When Your Best Friend Becomes Your Worst Boss: A Coffee Talk About Career Survival

 

Last week, I had a long phone call with my old friend, Farid (not his real name). We haven't caught up properly in months. What started as casual "how are you bro" quickly turned into a two-hour deep conversation about work, life, and some hard truths about the corporate world.

I'm sharing this because honestly, there's too many good lessons here to keep to myself.

 

The Two-Hour Interview: Good Sign or Red Flag?

Farid told me he just went for an interview. Aviation management team position. Quite senior role.

"Bro, the interview took almost two hours," he said.

"Two hours? Serious?"

"Yeah. Other candidates only 20 minutes. I don't know if that's good or bad."

I told him honestly — it can go both ways. Maybe they really interested in you. Maybe they grilling you because they not sure. But two hours? That means something caught their attention.

Then he shared some of the questions they asked. And wah, these are not your typical "tell me about yourself" questions.

Question 1: "You are a single father. How will you handle 30 female bachelor staff under you?"

I nearly choked on my coffee when he told me this. What kind of question is that? But you know what, it's actually clever. They want to see if he will panic. If he will say something inappropriate. If he understands boundaries and professionalism.

Question 2: "Let's say all your team members are your best friends. One of them is underperforming. How do you handle it?"

This one is tricky. Because we all know — friendship and work sometimes don't mix well. Can you be firm with your buddy? Can you separate personal from professional?

Question 3: "How would you handle a sexual harassment case in your team?"

Straightforward but heavy. They want to know if you understand policy, procedure, and most importantly — will you protect your people or protect the company's image?

Question 4: "You have a good worker, but they have a medical problem. How do you manage this?"

This shows if you have compassion. Do you see staff as humans or just numbers on KPI sheet?

Question 5: "If we hire you, what new things will you bring to the company?"

Classic. But important. Are you just here to collect salary, or you actually want to contribute something?

I told Farid, "Bro, if they asking you all this, they seriously considering you. These are leadership questions."

 

 

The Story Behind His Two Resignations

After the interview talk, I asked him something I've been curious about.

"Eh, what happened to your previous jobs? I heard you left two companies already."

He went quiet for a moment. Then he said, "It's a long story, bro."

And what he told me next — I think everyone needs to hear this.

The First Job: When Integrity Costs You Everything

Farid used to work for a company that managed and funded a religious school. Good job. Stable. Respected.

His own son was a student there.

One day, his son came home with injuries. Bad ones. Turns out, a teacher had physically punished him so badly that the boy had to be hospitalised.

As a father, Farid was furious. As an employee, he wanted to report it properly.

But the management called him in.

"Farid, we understand you're upset. But please, let's settle this internally. Don't make a police report. Don't go to the media. It will damage the school's reputation. It will affect our funding."

They basically asked him to shut up. To protect the company's name. To sacrifice his son's justice.

"I cannot do that, bro," he told me. "That's my son. How can I stay in a company that asks me to cover up abuse?"

So he resigned.

No drama. No big announcement. He just walked away.

"Sometimes," he said, "your principles cost you your paycheck. But at least I can sleep at night."

The Second Job: When Your Friend Becomes Your Enemy

After that, Farid was quite lost. No job. Bills piling up. Single father, remember.

Then an old friend approached him.

"Bro, come work with me. I'm in this organization now. The pay is good. I'll take care of you."

Farid was hesitant. The job scope wasn't his expertise. He's more of operations and management guy. This new role was completely different field.

But the salary was attractive. And his friend kept pushing. "Don't worry, I'll guide you."

So he joined.

Big mistake.

The first few months were okay. But slowly, things changed.

His friend — now his boss — started to pressure him. Complained about his performance. Set unofficial KPIs that were impossible to achieve.

"He never gave me proper training or resources," Farid said. "But he expected me to perform like I've been doing this job for 10 years."

And here's the worst part.

Farid is a friendly guy. He gets along with people easily. Soon, he became quite popular among other staff. People liked him. Respected him.

And his boss? Got jealous.

"I could feel it, bro. Everytime I joke with colleagues, he would give me that look. When people come to me for advice instead of him, he got irritated."

The boss started to sabotage him. Talked bad about him to board members. Made him look incompetent in meetings. Created situations where Farid would fail.

Finally, Farid was "advised" to resign.

"When I left, some staff actually cried. A few even said they wanted to resign too. That's when I knew — the problem was never me."

 

The Lessons I Took From This Conversation

After we hung up, I couldn't stop thinking about Farid's stories. There's so much to unpack here.

1. Know what you're good at — and stick to it.

Farid struggled in his second job because it wasn't his strength. Yes, the money was good. But money means nothing if you're miserable and failing everyday. Your "bread and butter" skills exist for a reason. Don't abandon them just for a bigger paycheck.

2. Never mix friendship with hierarchy.

This is painful but true. Your best friend can become your worst boss. When power dynamics enter a friendship, things get complicated. Not everyone can separate personal feelings from professional decisions. Be very careful when a friend offers you a job under them. Ask yourself — can this friendship survive if things go wrong at work?

3. Jealousy in the workplace is real.

Some bosses feel threatened when their subordinates shine. Instead of being proud, they feel challenged. If your boss starts acting cold when you get praised by others, that's a red flag. Protect yourself.

4. Impossible KPIs without resources is just setting people up to fail.

How can you expect someone to climb a mountain if you don't give them proper shoes? Some managers set high targets but provide zero support. No training. No budget. No manpower. Then they blame the staff when targets are not met. That's not leadership. That's cruelty.

5. Look after your people's welfare — including their health.

A good worker with medical problems is still a good worker. Don't throw people away just because they're going through tough times. Show compassion. Adjust their workload. Be human.

6. Your integrity is not for sale.

Farid could have stayed quiet about his son's case. He could have kept his job, kept his salary, kept his comfortable life. But he chose to walk away because he couldn't live with himself otherwise. In the end, we all have to answer to ourselves. Can you look in the mirror and be proud of who you are?

7. Communication and humility go a long way.

Talk to your team. Ask questions. Don't pretend you know everything. The best leaders are those who say, "I don't know, but let's figure it out together."

 

Final Thoughts

Before we ended the call, I asked Farid, "Any regrets?"

He laughed softly.

"Regret? No, bro. I learned so much from both experiences. Painful, yes. But I know now what kind of workplace I want. What kind of leader I want to be. And most importantly — what kind of person I refuse to become."

That hit me hard.

Sometimes the worst jobs teach us the best lessons.

To Farid, wherever your next chapter takes you — I'm rooting for you, brother.

And to whoever reading this: protect your peace, know your worth, and never let anyone make you compromise who you are.

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Have you ever been in a similar situation? A friendship that got ruined by work? A boss who made your life miserable? Drop your thoughts. Sometimes sharing helps us heal.

Shamyl Shalyzad, PhD, is a freelance writer, HR advisor, and social science researcher. He resides in Seremban, Negeri Sembilan