

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.
But this isn’t just a cringe-fest—it’s a redemption story.
Episodes
Mentioned books

Aug 27, 2025 • 32min
06: When Emotions Hijack Your Leadership: Learning to Respond vs. React
Jill Young, an EOS expert and creator of Coaching Magic, shares her transformative leadership journey with Beth Fahey. They discuss cringe-worthy leadership moments, including mishandling employee salary requests and unexpected firings. Jill emphasizes the importance of emotional awareness, thoughtfully responding rather than reacting. The conversation also touches on the significance of personal growth, navigating difficult conversations, and her whimsical tattoo that reminds her of her potential. It's a powerful reminder that even seasoned leaders can learn from their missteps.

Aug 20, 2025 • 30min
05: When Employee Feedback Feels Like a Gut Punch
Miranda Barrett, founder of Mind the Mic Consulting, shares her tumultuous journey through leadership challenges that tested her confidence. She recounts cringe-worthy onboarding fails and harsh feedback that reshaped her career. Miranda emphasizes the importance of transparency and effective communication while navigating employee dynamics. She also discusses modernizing performance reviews and fostering core values in the workplace. Finally, she reflects on lessons learned from rock climbing about trust and intuition in leadership.

8 snips
Aug 13, 2025 • 59min
04: Why Visionaries Shouldn't Hire People
Jonathan Reynolds, CEO of Titus Talent, shares his insights on leadership and hiring decisions. He discusses the pitfalls of hiring for personal bias and the importance of cultural fit. Jonathan emphasizes the 'Hire for Performance' strategy, showcasing how effective onboarding boosts team success. He also touches on the significance of vulnerability in leadership, the art of communication, and fostering trust within teams. Through personal stories, he illustrates how embracing calculated risks can lead to innovation and growth.

Aug 6, 2025 • 48min
03: Going Down with My Flipchart
Join Francine Lasky, a Vistage chair and facilitation expert from Chicago, as she shares her leadership blunders and insights. She dives into the importance of clear communication and the weight of expectations in creative discussions. Francine opens up about her most cringeworthy moments in meetings and how vulnerability can foster trust within teams. Discover strategies for effective meeting facilitation, the power of purposeful gatherings, and personal growth beyond 50. It's a candid look at leadership that balances humor and authenticity.

Jul 30, 2025 • 43min
02: Broken, Better, and Whole: A Coach’s Journey to Heart-Led Leadership
Shasheen Shah, a coach for founders and leaders, shares his transformative journey from high-powered hustler to heart-led healer. He candidly discusses how the pursuit of success almost shattered him, prompting raw self-reflection and emotional growth. Shasheen touches on ego traps, the inner critic, and the profound loneliness often found in achievement. He emphasizes the importance of authentic self-care and shadow work, highlighting how embracing vulnerability can lead to genuine joy and connection.

4 snips
Jul 23, 2025 • 50min
01: Too Busy to Lead
René Boer, author of 'How to Be a Great Boss' and EOS implementer, dives into the chaotic world of leadership. He shares personal stories about navigating leadership failures, highlighting the importance of empathy and communication. René emphasizes that effective leadership is about serving others rather than wielding authority. He challenges the modern leader to prioritize listening and building genuine connections. With practical tools and insights, he reassures anyone feeling overwhelmed that they have what it takes to lead well.