7 Tough Interview Questions That Actually Get To The Core Of Whether A Person Has A Work Ethic Or Not

Tired of fluffy interview answers? These questions reveal who's actually willing to do the work.

Written on Jul 07, 2025

Man asking questions during interview. Jason Goodman | Unsplash
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I have been on hundreds of interviews, and with very few exceptions, the conversations have been pretty much the same, at least in finding out whether we’re a good match. That’s when I realized that instead of businesses asking the standard questions, we could dive deeper beyond the job requirements and get to know the actual candidate.

When we consider that millennials, according to Deloitte’s research, stay in a job for an average of about 2.8 years, it’s time to rethink the typical interview process. As a Millennial, I have given the matter some thought and found that part of the main issue starts with not asking the right questions in the interview.

Here are seven interview questions that get to the core of whether a person has a work ethic or not:

1. 'What do you do in your free time?'

woman with the interview question of what do you do in your free time insta_photos / Shutterstock

Purpose: To break the ice and see who the person is outside of work.

A good icebreaker is essential for any interview. The best icebreaker I saw, which In-n-Out uses, is asking the candidates what they do in their free time.

Are they someone who enjoys the outdoors? Do they have a family vacation spot they go to every year? Do they make shirts for a local charity?

Millennials value authenticity. And the best way to find out how authentic they are is by diving deeper into who they are.

RELATED: The Two Best Ways To Answer The Most Common Interview Question, According To A Career Expert

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2. 'What would you do if you won $1000 or anything beyond that?'

woman asking the interview question what would you do if you won money insta_photos / Shutterstock

Purpose: To see how they react to money.

Millennials grow up in an unstable economic environment right out of school, which affects their attitude toward money. But that doesn’t mean we are all financially illiterate.

Someone may have an active imagination. Or, if they are applying for a sales position, perhaps they have a better way to spend a thousand dollars than another candidate.

All options are possible, and it’s a unique way to see if they fit your company culture.

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3. 'What does your best work environment look like?'

woman asking the interview question like what their best work envirnoment us fizkes / Shutterstock

Purpose: To see if an employee’s work environment matches the job.

Everyone succeeds in a particular work environment, but only some candidates who come through the door are made for the environment the job requires.

I learned the hard way that I succeed in a quiet and calm work environment compared to the loud and chaotic ones in the fast food jobs I applied for.

So, it is essential to ensure that your company’s work environment and the position they are applying for give them the best resources to succeed.

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4. 'Name a time you felt challenged at your job, and did you succeed or fail?'

man with the interview question of name a time the woman was challenged at work DC Studio / Shutterstock

Purpose: To see how they handle a curveball.

Knowing how the candidate will perform is essential, whether they were successful or not. We tend to learn more about ourselves through our failures than our successes.

Millennials have been given the short stick for a while, so our failures make our generation stronger and more resilient than most think.

If there is a problem, focus on how the candidate approached it and what they did afterward. If they get hired, they may encounter a similar situation.

RELATED: The Subtle Red Flag That Made Me Leave A Job Interview Before It Even Started

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5. 'What three contributions or ideas will you add to the job?'

man with the interview question of what ideas would you add to the job Yuri A / Shutterstock

Purpose: To see if they have ideas or will follow directions.

From my experience of the ten-plus jobs I’ve had, every millennial I ran into wanted to improve the business. They put their time and energy into doing their jobs because they are a generation that cares.

It only makes sense that they want to improve the next job, even if they need to learn how the entire company functions or works, listening to their feedback is still important.

RELATED: 10 'Weaknesses' Bosses Want To Hear About In Job Interviews

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6. 'What about the position excites you?'

man asking the interview question what about this position excites you fizkes / Shutterstock

Purpose: To see what caught their attention and keeps them motivated.

No matter if they are Millennials, Gen-Xers, Boomers, or even Gen-Zers, everyone eventually gets excited about a job. And when a job gets posted that satisfies all the skills and requirements a person has worked hard for, it’s hard not to get excited.

When a candidate is in the interview, ask them specifically about what excites them. This may reveal more about their strengths, weaknesses, motivations, and other details that determine if they are a good fit.

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7. 'Was there anything about the company that stood out to you positively? Or even a negative way?'

woman asking the interview question what about the company stands out Amnaj Khetsamtip / Shutterstock

Purpose: If employees need constructive criticism, so do companies.

What companies don’t consider is constructive criticism for them. Millennials need companies to be more transparent. And the best way to do that is to allow constructive feedback rather than blatantly dismiss a candidate who sees a problem management refuses to acknowledge.

Whether you are hiring a Millennial, Gen Zer, or any other generation, it’s important to remember that we are all individuals. Like any worker, we have different goals, histories, and skills.

People want to succeed in their jobs. When people have the resources to grow, we tend to stick around longer than a few years. Once we understand how to ask the right questions and get what we seek, we’ll eventually find a happy middle ground.

RELATED: I Was Denied A Job Interview For The Most Frustrating Reason — 'I Felt Like An Inconsequential Piece Of Dirt'

J.C. Kersh is a freelance writer and contributor to Medium. She is currently a 3x CEO Administrative Assistant at three different companies.

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