Great Mondays Radio

Josh Levine
  • 4.8 (19)
  • Business
  • Updated Weekly

AI, distributed work, and technology are changing how organizations operate. Leaders are discovering that the mechanisms they inherited to manage their teams weren’t built for this environment. Every week, host Josh Levine interviews a business leader about their experiences integrating AI into their team and company's work. If you know a director, VP, or people leader grappling with teams, AI, and the future of work, tell them to apply to be a guest on the show at https://radio.greatmondays.com/podcast-guest

  1. 1d ago

    Are We Using AI Backwards? An Improv Coach Says We’re Doing It Wrong. (Substack preview)

    The instinct is always the same. Ask AI to complete the task, assemble the deck, execute the command. Josh thinks that's backwards, and the bill for that mindset is already coming due. So Josh went looking for a different way to use the tool, one built on opening ideas up instead of closing them down. He found it in leadership coach and improviser Aidan Nepon. She once coached a singing student without a single technical note, just told her to sing like Beyoncé. The persona did more work than any correction could, and it's the same principle Josh thinks we're missing with AI. Josh breaks down three improv games Aidan uses with clients, and turns each into a way of prompting AI that pushes past the obvious answer. The real question was never how to get AI to finish your thought. It's how to get it to argue with you instead. Follow The Job Sh*t Show investigation at https://joshlevine.substack.com About The Job Sh*t Show The Job Sh*t Show is an investigation into how finding, keeping, and doing work is changing faster than anyone is admitting — and what that actually looks like for real people on the ground. The Sh*t List is a paid Substack for leaders who want to stay ahead of what AI is doing to the workplace — and actually do something about it. Every other week, subscribers get a new AI Manager Skill: one practical, field-tested move for leading your team better in an AI world.

    Are We Using AI Backwards? An Improv Coach Says We’re Doing It Wrong. (Substack preview)

  2. 4d ago

    AI Isn’t the Enemy. Your Anxiety Is.

    Zhou Fang, founder of Intersectional Group, spent this year testing whether abundance thinking actually holds up against a job market that feels like scarcity. She still gets asked to prove it. On Great Mondays Radio we get into all of it: Why she says two people sharing five job leads each end up with ten opportunities, not fiveThe question she asks anyone in a job search spiral: are you being strategic, or just anxious and calling it strategyWhy companies keep cutting roles for AI, then quietly hiring the same roles back About Zhou Fang Zhou Fang teaches abundance mindset and intersectionality to leaders navigating change. She's watched company after company treat AI layoffs as a plan when they were really a guess, and she has a clear read on what leaders should be doing instead. About Great Mondays Radio → Think you'd be a great guest on the show? Apply here. → I’ve spent two decades helping leaders fix their culture. Learn how I can support your work Great Mondays. → Want sharp takes on AI and the future of work? Read The Job Sh*t Show on Substack. → Watch Great Mondays Radio episodes on YouTube.

    AI Isn’t the Enemy. Your Anxiety Is.

  3. Jul 13

    Your Dev Team Is 70% Faster. Now What?

    How far can “AI does more” go before “we need fewer people” becomes true? Anthony Rose, founder and CEO of Seedlegals, a legal tech platform, spent a year testing that exact question, and he still doesn’t know. On Great Mondays Radio we get into all of it: Why he refused to cut 20 percent of his team just because everyone else didHow his team turned a checklist built from thousands of filings into an AI system that catches almost every error before it ever reaches a human Why he’d still bet against AI ever inventing something truly new About Anthony Rose Anthony Rose has built and sold multiple companies before this one. Over the past year he’s rebuilt his team’s workflows around AI without cutting a single job, and he has strong opinions about which roles are actually safe right now, and which ones just feel that way. About Great Mondays Radio → Think you'd be a great guest on the show? Apply here. → I’ve spent two decades helping leaders fix their culture. Learn how I can support your work Great Mondays. → Want sharp takes on AI and the future of work? Read The Job Sh*t Show on Substack. → Watch Great Mondays Radio episodes on YouTube.

    Your Dev Team Is 70% Faster. Now What?

  4. Jul 9

    Will We Ever Stop Work-Maxxing? The False Promise of Infinite Productivity

    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 time or energy for the work already on their plate. One fractional executive on a call put it plainest. "I'm 53 and I am tired." Josh's grandfather used to joke that owning a business meant working any 24 hours you wanted. Josh built a bot this year to book his own podcast guests. It's faster. He's not any less tired. The question was never how to work faster. It's what happens when a species that needs sleep gets asked to keep pace with something that doesn't. Josh shares where he's drawing his own line between speed and rest. Follow The Job Sh*t Show investigation at https://joshlevine.substack.com About The Job Sh*t Show The Job Sh*t Show is an investigation into how finding, keeping, and doing work is changing faster than anyone is admitting — and what that actually looks like for real people on the ground. The Sh*t List is a paid Substack for leaders who want to stay ahead of what AI is doing to the workplace — and actually do something about it. Every other week, subscribers get a new AI Manager Skill: one practical, field-tested move for leading your team better in an AI world.

    Will We Ever Stop Work-Maxxing? The False Promise of Infinite Productivity

  5. Jul 6

    Your Voice. Everywhere. Without You. Your first sales hire used to be inevitable. Now it’s optional.

    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 when a founder who has been running sales out of their own head has to hand that function to someone else. As founder of Melia Strategy, she works with founders who are wall-to-wall in meetings, running on institutional knowledge they have never written down, selling through relationships and instincts a new hire cannot inherit. Her method is not to clone the founder. It is to extract what is actually working, edit out what is not, and build a playbook that survives the transition. She does that with AI and without the founder in the room. About Morgan Abreu Morgan Abreu is a fractional sales consultant and founder of Melia Strategy, specializing in the transition from founder-led sales to a scalable sales organization. She works with founders across industries to capture, refine, and systematize how they sell — using AI to surface communication patterns that founders themselves cannot always articulate. Connect with her on LinkedIn at Morgan Abreu. Morgan is also building Referral Reef — a trust layer for fractionals and freelancers built around transparency and accountability in warm introductions. Whether you're looking to build your own referral system or be part of a high-trust talent network, the founding cohort is open now. About Great Mondays Radio → Think you'd be a great guest on the show? Apply here. → I’ve spent two decades helping leaders fix their culture. Learn how I can support your work Great Mondays. → Want sharp takes on AI and the future of work? Read The Job Sh*t Show on Substack. → Watch Great Mondays Radio episodes on YouTube.

    Your Voice. Everywhere. Without You. Your first sales hire used to be inevitable. Now it’s optional.

  6. Jul 2

    Should AI Be Allowed In School? We’re asking the wrong question. (Substack preview)

    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 publishers who pulled Mia Ballard's horror novel Shy Girl over AI accusations her author denied — aren't protecting learning. They're avoiding the harder conversation about where the guardrails actually belong. Anne figured out her own. Research, yes. Writing, no. Checking a paper for errors, yes. She named her AI Otis. And by semester two, she'd built a working relationship with it that her distributed, at-times-lackluster teachers couldn't come close to matching. The question was never should AI be allowed. It's where do we install the guardrails — and who gets to decide. Josh shares a framework for developing your own boundaries around AI use, for yourself and your team. The full essay and the framework are on The Sh*t List. Follow The Job Sh*t Show investigation at https://joshlevine.substack.com About The Job Sh*t Show The Job Sh*t Show is an investigation into how finding, keeping, and doing work is changing faster than anyone is admitting — and what that actually looks like for real people on the ground. The Sh*t List is a paid Substack for leaders who want to stay ahead of what AI is doing to the workplace — and actually do something about it. Every other week, subscribers get a new AI Manager Skill: one practical, field-tested move for leading your team better in an AI world.

    Should AI Be Allowed In School? We’re asking the wrong question. (Substack preview)

  7. Jun 29

    1,300 Beds. Zero Prepared Nurses. Why the People Closest to the Work Already Know What Training They Need

    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 workers for a clinical environment that is already deep into AI deployment — virtual nursing, AI-assisted imaging, pharmaceutical systems. Before that, he sat inside Siemens Healthineers, one of the organizations that has been using AI in medical technology for longer than most companies have been talking about it. He is not a theorist. He is someone who has watched the gap between industry readiness and institutional preparation widen in real time, in a field where that gap has direct consequences for patients. About Geoffrey Roche Geoffrey Roche is a healthcare workforce strategist, speaker, and Senior Vice President of Healthcare Solutions at RisePoint, an educational and workforce solutions company serving universities and academic institutions across the country. He has spent his career on both sides of the academia-industry divide — including a tenure at Siemens Healthineers — and is a regular voice at Chief Learning Officer events on AI, workforce preparation, and the future of healthcare education. Geoffrey's work is rooted in a simple belief: the gap between what hospitals are building and what schools are teaching is a leadership problem, not a technology one. Connect with him on LinkedIn at geoffrymroche. About Great Mondays Radio → Think you'd be a great guest on the show? Apply here. → Running our show takes a lot of coffee. Support us for just $3/month. → Watch Great Mondays Radio episodes on YouTube. → Want to learn more about Josh's work at Great Mondays? Visit greatmondays.com.

    1,300 Beds. Zero Prepared Nurses. Why the People Closest to the Work Already Know What Training They Need

  8. Jun 25

    Is AI changing hiring for better or worse? Yes.

    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 the same questions. No primacy bias, no 4pm fatigue, no inconsistency. Done well, it might actually be fairer than what we have now. The second is a Stanford study on algorithmic bias that found 26% of Black applicants and 15% of Asian applicants applied to positions where AI discriminated against their racial group. Over 60% of Fortune 100 companies use the same third-party hiring algorithm. When one vendor mediates hiring at that scale, bias doesn't just exist — it compounds. Quietly. Invisibly. Across every company using the same tool. The third is what happens when candidates stop trusting the process. They go around it. Build something. Show up with proof of work instead of a resume. It's smart. And it's also a signal. Because if it's a process people don't trust, it will become a process people game. And a process people game stops working for everyone. The question in the future isn't whether AI should be involved in hiring. It's what kind of AI, built by whom, and accountable to who. Nobody's answered that yet. But at least now we're asking. About The Job Sh*t Show The Job Sh*t Show is an investigation into how finding, keeping, and doing work is changing faster than anyone is admitting — and what that actually looks like for real people on the ground. The Sh*t List is a paid Substack for leaders who want to stay ahead of what AI is doing to the workplace — and actually do something about it. Every other week, subscribers get a new AI Manager Skill: one practical, field-tested move for leading your team better in an AI world.

    Is AI changing hiring for better or worse? Yes.
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4.8
out of 5
19 Ratings

About

AI, distributed work, and technology are changing how organizations operate. Leaders are discovering that the mechanisms they inherited to manage their teams weren’t built for this environment. Every week, host Josh Levine interviews a business leader about their experiences integrating AI into their team and company's work. If you know a director, VP, or people leader grappling with teams, AI, and the future of work, tell them to apply to be a guest on the show at https://radio.greatmondays.com/podcast-guest

Information

  • Creator
    Josh Levine
  • Years Active
    2023 - 2026
  • Episodes
    192
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Josh Levine
  • Show Website
    Great Mondays Radio

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