Bad Boss Confessional
By Speakeasy Podcast Network
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Category: Management
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Episodes: 43
Description
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.
| Episode | Date |
|---|---|
|
43: Fixing the Problem, Losing the Person
|
May 20, 2026 |
|
42: What Got You Here Won't Get You There
|
May 13, 2026 |
|
41: The Feedback Nobody Should Have Given
|
May 06, 2026 |
|
40: What Gets Lost When You Move Too Fast
|
Apr 29, 2026 |
|
39: You Can't Want It More Than They Do
|
Apr 22, 2026 |
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38: Every Coach Has to Learn to Lead
|
Apr 15, 2026 |
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37: When Growth Gets Ahead of Connection
|
Apr 08, 2026 |
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36: The Culture You Create When You're Not Looking
|
Apr 01, 2026 |
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35: When Your Team Tells You The Truth
|
Mar 25, 2026 |
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34: When a Star Player Stops Being a Teammate
|
Mar 18, 2026 |
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33: The Cost of Skipping the Details
|
Mar 11, 2026 |
|
32: Letting Go of the Vine
|
Mar 04, 2026 |
|
31: Building a Business Without Burning Out
|
Feb 25, 2026 |
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30: The High Price of Saying Yes
|
Feb 18, 2026 |
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29: Rollout: A Book Born From Bad Boss Moments
|
Feb 11, 2026 |
|
28: Getting Out of Your Own Way
|
Feb 04, 2026 |
|
27: Paying Attention to the Red Flags | Bad Boss Confessional
|
Jan 28, 2026 |
|
26. When Good Intentions Go Wrong
|
Jan 21, 2026 |
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25. The Hidden Cost of Doing the Right Thing
|
Jan 14, 2026 |
|
24. The Shift from Peer to Boss with Jessenia Flores-Gayle
|
Jan 07, 2026 |
|
23. Owning It: A Year of Leadership Confessions
|
Dec 31, 2025 |
|
22. The Role of Honest Dialogue in Healthy Leadership Teams
|
Dec 17, 2025 |
|
21: Be Their Boss, Not Their Buddy
|
Dec 10, 2025 |
|
20: From Positional Power to Humanized Leadership
|
Dec 03, 2025 |
|
19: Empathetic Leadership Without Compromising Accountability
|
Nov 26, 2025 |
|
18: Startup Fails, Shark Tank Tales, and Bad Boss Moments
|
Nov 19, 2025 |
|
17: Perfectionism, Pivoting, and Perseverance
|
Nov 12, 2025 |
|
16: Leadership Lessons from a Firing Gone Wrong
|
Nov 05, 2025 |
|
15: I Am Enough: Embracing Authentic Leadership
|
Oct 29, 2025 |
|
14: Bad Boss Moves, Better Boss Lessons
|
Oct 22, 2025 |
|
13: How Process Turns Chaos into Clarity
|
Oct 15, 2025 |
|
12: Lessons from a Meeting Gone Wrong
|
Oct 08, 2025 |
|
11: Why Straying from Your Core Focus Can Cost You Everything
|
Oct 01, 2025 |
|
10: When Loyalty Hurts: Hiring, Firing, and Hard Lessons
|
Sep 24, 2025 |
|
09: From Bulldozer to Breakthrough
|
Sep 17, 2025 |
|
08: Clarity is Key
|
Sep 10, 2025 |
|
07: Letting Go of Managing People
|
Sep 03, 2025 |
|
06: When Emotions Hijack Your Leadership: Learning to Respond vs. React
|
Aug 27, 2025 |
|
05: When Employee Feedback Feels Like a Gut Punch
|
Aug 20, 2025 |
|
04: Why Visionaries Shouldn't Hire People
|
Aug 13, 2025 |
|
03: Going Down with My Flipchart
|
Aug 06, 2025 |
|
02: Broken, Better, and Whole: A Coach’s Journey to Heart-Led Leadership
|
Jul 30, 2025 |
|
01: Too Busy to Lead
|
Jul 23, 2025 |