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. 48: Two Million Reasons to Ask More Questions

    13h ago

    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

    59 min
  2. 47: One Workshop, Four Confessions

    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

    38 min
  3. 46: When Confidence Becomes a Liability

    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

    33 min
  4. 45: Ask Me Anything: Real Questions, Real Answers

    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

    32 min
  5. 44: How a Visionary Becomes a Bottleneck

    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

    41 min
  6. 43: Fixing the Problem, Losing the Person

    May 20

    43: Fixing the Problem, Losing the Person

    In this episode of Bad Boss Confessional, Beth Fahey sits down with Raina Fryer, head of talent strategy at Titus Talent Strategies. Raina's confession takes her back to a training room early in her career, where she was young, eager to prove herself, and co-facilitating alongside someone she was supposed to be developing. Every time her teammate made a misstep, she stepped in. Mid-sentence, in front of the room, again and again. She told herself it was about safety. Looking back, she knows it was also about ego. Two months later, her teammate quietly asked for a new manager. That was the moment that stuck. Her lesson is simple and hard-earned: the points that actually count are the ones that make people feel safe enough to trust you.     Timestamps 00:00 Introduction to Raina Fryer 03:19 Raina’s Bad Boss Confession 09:54 The Impact of Imposter Syndrome 13:01 Training and Role-Playing for Managers 16:47 Titus Talent’s Holistic Approach 19:26 Top People Issues: Accountability Chart 23:07 Culture Integration & Manager Elevation 28:56 Continuous Learning & Personal Insights   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

    33 min
  7. 42: What Got You Here Won't Get You There

    May 13

    42: What Got You Here Won't Get You There

    In this episode of Bad Boss Confessional, Beth Fahey sits down with Ben Stern, EOS implementer and former integrator who helped scale a transmission remanufacturing company from 300 employees and $40 million in revenue to 850 people and $190 million. Ben's confession starts long before that chapter, back on a construction crew where being the hardest worker in the room felt like a leadership strategy. The conversation explores what happens when intensity without emotional intelligence becomes the culture, why the habits that make someone a standout performer can quietly poison a team, and what it actually took to close the gap. Ben reflects on nearly two decades of deliberate work, the people who helped him see what he couldn't see himself, and why learning Spanish to connect with his team is one of the things he's most proud of. His lesson is one every high performer eventually has to face: what got you here won't get you there.     Timestamps 00:00 Ben Stern’s Background 02:13 From Hammer to CEO 06:17 Reflecting on Growth and Wins 10:12 The Hard-Charging Boss 14:59 Journey to Emotional Intelligence 19:17 Work-Life Balance and Gen Z 22:01 Leadership Through Parenthood 26:27 Deprogramming and Human Connection 30:12 Scaling Leadership and GWC 35:15 Continuous Learning and Empathy   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

    41 min
  8. 41: The Feedback Nobody Should Have Given

    May 6

    41: The Feedback Nobody Should Have Given

    In this episode of Bad Boss Confessional, Beth Fahey sits down with Jeanet Wade, Expert EOS Implementer, ForbesBooks author of The Human Team, and one of the top 100 innovators and entrepreneurs in her region. Jeanet comes with two confessions, and they both involve the same person. The conversation explores what happens when dysfunction travels downhill, why secondhand feedback is its own kind of leadership failure, and what it looks like to stop the madness in real time and just tell the truth. Her lesson cuts through the noise: when the feedback doesn't feel right, it probably isn't.     Timestamps 00:00 Introduction & Jeanet's Background 03:10 The Allure of Entrepreneurship 07:52 First Bad Boss Confession: Task Management 11:56 Second Bad Boss Confession: Secondhand Feedback 15:41 The Human Team: Bridging Nature to Nurture 22:06 Team Dynamics in Entrepreneurial Settings 27:30 Bossing Bosses & Overcoming Dysfunctional Teams 33:00 Growth Optimization & Vulnerability 39:19 Leadership Evolution & Personal Tattoo   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

    41 min
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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
    48
  • Rating
    Explicit
  • Copyright
    © Copyright Speakeasy Podcast Network
  • Show Website
    Bad Boss Confessional

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