In this episode, host Josh Levine and AWS technology executive Robin Goad unpack the unwritten rules of corporate America that most people don't figure out until their mid-40s — and how AI is now adding a new layer to all of them. They dig into why visibility is fuel, how to build an internal power map that gets the right people telling your narrative in rooms you're not in, and why not talking openly about how you use AI is quickly becoming a career liability.

If you lead a team — or you're trying to move up inside one — the soft skills still matter. But the floor just got higher, and knowing how to play both games at once is what separates who gets promoted from who gets passed over.

About Robin Goad Robin Goad is a technology executive at Amazon Web Services, speaker, author, and growth consultant with over 32 years of experience in corporate America. She began working with AI companies in 2014 — long before most organizations knew what to do with the technology — and has spent her career studying how high performers actually get ahead inside large organizations. She is the author of Girl by Birth, Woman by Fire. Learn more at therealrobingoad.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.

Most business leaders say their people are their greatest asset. Very few build a company that actually proves it.

Bob Whalen has spent 15 years doing exactly that. As CEO of HB Global, he took a $25 million mechanical contracting company with 150 employees and turned it into an employee-owned holding company with one stated goal: make every employee a millionaire. Not as a tagline. As a financial commitment backed by a plan, a structure, and a track record that's already delivering.

In this episode, Josh and Bob dig into what it actually takes to build a culture of ownership — not the poster-on-the-wall version, but the kind that reaches field technicians who never sit at a desk, spans multiple acquired companies, and compounds in value over decades. They talk about why the ESOP is a tool, not the culture itself, why Bob spends 50% of his time on culture, and why the hardest problem he still hasn't solved is getting employees to push back when something's wrong.

If most companies are moving toward short-termism and disposable workers, this episode is a clear-eyed look at what the opposite actually requires.

About Bob Whalen

Bob Whalen is the CEO of HB Global, an employee-owned holding company operating across commercial mechanical contracting, 5G infrastructure, and real estate services. Since acquiring his first stake in HB McClure in 2008, Bob has built HB Global around a single organizing principle: that retirement is the company's responsibility, not the employee's. He is a vocal advocate for the ESOP model as a tool for keeping businesses locally owned, rewarding the people who build them, and competing against private equity on terms that don't require selling out the workforce. Learn more at hb-global.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.

The résumé was already broken before AI showed up. Now it might actually be on its way out.

In this episode, Josh looks at the first viable replacement he's seen — not a shinier LinkedIn profile or a better-optimized PDF, but something closer to a behavioral fingerprint. A system that stays with you across your career, learns how you actually work, and advocates for you to employers using verified evidence instead of bullet points you stretched to fit a job description. Drawing on a lecture from the founder of Inspire AI, Josh explores what longitudinal profiling could mean for candidates, why the two-sided market problem is the real obstacle, and what you can start doing right now before the technology catches up. The résumé isn't just a formatting problem. It's a representation problem. And for the first time, there's a hint of something better.

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 job seekers think finding work is a numbers game. Send out enough applications, hit enough easy apply buttons, and eventually something sticks. But in today's market, that approach isn't just ineffective — it's actively working against you.

Mac Prichard has spent 25 years at the center of how people find work and how employers find talent. What he's learned cuts against the conventional wisdom: the fundamentals of a great job search haven't changed, but the noise surrounding them has never been louder. And the candidates who get hired aren't the ones sending the most applications — they're the ones who did the work before they ever applied.

In this episode, Josh and Mac unpack what actually drives hiring decisions, why specificity beats volume every time, and how the easy apply button has made a hard problem significantly worse. They dig into the three questions every job seeker needs to answer, why referrals matter more than credentials, and what a candidate who landed offers at all three companies she interviewed with did differently than everyone else.

If you're navigating a job search — or responsible for hiring — the fundamentals haven't changed. But knowing how to use them right now makes all the difference.

About Mac Prichard

Mac Prichard is a career expert, speaker, and founder of Mac's List, a niche job board serving employers and job seekers across Oregon and Washington for over 25 years. He is also the host of Find Your Dream Job, a weekly podcast featuring conversations with hiring experts and career coaches. Mac's work is rooted in a simple belief: job searching is a skill, and like any skill, it can be learned. Learn more at macslist.org.

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.

The last thing your people need is another training.

This week Josh previews AI Leadership Skill #2: Let Your Team Lead, the latest entry in The Sh*t List, the paid Substack companion to The Job Sh*t Show.

It's built around a conversation with Geoffrey Roahe, SVP of Healthcare Solutions at RisePoint, where he helps colleges and universities modernize for the real world. When Jeffrey asks leaders how often they're actually teaching AI, the answer is almost always the same: "Well, we talk about it."

Talking about AI and actually learning it together are not the same thing. And the gap between them is bigger than most leaders realize.

His advice? Ask your team. Not a survey — a real conversation. Jeffrey did exactly that with his own team of 13 and discovered some of them had access to a resource he didn't even know existed. He'd been managing them for months.

Your team already knows more than you think. You just don't know who's ahead and who's stuck — because you haven't made it something you do together.

The full piece on The Sh*t List walks through three specific moves to turn your team from an audience into co-designers of their own AI fluency. Link in the description. If you're not on The Sh*t List yet, this is a good week to start.

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 leaders try to fix performance problems with better systems, clearer processes, or new hires. But what if the real bottleneck is something far more fundamental — and it starts with you?

Linda Perry spent 17 years as a federal criminal defense attorney studying what drives human behavior before becoming a leadership and executive strategist. In that courtroom work, she discovered something that now shapes how she helps organizations scale: everyone operates from a core motivation — a hidden "why" that determines how they make decisions, communicate, lead, and get stuck.

In this episode, Josh and Linda explore what happens when leaders finally understand their own operating system — and what it costs when they don't. They dig into how core motivations shape the cultures leaders build (often without realizing it), why the "problem employee" is usually just wired differently, and how a team's collective why can reveal exactly where growth will stall.

If your organization has hit a plateau, the answer probably isn't a new strategy. It's a clearer understanding of the people already in the room.

Reference: 9 Whys

About Linda Perry

Linda Perry is a former federal criminal defense attorney turned leadership and executive strategist. After 17 years in the federal court system, she shifted her focus from defending clients to understanding what drives human behavior — and how those same patterns shape organizational performance. Today she works with executives and leadership teams to uncover their core motivations, break through growth plateaus, and build cultures that leverage who people actually are. Learn more at lindamperry.com.

About Great Mondays:

→ 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.

When Anthropic dropped Claude Design and OpenAI released Images 2.0, something shifted. The ability to create professional-grade visuals — the kind that used to require years of training and hard-won expertise — got handed to everyone.

In this episode, Josh argues that AI isn't replacing creative experts. It's promoting them. The people with real taste, real vision, and the language to describe what they want are about to have a very good 12 to 18 months. After that, the tools catch up. And the only thing left that can't be automated is the ability to imagine something that doesn't exist yet. The new currency isn't who can use the tools best. It's who can see what hasn't been made.

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.

Most cultures don’t fail loudly. They erode in small moments—a comment in a meeting, a policy that signals distrust, a leader who thinks they’re being clear but shuts the door instead. On this episode of Great Mondays Radio, Josh Levine sits down with Aoife O’Brien to unpack how these seemingly minor signals shape whether people thrive or disengage.

Aoife shares how her own experience in a toxic workplace led her to question what actually drives performance. Not perks or motivation, but the conditions leaders create every day. From psychological safety to workplace systems, she challenges the assumption that culture is working just because no one is complaining. In reality, silence is often the clearest sign something is off.

They dig into the moments that matter most: why phrases like “that’s not how we do things here” shut down innovation, how return-to-office policies can quietly erode trust, and why leaders misunderstand autonomy. The takeaway is practical and direct—set clear expectations, focus on outcomes, and give people the space to deliver. Culture isn’t built in big initiatives. It’s built in how leaders show up, every day.

About Aoife O’Brien

Aoife O’Brien is the founder of Happier at Work, a leadership consultant, and host of the Happier at Work podcast. With a background in market research and a master’s in organizational behavior, she helps organizations build psychologically safe, high-performing cultures. She is the author of Thriving Talent, a book focused on how leaders drive performance, engagement, and retention by creating the right conditions for people to succeed.

About Great Mondays:

→ 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.

Most leaders are using AI to go faster. This skill is about going deeper.

Coach Your People Better With AI is the first entry in The Sh*t List, the paid Substack companion to The Job Market Sh*t Show. It starts with a simple question: what if, before your next difficult one-on-one, you spent 15 minutes with an AI tool working through everything you actually know about that person?

This one's built around a conversation with Kathrin Fleer, who spent 12 years leading luxury retail teams for Saint Laurent and Tiffany & Co across Europe. What she said about the ceiling every manager eventually hits — and where AI fits in — stuck with Josh.

The full piece includes four specific prompts and a framework you can use before your next one-on-one. If you're not on The Sh*t List yet, this is a good week to start.

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. 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.

In a world full of leadership frameworks and culture playbooks, why does so much of it fail to stick? What if the issue isn’t strategy, but the way we develop leaders in the first place?

On this episode of Great Mondays Radio, host Josh Levine talks with leadership coach and founder of The Art of Learned Intelligence, Cara-Lyn Giovanniello, about the gap between intention and behavior inside organizations. She introduces her model of whole person leadership—integrating emotional, relational, and strategic intelligence—and explains why siloed development keeps teams stuck at the surface. Through a story from her work at UC Berkeley, she shows how real change happens when leaders are understood before they’re aligned.

They also explore how AI is reshaping expectations of leadership, making certainty less valuable and curiosity, vulnerability, and honesty essential. The takeaway is simple: culture changes through behavior, and leaders who can integrate how they think, feel, and act are the ones who move things forward.

About Cara-Lyn Giovanniello

Cara-Lyn Giovanniello is a leadership coach, consultant, and founder of The Art of Learned Intelligence. With over 20 years of experience in leadership development, she works with executives and teams to build whole person leadership by integrating emotional, relational, and strategic intelligence. Her work focuses on helping leaders create meaningful, lasting change by addressing the root of how people show up and work together.

About Great Mondays:

→ 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.