Bad Boss Confessional

Speakeasy Podcast Network
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Feb 4, 2026 • 37min

28: Getting Out of Your Own Way

In this episode of Bad Boss Confessional, Beth Fahey sits down with EOS Implementer Amanda Matthews to unpack a painfully relatable leadership moment driven by ego, insecurity, and a lack of self-awareness. After years of corporate leadership training, Amanda found herself out of her depth while managing in a high-volume restaurant environment. What she thought was confident leadership quickly turned into public shaming. Even experienced leaders can lose their way when ego and self-doubt take over. Great leadership requires pausing, reading the room, and remembering that praise belongs in public while criticism belongs in private. Growth begins when leaders learn to get out of their own way.   Timestamps 00:00 Introduction to Amanda Matthews 01:45 Amanda’s Love for Swing Dancing 04:36 Corporate to Restaurant World Shift 09:02 The Tobacco Chewer Incident 16:11 Lessons from the Incident 22:55 Recommended Management Books 26:08 The Simplicity of Direct Feedback 31:57 A Tattoo for Ego Check   About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Amanda Matthews coaches entrepreneurs on how to be wildly successful while also having time for what matters most in their lives using the Entrepreneurial Operating System (EOS). She describes herself as a dance enthusiast, book nerd and interpersonal knot detangler.  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.
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Jan 28, 2026 • 39min

27: Paying Attention to the Red Flags | Bad Boss Confessional

In this episode of Bad Boss Confessional, Beth Fahey sits down with EOS Implementer Ken DeWitt, also known as “Hurricane,” to unpack a leadership lesson that quite literally required warning flags. Early in his career, Ken’s intensity and drive created an environment where employees tracked his moods to protect themselves. What he didn't realize was that his passion was being met with fear and anxiety. Leaders are always on stage, whether they realize it or not. Self-awareness, emotional control, and humility matter as much as vision and results. Successful managers will never stop growing, even if it means facing some painful gut checks. Timestamps 00:00 Introduction to Ken ‘Hurricane’ DeWitt 02:27 From Accountant to EOS Implementer 05:08 The Psychologist’s Revelation 07:22 The ‘Hurricane’ Nickname 10:55 Dealing with the ‘Hurricane’ 14:58 Learning Calmness and Self-Awareness 19:04 The Impact of Personal Change 23:55 Understanding Different Communication Styles 28:59 Trust, Care, and Excellence in Leadership 32:56 Legacy and Learning: The Hurricane Tattoo   About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Over the past 40 plus years, Ken DeWitt has built, grown, and successfully exited companies across multiple industries, including accounting, agriculture, consumer finance, real estate, and consulting. He has worked with more than 100 owners and leadership teams to install EOS across seven states, helping them gain control, strengthen leadership, and build businesses that work for them rather than because of them. 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.
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Jan 21, 2026 • 31min

26. When Good Intentions Go Wrong

In this episode of Bad Boss Confessional, Beth Fahey sits down with EOS Implementer Carolyn Mitchell for an honest conversation about leadership, ego, and the hidden cost of trying to help too much. Carolyn shares a moment many leaders will recognize. As the unofficial “company therapist,” she believed stepping in and sharing sensitive information was for the greater good. Instead, it backfired. The employee she tried to protect walked it back, leaving Carolyn exposed, frustrated, and humbled. What felt like service was actually ego at work. The need to fix, to be needed, and to save the day created more dysfunction, not less. The lesson is simple and hard-earned. Great leaders coach people to speak for themselves instead of carrying their burdens. Growth happens when leaders pause, listen, and ask whether the problem is truly theirs to solve. Sometimes the best leadership move is letting go and letting it be easy.   Timestamps 00:00 Introduction to Carolyn Mitchell 02:08 Career Journey: Engineer to EOS Implementer 08:39 The Unofficial Company Therapist 12:09 Ego and the Hero Complex 19:02 Learning to Pause and Listen 23:33 Coaching vs. Fixing, and Tattoos   About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Guest Links: Website:  https://implementer.eosworldwide.com/carolyn-mitchell/ LinkedIn:  https://www.linkedin.com/in/carolyn-mitchell-coach Carolyn Mitchell is an EOS® Implementer, business coach, and speaker with a background in sales and marketing leadership. She’s been in the founder and leadership seats, implemented EOS, and now helps teams build clarity, accountability, and trust. She’s also a personal development junkie, a certified yoga teacher and believer in leadership that grows people, not just results. 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.
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Jan 14, 2026 • 36min

25. The Hidden Cost of Doing the Right Thing

In this episode of Bad Boss Confessional, Beth Fahey talks with EOS Implementer Michael Deutsch about a leadership failure that tested his ethics, his systems, and his gut. After landing the biggest client in his electronics recycling business, Michael discovered that valuable materials were being stolen somewhere in the supply chain. The mistake was not driven by bad intent, but by gaps in people and process that he ultimately owned as the leader. Michael shares the uncomfortable moment of choosing to proactively tell a Fortune 500 client the truth, knowing it could cost the relationship. Looking back, Michael points to right person, wrong seat decisions, weak project oversight, and the danger of trusting without the right structure in place. The lesson is clear: Core values are not words on a wall. They are tools that guide decisions when things go wrong. Doing the right thing does not always protect the outcome, but it protects who you are as a leader. Timestamps 00:00 Introduction to Bad Boss Confessional 01:28 Michael Deutsch’s Diverse Career Path 05:51 The Electronics Recycling Business 07:46 The Biggest Client Scandal 12:54 Owning the Mistake and Lessons 16:32 People, Process, and System Building 21:31 Applying Core Values and EOS 27:53 Personal Core Values and Self-Reflection 33:09 The ‘Let Them’ Tattoo and Farewell About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Guest Links: Website:  https://implementer.eosworldwide.com/michael-deutsch/ LinkedIn:  https://www.linkedin.com/in/michaeldeutsch/ Michael has been part of senior management for over 25 years - first as a leader for several high-growth organizations and then as a business owner. Now, as an EOS Implementer, he helps other business owners avoid the mistakes he made and get what they want from their business that they're not getting right now. 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.
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Jan 7, 2026 • 29min

24. The Shift from Peer to Boss with Jessenia Flores-Gayle

On this episode of Bad Boss Confessional, Beth Fahey sits down with marketing executive and general manager Jessenia Flores-Gayle to explore what happens when you suddenly become the boss of people who used to be your peers. Jessenia describes the emotional and practical challenges of stepping into an integrator role inside a close-knit, all-female leadership team. She talks about the pressure to be liked, the discomfort of holding friends accountable, and the self-doubt that surfaces when you feel caught between belonging and leading. Jessenia shares how her background in dance shaped her natural ability to bring people together and build strong relationships that support collective goals. She and Beth discuss boundaries, decision making, and the importance of vulnerability when the demands of leadership feel heavy. Jessenia stays grounded with a personal mantra that guides her work: forgive, learn, and move forward with intention. Timestamps 00:00 Introduction to Bad Boss Confessional 01:56 Jessenia’s Career Journey and Integrator Role 06:36 Challenges of Leading Friends 12:12 The Skill of Relationship Building 15:35 Vulnerability and Saying No 20:18 Influences and Decision-Making 24:08 Tattoos and Leadership Lessons   About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Guest Links Jessenia Flores-Gayle is a marketing executive and General Manager with over 13 years of experience in the haircare industry, recognized for building impactful brands and leading philanthropic campaigns, including a Shorty Award for her work with nonprofit partners. Throughout her career, she has championed culture, language, and representation, creating inclusive experiences that resonate with diverse audiences. She is also the co-creator of Mighty Big Love, a bilingual children’s brand designed to celebrate identity and heritage from an early age. 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.
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Dec 31, 2025 • 21min

23. Owning It: A Year of Leadership Confessions

This year-end episode of Bad Boss Confessional is a look back, a deep breath, and a heartfelt thank you. After launching the show in July, Beth reflects on what it has meant to create a space where leaders tell the truth about the moments they got it wrong. Across the year, listeners heard confessions about emotional outbursts, fear-driven decisions, people pleasing, missed conversations, and leadership mistakes that still linger. They also heard redemption stories, hard-earned self-awareness, and the quiet shifts that turn bad bosses into better ones. This episode weaves together clips from the past six months while Beth shares what she has learned from hosting these conversations. Every leader messes up. What matters is what you do next. Most of all, this episode is about gratitude for the guests who were brave enough to confess and for the listeners who showed up, shared the show, and reminded each other that growth starts with honesty. Timestamps 00:00 Welcome to Bad Boss Confessional 01:54 Mary Pat Knight’s Explosive Reaction 03:59 Dominic Sergi’s Empathy Challenge 06:58 Matt Haney’s Difficult Termination 09:16 Lisa Gonzalez’s Binder Blunder 11:15 Mike Shannon’s Scaling Challenges 15:11 Kathy Bresler’s COVID Launch 17:57 John McMahon’s Power of Silence 19:04 Rhonda Myers’ ‘I Am Not Enough’   About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  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.
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Dec 17, 2025 • 33min

22. The Role of Honest Dialogue in Healthy Leadership Teams

This week on Bad Boss Confessional, Beth Fahey welcomes Dennis Purcell, Chief Human Resources Officer at Skidmore Sales & Distributing Co., Inc., for a conversation about what happens when leaders develop talent without asking the questions that matter most. Dennis shares the painful lesson he learned after mentoring a high potential team member for years, only to discover in a heated leadership meeting that others had been struggling with that relationship all along. What began as a well intentioned effort to coach performance became a wake up call about trust, communication, and the difference between being nice and being kind. Dennis explains how his team rebuilt leadership health by normalizing people issues in their weekly meetings, creating language that makes hard conversations safer, and using one simple prompt, “What else?” to invite the truth before it is too late. Timestamps 00:00 Introduction to Bad Boss Confessional 02:33 Dennis Purcell’s Career Journey 06:28 A Painful Leadership Lesson 11:18 Building a Healthier Leadership Team 15:17 Navigating ‘Nice’ vs. ‘Kind’ Teams 20:10 Biggest Misconceptions of Leadership 26:35 The ‘What Else’ Tattoo and Retirement About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Guest Links For the past 13 years, Dennis has served as the HR leader at Skidmore Sales and Distributing, a food ingredient distributor.  Prior to Skidmore, Dennis spent 23 years at The Hennegan Company, a commercial printer, handling HR functions, including labor negotiation, as well as managing administrative and operational departments. Dennis is a graduate of Williams College and obtained an MBA in finance from Xavier University. Website: https://skidmoresales.com/ LinkedIn: https://www.linkedin.com/in/dennispurcellssdc 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.
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Dec 10, 2025 • 43min

21: Be Their Boss, Not Their Buddy

On this episode of Bad Boss Confessional, Beth Fahey sits down with lifelong entrepreneur and EOS Implementer Dan Heuretz to share a story about betrayal, accountability, and healing. Dan explains how he handed full control of a multimillion dollar real estate project to his trusted right hand, only to discover that the person he supported and believed in had been stealing from him. The fallout was immediate. The financial records were wiped. Investors were furious. Dan felt alone and overwhelmed. He describes the moment he stopped hiding and chose to face everyone in person, even when it meant anger, blame, and hard conversations. Dan reflects on the mentors who helped him find courage, the light he discovered in the darkest moments, and the forgiveness journey that freed him. Today, he still leads with trust and anchors his life in one purpose: do more good things with good people. Timestamps 00:00 Introduction to Dan Heuretz 04:48 Personal vs. Professional Betrayal 08:04 The Betrayal and Its Immediate Aftermath 13:58 Facing the Music and Rebuilding Trust 17:14 The Impact on Core Values and Trust 20:58 Finding Light in the Darkness 25:42 The Hard-Earned and Easily Lost Trust 29:26 The Journey of Forgiveness and Freedom 36:29 Reaffirming Trust and Moving Forward 38:48 Do More Good Things with Good People   About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Guest Links Dan Heuretz is a lifelong entrepreneur with nearly a decade of experience as an EOS Implementer. He has built and led companies across hospitality, real estate development, and consumer brands, earning a reputation for candor, resilience, and people focused leadership. Dan is also the co founder of the Skinny Book Company, where he helps entrepreneurs learn faster through concise, actionable content. His work centers on truth, learning, and doing good things with good people. Website: https://implementer.eosworldwide.com/dan-heuertz/ LinkedIn: https://www.linkedin.com/in/dheuertz 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.
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Dec 3, 2025 • 39min

20: From Positional Power to Humanized Leadership

On this episode of Bad Boss Confessional, host Beth Fahey sits down with Mary Pat Knight, author of The Humanized Leader, to unpack a career-defining moment of shame. Mary Pat tells how, at 19 and newly promoted in a troupe of performers, she lost control, hurled objects, and verbally exploded at a colleague. She reflects on how that moment taught her the limits of positional power and the lifelong work of emotional regulation. Conversation moves from the sting of shame to practical repair: naming triggers, practicing box breathing, learning the drama triangle, and choosing empathy and accountability. You’ll leave with a clear leadership takeaway: own your mistakes, learn your triggers, and wear the world like a loose garment so shame cannot stop your growth. 00:00 Introduction to Mary Pat Knight 03:04 Mary Pat’s Bad Boss Moment 07:39 Triggers, Shame, and Loose Garments 11:26 The Humanized Leader System 15:20 Empathy in a Wound-Up World 18:35 Common Leadership Issues and Willingness 22:21 Understanding the Drama Triangle 29:00 The Power of Frameworks 31:22 Future Books and Meditation 35:10 Tattoos and Final Thoughts About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Guest Links Mary Pat Knight, author of the international best seller, The Humanized Leader, is on a mission to develop more humanized leaders inside workplaces all over the world. She is the CEO and Founder of Leaders Inspired, a global training and development firm dedicated to personal and leadership transformation, and a speaker, author, coach, and consultant who is an expert in leadership and emotional intelligence. Leaders Inspired exists with a simple goal in mind – When inspired leaders inspire others, they have the capacity to change the world. Website: https://leadersinspired.com/about/ LinkedIn: https://www.linkedin.com/in/mpknight 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.
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Nov 26, 2025 • 32min

19: Empathetic Leadership Without Compromising Accountability

This week on Bad Boss Confessional, Beth Fahey welcomes Dominic Sergi, CEO of Clear Height Properties, for a conversation about how unchecked empathy almost held his company back. Dominic shares the hard lesson he learned from keeping the wrong people in the wrong seats for too long, all because he cared too much. What began as a culture built on patience and compassion evolved into one grounded in clarity, accountability, and authentic care. Dominic reveals how a mindset shift from fear to candor transformed his leadership, accelerated growth, and created a workplace where radical honesty builds trust, not resentment. It's a story about letting go, leaning in, and learning to say “yes, and…” instead of “yes, but.” Chapters 00:00 Empathy: Superpower or Kryptonite? 05:09 Learning from a Mentor 09:00 Empathy’s Double-Edged Sword 12:35 Right People, Right Seats 17:29 Mastering the EOS Journey 20:49 Building an Authentic Culture 26:52 The ‘Yes And’ Mindset About:  Beth Fahey is a leadership coach, Expert EOS Implementer, and co-creator of the How to Be a Great Boss Workshops. With nearly 40 years of hands-on leadership experience, Beth has worn many hats: from working in film and owning a bakery to leading a national trade association.   Now, as the host of The Bad Boss Confessional, she shares candid stories about the challenges of leadership, mistakes made, lessons learned, and the path to becoming the kind of boss your team actually wants to follow. Through humor, honesty, and heart, Beth is on a mission to help leaders grow, one confession at a time.   Show Links For more information about Beth Fahey follow the links below. Website: www.eosworldwide.com/beth-fahey  Facebook: www.facebook.com/BethFaheyEOS Instagram: www.instagram.com/bethfaheyeos/ TikTok: www.tiktok.com/@bethfaheyeos LinkedIn: www.linkedin.com/in/bethfahey/ Bad Boss Confessional YouTube:  https://www.youtube.com/@badbossconfessional  Beth's Youtube:  https://www.youtube.com/@bethfaheyeos  Guest Links Dominic Sergi is an entrepreneur and investor with a passion for building enduring companies. As CEO of Clear Height Properties, he’s led over $1 billion in industrial real estate transactions, co-founded Cresco Labs, one of the nation’s leading cannabis companies, and launched Westshore Capital Group, his family office built on the belief that patient capital can outperform the market while leaving a lasting legacy. Clear Height Properties: https://www.clearheight.com/ LinkedIn: https://www.linkedin.com/in/dominic-sergi-8b5ba24 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.

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