for help beyond the book? See if our coaching community is right for you. 

Access more resources from Lawyerist at lawyerist.com. 

Chapters / Timestamps:  

00:00 – Introduction 

08:45 – Meet Graydon 

11:10 – Practical AI in Law Firms 

16:40 – Myths, Fears & Privacy 

19:00 – Real AI Workflows 

23:00 – Productive Laziness 

31:00 – AI in the Courtroom 

34:45 – Faster Discovery & SOPs 

38:50 – Flat Fees & the Future 

45:13 – Closing Thoughts 

Security, security, security. In your law firm’s tech package, there is probably no more important word than security. Your clients depend on it. Your business depends on it. 

You and your firm can get hacked. It happens. Bad people want to get into your firm. They can dig through your email. They can get into your Microsoft 365 One Drive or Google accounts. Guest Adam Alexander, president of the Orlando-based IT firm Internetwork IT, explains two recent breaches, how they happened and how much damage hackers can do. 

Once inside, hackers can hold your business – and your reputation – for ransom. The scary part? While evil doers are worming through your data, you may not even know it.   

In this important episode, even if you think you know all about security, take a moment to get your head around the latest threats and safeguards. What’s an admin account? What’s two-factor authentication? Who holds the key to your kingdom? If you haven’t thought about this for a while, today’s the day. 

Questions or ideas about solo and small practices? Drop us a line at [email protected], 

Topics:

Mentioned in This Episode:

Previous appearance on New Solo, “AI And The Evolving Security Threats (And Protections)” 

Previous appearance on New Solo, “The Microsoft 365 Special: Your Questions, Expert Answers”

Microsoft 365

Microsoft 365 Premium

Microsoft Defender Threat Intelligence

“Set up multifactor authentication for Microsoft 365”

Google OAuth

1Password

RoboForm

American Bar Association, “Insurance Strategies to Mitigate AI and Cyber Risks”

Clio

ABA Techshow 2026

Clio Cloud Conference 2026

John Simon remarked, “If the jury thinks this case is about rocks, you’re in trouble.”  How we creatively framed the case and presented punitives set our client up for amajor win.

Bonuses and botched prosecutions.

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Bonus season is underway, and Biglaw firms are lining up to reward associates for a year's worth of effort. The market scale -- unless some firm breaks rank and crashes the party -- tracks last year, which can be a bit anticlimactic, but with the economy possibly resting on the precipice of recession, this was probably all we could hope for. Also, we discuss Lindsey Halligan's epic fail in the James Comey case -- and we recorded this before the judge tossed the case. Finally, Judge Jerry Smith decided to commit his unhinged conspiracy theories to paper in a massive, doorstop of a dissent in the Texas redistricting case. And we discuss Thanksgiving sides.

Today’s episode is about you and your mindset as it pertains to generating wealth through your business. Guest Lauren A. Klein was a corporate attorney when she came to a crossroads, would she follow the corporate path and accept a paycheck, or strike out on her own and build wealth on her terms.

She started by asking questions about how lawyers make money and build wealth. What does it actually mean to make partner at a firm? And she came to the conclusion that there had to be more, that she could do better on her own, knowing full well, as she says, running a law firm is “not for the weak of heart.”

In addition to driving the elder law and estate planning firm Flourish Law Firm she co-founded with her best friend, she’s also the host of the podcast “The Wealthy Law Squad.” She learned from corporate law that getting a salary and spending it on lifestyle isn’t wealth. Wealth is investing, creating tools that generate passive income, and building net worth. 

What can you invest in today that gives you the financial freedom to do whatever you want later? A “wealth mindset” is about creating freedom, not being chained to the golden handcuffs of a paycheck. What are you working toward?

Ask us anything for the Community Table. Leave us a question online!

Join the next Community Table discussion live! Always the third Thursday of the month at 3pm Eastern.

Mentioned in This Episode:

The Wealthy Lawyer Squad podcast

Clio

Have you ever thought about writing the perfect legal brief? Guest David N. Greenwald has, so much so that the retired partner from the firm Cravath, Swaine & Moore wrote a book on the subject, titled “Sentence, Paragraph, Argument, Brief: Meeting the Four Challenges of Legal Writing.”

The book is the culmination of a 30-year legal career, beginning with a clerkship and the lessons learned under the guidance of the Hon. Richard A. Posner, Chief Judge of the United States Court of Appeals for the Seventh Circuit. Reading, digesting, and understanding everything related to each brief proved to be the foundation of good legal writing, Greenwald says.

Throughout his career, Greenwald intentionally honed his skills, from writing briefs to eventually, as a partner, editing them. With each paragraph and edit, he focused on the construction and flow of each argument.

Writing, Greenwald explains, is a linear process, putting ideas and sentences in a logical progression. A brief, he says, is a special kind of writing that must be learned. It starts with a statement of fact or history, building a narrative. But it’s also a work focused on clarity, without surprises or suspense. Hear Greenwald’s discussion of the art, and science, of legal writing and the principles of a clear, persuasive argument.

Have a question, comment, or suggestion for an upcoming episode? Get in touch at [email protected] and [email protected].

Resources:

Hon. Paul R. Michel, Chief Judge (Retired), U.S. Court of Appeals for the Federal Circuit on C-SPAN 

2026 Women in Litigation CLE Conference

American Bar Association

American Bar Association Litigation Section

 “Sentence, Paragraph, Argument, Brief: Meeting the Four Challenges of Legal Writing,” by David N. Greenwald

A recent report from LSC's Rural Justice Task Force, “Justice Where We Live: Promising Practices from Rural Communities,” dives into a multitude of programs and approaches that address the biggest challenges to accessing civil justice in rural America. One issue is the scarcity of attorneys in rural areas, often called “legal deserts.” This episode highlights three programs working to create a pipeline of new rural lawyers.

Causation and Workers’ Compensation? It’s complicated, and it varies by state. The concept is that to qualify for Workers’ Comp there must be a direct link between the injury (or illness) and the workplace. But how do you prove what’s a direct result of the workplace and what was the result of a prior injury or condition? 

Here’s where it gets confusing. Every state has its own rules. There are varying degrees of required proof, pre-existing conditions, mental trauma, contributing causes, and it can be a challenge to sift through each jurisdiction’s standards. 

Hosts Judson and Alan Pierce dissect how pre-existing conditions complicate work-related injury claims. It’s not always as clear as it seems, and state-by-state regulations create even more confusion. Add in workplace psychological stresses and it goes even deeper.

If you have thoughts on Workers’ Comp law or an idea for a topic or guest you’d like to hear, contact us at [email protected] or [email protected]. 

Mentioned in This Episode:

“AMA Guides® to the Evaluation of Permanent Impairment: An Overview” 

“AMA Guides to Disease and Injury Causation,” by J. Mark Melhorn

In this special episode of On the Road, Nexl Chief Growth Officer Ben Chiriboga explains why the future of legal practice hinges on what AI can’t replicate: strong client relationships. He introduces the concept of “relationship intelligence” and shows how lawyers can use simple data points—from communication patterns to internal connections—to focus their limited time on building deeper, more strategic client relationships. Learn how a data-informed approach to business development can help lawyers move from service providers to true trusted advisors.

Ben Chiriboga is the Chief Growth Officer at Nexl and a former practicing attorney.