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 did
• How 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.

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.

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.

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.

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.

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.

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 aligning people, places, and client experiences. And as AI reshapes how leaders hire, coach, and communicate, she has strong opinions about what gets lost when we let the technology do too much of the work.

In this episode, Josh and Kathrin unpack why in-person hiring still matters even in a remote world, how AI can make managers better coaches without replacing human judgment, and why the emotional logic of luxury retail is a blueprint for any business trying to build loyalty. They dig into her three leadership principles — Know Your Why, Action Creates Energy, and People Need People — and land on a shared concern: in the race to automate everything, companies are stripping out the exact things that drive performance and meaning.

If you lead a team — or are thinking hard about where AI belongs in your culture — the most important insight here is also the most counterintuitive. The technology works best when it pulls you closer to your people, not further away.

About Kathrin Fleer

Kathrin Fleer is an international luxury brand expert and founder of Studio Fleer, where she helps brands grow by aligning people, places, and client experiences. She has led retail teams across Europe and internationally for over a decade, including director-level roles at Tiffany and Saint Laurent. Her leadership philosophy is built on three principles: Know Your Why, Action Creates Energy, and People Need People. Learn more at studio-fleer.com.

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.

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 Block's workforce and then told the world most companies would follow within a year. That's not a prediction — it's a frame that spreads. The story of not enough jobs, not enough capital, not enough time is landing in boardrooms and news feeds and heads at 11pm. And if you're a leader absorbing it, it is reaching your team whether you mean it to or not.

But at a roller derby match in Portland, Josh met a software engineer from Stripe. Same industry. Same moment. Completely different tone. Cautious. Deliberate. Not panicking. And $2.2 billion in free cash flow.

The difference isn't resources. It's the mindset behind the decisions.

Josh introduces a new framework — the panic trap — a two-by-two that helps leaders identify what kind of decision they're actually making before they make moves that can't be undone. Because some decisions you can walk back. And some you can't.

About The Job Market Sh*t Show

The Job Market Sh*t Show: How AI Broke Hiring and What Might Be Next is an investigation into how hiring actually works now, how AI and automation have upended the process, and why the old rules no longer apply. It blends reporting, analysis, and firsthand stories from inside a labor market that’s increasingly algorithmic, opaque, and indifferent to the people moving through it—while asking what, if anything, might replace a system that no longer seems to work for humans on either side of the process.

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 build an AI-native company, why every employee should be trying to automate their own job, and what a $14 million duplicate wire transfer taught Gary about the hidden cost of code that nobody in the industry is measuring.

If you lead an organization navigating AI — or you're trying to figure out whether to lean into it or protect what you have — the fear is understandable. But leaning back is how you fall.

About Gary Hoberman

Gary Hoberman is the CEO and founder of Uncork, an enterprise software company built to eliminate the technical debt and bureaucracy that holds large organizations back. Before founding Uncork, Gary served as Global CIO at MetLife, one of the world's largest insurance companies, and held senior technology leadership roles at Citigroup and Bankers Trust. He has spent his career at the intersection of technology, enterprise operations, and organizational change. Learn more at uncork.com.

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.

→ Subscribe to The Sh*t List on Substack for biweekly AI Leadership Skills content.

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 all inside one organization. That logic built every large firm you've ever worked at.

AI is now dismantling it from the outside.

A lawyer profiled in the New York Times mounted four Mac minis under his desk and runs five AI agents simultaneously — reading court notices, messaging clients in Spanish, drafting counter proposals. No firm. No overhead. No coordination tax.

The same lift that solopreneurs and small teams are feeling right now? Large organizations aren't getting it. Not because AI doesn't work — but because the friction that protects big companies from chaos is the same friction preventing AI from doing anything remarkable inside them.

The capability ceiling just got very crowded. And the large firms that built their advantage on scale are now finding out that scale might be the vulnerability.

About The Job Market Sh*t Show

The Job Market Sh*t Show: How AI Broke Hiring and What Might Be Next is an investigation into how hiring actually works now, how AI and automation have upended the process, and why the old rules no longer apply. It blends reporting, analysis, and firsthand stories from inside a labor market that’s increasingly algorithmic, opaque, and indifferent to the people moving through it—while asking what, if anything, might replace a system that no longer seems to work for humans on either side of the process.

Correction: In this episode Josh refers to "Robert Coase." The economist's name is Ronald Coase. Apologies for the error.