Micro-Hard for Microsoft: AI, Copilot & The Future of Legal Tech (Feat. Ben Schorr)

Welcome back, late nighters! Make sure the kids are asleep, because we're going hard this week.  Or kinda of micro-hard, specifically.  This week, Jared is joined by Ben Schorr, Innovation Strategist at Affinity Consulting, who spent nine years working at Microsoft.

First, Jared shares his monologue on the seminal sci-fi anthology series, The Twilight Zone. He discusses creator Rod Serling's history as a WWII paratrooper and his commitment to addressing taboo subjects like fascism and war. Jared then lists his Top 10 Twilight Zone Episodes—from "Time Enough at Last" to "The Monsters Are Due on Maple Street"—without spoilers, of course!

Then, Ben Schorr takes us deep into the world of Microsoft. He clarifies the confusing reality of Microsoft 365 Copilotlicensing and explains why lawyers are slow to ditch desktop apps. Ben shares his thoughts on the broader AI landscape, advising lawyers to be monogamous with their two or three best tools to avoid "tech paralysis". He also offers clear answers on the difference between OneDrive ("me files") and SharePoint ("we files").

Finally, stick around for our Counter Program segment, "Ben Rates the 80s." Ben shares stories from his early career, including working for Alex Trebek, and then rates 80s staples like hair styles, movie soundtracks (hello, Top Gun!), his favorite movie (Real Genius!), and which defunct store he misses most.

Be sure to connect to with Ben Schorr on LinkedIn.
And learn more about Affinity Consulting.

And don't think we're not giving you that sweet, sweet Spotify love this week.  Check out our playlist here.

Thanks to those supporting this episode:

• Assembly Neos. Visit assemblysoftware.com to learn more and schedule your consultation today.
• Captain Compliance.  Visit captaincompliance.com to easily manage your company's privacy compliance.
• Attorney at Work. Head to Attorney at Work for your one really good idea each day.  Check out their new podcast Attorney at Work Today on Apple, Spotify, or wherever you listen to podcasts.

• (00:00) - Intro & Monologue: The Fifth Dimension of The Twilight Zone
• (02:25) - Rod Serling's WWII History & Fight Against Censorship
• (06:09) - Rules for Jared's Top 10 Twilight Zone Episodes
• (07:00) - Jared's Top 10
• (12:15) - More Obscure Twilight Zone Selections (The Beholder, The Invaders)
• (15:34) - The Singular Power of Rod Serling’s Closing Narration
• (18:01) - Introducing Guest: Ben Schorr of Affinity Consulting
• (18:40) - Ben’s Career Path: From Law Firm Admin to Consulting to Microsoft
• (20:01) - Working for Alex Trebek (The Jeopardy! Story)
• (22:57) - The Move from Microsoft to Affinity Consulting
• (24:26) - Ben’s Role as Innovation Strategist & AI Beyond Copilot
• (25:33) - Microsoft 365 Copilot Licensing Explained
• (29:04) - The Broader AI Landscape: Why You Need Multiple Tools
• (31:02) - AI Research: Tuning vs. Data Sets
• (32:19) - Practice-Specific AI: Medical Chronologies
• (34:19) - Custom GPTs & The Daily News Briefing Use Case
• (35:53) - Notebook Tools (Copilot Notebooks & Google Notebook)
• (37:36) - Why Lawyers Still Use Desktop Apps (The Add-in Problem)
• (38:56) - Jared Hates Microsoft Teams: The Debate
• (42:11) - OneDrive vs. SharePoint Explained
• (45:30) - Counter Program Intro: "Ben Rates the 80s"
• (46:38) - Best 80s Hairstyle
• (47:45) - Favorite 80s Movie Soundtrack
• (49:41) - Favorite 80s Movie
• (52:05) - Favorite 80s Tech Device
• (54:23) - Favorite Defunct 80s Store
• (55:50) - Conclusion & Outro