When hiring for a position, the skills and qualifications listed on a candidate’s résumé are important, but they don’t tell the whole story. To make a more informed hiring decision and gain a deeper understanding of the candidate, employers must look beyond the credentials and ask insightful questions. The right questions can help assess a candidate’s character, work ethic and problem-solving abilities.
Below, 20 Forbes Business Council members share the most insightful questions to ask job applicants and the results that can be expected.
1. ‘What’s Your Why?‘
I’ve been in executive search for 16 years and the line of questioning all depends on the task at hand. However, if you want to dive into the psyche of a candidate, ask them, “What’s your why?” At that moment, you will see the wheels turning as it is an unexpected question and one that is not easily answered. You can learn a lot from someone based on that question. – Joe Carbone, Eastward Partners
2. ‘What Social Cause Or Issue Is Important To You?’
As a gifting company steeped in social impact, our employees need to care about doing good. It’s a foundational core value that every employee must have. It’s clear when a candidate invents a cause on the spot. I don’t care what the cause is; I just care that social impact is a value they live every day. – Leeatt Rothschild, Packed with Purpose
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3. ‘Can You Describe A Time When You Faced A Setback?’
One question that can provide valuable insights into a candidate’s work ethic and motivation is asking them about a time when they faced a difficult challenge or setback at work and how they handled it. This reveals 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 accomplish. I always ask what their personal non-negotiables are for their profession. This will enable me to see what they really find important and if those traits meet the core values of the company. – Ralph DiBugnara, Home Qualified
5. ‘How Have You Taken A Concept And Made It Concrete?’
Regardless of how experienced they are, I always ask people how they’ve taken a concept and turned it into a concrete result. This helps me understand their thought process, how they work independently and when they seek support. – Nell Callahan, Frontwood Strategies
6. ‘How Do You Stay Updated On Trends And Developments?’
Ask, “”How do you stay up-to-date with industry trends and developments?” This question provides insight into the candidate’s passion for the job and their dedication to continuous learning and improvement. – Trey Ferro, Spot Pet Insurance
7. ‘Can You Describe A Time When You Had To Overcome A Significant Challenge?’
By asking candidates to describe a time when they had to overcome a significant challenge and how they handled it, I was able to gauge their problem-solving skills, adaptability and resilience. The responses varied; some candidates demonstrated ingenuity and determination, while others showed their ability to collaborate and communicate effectively. It provides insight into their mindset and capabilities when tackling complex situations. – Leigh Burgess, Bold Industries Group, Inc.
8. ‘What Is The Toughest Experience You Have Faced In Life?’
We use the interviewing process as a dynamic opportunity to gain deeper knowledge and understanding of a candidate’s motivations. Ask, “What is the toughest experience you have faced in life, and what did you learn from it?” By asking this question, you will be amazed at the wealth of insightful information you get from a candidate. – Francisco Ramirez, The ACE Group (TAG)
9. ‘Why Did You Quit Your Last Job?’
This question catches them by surprise and gives me 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 perhaps they were sensitive and would not mingle well with co-workers. I was expecting the “I found a better-paying job” answer. This has been highly effective for my interview process. – Tammy Sons, Tn Nursery
10. ‘Tell Me About A Time That You Used Critical Thinking To Solve A Work Problem?’
I won’t hire a candidate if they cannot answer this simple question. Those who can answer it have always shown 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’ve Failed At?’
I always ask future candidates about three things they’ve failed at. I don’t care about failure, but if they smile when they share, then that person could be someone who will try and fail at things, which is invaluable in an organization. Not trying and always playing it safe will suffocate a company. – Joseph Edgar, SnapAds
12. ‘Have You Ever Worked With A Troublesome Colleague?’
I like to ask whether they have ever been in a situation where they had to work with a troublesome colleague or someone they hated and how did they handle it. These questions will give you deep insights into the professionalism of the candidate and their ability to put aside personal grievances for the company’s sake. It’s an incredibly crucial trait to have for folks who wish to work in highly dynamic and diverse organizations. – Erik Pham, Health Canal
13. ‘What Motivates You?’
I ask job candidates what motivates them to gain insight into their values and work ethic. One candidate said they’re motivated by creating a positive impact, aligning with our company culture. We hired them and they’ve been a valuable addition to our team. – Ifiok Nkem, Snapilabs
14. ‘Are There Any Questions You Wish I’d Asked That I Didn’t?’
At the end of an interview, I always ask, “Are there any questions you wish I’d asked that I didn’t?” It gives the candidate the opportunity to showcase what they’ve researched about our company, what they want to spotlight about themselves and what matters to them as a human. It can also give you a nice way to end the interview on a positive note. – Julie Williamson, Karrikins Group
15. ‘What’s Your Proudest Achievement?’
When hiring, don’t just skim the résumé. Dig deeper by asking, “What’s your proudest achievement?” The answer will reveal 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 demonstrated leadership, dedication and a commitment to making a positive impact. That’s what companies need. – Chris Kille, Payment Pilot
16. ‘Why Do You Want To Work Here?’
The “Tell me about a time” questions are a great way to arrive at rote and practiced responses. Asking, “Why do you want to work here?” lets you gauge how people see themselves impacting your business in meaningful ways. It also helps filter out the people looking for a cash grab and often uncovers the people who have actually performed meaningful research about the company and its role. – Ty Allen, SocialClimb
17. ‘Is That Correct?‘
I ask candidates something that they should know isn’t accurate to see if they’ll politely and professionally disagree with me. It’s essential to have a team that will remedy your erroneous positions to keep your business healthy. I used this approach in a CFO search and, surprisingly, only two out of 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?’
By asking this question, it helps me understand a candidate’s priorities and what they value. You should take pride in your work but also take pride in how you live your life outside of work. – Natasha Koifman, NKPR
19. ‘Where Will We See You At Your Best?’
One question I ask and always find the answer insightful is, “Where will we see you at your best?” It’s a question that applicants need to think on their feet to answer, and it gives a peek into what they gravitate toward and the work they find most fulfilling. – Lindy Tentinger, VGM Forbin
20. ‘Would You Rather Be A Tree Or A River, And Why?’
It is imperative that you take quantitative metrics on a résumé into account, but always remember that as a leader, you are hiring a team member, not just an employee. Look at teams within your business as parts of an ever-growing ecosystem that are meant to flourish daily. There is no right or wrong answer to our favorite question that drives thought—”Would you rather be a tree or a river and why?” – Christian Brown, Glewee
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