My most embarrassing interview experience

What’s the most embarrassing thing that has ever happened to you during an interview?

For me, it was breaking down uncontrollably in tears.

No, it wasn’t a tough question that stumped me. And it wasn’t the interviewer being an ass.

I was the interviewer. I felt like the ass.

Here is the story of what led to my breakdown.


The context

Sam (not his actual name) had applied to join an online learning organization I was helping.

I show up on Zoom at the appointed time. 5 minutes in, Sam is nowhere to be seen.

I ping him. No response.

A few minutes later, I give up and leave – slightly annoyed.

Half an hour later, I receive an apologetic email from Sam. He doesn’t give a real excuse. Just says sorry and asks to reschedule.

I’m somewhat curious. Plus, the organization I’m helping is short on candidates.

So I decide to give Sam another chance. We hop on Zoom a couple of hours later.


First impression

Sam’s camera turns on. I quickly notice 4 things.

  1. I see that he is using a cellphone rather than a laptop for this professional video interview.
  2. The name at the bottom of his icon says “Sam’s iPhone” rather than his full name.
  3. His iPhone camera is at an odd angle.
  4. And I can barely see his face due to his complexion coupled with the bad lighting in the room.

Not a good first impression.

I immediately think to myself:

Man, this guy is a dud. I shouldn’t have even agreed to reschedule this…

But since I’m here, I might as well continue.

In the first few minutes, we introduce ourselves. I start with a standard set of questions, and my impression doesn’t change much. English is not Sam’s first language, and it’s slightly difficult for me to understand him.

But something about this situation, his story, and my initial impression just feels incongruous. So I dig in.

I ask him to tell me the story of where he is from and how he got to America.

Sam tells me:

I came here at age 26 from [country name redacted]. I am 46 now.

I came to the US with basically nothing after finishing my law degree. I had to flee my country after the civil war. My best friend was killed by the military during the protests. I was lucky to only be thrown in jail.

In America, I started out as a dishwasher.

I later became a special ed teacher for 13 years.

But I’ve always wanted to be a businessman, so I started my own business.

I had actually taken a look at Sam’s business website right before the interview. I hadn’t thought much of it. It was poorly designed, and it didn’t even have an SSL certificate. 

“Amateur hour”, I had thought.

Plus, his LinkedIn wasn’t polished at all. He didn’t have a profile picture. He had <10 connections, and only one position listed. 

I had no idea that he had founded the company, as his listed title for that position wasn’t CEO or founder.


Illusion shattered

Curious now, I ask him to tell more about his company.

Sam proudly tells me:

My business helps disabled people.

Our revenues grew by $2 million this year!

Shock passes through me. My impression of Sam flips a 180.

How could I have been so wrong?

He wasn’t a dud. He was a successful, self-made businessman.

I feel like an utter fool.

Breaking down

As Sam tells me more about himself, such as how he created a LinkedIn profile for the first time just for this application–my mind continues to spin.

This is where I breakdown. My eyes first start getting watery.

My mind wanders to my parents.

Sam started out washing dishes when he first came to America. My mother did the same thing when we came to this country.

Just like Sam, both my parents have thick accents. Neither are tech savvy. 

That doesn’t make them any less hardworking, any less intelligent, and any less deserving of opportunity.

I had thought highly of my own ability to read people. But I had misjudged Sam, badly. 

I can’t believe myself. I nearly deprived this man of an opportunity. I feel angry. I feel disappointed.

I am overwhelmed by emotion, and my tears now flow uncontrollably.

Now I’m the one apologizing to Sam. I try to explain myself but I have no words.

The interview candidate I thought was unprofessional is now reassuring me in my extremely vulnerable, unprofessional state.

It’s okay Yishi, don’t worry”

As Sam gently comforts me over Zoom, I think to myself:

“People work in special ed because they want to help people. And now, he’s built a business helping disabled people. This is a very kind, empathetic, and caring person.

And now he is taking care of me”

I feel embarrassed. I feel self conscious. I have never broken down like this in an interview with a stranger before, but I can’t stop my tears.

No one ever taught Sam basic Zoom etiquette.

No one ever taught Sam how to make a proper LinkedIn.

No one ever taught Sam how to tell his story of escaping a war-torn country in a compelling way. 

Sam is the epitome of the American Dream, and a kind-hearted person to boot. He built a successful business in the social sector and has dedicated most of his career to helping others.

I judged him just as countless people surely must have over the years. Just like how countless people must have judged my parents. Just like people have judged me.

And here I was perpetuating these biases. I had attended some of the best schools in the world. I had held great jobs. I had arrived at a position of privilege. And here was someone who started with way less than I did and has made it incredibly far. 

I feel shame. I feel guilt.

As I pull myself together, he tells me that he is applying to this organization I’m working with because he just wants to learn. 

I give him a few tips, and offer him my gratitude, a few bits of advice, and promise of future help.

And so that’s how the most unique interview experience of my life comes to an end.

It was quite a learning experience for me, and I can only hope that I’ve made a positive impact on Sam. 

Subscribe for the latest updates

July 12th, 2023

More essays

My personal journey, Poker

My evolving relationship with poker

When I first started playing poker regularly in 2019, I was looking for fun. I wanted a new hobby to get good at – with the bonus hope of making...

My personal journey, Poker

What writing does for me (and perhaps you as well)

I write to explore my own thoughts. It’s a creative outlet. Some of my most enjoyable-to-write articles were about niche, eclectic topics that have received very few clicks: While I’m...

My personal journey, Investing

Run-in with a con man

A while back, I met an entrepreneur. Let’s call him Gary (not his real name). I took a liking to Gary, and I took a small amount of funds from...