Great Mondays Radio

Hosted by Josh Levine

Business EntrepreneurshipInterviews guests

Website RSS feed

Episodes

200

Latest episode

Oct 2026

Language

About the show

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

Listen to episodes

60 recent

October 23, 202634 min

Who’s To Blame When AI Decides? Christopher Bylone on AI Accountability.

Christopher Bylone is a People Experience Practitioner at Innovation Unbiased and the former Global Head of Belonging at Krispy Kreme. After Claude read his silence on 20 decisions as a yes and ran a project to a critical failure, he wrote a rule that stops all work until he signs off on every call. Here’s what we talk through: Why he tells leaders to expect at least three years of falling belonging scores once they start doing the work right How he held Krispy Kreme shops in West Virginia and Atlanta to different diversity expectations, because each should reflect the market it serves Why he shelved a company’s unconscious bias training until it could say what happens when someone reports a racist act About Christopher Bylone Christopher Bylone is People Experience Practitioner at Innovation Unbiased and host of the I Know I Belong When podcast. He created the title Global Head of Belonging for himself at Krispy Kreme in 2023 and launched the company’s first global belonging strategy. He argues belonging is a birthright, bigger than any workplace initiative. He’s even built it into a formula where justice sits in the denominator, because it decides whether belonging spreads across a company or pools with the people who already have privilege. 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 .

October 16, 202630 min

Another Reorg? AI Enablement Director Jim Spignardo on What’s Driving It.

Jim Spignardo is Director of Cloud Services and AI Enablement at ProArch, and he thinks AI’s worst answers are the most useful thing it gives you. When the tool gets your company confidently wrong, he treats that as a red flag pointing straight at a process nobody ever wrote down. Here’s what we talk through: Why his first request to clients is “show me where it’s documented,” and why an offer to get a bunch of people on the phone doesn’t count How he uses the dull, the draining, and the distracting to pick a real use case before anyone gets a Copilot license Why saying “we’re still working through it” during a reorg beats silence, because people fill the gap with the layoff story About Jim Spignardo Jim Spignardo is Director of Cloud Services and AI Enablement at ProArch , where he leads the AI governance council. He has more than 25 years in IT, much of it on Microsoft’s platform and Copilot. He wrote The AI Turning Point, a business book told through a fictional company, cartoons included. He doesn’t buy the idea that any company that hasn’t started on AI is already finished. His window is 12 to 18 months. If you still don’t have someone who owns automation and AI by then, that’s when you fall behind. 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 .

October 13, 20264 min

Should AI Make Your Work Harder?

AI Leadership Skill #8 (Substack Preview) I spent two hours prompting my way to a client deck. Then I threw it out. The story was clean and the slides looked great, but I couldn’t defend a single one of them. That’s where AI Manager Skill #8 starts. Let AI do the making. Keep the thinking for yourself. In this episode A report, a deck or a strategy used to prove someone did the thinking. It doesn’t anymore. My colleague Scott paid an expert he trusted for a nonprofit plan. He got back a long, muddy document stuffed with AI phrases. Ellie Hartman at Agile One uses AI to add friction, not remove it. Paid subscribers get the full skill and a downloadable cheat sheet. Go look at the last thing you shipped. Could you defend every line? Check out the full article at 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.

October 9, 202640 min

Domain Expertise is the New Oil

Tim Shea is founder and CEO of LatticeWork Insights, a data science agency for retail and direct to consumer brands. Everyone says data or compute is the new oil. Tim thinks it's domain expertise, because when your best, average and weakest people use the same AI, they get wildly different results. Here's what we talk through: Why one of his clients made a rule that anyone who ships work made with AI puts their name at the top and goes down with the ship if it's wrong How an engineering team writing 10x more code with AI ended up exhausted from checking 10x more edge cases Why calculating customer lifetime value went from six months of work to about a week, and why that's no reason to cut your analysts About Tim Shea Tim Shea is founder and CEO of LatticeWork Insights , a data science agency that helps retail and direct to consumer brands reach their next stage of growth. He's run it for about a decade on top of 25 years in the field, with clients like the NBA, the UFC, Sweetgreen, Princess Cruises and Reddit. AI changed how he sells it. He now pitches return on analytics spend, because he says clients should judge him on whether he made them more money, not on whether they got a Tableau dashboard. 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 .

October 6, 20269 min

Is AI Making Us Make Too Much?

Is AI making us make too much? I designed a workshop with AI for the first time, and it buried a good idea under a pile of stuff nobody will ever open. In this episode: How a Notion page, a work pack and a stack of worksheets made my workshop worse, not better Why Jevons Paradox breaks when AI makes content almost free but your hours and attention stay the same Why output no longer proves you're productive, and the question a colleague asked that I can't shake. What is worth rejecting? The next time AI hands you more, ask what you'd cut. 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.

October 2, 202638 min

Is Your Team Faking AI Adoption?

Sheryl Anjanette is founder and CEO of Parsley360, with a background in cognitive behavioral neuroscience. She told me about a senior sales exec at one of the big tech companies whose team was asked to teach their AI everything they know, and he admitted they're all teaching it the minimum. Here's what we talk through: Why the adoption numbers on your dashboard might be measuring compliance, because people tell leaders what they think leaders want to hear How the adoption curve drops into a valley, and why she says motivation is the last lever to pull to get it back up Why leaders who cut headcount for AI need to check whether AI picked up the work or their best people did About Sheryl Anjanette Sheryl Anjanette is founder and CEO of Parsley360 , with over three decades of leadership experience and a background in cognitive behavioral neuroscience. She gave a TEDx talk called How Empathetic AI Can Change the World. She argues empathy is a cognitive skill any leader can practice, because you don't have to feel what someone feels to imagine standing in their shoes. 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 .

September 29, 20267 min

It’s Not My Fault—The AI Did It.

Another solo one. No guest, just me chewing on something that's been bugging me for months, which is the way we talk about AI. My complaint is about language. We say AI thinks, decides, and acts on its own. Most people know it isn't alive. But when we talk about a tool like it has agency, we quietly hand it the blame too. So I went back and read what the people building it have said. In 2024, Dario Amodei wrote that AI could take on tasks the way a smart employee would. A few months later, Jensen Huang said IT departments would become the HR department for AI agents. That's the language of hiring, not software. Then things got weird. In one of Anthropic's own lab tests, Claude deceived the people running it. And when an OpenAI agent broke into a government website, the company's explanation made the model the one doing the acting. Same move both times. Give the machine a personality, and the humans behind it get to step out of the frame. Here's where I land. Whoever builds and prompts the AI owns what it does. I'm not done with this one. Next I want to get into what owning it actually looks like at work. 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.

September 21, 202649 min

Is Everyone About to Become a Manager?

Boris Berenberg is CEO of Z0.ai, and when he built his own outreach system he didn't try to hide that it was automated. He decided to say so up front, and found that up to 40 percent of the people who responded brought up the disclosure before anything else. Here's what we talk through: Why he thinks cutting headcount to save money on AI is proof you couldn't think of anything better to do with it How Ikea moved 1,500 customer support reps into a new role instead of laying them off, and turned it into over a billion dollars in revenue Why the fastest way to tell if someone's scared of AI is to ask whether they manage people About Boris Berenberg Boris Berenberg is founder and CEO of Z0.ai , built on the idea that AI should grow a company's top line, not just cut its costs. Before that he ran a consulting business that walked into massive tech installations and told clients up front when a project was going to fail, because he says the real thing he was selling wasn't the outcome, it was someone to blame if it went wrong. 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 .

September 17, 202610 min

Lightening Case Study:️ Fusion Reactors + Plant Milk

Fusion plasma has been thirty years away for seventy years. In 2022, DeepMind actually cracked part of it. Not by teaching the physics. They just described the shape they wanted and let the AI figure out the steps. This caught my attention, so I went looking for more examples like these. Food scientists did the same thing trying to build a better milk substitute. Measured everything about real milk, handed it to AI, and asked for a formula. It came back with pineapple and cabbage - nobody would guess that it would work but it does. Perfumers are doing it too. Feed AI what's popular and what's in it, and it suggests combinations no human nose would try. Most of us use AI to do our same old work a little faster. That's the ceiling. That's why the ROI never shows up. But fusion plasma is different. Nobody handed over the steps for this one, they handed over the destination and let AI find its own way there. Give AI the destination, not the directions. That's the rule I'm testing this week. 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.

September 14, 202638 min

AI Can Replace Coordination. It Can’t Make People Feel Motivated.

Jason Lauritsen, CEO of Connected Performance Group, spent close to two years building a study on workplace connection with almost 300,000 employee responses, and what he found upends the assumption that the manager relationship matters most. Here's what we cover: Why connection to a company's purpose beat manager connection as the strongest predictor of motivation, even though almost nobody bet on it How highly connected employees turned out to be 6.7 times more motivated and 7 times more likely to recommend their company as a place to work Why Jason argues AI won't flatten management, because if a bot can do what a manager does, that manager was never doing the real job About Jason Lauritsen Jason Lauritsen (connectedperformancegroup.com) has spent two decades studying what makes work relationships function, going back to his book Social Gravity. His new research argues connection isn't a byproduct of good culture, it's the fuel that produces it, and he has a specific theory about which type of connection actually moves the needle and why almost no company is building for it. 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 .