Bad Boss Confessional

Speakeasy Podcast Network
  • 5.0 (5)
  • Management
  • Updated Weekly

Bad Boss Confessional is the podcast where entrepreneurs, founders, and leaders fess up to their most cringeworthy management moments—the times they micromanaged, blew up in meetings, or simply got it dead wrong. With names changed (to protect the innocent...and guilty), guests walk us through their “bad boss” moment in all its messy glory. But this isn’t just a cringe-fest—it’s a redemption story.

  1. 3h ago

    51: Falling in Love With Your Own Idea

    In this episode of Bad Boss Confessional, Beth Fahey sits down with Chris Hallberg, expert EOS implementer, founder of GoXpand, and someone who learned his most expensive lesson long before he ever walked into a session room. Chris's confession is about a venture he poured everything into, including his house, his savings, and his team, built on assumptions nobody tested and a structure nobody controlled. The conversation explores what happens when a visionary gets so sold on an idea that warning signs become background noise, why minority ownership in your own vision is a trap, and what it costs a team when the person at the top stops listening. Chris also reflects on how that failure rewired the way he asks questions, invites dissent, and shows up for the people around him. Timestamps 00:00 Welcome and Introductions 05:08 A Visionary’s Misstep 11:00 The High Cost of Poor Structure 17:23 Lessons Learned and New Beginnings 23:36 Turning Failure into Growth 33:29 Using the VTO for Alignment 37:24 Departmental Planning and Accountability 43:06 The Crucial Role of Mid-Managers 48:45 Innovative Tools and Veteran Leadership 55:18 Closing Thoughts and Mantras Guest Links: EOS Site: https://implementer.eosworldwide.com/chris-hallberg/ LinkedIn: https://www.linkedin.com/in/chris-hallberg-01516315/ Subscribe to the Bad Boss Confessional podcast: 🎙️ Podbean: https://www.badbossconfessional.podbean.com ▶️ YouTube: https://www.youtube.com/@badbossconfessional The Bad Boss Confessional is where leaders come to tell the truth about the moments they rarely talk about out loud. The mistakes, the hard lessons, and what it actually takes to become a great boss. Hosted by Beth Fahey, Expert EOS Implementer, co-author of ROLLOUT, and creator of the Great Boss Workshop. Connect with Beth Fahey: 🌐 https://www.bethfahey.com ▶️ https://www.youtube.com/@bethfahey Want to be a guest on the show? Visit https://www.bethfahey.com/podcast to inquire. Pick up a copy of ROLLOUT: Get Your Entire Team Running on EOS to Achieve Your Vision at https://www.rolloutbook.com/order Download free Rollout resources at https://www.rolloutbook.com Join Beth at the next Great Boss Workshop at https://www.bethfahey.com/events

    51: Falling in Love With Your Own Idea

  2. Jul 8

    50: When Hustle Becomes the Enemy

    In this episode of Bad Boss Confessional, Beth Fahey sits down with Travis Townsend, president of North Star Refrigeration, who built his company from a used van to a 100-person operation across New England. Travis's confession comes from the early days, when lean meant running a skeleton crew at full speed and hoping nobody broke. The conversation explores what it costs a team when the owner assumes everyone shares the same drive, why the pacesetter mentality can quietly demoralize the people trying to keep up, and what it took to go from six employees grinding themselves down to a culture built to last. His lesson is one every growth-stage founder eventually has to face: you can't build a great company by burning through the people inside it. Timestamps 00:00 Introduction to Travis Townsend 03:02 From Landscaper to Entrepreneur 06:11 The Josh Hill Wake-Up Call 09:51 Understanding Visionaries and Integrators 12:33 Navigating Entrepreneurial Fears 15:20 Preventing Burnout and Leading by Example 19:01 Future Vision: Employee-Owned Company 21:30 Culture, Growth, and Leadership Evolution 26:13 The Importance of EOS Implementers 30:22 Burn the Boats Mentality and Conclusion Subscribe to the Bad Boss Confessional podcast: 🎙️ Podbean: https://www.badbossconfessional.podbean.com ▶️ YouTube: https://www.youtube.com/@badbossconfessional The Bad Boss Confessional is where leaders come to tell the truth about the moments they rarely talk about out loud. The mistakes, the hard lessons, and what it actually takes to become a great boss. Hosted by Beth Fahey, Expert EOS Implementer, co-author of ROLLOUT, and creator of the Great Boss Workshop. Connect with Beth Fahey: 🌐 https://www.bethfahey.com ▶️ https://www.youtube.com/@bethfahey Want to be a guest on the show? Visit https://www.bethfahey.com/podcast to inquire. Pick up a copy of ROLLOUT: Get Your Entire Team Running on EOS to Achieve Your Vision at https://www.rolloutbook.com/order Download free Rollout resources at https://www.rolloutbook.com Join Beth at the next Great Boss Workshop at https://www.bethfahey.com/events

    50: When Hustle Becomes the Enemy

  3. Jul 1

    49: When The Expert Gets It Wrong

    In this episode of Bad Boss Confessional, Beth Fahey sits down with CJ Dube', expert EOS implementer, author, and someone who has spent more than 40 years in the people business. CJ's confession is one that will hit close to home for anyone who has ever hired against their better judgment. The conversation digs into what it actually means to hire slow and fire fast, why the tools only work when you use them, and what it costs a team when a leader keeps someone in the wrong seat for the sake of convenience.  Her lesson is one she now coaches every client on: the red flags in a reference check are there for a reason.     Timestamps 00:00 Introduction to CJ DuBe' 02:12 CJ’s Journey: From Placement to EOS 06:05 The Confession: Hiring Mistakes and Lessons 10:47 The ‘Hire Slow, Fire Fast’ Philosophy 13:04 Deep Dive into Hiring Process 18:00 Addressing People Issues: Timing and Empathy 22:56 Leadership Credibility and Outgrowing Seats 25:25 Strategies for Organizational Growth and Tools 31:19 Aha Moments from ‘The People Book’ 35:45 Tattoo Confession and Closing Remarks   Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.   Subscribe to the Bad Boss Confessional podcast: 🎙️ Podbean: https://www.badbossconfessional.podbean.com ▶️ YouTube: https://www.youtube.com/@badbossconfessional The Bad Boss Confessional is where leaders come to tell the truth about the moments they rarely talk about out loud. The mistakes, the hard lessons, and what it actually takes to become a great boss. Hosted by Beth Fahey, Expert EOS Implementer, co-author of ROLLOUT, and creator of the Great Boss Workshop. Connect with Beth Fahey: 🌐 https://www.bethfahey.com ▶️ https://www.youtube.com/@BethFahey Want to be a guest on the show? Visit https://www.bethfahey.com/podcast to inquire. Pick up a copy of ROLLOUT: Get Your Entire Team Running on EOS to Achieve Your Vision at https://www.rolloutbook.com/order Download free Rollout resources at https://www.rolloutbook.com Join Beth at the next Great Boss Workshop at https://www.bethfahey.com/events

    49: When The Expert Gets It Wrong

  4. Jun 24

    48: Two Million Reasons to Ask More Questions

    In this episode of Bad Boss Confessional, Beth Fahey sits down with Dan Wallace, one of the first EOS implementers and a former turnaround operator with a background spanning Harvard Business School, investment banking, and strategy consulting. Dan's confession is a good one: six weeks into a new role, he green-lit a $2 million software build that the company never launched. The conversation explores what happens when a high quick start moves before they've truly understood the problem, why buying is almost always better than building, and what it costs a team when the person at the top has no one to slow them down. Dan also reflects on the two leadership lessons he stumbled into by accident, both of which still shape how he coaches teams today.     Timestamps 00:00 Introduction to Dan Wallace 02:50 Career Shift to Turnarounds 07:39 Joining EOS and Growth 11:25 The Niche Lending Company Challenge 15:05 The $2 Million Software Mistake 24:50 Visionary-Integrator and Empathy 33:32 Lessons: Do Ask, Don’t Tell 40:09 Preparing for Departure 43:02 The Need for Operating Systems 50:47 Walmart Missionary Mix-Up 53:11 Humility and Kindness   Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.   Subscribe to the Bad Boss Confessional podcast: 🎙️ Podbean: https://www.badbossconfessional.podbean.com ▶️ YouTube: https://www.youtube.com/@badbossconfessional The Bad Boss Confessional is where leaders come to tell the truth about the moments they rarely talk about out loud. The mistakes, the hard lessons, and what it actually takes to become a great boss. Hosted by Beth Fahey, Expert EOS Implementer, co-author of ROLLOUT, and creator of the Great Boss Workshop. Connect with Beth Fahey: 🌐 https://www.bethfahey.com ▶️ https://www.youtube.com/@BethFahey Want to be a guest on the show? Visit https://www.bethfahey.com/podcast to inquire. Pick up a copy of ROLLOUT: Get Your Entire Team Running on EOS to Achieve Your Vision at https://www.rolloutbook.com/order Download free Rollout resources at https://www.rolloutbook.com Join Beth at the next Great Boss Workshop at https://www.bethfahey.com/events

    48: Two Million Reasons to Ask More Questions

  5. Jun 17

    47: One Workshop, Four Confessions

    In this episode of Bad Boss Confessional, Beth Fahey is joined by four fellow EOS implementers right off the back of a Great Boss Workshop. Mary Reilly-Magee, Jordan Regas, Phil Ouellette, and Barb Reimbold each bring their own confessions to the table, and none of them hold back. The conversation covers public callouts, unclear roles, avoided confrontations, a deleted dataset, and the slow damage of being too nice to have the hard conversation. They also dig into what they saw in the workshop that day, why so few leaders ever receive formal management training, and what it actually takes to give feedback people can hear and act on. Four leaders, four stories, one honest conversation about what it really takes to get better.     Timestamps 00:00 Welcome and Introductions 06:47 Early Management Mistakes 09:43 Role Clarity and Buddy vs. Boss 14:14 Addressing Confrontation and Epiphanies 17:47 Leadership vs. Management & Nice Cultures 23:22 Conflict Debt and Communication 25:58 Positive to Negative Feedback Ratio 35:06 No Poop Sandwiches and Conclusion   Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.   Subscribe to the Bad Boss Confessional podcast: 🎙️ Podbean: https://www.badbossconfessional.podbean.com ▶️ YouTube: https://www.youtube.com/@badbossconfessional The Bad Boss Confessional is where leaders come to tell the truth about the moments they rarely talk about out loud. The mistakes, the hard lessons, and what it actually takes to become a great boss. Hosted by Beth Fahey, Expert EOS Implementer, co-author of ROLLOUT, and creator of the Great Boss Workshop. Connect with Beth Fahey: 🌐 https://www.bethfahey.com ▶️ https://www.youtube.com/@BethFahey Want to be a guest on the show? Visit https://www.bethfahey.com/podcast to inquire. Pick up a copy of ROLLOUT: Get Your Entire Team Running on EOS to Achieve Your Vision at https://www.rolloutbook.com/order Download free Rollout resources at https://www.rolloutbook.com Join Beth at the next Great Boss Workshop at https://www.bethfahey.com/events

    47: One Workshop, Four Confessions

  6. Jun 10

    46: When Confidence Becomes a Liability

    In this episode of Bad Boss Confessional, Beth sits down with Scott Rusnak, expert EOS implementer, Olympic team coach, and author of the Audible bestseller "Who Is the Architect of Your Life?" Scott's confession starts at a Canadian Tire warehouse in 1979 and ends with a million-dollar mistake decades later that nearly cost him everything. The conversation explores what happens when a leader stops listening, charges ahead on gut instinct alone, and finds out too late that the team saw it coming. Scott reflects on the moment he flipped the boat, what it cost him, and why the right people around you are only useful if you actually let them speak.     Timestamps 00:00 Introduction to Bad Boss Confessional 02:29 The Root Cause of Business Issues 05:10 Early Bad Boss Experience 08:12 Ego and Colossal Failure 12:25 Surrounding Yourself with Right People 17:39 The Art of Saying No 24:55 Fourth Quarter Mindset and Legacy   Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.   Subscribe to the Bad Boss Confessional podcast: 🎙️ Podbean: https://www.badbossconfessional.podbean.com ▶️ YouTube: https://www.youtube.com/@badbossconfessional The Bad Boss Confessional is where leaders come to tell the truth about the moments they rarely talk about out loud. The mistakes, the hard lessons, and what it actually takes to become a great boss. Hosted by Beth Fahey, Expert EOS Implementer, co-author of ROLLOUT, and creator of the Great Boss Workshop. Connect with Beth Fahey: 🌐 https://www.bethfahey.com ▶️ https://www.youtube.com/@BethFahey Want to be a guest on the show? Visit https://www.bethfahey.com/podcast to inquire. Pick up a copy of ROLLOUT: Get Your Entire Team Running on EOS to Achieve Your Vision at https://www.rolloutbook.com/order Download free Rollout resources at https://www.rolloutbook.com Join Beth at the next Great Boss Workshop at https://www.bethfahey.com/events

    46: When Confidence Becomes a Liability

  7. Jun 3

    45: Ask Me Anything: Real Questions, Real Answers

    In this episode of Bad Boss Confessional, there's no guest... just Beth!  Listeners sent in their questions and she answered them, from EOS deep dives to career what-ifs to a heartfelt moment about the baking industry she'll always call home. She also shares a confession of her own about a pastry chef, a walk-in cooler, and a moment she wishes she could take back. It's the most personal episode yet, and proof that nobody is off the hook on this podcast... not even the host. Timestamps 00:00 Introduction & Career What-Ifs 03:39 My Bad Boss Confession 06:09 Favorite Non-EOS Leadership Book 07:37 Connecting Diverse Career Paths 10:20 Ideal Kolbe Score for an Integrator 12:51 Visionary-Integrator Authority Dynamic 17:37 Common Leadership Team Mistakes 20:18 Running EOS During Major Change 23:09 Baking Industry Crisis & Adaptation 29:51 Lessons as an EOS Implementer Subscribe to the Bad Boss Confessional podcast: 🎙️ Podbean: https://www.badbossconfessional.podbean.com ▶️ YouTube: https://www.youtube.com/@badbossconfessional The Bad Boss Confessional is where leaders come to tell the truth about the moments they rarely talk about out loud. The mistakes, the hard lessons, and what it actually takes to become a great boss. Hosted by Beth Fahey, Expert EOS Implementer, co-author of ROLLOUT, and creator of the Great Boss Workshop. Connect with Beth Fahey: 🌐 https://www.bethfahey.com ▶️ https://www.youtube.com/@bethfahey Want to be a guest on the show? Visit https://www.bethfahey.com/podcast to inquire. Pick up a copy of ROLLOUT: Get Your Entire Team Running on EOS to Achieve Your Vision at https://www.rolloutbook.com/order Download free Rollout resources at https://www.rolloutbook.com Join Beth at the next Great Boss Workshop at https://www.bethfahey.com/events

    45: Ask Me Anything: Real Questions, Real Answers

  8. May 27

    44: How a Visionary Becomes a Bottleneck

    In this episode of Bad Boss Confessional, Beth sits down with Mark C. Winters, Expert EOS Implementer, co-author of "Rocket Fuel", and author of the new book "Visionary." Mark confesses to something a lot of visionaries won't admit: he was burning his team out by diving deep into the details and staying there. The conversation explores what happens when a visionary's hyperfocus lands in the wrong place, why learning to let go is harder than it looks, and how finding the right integrator changed everything. Mark reflects on the moment a business partner pulled him out of a CRM rabbit hole and redirected him to where he actually belonged, and what that shift taught him about the best use of a visionary's time. His lesson is one every visionary eventually has to face: the work that feels effortless is often the work only you can do.     Timestamps 00:00 Introduction & Marc C. Winters’ Background 03:20 From Operator to Advisor & EOS 05:08 The Visionary-Integrator Obsession 06:29 Confessions of a Visionary Bottleneck 11:10 Trust & Control for Visionaries 14:46 Obsessive Focus: Superpower or Pitfall? 17:01 Visionary’s Highest Use & Team Dynamics 22:05 Tools for Visionary-Integrator Alignment 27:54 Building a Strong Leadership Team 32:18 Know Thyself: The Visionary’s Inner Work 35:10 The Tattoo Confession: Freedom 39:34 Upcoming Books & Closing Remarks   Sponsor Links Thanks to our Sponsors A big thank you to our amazing sponsors for making this episode possible: Titus Talent – Helping organizations make the best hiring decisions with performance-based talent strategies. Strety – Empowering teams through strategic planning and performance management tools built for modern workforces.   Subscribe to the Bad Boss Confessional podcast: 🎙️ Podbean: https://www.badbossconfessional.podbean.com ▶️ YouTube: https://www.youtube.com/@badbossconfessional The Bad Boss Confessional is where leaders come to tell the truth about the moments they rarely talk about out loud. The mistakes, the hard lessons, and what it actually takes to become a great boss. Hosted by Beth Fahey, Expert EOS Implementer, co-author of ROLLOUT, and creator of the Great Boss Workshop. Connect with Beth Fahey: 🌐 https://www.bethfahey.com ▶️ https://www.youtube.com/@BethFahey Want to be a guest on the show? Visit https://www.bethfahey.com/podcast to inquire. Pick up a copy of ROLLOUT: Get Your Entire Team Running on EOS to Achieve Your Vision at https://www.rolloutbook.com/order Download free Rollout resources at https://www.rolloutbook.com Join Beth at the next Great Boss Workshop at https://www.bethfahey.com/events

    44: How a Visionary Becomes a Bottleneck
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About

Bad Boss Confessional is the podcast where entrepreneurs, founders, and leaders fess up to their most cringeworthy management moments—the times they micromanaged, blew up in meetings, or simply got it dead wrong. With names changed (to protect the innocent...and guilty), guests walk us through their “bad boss” moment in all its messy glory. But this isn’t just a cringe-fest—it’s a redemption story.

Information

  • Creator
    Speakeasy Podcast Network
  • Years Active
    2025 - 2026
  • Episodes
    51
  • Rating
    Explicit
  • Copyright
    © Copyright Speakeasy Podcast Network
  • Show Website
    Bad Boss Confessional

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