Great Mondays Radio

Josh Levine
  • 5.0 (17)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

There is only one sustainable competitive advantage in business today—company culture—and I’m on a mission to help organizations harness its power. Josh Levine, here, the host of Great Mondays Radio. I’m an author, consultant, and educator with over fifteen years of experience helping hyper-growth technology companies become more effective, aligned, and profitable. My book, Great Mondays: How To Design A Company Culture Employees Love, was listed as one of BookAuthority’s best culture books of all time. Great Mondays Radio is my way of elevating the people and stories behind tech’s best company cultures so that more leaders can apply this powerful business tool to improve employee lives and their bottom line. If you're an experienced people leader or HR professional, apply to be a guest on the show at https://radio.greatmondays.com/podcast-guest

  1. The Job Market Sh*t Show: Is It Who You Know?

    2H AGO

    The Job Market Sh*t Show: Is It Who You Know?

    Applying to hundreds of jobs feels like progress—but it might just be noise. In this episode, Josh looks at the two strategies job seekers are using right now: scale and signal. Some people are flooding the system with applications, hoping one slips through. Others are doing the opposite—only applying when they can get a human introduction inside the company. Through conversations with job seekers who’ve tried both approaches, Josh explores why referrals seem to matter more than ever, why charm alone isn’t enough in this market, and what happens when the only way to stand out is to prove you’re not a bot. 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.

    16 min
  2. The Career Mistake AI Can’t Fix — Leaders Who Don’t Know What They Stand For: Voice as the New Differentiator

    3D AGO

    The Career Mistake AI Can’t Fix — Leaders Who Don’t Know What They Stand For: Voice as the New Differentiator

    In a world where anyone can publish, post, or prompt their way to polished prose, standing out no longer comes down to volume. It comes down to voice. But what if the real career risk isn’t being replaced by AI—it’s becoming indistinguishable from everyone else? On this episode of Great Mondays Radio, host Josh Levine talks with nonfiction ghostwriter and thought leadership strategist Jamie Dykstra about the one thing AI can’t manufacture: conviction. Jamie helps executives and founders uncover their authentic voice—the durable throughline that carries across roles, industries, and seasons of a career. Together, they explore why authenticity is more than a buzzword, how defining one specific audience sharpens your positioning, and why leaders who don’t know what they stand for risk blending into the noise. They also dive into the evolving role of AI in writing and leadership, where it’s a powerful tool, and where it falls short. The takeaway is clear: technology can amplify your message, but it cannot supply your clarity. In a marketplace saturated with content, voice is the differentiator—and clarity is the work. About Our Guest: Jamie Dykstra is a nonfiction ghostwriter and thought leadership consultant specializing in business, leadership, and personal development books. With a background in corporate finance and operations, she brings both strategic rigor and storytelling craft to her work. Jamie helps leaders clarify their message, articulate their expertise, and share ideas that resonate. Learn more at jamiedykstra.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.

    32 min
  3. The Job Market Sh*t Show: What is Grammarly's AI Ad Trying to Tell Us?

    FEB 26

    The Job Market Sh*t Show: What is Grammarly's AI Ad Trying to Tell Us?

    AI used to promise better work. Now it’s starting to promise no work at all. In this episode, Josh unpacks a deceptively cheerful Grammarly ad that suggests AI can handle your tasks so you can “get back to what matters.” Cute on the surface. Slightly terrifying underneath. He connects the dots to a viral essay arguing that AI is already replacing large chunks of knowledge work—from coding to law—and asks what happens when the tools don’t just assist us, but quietly outperform us. If AI can do the job, are we being freed… or phased out? And if the future belongs to those who know how to orchestrate machines, what does that mean for everyone else? 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.

    11 min
  4. You’re Over-Investing in Software and Under-Investing in Humans. A CIO’s Case for the Most Underrated Leaders in Your Company.

    FEB 23

    You’re Over-Investing in Software and Under-Investing in Humans. A CIO’s Case for the Most Underrated Leaders in Your Company.

    We are pouring money into AI, automation, and digital tools. But what if the real bottleneck isn’t your tech stack. What if it’s your human stack. On this episode of Great Mondays Radio, Josh Levine sits down with award-winning author, fractional CIO, and founder of Digital Wisdom Collective, Barbara Whitman, to explore why most transformation efforts fail for one simple reason: we upgrade the software and forget to upgrade the people. Drawing on 25 years of rescuing broken transformation projects, Barbara makes the case for investing in “human infrastructure” — the trusted middle leaders who turn strategy into execution. Together, they unpack how empowering just a small cohort of these quiet operators can reduce reliance on consultants, strengthen collaboration, and build the collective intelligence organizations need to thrive in an AI-driven world. If you are leading change and wondering why adoption lags or strategy stalls, this conversation offers a practical, human-centered path forward. About Our Guest: Barbara Whitman is an award-winning author, fractional CIO, and founder of Digital Wisdom Collective. For more than two decades, she has helped organizations repair stalled transformation efforts by strengthening leadership from the middle out and building the human capabilities required to sustain change. 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.

    31 min
  5. The Job Market Sh*t Show: Is the Job Market a Market Failure?

    FEB 19

    The Job Market Sh*t Show: Is the Job Market a Market Failure?

    Job searching used to feel like a transaction: effort in, opportunity out. Now it often feels like shouting into a void. In this episode, Josh argues that hiring isn’t just dysfunctional—it’s starting to resemble a classic market failure, where companies absorb almost no cost for bad behavior while candidates absorb all of it. He breaks down how ghost jobs, opaque AI screening, and endless silence create a system built on information asymmetry and misaligned incentives. And then, a rare twist: Ontario, Canada introduces a new law that forces employers to disclose salary ranges, admit when AI is used, confirm whether a job is actually vacant, and stop ghosting candidates—or face serious fines. It’s a reminder that when the market won’t fix itself, something else has to. 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.

    20 min
  6. When Smart Leaders Self-Sabotage and Call It “High Standards”. Plus, Why insight doesn’t automatically lead to behavior change.

    FEB 16

    When Smart Leaders Self-Sabotage and Call It “High Standards”. Plus, Why insight doesn’t automatically lead to behavior change.

    In leadership, we like to believe our biggest challenges are external. Market shifts. Economic pressure. Disruption. Competition. But what if the real friction isn’t "out there"? On this episode of Great Mondays Radio, host Josh Levine sits down with certified executive coach Rob Wise to explore the concept of leadership saboteurs—the hidden patterns of thinking that quietly shape our behavior when we’re stressed, tired, or feeling threatened. From the ever-present Judge to the Controller, the Hyper-Achiever, the Pleaser, and more, Rob breaks down how the very traits that fueled your success can, under pressure, start to erode trust, culture, and clarity. Together, Josh and Rob unpack the difference between judgment and discernment, reaction and response, insight and actual behavior change. They also dig into the practical side of transformation. Why awareness alone rarely rewires behavior. Why physical interruption matters. And how a simple pause can shift you from critique to curiosity in moments that matter most. This conversation is not about eliminating your shadow side. It’s about integrating it. Because leadership is not the absence of triggers. It’s the ability to navigate them with intention. If you’ve ever fired off an email you regretted, defaulted to control when things felt uncertain, or called your defensiveness “high standards,” this episode will feel uncomfortably familiar—in the best possible way. About Our Guest: Rob Wise is a certified business and executive coach specializing in leadership development, emotional intelligence, and organizational effectiveness. Through his work with leaders and teams, Rob helps high performers identify the internal patterns that limit their impact and build the habits that unlock wiser, more grounded leadership. Learn more at Focal Point Coaching. 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.

    31 min
  7. The Job Market Sh*t Show: Is Fractional Work the Uber-fication of Jobs?

    FEB 12

    The Job Market Sh*t Show: Is Fractional Work the Uber-fication of Jobs?

    Work is starting to behave like a scarce resource—and companies are adjusting their metabolism accordingly. In this episode, Josh explores how AI, short-term incentives, and belt-tightening are accelerating the unbundling of jobs into fractional roles, contractors, and piecemeal tasks. What once looked like flexibility and “portfolio careers” is starting to resemble something else: an uberification of work where organizations can buy talent in slices, avoid long-term commitments, and offload risk onto individuals. Josh unpacks why this shift feels sudden, why it may be structural rather than temporary, and what it means when stability becomes a perk instead of the baseline. 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.

    14 min
  8. The Stories We Tell Ourselves. Emotional Intelligence at Work with Performance Psychotherapist Jade Wood. Plus Why 360 Reviews are Broken.

    FEB 9

    The Stories We Tell Ourselves. Emotional Intelligence at Work with Performance Psychotherapist Jade Wood. Plus Why 360 Reviews are Broken.

    What if your biggest leadership blind spot isn’t strategy but self-awareness? On this episode of Great Mondays Radio, host Josh Levine talks with performance psychotherapist Jade Wood, MA, LMFT, MHSA about the overlooked power of emotional intelligence at work. They explore how trust breaks down when leaders lack self-awareness, why most 360 reviews fall flat, and what actually helps people grow: understanding how others experience you. Jade shares practical ways to build emotional fluency, explains why most conflict is unhealed trauma in disguise, and offers two deceptively simple questions that can shift how you lead. If you're building culture or managing people, this episode reframes EQ as a critical leadership muscle—one that separates good teams from great ones. About Our Guest: Jade Wood, MA, LMFT, MHSA is a clinical psychotherapist and performance coach who helps leaders and organizations build emotional intelligence from the inside out. Learn more about her work or get in touch via LinkedIn. 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.

    39 min
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5
out of 5
17 Ratings

About

There is only one sustainable competitive advantage in business today—company culture—and I’m on a mission to help organizations harness its power. Josh Levine, here, the host of Great Mondays Radio. I’m an author, consultant, and educator with over fifteen years of experience helping hyper-growth technology companies become more effective, aligned, and profitable. My book, Great Mondays: How To Design A Company Culture Employees Love, was listed as one of BookAuthority’s best culture books of all time. Great Mondays Radio is my way of elevating the people and stories behind tech’s best company cultures so that more leaders can apply this powerful business tool to improve employee lives and their bottom line. If you're an experienced people leader or HR professional, apply to be a guest on the show at https://radio.greatmondays.com/podcast-guest

Information

  • Creator
    Josh Levine
  • Years Active
    2023 - 2026
  • Episodes
    154
  • Rating
    Explicit
  • Copyright
    © Copyright 2026 Josh Levine
  • Show Website
    Great Mondays Radio

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