Bad Boss Files: Lessons From The Worst

In this episode, The Side Eye Supervisor , we hear a story from a front desk employee in a busy healthcare office where micromanagement went way too far. From being constantly watched to having bathroom breaks tracked and empathy discouraged, this “hall monitor” leadership style created a high-stress, low-trust environment. When a moment of compassion toward a struggling patient was criticized as...

In this listener story, a People Ops leader at a startup is told to be more “aggressive” but when she applies that feedback, she’s publicly shut down and later dismissed by her manager. With unclear expectations, mixed messages, and a toxic, male-dominated leadership dynamic, her confidence takes a hit and she ultimately leaves after six months. This episode highlights how poor leadership, vague f...

In this episode, we unpack a real-world story that highlights a growing issue in today’s workplace: employee misclassification. What happens when someone is labeled as an independent contractor but treated like an employee? We walk through the experience of a worker who initially loved their role, only to discover over time that they were responsible for their own taxes, received no benefits, had...

In this episode, we share a real story about a department manager dealing with a toxic, bullying boss in a retail environment. Over time, the manager faced constant criticism, public humiliation, and unfair treatment especially around serious health issues that required ongoing medical care. Instead of support, the boss used intimidation, made inappropriate comments, and even shared private inform...

In this episode, we talk about how workplace behavior is learned by watching others, especially leaders, and how quickly culture can be shaped by what managers say and do. When a manager makes inappropriate comments or crosses personal boundaries, it doesn’t just affect one person: it impacts trust, safety, and the entire team. We also explore what happens when an employee shows up, works hard, an...

In this episode of Bad Boss Files, we dive into a workplace where communication is one-sided, leadership is checked out, and accountability is nowhere to be found. What starts with a boss casually showing up to meetings “a little tipsy” quickly unravels into a pattern of behavior that erodes trust across the team. It shows how leadership sets the standard for culture and leaves once-happy employee...

In this episode of Bad Boss Files, we dive into a workplace where communication is one-sided, favoritism runs deep, and retaliation is real. When a sales team is asked to share the good, bad, and ugly, a woman is cut off mid-sentence while her male coworker gets triple the time and the boss’s full attention. What follows is two months of silent treatment, ignored emails, and a growing list of red...

In this powerful live episode, we welcome our first-ever guest who bravely shares what it was like to work for a boss who regularly made inappropriate comments about her clothing and appearance. The lines kept getting crossed and she often found herself embarrassed, uncomfortable, and unsure how to respond. Sheri and Kate open up about their own experiences with workplace harassment and the ways s...

In this episode, we explore the complicated transition of power when a long-time owner steps away and a senior leader, whose only leadership example is the outgoing boss, steps in. Communication gaps, top-down decisions, and a legacy of poor leadership create a shaky start. But when employees bravely speak up, the new owner begins to listen. We dig into what it takes to break the cycle, build trus...

After a long career in government service, one employee finally landed a temporary role they loved thanks to a supervisor who unknowingly bypassed a gatekeeping process. They excelled, earned praise, and was invited to extend. When the regular supervisor was asked for approval, the answer was a firm 'no'. And the next time around, the employee wasn’t even permitted to apply for a position...

This episode spotlights a boss who brought in a highly-qualified new manager only to undermine her at every turn. Despite her competence and the team's steady progress, he inserted himself into projects unnecessarily, caused delays, and ultimately claimed credit for work she and her team completed. We break down the insecurity-fueled sabotage, the leadership damage it caused, and ask: Was this coa...

In this episode, we unpack the story of a manager who constantly changed the work schedule without informing staff, then had the audacity to blame his team for being “undependable.” As frustration grew, it became clear he played favorites—giving select employees insider info while leaving others scrambling. We dig into the impact of poor communication, inconsistent expectations, and favoritism on...

In this episode, we unpack the story of an employee at a small business who was eager to grow, stepping up to take on new responsibilities after a teammate left. But when she sent one marketing email, her boss responded with yelling, profanity, and an ego-fueled lecture. Despite her dedication, she consistently felt singled out—and as a minority, she finally asked the question that had been weighi...

In this episode, we explore the story of an employee who was encouraged to pursue education and career advancement—until she actually tried. When she submitted her tuition reimbursement form, it mysteriously vanished, her manager deflected blame to HR, and the HR contact conveniently left. What followed was a textbook case of passive resistance, lost trust, and silent sabotage. She ended up invest...

In this episode of Bad Boss Files, a long-time high-performer finds herself micromanaged, blocked from leadership, and slowly erased after a new manager takes over. Delegated to, ignored, and devalued, she finally gives notice — only to have her boss finally ask what salary might have kept her. At her farewell lunch, the micromanaging doesn't stop. The kicker? “ Order whatever you want — but you H...

Before the stories roll in, we’re pulling back the curtain on how Bad Boss Files came to be. In this kickoff episode, Sheri and Kate share the inspiration behind Bad Boss Files, why this podcast matters, and what you can expect in future episodes. Whether you’ve survived a bad boss, been one, or want to avoid becoming one — you’re in the right place. #BadBossFiles #LessonsFromTheWorst #BadBossFile...

In this kickoff episode, Sheri and Kate introduce The Bad Boss Files the podcast where workplace horror stories meet coaching wisdom and real talk. They share why the show exists, what you can expect in each episode, and how your stories (yes, yours!) can help others lead better. From HR confessions to laugh-out-loud leadership fails, this podcast digs into whether bad behavior is coachable, train...