Great Mondays Radio

In this episode, Josh challenges the question everyone keeps asking about AI and work, and makes the case that it's the wrong one. The framing is always the same. AI helps us do more, or it burns us out. Faster or exhausted. Pick one. But that's a biology problem, not a software problem. Microsoft's 2025 Work Trend Index shows the split. Eighty percent of the workforce says they don't have the tim...

Most fractional consultants walk into a founder's business and ask them to explain themselves. Morgan Abreu runs a note taker in the background instead. The difference is not a workflow preference. It is the whole point. The moment you ask someone to describe their own voice, they stop using it. Morgan Abreu has spent her career at the handoff point that breaks most growing companies — the moment...

In this episode, Josh challenges the question everyone keeps asking about AI in school — and makes the case that it's exactly the wrong one to be asking. The yes-no binary is a dead end. AI in school: allowed or banned. AI in writing: authentic or cheating. These are crude frames for a genuinely complicated problem. And the institutions drawing the hardest lines — the grad school deans, the publis...

Every organization is telling its people that AI matters. Almost none of them are asking their people what they actually need from it. That gap — between the announcement and the ask — is where most AI training programs quietly die. Geoffrey Roche has spent years on both sides of that gap. As SVP of Healthcare Solutions at RisePoint, he works with academic institutions trying to prepare healthcare...

In this episode, Josh weaves together three stories about where AI-driven hiring is actually headed — and why the answer to whether it's making things better or worse is: yes. The first is a conversation with someone building a high-volume AI hiring tool for a major tech company. The premise is simple: skip the resume, go straight to an AI-hosted interview. Everyone gets to speak. Everyone gets th...

Kathrin Fleer spent 12 years leading retail teams at Tiffany and Saint Laurent. She has seen firsthand what separates stores that hum with energy from ones that flatline — and it has nothing to do with the product on the shelf. It comes down to the people, how they were hired, how they were led, and whether the culture actually breathes. Now she runs her own studio advising luxury brands on aligni...

Josh hit a Claude Design usage limit this week. Four hours locked out of a presentation he was mid-build on. The feeling that came with it — that he didn't own it, couldn't just keep going — told him something about the moment we're all in. In this episode, Josh argues that scarcity thinking isn't just a feeling. It's becoming a leadership strategy. And it's contagious. Jack Dorsey cut 40% of Bloc...

In this episode, host Josh Levine and Uncork CEO Gary Hoberman unpack why most AI deployments fail before they start, how the compensation models inside large enterprises are actively sabotaging the automation they're trying to deploy, and why the switching cost moat that protected businesses for decades is disappearing faster than most CEOs want to admit. They dig into what it actually means to b...

This week Josh covers why AI is doing something economists didn't see coming — collapsing the coordination costs that made large firms powerful in the first place. It starts with a 1937 paper by economist Ronald Coase called The Nature of the Firm. His argument: companies exist because coordinating through the market is expensive. Search, negotiate, contract, repeat. It's cheaper to just put it al...

In this episode, host Josh Levine and entrepreneur Brian Sampson unpack what actually happens when you try to roll out AI across multiple businesses at once — a contract recruiting firm, a locksmith company, a cleaning business, and an AI agency he built specifically because of what he learned along the way. They dig into why employees resist tools that would make their lives easier, how proximity...

If a person produces X and AI produces X faster and cheaper, the math is simple. Replace people with AI. Except the equation isn't true. This week Josh covers AI Leadership Skill #4: Know the Value of Your People — the latest entry in The Sh*t List , the paid Substack companion to The Job Sh*t Show. It starts with a simple question: what does a doorman actually do? Holding the door is the job desc...

In this episode, host Josh Levine and operations expert Paul Swaney unpack what a two-hour factory tour can tell you about a company's culture, why AI is making it more important — not less — to get off your desk and show up in person, and why the leaders who think AI means less travel are about to lose significant ground to the ones who do the opposite. They dig into how to introduce AI into a re...

Mark Zuckerberg called it a budget trade-off. Jack Dorsey cut 4,000 jobs. Salesforce slashed its support headcount from 9,000 to 5,000. ServiceNow's CEO celebrated agents that don't need lunch or healthcare. The story these CEOs are telling is that AI made the cuts necessary. But the productivity numbers don't show it — and the pattern of how new technology actually gets adopted suggests we've bee...

In this episode, host Josh Levine and executive coach Dr. Gary Crotaz unpack why employees don't come to work for your purpose — they come for their own — and why most leaders have never once asked what that is. They dig into what an unlock moment actually is, how two questions can reveal more about a person than any engagement survey, and why the culture you're trying to build already exists insi...

For 50 years, organizations have chased one thing: efficiency. More output, less friction, faster everything. And it worked — until it didn't. In this episode, Josh sits down with organizational change expert Josh Allen Dykstra at a live conference to trace how we got here: from Milton Friedman's 1970s shareholder mandate to a workplace so optimized for productivity that there's no room left to th...

In this episode, host Josh Levine and AWS technology executive Robin Goad unpack the unwritten rules of corporate America that most people don't figure out until their mid-40s — and how AI is now adding a new layer to all of them. They dig into why visibility is fuel, how to build an internal power map that gets the right people telling your narrative in rooms you're not in, and why not talking op...

Most business leaders say their people are their greatest asset. Very few build a company that actually proves it. Bob Whalen has spent 15 years doing exactly that. As CEO of HB Global, he took a $25 million mechanical contracting company with 150 employees and turned it into an employee-owned holding company with one stated goal: make every employee a millionaire. Not as a tagline. As a financial...

The résumé was already broken before AI showed up. Now it might actually be on its way out. In this episode, Josh looks at the first viable replacement he's seen — not a shinier LinkedIn profile or a better-optimized PDF, but something closer to a behavioral fingerprint. A system that stays with you across your career, learns how you actually work, and advocates for you to employers using verified...

Most job seekers think finding work is a numbers game. Send out enough applications, hit enough easy apply buttons, and eventually something sticks. But in today's market, that approach isn't just ineffective — it's actively working against you. Mac Prichard has spent 25 years at the center of how people find work and how employers find talent. What he's learned cuts against the conventional wisdo...

The last thing your people need is another training. This week Josh previews AI Leadership Skill #2: Let Your Team Lead , the latest entry in The Sh*t List, the paid Substack companion to The Job Sh*t Show. It's built around a conversation with Geoffrey Roahe, SVP of Healthcare Solutions at RisePoint, where he helps colleges and universities modernize for the real world. When Jeffrey asks leaders...

Most leaders try to fix performance problems with better systems, clearer processes, or new hires. But what if the real bottleneck is something far more fundamental — and it starts with you? Linda Perry spent 17 years as a federal criminal defense attorney studying what drives human behavior before becoming a leadership and executive strategist. In that courtroom work, she discovered something tha...

When Anthropic dropped Claude Design and OpenAI released Images 2.0, something shifted. The ability to create professional-grade visuals — the kind that used to require years of training and hard-won expertise — got handed to everyone. In this episode, Josh argues that AI isn't replacing creative experts. It's promoting them. The people with real taste, real vision, and the language to describe wh...

Most cultures don’t fail loudly. They erode in small moments—a comment in a meeting, a policy that signals distrust, a leader who thinks they’re being clear but shuts the door instead. On this episode of Great Mondays Radio, Josh Levine sits down with Aoife O’Brien to unpack how these seemingly minor signals shape whether people thrive or disengage. Aoife shares how her own experience in a toxic w...

Most leaders are using AI to go faster. This skill is about going deeper. Coach Your People Better With AI is the first entry in The Sh*t List, the paid Substack companion to The Job Market Sh*t Show. It starts with a simple question: what if, before your next difficult one-on-one, you spent 15 minutes with an AI tool working through everything you actually know about that person? This one's built...

In a world full of leadership frameworks and culture playbooks, why does so much of it fail to stick? What if the issue isn’t strategy, but the way we develop leaders in the first place? On this episode of Great Mondays Radio , host Josh Levine talks with leadership coach and founder of The Art of Learned Intelligence, Cara-Lyn Giovanniello, about the gap between intention and behavior inside orga...