x

75% of people globally want unbiased news (Pew Research) but are concerned they're not getting that.

Get balanced coverage with Symby. See how stories are covered across diverse outlets and spot when one side covers a story the other skips.

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

30:50

26. When Good Intentions Go Wrong

Bad Boss Confessional ·

2026/01/21

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

en

36:19

25. The Hidden Cost of Doing the Right Thing

Bad Boss Confessional ·

2026/01/14

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

en

28:56

24. The Shift from Peer to Boss with Jessenia...

Bad Boss Confessional ·

2026/01/07

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

en

21:20

23. Owning It: A Year of Leadership Confessions

Bad Boss Confessional ·

2025/12/31

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

en

32:43

22. The Role of Honest Dialogue in Healthy Leadership...

Bad Boss Confessional ·

2025/12/17

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

en

43:29

21: Be Their Boss, Not Their Buddy

Bad Boss Confessional ·

2025/12/10

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

en

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

en

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

en

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

en

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

en

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

en

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

en

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

en

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

en

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

en

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

en

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

en

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

en

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

en

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

en

27 results

Similar Podcasts

TaxTalent.com The Golden Rule Podcast

Adam Golden

TaxTalent.com Podcast

Tony Santiago

Handelsblatt Crime - spannende Streitfälle der deutschen Wirtschaft

Ina Karabasz, Solveig Gode, Sönke Iwersen

Deffner und Zschäpitz – Der Wirtschafts-Talk von WELT

WELT

Black Box - La scatola nera della finanza

Guido Brera e Gian Luca Comandini -...