Great Mondays Radio

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...

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 coll...

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 an...

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 colle...

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 ...

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 ...

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 sup...

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...

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 employee...

Michael Villegas leads generative AI strategy for one of the country's largest interior architecture firms, and when he started testing these tools on real design work, he found the biggest risk wasn't bad output, it was that the tool felt too human to question.

Here's what we talk through:

• Why he thinks AI sounding like a person instead of a calculator is a "slippery slope" that quietly lowers our guard
• How his best prompt isn't ...

I tried something new this week. No guest, no interview, just me thinking out loud about a talk I'm building on how companies actually get value from AI.

My complaint is simple. Most of us use AI to do the same work faster, and that shortcut has a ceiling. It's why the ROI never shows up the way it's promised.

So I went looking at how scientists use AI instead. Google DeepMind's weather model, GenCast, never got taught a single rule ...

Eric Tabone, runs AI powered recruiting pipelines that process hundreds of applications a day for US companies. When we got into where the system still fails, he landed on a problem no amount of automation fixes.

Here's what we go over:

• Why he'd bet on someone who sold used cars for ten years over someone who coasted ten years at Salesforce, and what that says about how most companies screen for pedigree instead of grit
• Why he thi...

Uber burned through its entire 2026 AI budget in four months and still can't tie the spend to results. Starbucks pulled its AI inventory agent. Ford hired back 350 engineers to clean up after automated inspection. So what's actually going on?

I think most of us are stuck in mode one and mode two thinking — using AI to automate tasks or do things faster ourselves — when the real payoff is in mode three: changing what work...

What if the algorithm screening your applicants is designed to reject your best ones?

Aden Nepom, president of Art of Change, has spent almost two decades teaching executives to communicate under pressure using tools built from improv. When we got into what AI does to creativity, she landed on a problem she doesn't have a fix for yet.

Here's what we go over:

• Why she thinks LLMs are structurally built to average, and what that's do...

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 som...

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 mo...

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 communi...

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 ...

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 sa...