20 insightful questions to ask job applicants


When hiring for a position, the skills and qualifications listed on a candidate’s resume are important, but they don’t tell the whole story. To make a more informed decision to hire a candidate and gain a better understanding of the candidate, employers should look beyond the references and ask insightful questions. The right questions can help assess a candidate’s character, work ethic, and problem-solving ability.

Below, 20 gotechbusiness.com Business Council members share the most insightful questions applicants can ask and the results that can be expected.


1. ‘What is your why?

I have been in executive search for 16 years and the questioning all depends on the task at hand. However, if you want to delve into a candidate’s psyche, ask them, “What’s your why?” That’s when you see the wheels turning, because it’s an unexpected question that isn’t easy to answer. You can learn a lot from someone based on that question. – Joe Carbone, Eastbound Partners

2. “What social cause or issue is important to you?”

As a giving company steeped in social impact, our employees should care about doing good. It is a fundamental core value that every employee should have. It is obvious when a candidate makes up a cause on the spot. I don’t care what the cause is; I only care that social impact is a value they live by every day. – Lee Rothschild, Packed with a purpose

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3. “Can you describe a time when you faced adversity?”

One question that can provide valuable insight into a candidate’s work ethic and motivation is to ask them about a time when they faced a difficult challenge or setback at work and how they handled it. This demonstrates the candidate’s problem-solving skills, resilience and ability to work under pressure. It also helps to evaluate the candidate’s interpersonal and communication skills. – Yasmin Walter, KMD Books

4. “What are your non-negotiables?”

I like to make the interview about their values ​​to see what they really want to achieve. I always ask what their personal non-negotiables are for their profession. This way I can see what they really find important and whether those characteristics are in line with the core values ​​of the company. – Ralph Di Bugnara, Qualified at home

5. ‘How did you take a concept and make it concrete?’

No matter how experienced they are, I always ask people how they turned a concept into a concrete result. This helps me understand their thought process, how they work independently and when to seek support. – Nelle Callahan, Frontwood Strategies

6. ‘How do you keep abreast of trends and developments?’

Question: “How do you keep abreast of trends and developments in the industry?” This question provides insight into the candidate’s passion for the job and their commitment to continuous learning and improvement. – Trey Ferro, Spot Pet insurance

7. “Can you describe a time when you had to overcome a great challenge?”

By asking candidates to describe a time when they had to overcome a major challenge and how they handled it, I was able to gauge their problem solving, adaptability and resilience. Reactions varied; some candidates showed resourcefulness and determination, while others demonstrated their ability to collaborate and communicate effectively. It provides insight into their mindset and capabilities when tackling complex situations. – Leigh Burgess, Grease Industries Group, Inc.

8. “What is the most difficult experience you have had in life?”

We use the interview process as a dynamic opportunity to gain deeper knowledge and understanding of a candidate’s motivations. Question: “What is the most difficult experience you have had in your life and what have you learned from it?” By asking this question, you’ll be amazed at the wealth of insightful information you’ll get from a candidate. – Francisco Ramirez, The ACE group (TAG)

9. “Why did you quit your last job?”

This question surprises them and gives me a quick insight into their temperament. For example, one person said, “They didn’t like me because I was quiet.” That answer led me to believe that maybe they were sensitive and wouldn’t get along well with colleagues. I expected the answer “I found a better paying job”. This has been very effective for my interview process. – Tammy sons, Tn Nursery

10. “Tell me about a time you used critical thinking to solve a work problem?”

I won’t hire a candidate if they can’t answer this simple question. Those who can answer it have always demonstrated the ability to solve problems in our offices and on our film sets. – ‘Smitty’ Robert J. Smith, Robert J. Smith Productions

11. “What are three things you failed to do?”

I always ask prospective candidates about three things they failed to do. I don’t care about failure, but if they smile when they share, then that person may be someone who will try to fail, which is invaluable in an organization. Not trying and always playing it safe will suffocate a business. – Joseph Edgar, SnapAds

12. “Have you ever worked with a difficult colleague?”

I like to ask if they’ve ever been in a situation where they had to work with a difficult colleague or someone they hated and how they handled it. These questions will give you in-depth insights into the candidate’s professionalism and their ability to put aside personal grievances in the best interest of the company. It’s an incredibly crucial trait for people who want to work in highly dynamic and diverse organizations. – Eric Pam, Health channel

13. “What Motivates You?”

I ask applicants what motivates them to understand their values ​​and work ethic. One candidate said they are motivated by creating a positive impact, in line with our corporate culture. We hired them and they have been a valuable addition to our team. – Ifiok Nkem, Snapilabs

14. “Are there any questions you wish you hadn’t asked?”

At the end of an interview, I always ask, “Are there any questions you wish I had asked that I hadn’t?” It gives the candidate a chance to show what they’ve researched about our company, what they want to highlight about themselves and what’s important to them as a human being. It can also give you a nice way to end the interview on a positive note. – Julia Williamson, Karrikin’s Group

15. “What is your proudest achievement?”

Don’t just browse the resume when hiring. Dig deeper by asking, “What is your proudest achievement?” The answer reveals more than just skills: it shows passion, creativity and work ethic. The most memorable response I got was, “I organized a community fundraiser that raised over $10,000.” It showed leadership, dedication and dedication to making a positive impact. That’s what companies need. – Chris Kille, Pay pilot

16. “Why do you want to work here?”

The “Tell me about a time” questions are a great way to get memorized answers. Asking: “Why do you want to work here?” lets you gauge how people see themselves as having a meaningful impact on your business. It also helps filter out the people looking for cash grabs and often reveals the people who have actually done meaningful research on the company and its role. – Ty Allen, SocialClimb

17. Is that correct?

I ask candidates something they need to know isn’t right to see if they disagree with me politely and professionally. It is essential to have a team that will fix your erroneous positions to keep your business healthy. I used this approach on a CFO search and surprisingly only two of the many candidates corrected me. This showed me that they were both qualified to join our team. – Dr. David Lenihan, Tiber Health

18. “What does a successful life look like to you?”

Asking this question helps me understand a candidate’s priorities and what is important to them. You should be proud of your work, but also proud of how you live your life outside of work. – Natasha Koifman, NKPR

19. “Where do we see you at your best?”

One question I ask and always find the answer to be enlightening is, “Where do we see you at your best?” It’s a question that applicants should think carefully about answering, and it gives a glimpse into what they’re looking for and the work they find most satisfying. – Linda Tentinger, VGM Forbin

20. “Would you rather be a tree or a river, and why?”

It is imperative that you consider quantitative metrics on a resume, but always remember that as a leader you are hiring a team member, not just an employee. Think of teams within your company as part of an ever-growing ecosystem that is meant to thrive on a daily basis. There’s no right or wrong answer to our favorite question that makes us think, “Would you rather be a tree or a river and why?” – Christian Brown, Glewee