On the Road with Legal Talk Network

Across a week of conversations in Missoula, one theme kept resurfacing no matter who was in the chair: AI is forcing every bar leader in the country to rethink risk, mentorship, and what it means to serve solo and small firm attorneys who are already stretched thin. Chris Newbold, COO of ALPS Insurance, opens this compilation with a thank you to the bar leaders who made the retreat what it was. From there, the episode pulls together moments from across the series focused on solo and small firm practice: Rachel Okun on why relationships built through bar leadership matter more than marketing, Kevin Maxim on the collision between attorney-client privilege and AI, Mark Bassingthwaighte on why succession planning has become a quiet crisis for solos, and Susan Carns Curtiss on the anonymous posts revealing how many newer attorneys are struggling to find mentorship. John Mudd, Alison Gee, Angela Armstrong, and Susan Bradford Tarley round out the conversation with their own takes on wellness, hallucinated case law, and the legal deserts still waiting to be served. Together, these voices paint a picture of a profession adapting in real time, uncertain but not without hope.

Proving once again that ALPS Insurance puts the "treat" in retreat, they gathered leaders in law from across the country this summer. These sit-down conversations reveal flavors of leadership and legal trends from a variety of perspectives. Cool takes, one scoop at a time, recorded live at the 2026 ALPS Bar Leaders Retreat in Missoula, MT.

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After 28 years as ALPS Insurance's Risk Manager, Mark Bassingthwaighte says cybersecurity now worries him more than legal malpractice, and he's tired of hearing solo and small firm lawyers insist they're too small to be a target. Bassingthwaighte, who's worked with more than 1,200 law firms and delivered over 700 CLE seminars, traces a quieter crisis behind the numbers: he estimates some form of attorney impairment, burnout, depression, addiction, or dementia, plays a role in as many as half to 70% of malpractice claims, including one case where an attorney was found hiding client files in the trunk of his car. He also breaks down how generative AI is supercharging phishing attacks at a scale small firms have never had to defend against, and pushes back on the fear that AI itself will replace lawyers, arguing it will only take out the ones who refuse to adapt. Bassingthwaighte closes on a message he repeats often to lawyers facing a claim: you're not judged by the mistake you made, you're judged by what you do about it.

Proving once again that ALPS Insurance puts the "treat" in retreat, they gathered leaders in law from across the country this summer. These sit-down conversations reveal flavors of leadership and legal trends from a variety of perspectives. Cool takes, one scoop at a time, recorded live at the 2026 ALPS Bar Leaders Retreat in Missoula, MT.

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In 2016, Susan Carns Curtiss added 46 women attorneys she knew to a Facebook group with no real plan behind it, and it's since grown into Girl Attorney, a network of more than 40,000 women lawyers trading practice advice, mentorship, and support across the country. A plaintiff's personal injury and wrongful death trial lawyer in Oklahoma City, Curtiss describes watching newer attorneys increasingly post anonymously about burnout and a lack of mentorship, even as most of the community is thriving, and shares her own recent experience nearly drowning in a growing litigation docket before a longtime colleague stepped in to help her offload cases. She credits two decades of showing up in her local bar and trial lawyer community for having someone to call when she needed it, and pushes back gently on the idea that women's push for work-life balance is a new trend rather than a fight that's been underway for years. Curtiss closes with a call not to look away from what she sees as a broader breakdown in the rule of law, and to find the others who are choosing to stand up rather than turn away.

Proving once again that ALPS Insurance puts the "treat" in retreat, they gathered leaders in law from across the country this summer. These sit-down conversations reveal flavors of leadership and legal trends from a variety of perspectives. Cool takes, one scoop at a time, recorded live at the 2026 ALPS Bar Leaders Retreat in Missoula, MT.

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One stretch of eastern Montana spans 75,000 square miles and has just 123 lawyers to cover it, and John Mudd, Executive Director and General Counsel of the State Bar of Montana, sees AI as one of the only realistic ways to close that kind of gap. A fifth-generation Montanan and national speaker on legal ethics and attorney wellness, Mudd lays out what he calls a "soup" of forces converging at once: rising distrust of institutions, a widening access to justice problem, and AI arriving into both at the same time. He points to recent structural shifts in the profession - Montana's newly adopted community justice worker program, modeled after a system Alaska pioneered, and to the broader wave of non-lawyer ownership entering law firms in addition to more immediate risks like attorneys filing briefs built on hallucinated case law. Mudd closes on the message he's carrying into the next year: when everything speeds up at once, the answer isn't panic, it's returning to the bedrock obligations, honesty with the court and loyalty to clients, that don't change no matter what tool is doing the work.

Proving once again that ALPS Insurance puts the "treat" in retreat, they gathered leaders in law from across the country this summer. These sit-down conversations reveal flavors of leadership and legal trends from a variety of perspectives. Cool takes, one scoop at a time, recorded live at the 2026 ALPS Bar Leaders Retreat in Missoula, MT.

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Some Wyoming counties have two practicing attorneys or fewer, and once you subtract the elected county attorney and public defenders, Alison Gee says there's barely enough left to keep a functioning legal system running. The incoming President of the Wyoming State Bar and a rural general practitioner, Gee describes fielding whatever problem walks through her door, a role she jokingly calls being a "law ninja," and explains how the state has leaned on remote hearings, online filing, and borrowed attorneys to patch gaps like its public defender shortage. She makes a case for moving law firms off local servers and onto cloud-based systems with real security controls, and pushes back on the instinct to let AI shortcut legal research given how easily it hallucinates case law. Gee closes on the balance she's trying to strike as incoming president, bringing Wyoming's legal profession into the future without losing the hands-on judgment that only comes from doing the work the hard way first.

Proving once again that ALPS Insurance puts the "treat" in retreat, they gathered leaders in law from across the country this summer. These sit-down conversations reveal flavors of leadership and legal trends from a variety of perspectives. Cool takes, one scoop at a time, recorded live at the 2026 ALPS Bar Leaders Retreat in Missoula, MT.

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As Virginia marks 250 years since its lawyers helped shape American democracy, Susan Bradford Tarley, President of the Virginia State Bar, is framing her term around what that legacy still demands of the profession today. A real estate and business law partner at Tarley Robinson PLC, she's built her presidency around four priorities: foundational ethics, attorney wellness, the bar's strategic plan, and Virginia's shortage of lawyers in underserved areas, detailed in the bar's own EGAD Report on where new attorneys are and aren't landing. She also weighs in on attorneys caught submitting briefs built on AI-hallucinated cases, some of whom doubled down even after a judge flagged them, arguing it's a symptom of skipping the work rather than a problem with the tool itself. Tarley closes on wellness as the precondition for everything else, arguing that lawyers can only take the small steps that sustain the rule of law if they put their own oxygen masks on first.

Proving once again that ALPS Insurance puts the "treat" in retreat, they gathered leaders in law from across the country this summer. These sit-down conversations reveal flavors of leadership and legal trends from a variety of perspectives. Cool takes, one scoop at a time, recorded live at the 2026 ALPS Bar Leaders Retreat in Missoula, MT.

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Maine has more legal work than it has lawyers to do it, and that gap grows every year even as rural opportunity grows with it. Rachel Okun, President of the Maine State Bar Association and a solo personal injury attorney at Okun Law, breaks down why she sees rural practice as a real career path, not a compromise, and why she taught herself AI tools so she could speak to her membership with real experience instead of theory. She also connects a less obvious dot: attorney burnout, she says, is one of the leading drivers behind bar complaints, since overextended lawyers start missing client communications long before anything more serious goes wrong. Okun closes on her defining message as bar president, that the profession loses something real every time a Zoom call replaces a handshake, and that relationships built through bar leadership, not marketing budgets, are what actually built her practice.

Proving once again that ALPS Insurance puts the "treat" in retreat, they gathered leaders in law from across the country this summer. These sit-down conversations reveal flavors of leadership and legal trends from a variety of perspectives. Cool takes, one scoop at a time, recorded live at the 2026 ALPS Bar Leaders Retreat in Missoula, MT.

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Federal judges are telling their own children not to answer the door to strangers, and that's the reality bar leaders are now building policy around. Kevin Maxim, national President-Elect of the Federal Bar Association and a commercial litigator in Atlanta, breaks down why judicial security has climbed to the top of the organization's Capitol Hill advocacy alongside judicial vacancies and court funding. He traces how the pandemic hollowed out the informal, in-person relationship-building that once held the profession together, and why rebuilding those connections, especially for newer members, has become part of his leadership philosophy. Maxim also raises a sharper concern facing the profession: what happens to attorney-client privilege once confidential communications start feeding into AI tools, particularly as a generational divide widens between attorneys who treat data protection as sacred and younger practitioners who see information differently. Law firms remain constant targets for phishing and cyberattacks, he says, and the profession's next real test is figuring out how much trust it can extend to the tools it's racing to adopt.

Proving once again that ALPS Insurance puts the "treat" in retreat, they gathered leaders in law from across the country this summer. These sit-down conversations reveal flavors of leadership and legal trends from a variety of perspectives. Cool takes, one scoop at a time, recorded live at the 2026 ALPS Bar Leaders Retreat in Missoula, MT.

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Rural legal deserts don't lack demand, they lack reach, and Angela Armstrong sees AI as one of the clearest ways to close that gap. Executive Director of the Maine State Bar Association since 2013, Armstrong describes how her members have moved past early AI hesitation into practical daily use, from legal research to marketing their own practices, while still needing to check every output against the same professional judgment they would apply to any junior associate's work. She also walks through the cybersecurity breach that reshaped her association's entire approach to risk, and shares why she pushed to get CLE credit approved for yoga after watching burnout and depression take a visible toll on members, including a past bar president who spoke openly about his own struggle. Armstrong closes on the throughline she keeps coming back to in her role: leadership in this profession isn't separate from service, it's the same instinct that pulled her into the Army years before it pulled her into bar leadership.

Proving once again that ALPS Insurance puts the "treat" in retreat, they gathered leaders in law from across the country this summer. These sit-down conversations reveal flavors of leadership and legal trends from a variety of perspectives. Cool takes, one scoop at a time, recorded live at the 2026 ALPS Bar Leaders Retreat in Missoula, MT.

Learn more about your ad choices. Visit megaphone.fm/adchoices

Fewer lawyers are gaining real courtroom experience, and the future of trial advocacy is at risk. In this special episode of On the Road, veteran trial attorney and educator Michael Schwartz examines why trial lawyers are becoming harder to find and what it takes to develop the skills true advocacy requires. Drawing on decades of experience trying hundreds of cases, Schwartz breaks down the foundations of effective trial lawyering, from witness examination and jury selection to professionalism, ethics, and strategy. He shares lessons from pivotal courtroom moments and explains why trials remain essential to the pursuit of justice and the search for truth.

Michael Schwartz is a trial lawyer, legal educator, and founder of Trial Advocacy Group, where he trains lawyers nationwide in trial advocacy.

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