13 Apr THE WORST BOSS I EVER HAD
Lessons From Bad Managers
Over the course of my career, I’ve worked for more than a few poor managers—enough that choosing just one as the worst would be nearly impossible. Instead, I’ve narrowed it down to three who left the deepest impression. Ironically, I’ve also been fortunate to work for some truly exceptional leaders, whom I’ll write about separately. The contrast couldn’t be sharper: the best managers elevated my career, respected me as a person, and recognized my strengths.
The three below did exactly the opposite.
Richard
I joined Richard’s petrochemical construction company as a Budget Manager after being referred by the Controller of my previous employer. From day one, Richard was an imposing presence—physically large, stern, and intimidating. Warmth was not part of his leadership style, at least not with me.
His high expectations didn’t bother me. What made him so difficult to work for was his constant inconsistency. He regularly contradicted his own instructions. I would present reports formatted exactly as he had requested—sometimes with his handwritten notes as proof—only to be told they were wrong. Even worse, he would arbitrarily change revenue or expense targets after I had already built the detailed budgets to support them.
This was before spreadsheets existed. Every number was calculated by hand across more than 100 paper spreadsheets, all compiled in a thick three-ring binder.
One day, enraged over the final budget, Richard picked up that binder and threw it at me.
After more than a year of silence—no feedback, no direction—I finally asked for a performance review and a raise. When it came, it was crushing. He told me my performance was unsatisfactory but offered no explanation, no examples, and no path to improve. My raise was minimal—around two percent. I walked away feeling blindsided and demoralized.
In over two years, I don’t recall a single positive comment from him. I lived in a constant state of stress, and I know that strain followed me home.
Things briefly improved when a new Controller, Galen, joined the company. He was everything Richard was not—supportive, encouraging, and genuinely invested in my growth. But after nine months, Galen was let go, and I was reassigned to Richard.
That’s when I knew it was time to leave. Soon after, I moved to Arizona.
David
I met David after flying from Chicago to Tucson for an interview. He hired me as a Financial Analyst for a land development company, and despite significant personal risk, I accepted.
At the time, my wife and I had just bought our first home, and she was eight months pregnant. I also signed a contract requiring me to repay relocation costs if I left within a year.
Almost immediately, red flags appeared. David had hired a team of six analysts but had no clear plan for what we were supposed to do. Two if us had relocated from across the country. The environment was chaotic—and worse, he was verbally abusive.
Like Richard, David often rewrote history. He would give me written instructions, then deny them later, claiming he had provided updated direction that simply didn’t exist.
The breaking point came around Election Day. A coworker and I asked for the day off together to support a candidate we all backed. David approved it.
The next day, I returned to work—and was fired for taking unauthorized time off. He said that he gave the other person authorization, but not me.
Madhavan
By the time I joined Madhavan’s company, I had more than twenty years of experience, including leadership roles as a Vice President of Sales and Regional Sales Manager. Madhavan recruited me to lead his technical support department, and I saw it as an opportunity to expand my skill set, even though my demonstrated expertise was in sales and finance.
He was undeniably intelligent—a PhD candidate turned entrepreneur—but he struggled with the human side of leadership. He lacked empathy, avoided delegation, and micromanaged relentlessly. Trust was not something he extended to his team.
In one company-wide meeting, he referred to employees as “interchangeable parts” and suggested salespeople could be replaced by “organ-grinder monkeys.”
When his leadership team proposed new ideas, he dismissed them outright: the team put together a thoughtful list of suggested improvements for the company, he took one look at them and said ”these are not suggestions…. they are an indictment of me and my company.” He then responded that if we didn’t like it, we could leave.
He didn’t just reject ideas—he punished initiative. When employees took risks that didn’t pan out, he publicly humiliated them. Over time, people stopped speaking up altogether.
I led a strong and committed technical support team, but challenges were inevitable. Instead of fostering solutions, Madhavan fostered fear. Eventually, I realized I could no longer work in that environment and chose to leave.
Final Reflection
If I had to choose, Richard was the worst. Two years under his leadership made daily work feel unbearable. But in truth, all three shared the same core failures. I was also singled out by him, whereas David and Madhavan mistreated everyone.
Key Lessons
These experiences taught me exactly what ineffective—and damaging—management looks like:
- They failed to coach, mentor, or develop their people.
- They used criticism and humiliation instead of constructive feedback.
- They provided little to no clarity on expectations or performance.
- They showed no interest in their employees’ goals or growth.
- They were either unaware of—or indifferent to—their impact on morale.
- They didn’t trust their teams, making success nearly impossible.