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Hiring Managers Share the Best Questions Asked by Candidates in Interviews

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  • Writer's pictureThe CareerBeacon Team

We asked hiring managers to share the best questions asked by candidates in interviews. Here’s what they had to say.

At some point in the job interview, usually, after they’re done asking their questions of you, the interviewer is going to ask if you have any questions for them.

You should never say “no” to this question, and you should have questions prepared beforehand. These should be around what you can bring to the table and the organization’s goals, rather than what the company can do for you.

We asked hiring managers to share the best question a job candidate has ever asked them in an interview and why the question was a good one. Here’s what they had to say.

Sean McPheat, CEO of MTD Sales Training

“What’s the biggest mistake you have made at work, and if I made it, how would you deal with it?”

McPheat says, “This put me on the back foot, and I liked it! She was testing to see if I was humble enough to mention a time when I had made a big mistake. At the same time, she wanted to know how I’d handle the situation, that mistakes were okay at my company, and that it’s viewed as a learning opportunity. She got the job and is with me nine years later.”

Willie Greer, founder of The Product Analyst

“What do you think is the biggest weakness of your company and one viable reason for why it would go bankrupt?”

Greer says, “What I felt when asked this question is that the person was looking for assurance on the company’s stability. Companies always look as if they are in a favourable and stable position during job hirings, given that they are looking for human resources. Still, it’s an applicant’s right to know whether this opportunity can bring them elsewhere.”

Andrew Roderick, CEO of

What are three company culture aspects it is important I learn before entering the workplace if I’m successful?”

This is a great question that showed me the potential employee was considering their role in the workplace, how the team interacts, and what we as a business expect from employees regarding communicating with others and how we go about our days. It shows a genuine interest in fitting in with the company’s ethos and community in the smoothest way that is beneficial for everyone.

James Jason, HR Manager and Financial Analyst at Mitrade

“If I was your daughter, would you recommend to me that I work here?”

“This was asked of me at a previous workplace, where I worked as a hiring manager. This is one of the most challenging questions that an interviewee asked me, but it was an excellent question. The candidate only sought to know whether her potential workplace was good enough. Honestly, I had been looking to exit the organization since there was a disconnect among the management, which made me uncomfortable. I told her I would recommend it, but it changed my way of handling hiring, and I quit the company before the applicants got their responses.”

Dan Kelly, Founder & Senior Partner at The Negotiator Guru

“How does your company work with their employees and leaders to incorporate mistakes into innovation and continuous growth without making them look like failures?”

“This question showed me that the candidate is passionate about continuous growth and understands the importance of creating opportunities out of failures.”

Timothy G. Wiedman, Associate Prof. of Management & Human Resources (retired), Doane University

“What is your company’s philosophy on employee training and continuing development, and is there any funding available to assist employees who want to upgrade their skills by taking job-related courses or certification exams during their free time?”

“When I worked as a hiring manager, I heard this question and enjoyed it because it indicated that an applicant was interested in continuing education and professional growth versus simply landing a job. And these days, all organizations need employees committed to keeping their job-related skills up to date.

Gene Caballero, Co-Founder of GreenPal

“The candidate asked, “What characteristics have you seen in successful individuals in this current role?’ I answered the question with ‘they are highly organized, motivated, and have great attention to detail.’ After my answer, he asked the interview panel, ‘Based on what you told me about the current successful individuals’ traits in this role and my strengths that align with these individuals, would you see any reason for not offering me this position?’

This happened with a candidate interviewing for a sales role at a Fortune 50 Tech company where I worked. These questions were great because they showed that he had a sales mentality and was closing the proverbial sale in the interview. He was hired on the spot.

Trind Nyland, Founder and CEO at Mattress Review

“What can I illuminate about myself to help decide to hire me an easy one?”

I loved this question because it’s bold and confident and leaves zero doubt about whether the candidate is genuinely interested in the position. It’s an intelligent play on the candidate’s part because it forces the interviewer to open up and reveal doubts, which can be addressed directly.

Michael Allen, CEO of the Fashion Jacket

“Where do you see your company in five years?”

“This is a very common question when asked by the employer during the interview, but we never expected it to come from the candidate. The one time a candidate asked me, it stood out. It was a good question because it showed his concern about the company’s future and that he was considering working there in the long run. It helps the candidate decide if he is a good fit by evaluating whether his planned trajectory fits with the company’s future.

Paul French, Managing Director, Intrinsic Search

“What would make someone not a good fit for the role?”

“Most candidates ask the opposite question — What qualities do successful employees in the company exhibit? Asking it the other way around showed that the candidate was less concerned about getting the job just for the sake of it and was instead more keen on whether the job would be a good fit based on his values and needs at that given time. This was also an impressive demonstration of self-awareness, a desired trait in modern-day leaders. Additionally, the candidate was trying to get an idea of what to do and not to do to set himself up for success should he get hired.”

Vincent Scaramuzzo, President, Ed-Exec, Inc.

“Where do people go to eat lunch?”

“The question caught me off guard, but I found it quite smart. The candidate wanted to learn about an important aspect of the organization’s culture. How employees treat lunch breaks says a lot about how the management treats employees. Someone looking for a flexible and interactive workplace might not be a good fit in a setting where employees are too busy to take a break and socialize and usually eat at their desks alone. The question also made for an interesting conversation about great places to have lunch. But, more importantly, the candidate was excited to learn that the culture at the organization was one in which employees were a close-knit group, hung out together frequently, and took breaks as needed.”

For a list of good questions to ask in the job interview, check out the 22 questions to ask in a job interview.

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