Great Mondays Radio

Hosted by Josh Levine

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198

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Aug 2026

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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

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60 recent

August 20, 202630 min

We need to talk about professional services.

My friend Lindsey Caplan buys professional services. She also sells them. Recently she opened a deliverable from someone she's paying real money, and found AI output staring back at her. What she landed on is something I keep coming back to. We've confused what we actually pay professional services people for. It was never really the output, even if it looked that way for years. It's the judgment, the pattern matching, the thing someone builds by doing this work long enough to see what you can't. I said something similar in a recent interview. Domain expertise is the new oil. Information is everywhere now. Knowledge is a utility. What's rare is someone who has seen enough of the pattern to tell you what it means. The disclosure question is where it got messy for us, and I've been here before. Five years ago it was whether your web guy only builds on WordPress. Now it's whether the person you hired is quietly routing your project through AI without telling you. Lindsey's take isn't that AI is the problem. It's that nobody's saying up front where they're using it and where they're not, and that silence is what kills the trust. Here's where I landed by the end of the conversation. AI was never built to help you do less work. It's not a shortcut, and treating it like one is exactly what's breaking down in the industries where time was always the product being sold. 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.

August 17, 202630 min

If We Could Replace You, We Already Would Have

What if the healthiest company in your industry has nothing to do with its stock price? Chase Sterling has spent almost 25 years inside workplace well-being, running Wellbeing Think Tank and pulling sentiment straight from Reddit and TikTok threads that never make it into a press release. When I asked her where things are headed, she didn't sugarcoat it. We haven't hit bottom yet. Here's what we go over: Why attrition tells you more about a company's health than its stock price ever will How CEO pay climbed from 10 times the average worker in the 80s to over 300 times today, and why Dr. Bronner's caps its own leadership at 20 times on purpose Why a leader saying "let's just ask AI" before anyone else speaks is the fastest way to kill a room About Chase Sterling Chase Sterling founded and runs Wellbeing Think Tank , a nonprofit focused on helping employers balance organizational performance with worker health. She's worked nearly every corner of the wellness industry, from vendor to broker to internal HR, and her core belief is simple. The worst behavior a company tolerates is its actual culture, no matter what's painted on the wall. 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 .

August 13, 202616 min

Episode Revist: If Everyone Hates LinkedIn, Why Are We Still There? The Role of Platforms In Our Search for Jobs

LinkedIn is noisy, frustrating, and often feels like a job search dead end—so why are we still using it? In this episode, Josh unpacks the tension we all feel about the platform, exploring what still works (profiles, networks, discovery) and what definitely doesn’t (spam, false leads, and the chaos of too much noise). Plus, a glimpse into how job seekers are starting to reclaim control—one Slack or Discord community at a time. 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.

August 10, 202644 min

Warm Body, Figma Skills, Good Luck. That’s Hiring Now.

Why do recruiters only need two minutes to decide if you're worth a call? I talked to Josh Silverman , founder of PeopleWork Partners, who has as spent 30 years connecting designers with opportunities, and recently placing candidates at companies like Target, Netflix, and OpenAI, and he told me the whole hiring system runs on guesswork dressed up as process. Here's what we go over: Why most recruiters spend one to two minutes on a portfolio before sorting a candidate into a yes or no pile How the entire burden of proving a good hire falls on the candidate, while nobody ever checks if the company or manager was actually the right fit Why your best work gets stuck in Jira tickets and Slack threads that disappear the moment you leave a job About Josh Silverman Josh Silverman is the founder and CEO of PeopleWork Partners (peoplework.partners). He spent a decade chairing the Master of Interaction Design program at California College of the Arts before the school's closure, and he now places designers and product people in roles at companies including Target, Cisco, Netflix, and OpenAI. He thinks the resume is a dead format and that soft skills, not technical ones, are actually the harder skills to master. 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 .

August 6, 202611 min

Am I a Crappy Boss to my AI?

Managing an AI agent is like speed running my worst management habits. I get frustrated, I start micromanaging, and I catch myself acting like the boss I used to complain about. Boris Berenberg, founder of Zero AI, told me we're turning everyone into a manager now. There's no such thing as a non managerial role anymore. Jack Dorsey disagrees. He called middle managers "an information routing protocol," cut 4,000 jobs at Block, and said he wants all 6,000 employees reporting straight to him. If a manager is just a router, sure, a computer can replace that. But that's the part of the job that sucks anyway. Here's the part that doesn't. Gallup says managers account for 70% of the variance in employee engagement. Google's own research found coaching was the top trait of their best managers, and technical skill was dead last. We just never train for it. There's also a hard cap. One person can really know maybe eight people well. That's why good teams stay small. It's slow. It's also the whole job. So middle management might be the last job that still requires you to give a shit. Now that we're all about to manage a team of bots, the question is whether we show up as a coach or a router. 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.

August 3, 202631 min

The Doorman Problem: What AI Actually Can't Replace

Casey Schaffer , a leadership coach who specializes in how professional identities shift, joined me this week, and she's watched companies make the same mistake twice, first with remote work, now with AI, and she's not convinced this round goes any better. Here's what we cover: Why I think the exact same trust collapse from "prove you're productive then get called back anyway" is about to repeat with AI cuts How one company Casey worked with onboards a new AI agent alongside every new hire, with the manager training both together Why the doorman problem shows you don't actually know what a job is until AI fails at replacing it About Casey Schaffer Casey Schaefer runs Definitions Coaching and Consulting , where she works with people leaders navigating identity shifts tied to career change. Her sharpest opinion in this one is that performance management systems haven't moved an inch even as the skills companies actually need have changed completely, and I think she's right that this gap sits squarely on HR's desk to fix. 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 .

July 30, 202610 min

Is AI the Light Bulb or the Loom?

Josh's instinct is always to reach for a matching disaster from history. He thinks that's a trap, because by the time you pick the analogy, you've already picked the answer. He found the proof in a New York Times episode his wife sent him. The chief economics correspondent Ben Casselman laid out two futures for AI. One matched the internet, which displaced travel agents slowly enough that most just aged out. The other matched the China shock, which flattened entire manufacturing towns overnight. Josh traced where these comparisons actually come from. Mary Daly at the San Francisco Fed reaches for electricity, because for a central banker the moral has to be patience. Journalist Brian Merchant reaches for the Luddites, because the real history is nine years of factory workers petitioning Parliament before anyone smashed a loom. Neither side is lying. They're just telling you what they think their job is by which wreck they pick. Josh built a timeline of these disruptions for a talk in Seattle and checked every date against a source. Three of the most repeated stories turned out to be folklore. He kept them in anyway, labeled, because a myth people keep reaching for still tells you something true about what they're scared of. 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.

July 27, 202641 min

97% Of Referral Hires Work. Why Everyone Still Posts On Indeed.

Fletcher Wimbush , CEO of Discovered, spent his career building a hiring platform meant to fix a broken system, and he'll still tell you nothing about hiring has actually improved in hundreds of years. On Great Mondays Radio we get into all of it: Why almost no hiring manager takes the 15 minutes to do a real job analysis, and just tells AI to "write me a job description" instead How his platform is 98.5 percent accurate at knowing who to reject, but leans on humans for structured interviews and reference checks to know who to actually hire Why he calls the AI hiring arms race mutually assured destruction, with employers adding more filters and candidates building their own bots to beat them About Fletcher Wimbush Fletcher is co-author of Hiring Talented Team Players and built Discovered as a new kind of applicant tracking system, one meant to replace the "old robots" with better ones. He's blunt that 87 percent of referral hires turn out good to phenomenal, that resumes are mostly embellishment, and that if you can cheat your way through every filter he's built, he still wants you on his team. 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 .

July 23, 202611 min

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.

July 20, 202634 min

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 five The question she asks anyone in a job search spiral: are you being strategic, or just anxious and calling it strategy Why 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 .