Podcast
Bad Boss Confessional
Hosted by Speakeasy Podcast Network · EN
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.
32episodes
Episodes
Newest firstAll episodes
25. The Hidden Cost of Doing the Right Thing
Jan 1400:36:19Tap to summarizeIn 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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24. The Shift from Peer to Boss with Jessenia Flores-Gayle
Jan 700:28:56Tap to summarizeOn 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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