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PODCAST

Bad Boss Confessional

Speakeasy Podcast Network

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.

business management

All Episodes

39:19

20: From Positional Power to Humanized Leadership

Bad Boss Confessional ·

2025/12/03

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

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32:12

19: Empathetic Leadership Without Compromising...

Bad Boss Confessional ·

2025/11/26

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

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42:20

18: Startup Fails, Shark Tank Tales, and Bad Boss...

Bad Boss Confessional ·

2025/11/19

This week on Bad Boss Confessional, host and EOS Implementor Beth Fahey sits down with Mike Shannon, CEO of Impruve and author of Sweaty Equity. From surviving Shark Tank to opening his first businesses, Mike opens up about his cringiest leadership missteps, the chaos of scaling to 120 employees, and how embracing systems thinking (and a few bad boss moments) helped him grow as a leader. Expect startup war stories, EOS insights, and a fresh look at how AI is transforming financial advising.00:00

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38:51

17: Perfectionism, Pivoting, and Perseverance

Bad Boss Confessional ·

2025/11/12

In this episode of Bad Boss Confessional, Beth Fahey welcomes Kathy Bresler, founder of Altar Community, a Chicago-based hub for connection, wellness, and growth. Kathy shares her journey from corporate strategist to reluctant boss and accidental entrepreneur. After years of envisioning a gathering space, she opened Altar in early 2020, just as the pandemic shut everything down. Forced to pivot, she and her community shifted online, building resilience through shared purpose.Kathy reflects on her

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40:28

16: Leadership Lessons from a Firing Gone Wrong

Bad Boss Confessional ·

2025/11/05

This week on Bad Boss Confessional, Beth Fahey sits down with Matt Haney, a seasoned fractional integrator who helps visionary-led teams cut through chaos and get traction. Matt shares the story of a firing he regrets to this day: an ungraceful exit of a 20-year employee during a pandemic downturn. Despite having let go of 15 others with care, this one moment turned combative, cold, and ultimately changed the way he leads forever.Matt unpacks the emotional aftermath, the gut-punch feedback he

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42:21

15: I Am Enough: Embracing Authentic Leadership

Bad Boss Confessional ·

2025/10/29

In this episode of Bad Boss Confessional, Beth Fahey, Expert EOS Implementer®, sits down with Rhonda Meyers for a raw and inspiring conversation about the realities of leadership. From navigating adversity and stepping into entrepreneurship, to the courage it takes to stand in your truth, Rhonda shares her journey of growth and resilience.Together, they unpack the challenges of wearing “six seats” in business, the hidden curse of being highly capable, and the bravery required to lead with both

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39:26

14: Bad Boss Moves, Better Boss Lessons

Bad Boss Confessional ·

2025/10/22

On this week’s episode of Bad Boss Confessional, Beth Fahey chats with EOS implementer John McMahon, who opens up about his toughest management, including the dreaded task of firing an employee. From learning that silence can speak louder than words to discovering the power of open-ended questions, John shares how missteps turned into lessons in empathy, communication, and leadership growth.01:37 Trial by Fire Leadership 05:22 First Lesson: What Took You So Long? 08:21 The Fear of Firing 11:06

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30:13

13: How Process Turns Chaos into Clarity

Bad Boss Confessional ·

2025/10/15

Do you think of “process” as boring, rigid, or suffocating? In this episode of Bad Boss Confessional, host Beth Fahey sits down with Lisa Gonzalez, EOS Implementer, lawyer-turned-entrepreneur, and co-author of Process: How Discipline and Consistency Will Set You and Your Business Free. Lisa shares her most cringeworthy leadership moment of secretly creating a six-inch binder of hyper-detailed processes that her team ignored, a project fueled by fear and perfectionism. She reveals the painful lessons

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32:52

12: Lessons from a Meeting Gone Wrong

Bad Boss Confessional ·

2025/10/08

We’ve all been there: fired up in a meeting, convinced our point is the only one that matters… until we realize the room has gone silent. In this episode of Bad Boss Confessional, host Beth Fahey sits down with Reid Hutchison, COO and integrator of HOH Technology, to unpack a moment he’s not proud of. Reid shares the time he let his emotions hijack a leadership meeting, turning collaboration into tension.The real lesson? How he owned the mistake, apologized in the moment, and rebuilt trust with his

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38:54

11: Why Straying from Your Core Focus Can Cost You...

Bad Boss Confessional ·

2025/10/01

This week, Beth Fahey sits down with Kelly Knight of EOS Worldwide to talk about the messy (and meaningful) side of leadership. From a vacation epiphany that reshaped her company’s mission to the tough call of laying off 38 employees, Kelly opens up about mistakes, lessons, and the power of vulnerability in business. Tune in for real talk on staying true to your core focus, building trust, and leading with courage.00:00 The Core Focus Dilemma 04:08 The Pitfalls of Software Expansion 08:49

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30:15

10: When Loyalty Hurts: Hiring, Firing, and Hard Lessons

Bad Boss Confessional ·

2025/09/24

In this episode of Bad Boss Confessional, host and EOS Implementer Beth Fahey sits down with Brian Dosal, CEO and co-founder of Strety, to talk about the messy side of leadership, ignoring red flags, hiring missteps, and the tough calls that come with rapid growth. Brian shares his entrepreneurial lessons on humility, adaptability, and why holding onto under performers can cost you your best people.03:11 The Difficult Decision to Let Go 07:34 Ignoring Red Flags and Outgrowing Roles 11:04 The

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34:38

09: From Bulldozer to Breakthrough

Bad Boss Confessional ·

2025/09/17

On this episode of Bad Boss Confessional, host and EOS Implementer Beth Fahey sits down with Lynda Martin to unpack the lessons learned from bulldozing through leadership missteps. From failed ventures and perfectionism to the power of slowing down, Lynda shares how embracing the physical, emotional, and spiritual sides of leadership transformed her career. Expect honest stories, big breakthroughs, and plenty of laughs as they explore what it really takes to grow as a leader.03:01 Integrating

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34:49

08: Clarity is Key

Bad Boss Confessional ·

2025/09/10

What happens when a fast-moving entrepreneur skips clarity and hires quickly? This week on Bad Boss Confessional, EOS Implementer Beth Fahey welcomes Drew Spurgers to unpack a hilariously painful hiring misstep, the chaos it created, and how clear communication (or lack thereof) can make or break your team. From titles that confuse to sales goals that actually work, Drew shares hard-won lessons about leadership, trust, and the power of saying exactly what you mean. This is your crash course in

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31:51

07: Letting Go of Managing People

Bad Boss Confessional ·

2025/09/03

Beth Fahey is joined by fellow EOS coach, implementer, and entrepreneur Jim Coyle, who shares his journey from childhood candy bar hustler to managing a Chicago bar. He opens up about the pitfalls of hiring friends, the emotional weight of leadership, and why management isn't for everyone. This episode brings laughs, lessons, and the wisdom every founder needs.00:26 Meet Jim Coyle 02:07 Jim’s Entrepreneurial Journey 04:06 The Challenges of Managing Friends 06:19 Lessons from the Bar

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32:18

06: When Emotions Hijack Your Leadership: Learning to...

Bad Boss Confessional ·

2025/08/27

Have your emotions ever hijacked your leadership? In this episode of Bad Boss Confessional, host Beth Fahey talks with Jill Young, EOS expert and creator of Coaching Magic, about three cringe-worthy moments that changed her approach to leadership. From losing her cool with an employee asking for a raise to firing someone who didn’t see it coming, Jill shares how these painful lessons taught her the power of responding thoughtfully instead of reacting emotionally. This candid conversation reminds us

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30:20

05: When Employee Feedback Feels Like a Gut Punch

Bad Boss Confessional ·

2025/08/20

In this episode of Bad Boss Confessional, EOS implementer Beth Fahey sits down with Miranda Barrett, founder of Mind the Mic Consulting, to unpack a leadership low point that rocked her confidence and reshaped her career. From onboarding fails and harsh feedback to a bombshell resignation that called her integrity into question, Miranda shares the painful—but powerful—lessons that helped her build trust, lead with transparency, and simplify management with EOS tools.01:45 Meet Miranda

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59:12

04: Why Visionaries Shouldn't Hire People

Bad Boss Confessional ·

2025/08/13

Jonathan Reynolds, CEO of Titus Talent, joins EOS Implementer Beth Fahey on Bad Boss Confessional to share the hard-earned lessons behind his biggest leadership missteps. From hiring failures to communication breakdowns, Jonathan reveals how applying EOS principles, empowering teams, and leading with clarity transformed his management style, and his company’s success. A must-listen for founders and business leaders seeking better hiring, smarter delegation, and stronger organizational

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48:27

03: Going Down with My Flipchart

Bad Boss Confessional ·

2025/08/06

When creative ideas crash and egos flare, even the most seasoned leaders can stumble spectacularly. This week, Vistage chair and facilitation expert Francine Lasky joins host and EOS Implementer Beth Fahey to confess her most cringeworthy leadership missteps—think brutally rejected ideas, painfully misunderstood meetings, and explosive clashes with powerhouse personalities. Tune in for raw, hard-won wisdom on vulnerability, buy-in, and building purpose-driven conversations that actually

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43:20

02: Broken, Better, and Whole: A Coach’s Journey to...

Bad Boss Confessional ·

2025/07/30

What happens when Beth Fahey’s own coach, Shasheen Shah, confesses his journey from high-powered hustler to heart-led healer? In this candid conversation, Shasheen reveals how chasing success nearly broke him—and how raw feedback, failure, and deep self-work rewired his path. From walking away from a tech industry failure to confronting childhood wounds and loneliness, he opens up about ego traps, emotional breakthroughs, and authentic self-care. It’s an honest talk about shadow work, self-worth,

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50:07

01: Too Busy to Lead

Bad Boss Confessional ·

2025/07/23

Can you lead when you're stuck in the chaos? In this episode, Beth Fahey chats with René Boer—author of How to Be a Great Boss—about ego, empathy, and the messy art of leadership. From cringe-worthy missteps to hard-won wisdom, René shares real stories and practical tools, revealing why soft skills might be your secret weapon. Perfect for anyone who's ever doubted their leadership abilities—spoiler alert: you probably are cut out for this, you just need better tools.00:00 Meet Rene Boer: The

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21 results

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