Adapting to AI and Technology: Strategies for Law Firm Resilience – 2026 ALPS Bar Leaders Retreat

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