

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 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.