How to Handle Difficult Bosses, Employees, and People

How to Handle Difficult Bosses, Employees, and People



How to Handle Difficult Bosses, Employees, and People

This past Mother’s Day was particularly poignant for me. This year marks the 10th year of my mother’s passing away in Bangalore, India, from a rare cancer.

Social media was filled with tributes to the world’s wonderful moms. My mother, Lakshmi, was also amazing.

And she was also… difficult.

Reflecting on my mother leaves me with lasting lessons about the impact of “difficult people” in our lives and careers. Calling someone “difficult” could seem pejorative, but it’s actually descriptive of the complex interpersonal dynamics that may not be as simple as we would like, but are active reflections of reality.

Mom gave my brother and me our strength, resilience, drive, and, above all, moral fiber. She was also kind and generous, especially to those less fortunate than us. She was a feminist in her own right, establishing boundaries for herself in the deeply traditional culture of South India’s Iyengar community. She was a big proponent of the education of working-class Indian women and paid for all our housemaids’ children’s schooling and kept track of their grades.

And my mother was also a difficult person. Stubborn, negative, pessimistic, and prone to bouts of anger and frustration. “No” was her default mode. But we knew how much she loved us.

Over time, my dad, brother, and I understood that Mom could never really be pleased, only managed. Married to her for 60 years, my dad became a master of stoicism. I could never figure out why she was the way she was.

Until one day, I was waiting for a prescription at my local pharmacy and browsing through a metal revolving book stand filled with paperbacks. I saw a book I think was titled How to Deal With Difficult People. My heart leaped. Wait, there was a category of people with psychological traits that made them “difficult people”? I instantly thought of mom, and everything fell into place.

I started flipping through the book. The message was clear. Being a “difficult person” is a personality trait that makes some people virtually impossible to please. It can also be shaped by her lack of self-determination and clear expression, manifesting as anxiety, depression, or loneliness. Looking back, I suspect that may have been part of my mother’s story, especially after her children moved to the United States.

Difficult people can create real strain on those around them, whether family members, friends, colleagues, employees, or bosses.

Managing Difficult Bosses and Employees

In my career, I’ve had my share of bosses who have been absolutely phenomenal and just a couple who, in retrospect, truly fell into the “difficult people” category. Negative, emotional, overly demanding, impossible to please.

Understanding that it’s a personality trait has made relationships much easier for me. When I am in a relationship or situation that seems impossible to navigate, I ask myself, “Am I dealing with a difficult person?”

It’s also made me acutely sensitive to the possibility that I might become my mom in my own relationships, so I often stop and try to recalibrate to see if I feel like I’m trending in that direction. I’ve also thought back to relationships and wondered how being “difficult” contributed.

The implications of this psychological trait are big for employers and employees. Employers have to deal with chronically negative people who spread toxicity in the workplace because they can never really be pleased. And their performance is often subpar. In many cases, they have to be removed quickly before they affect workplace culture.

On the flip side, if you are an employee who has a difficult boss, and you believe your performance has been superlative, understand first and foremost that it may not be you. They may just be a “difficult person.” So what do you do? Know that no matter how hard you work or how good you are at your job, they can never be pleased. They can only be managed, and only up to a point. The only options are to allow your resentment to fester over time or to leave and find a better boss. And there are so many great bosses out there in the world.

In my coaching, I often ask clients to think about the difficult people in their own lives or work. Are they exhausting themselves trying to please someone who can never really be pleased?

What are some steps you can take today to make your situation with difficult people easier?

On Mother’s Day, I sent lots of love to my mom for the lessons she taught me about meeting people where they are.



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About the Author: Tony Ramos

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