Great Mondays Radio

Why does every new priority land on top of the old ones instead of replacing them? A company that gives its leaders one protected AI hour a week has changed 2.5% of the week and left the other 97.5% right where it was.In this episode:Susan, a manager of 60, gets a CEO email telling her to “drive AI adoption” and types it at the bottom of a to-do list that hasn’t lost a single itemA 2021 study in Nature, including a university president whose call for ideas got about eight suggestions to add for every one to cutHow Atlassian swapped the memo for a working demo in design reviews, a real case of stopping one thing to start anotherBefore AI goes on your list, ask your boss what’s coming off it.About The Job Sh*t ShowThe 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.

What if work isn’t broken because we’re doing it wrong?What if it’s broken because of the story we’ve built our lives around?That’s where Josh Allan Dykstra landed. And he didn’t get there from a think tank. He got there the hard way. His tech company, #lovework, had a product people loved. Major clients. Everything you’re supposed to have.It couldn’t survive.So Josh went looking for what was really broken. For two decades he’d tried to fix work one level at a time. This time he went all the way down. What he found is in his new book, Work Will Kill Us All.Yes, that’s the title. And yes, he calls himself an optimistic futurist. Stick with him.In this episode we talk aboutWhy the postwar American middle class wasn’t luck, and what a 91 percent top tax rate and strong unions had to do with itHow AI fits a pattern that’s hundreds of years old, from the fenced fields of England to everything we’ve ever posted onlineWhy he gave up on universal basic income, and why he now thinks the answer is things communities own together, like a hospital owned by the town it servesAbout Josh Allan DykstraJosh is an optimistic futurist, keynote speaker, and host of the Hello Tomorrow podcast. His argument is one you won’t forget the next time you’re in line at the grocery store.The market is great at making things we want. Weird socks. Trader Joe’s snacks. It’s terrible at providing the things we need.So which one are you working for?Work Will Kill Us All comes out November 11.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 shoved every one of us through the hardest step of change, so the real question is whether you’re changing on purpose or getting changed. In this episode:How losing my anchor client in 2025 forced me to rethink my own career, and why 2026 became my year of experimentsKurt Lewin’s unfreeze, change, refreeze model, and why AI forced everyone through the step I spent 20 years pushing people towardA national healthcare retailer where everyone adopted AI and got more reports and more emails, not better workIf your company handed you an AI seat and said go experiment, listen up.About The Job Sh*t ShowThe 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.

Paul Wachtler is SVP of AI, Data and Strategy at Exiger, where his job is getting the whole company using AI. He spent more than 15 years in business intelligence, not software development. Once he started building with AI coding tools, he replaced Exiger’s legacy BI server so fully that the company retired it at renewal.Here’s what we talk through:Why finding time for AI is the leader’s job, and why “Tuesday mornings for an hour or two” beats telling people to go experimentHow a team moves past one person and a chat window, starting with a shared folder where the AI’s outputs get written back, not just pulled fromWhy, now that anyone can build an app, a flop is more likely a bad idea than a bad buildAbout 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.

A leader at a big tech company told me she spends hours in rooms where people can’t explain how they do their jobs today. So how are they supposed to reinvent them with AI?In this episode:A chief of staff who types the same “make this more concise” prompt 10 times a day and wonders if that’s all there isWhat Y2K got right. Companies hired experts instead of asking every employee to fix the system themselves.An HR leader’s warning that new tools stacked on old processes make work worse, and companies will have spent too much to back outHas a process at your work gotten worse since AI showed up? Check out the full article at joshlevine.substack.comAbout The Job Sh*t ShowThe 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.

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 rightHow he held Krispy Kreme shops in West Virginia and Atlanta to different diversity expectations, because each should reflect the market it servesWhy he shelved a company’s unconscious bias training until it could say what happens when someone reports a racist actAbout Christopher ByloneChristopher 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.

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 countHow he uses the dull, the draining, and the distracting to pick a real use case before anyone gets a Copilot licenseWhy saying “we’re still working through it” during a reorg beats silence, because people fill the gap with the layoff storyAbout Jim SpignardoJim 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.

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 episodeA 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.comAbout The Job Sh*t ShowThe 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.

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 wrongHow an engineering team writing 10x more code with AI ended up exhausted from checking 10x more edge casesWhy calculating customer lifetime value went from six months of work to about a week, and why that's no reason to cut your analystsAbout Tim SheaTim 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.

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 betterWhy Jevons Paradox breaks when AI makes content almost free but your hours and attention stay the sameWhy 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 ShowThe 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.