Interview questions always have a purpose behind them—whether it’s “What are your strengths?”, “Where do you see yourself in five years?” or “Why are you interested in this position?” Standard questions are generally considered standard for a reason, as they’ve been tried and tested at generating the information the hiring manager needs to make their decision.
However, it’s often the nonstandard questions that can really tell you a lot about a person. Here, 13 business leaders from Young Entrepreneur Council share the questions they love to ask during interviews and why. Consider adding one or more of these options to your list to see what you can learn about your next job candidate.
1. If you could be one item in the kitchen, what would it be and why?
This question always generates the most interesting responses—often things you hadn’t even considered. It is also unexpected, but in a fun way, and is meant to make you want to answer with what comes to mind first. Candidates’ answers can tell you a lot based on both the item they select and the reason why. It can also break the ice and give you the chance to see if the potential hire has a good sense of humor! – Kristy Knichel, Knichel Logistics
2. What’s a time in your life when you overcame the odds and succeeded?
“Tell me about a time in your life when the odds were stacked against you but you overcame them and succeeded.” This question is designed to help me understand how the candidate handles adversity. It can also reveal how well they handle pressure. – Mauricio Cardenal, Roofing Marketing Pros
3. Can you explain a time when you disagreed with a supervisor?
I find this question insightful because it allows candidates to showcase their ability to handle workplace conflicts professionally. It reveals their communication skills and their capacity to navigate disagreements in a constructive manner. Moreover, it shows whether they can balance their own perspective with the need to respect authority, which is essential in a collaborative work environment. Their answers often provide insight into their problem-solving abilities and willingness to learn from experiences. It allows candidates to demonstrate how they’ve handled past conflicts and whether they can reflect on those situations to improve their approach in the future. – Sujay Pawar, CartFlows
4. What don’t you like to do?
This question serves as a valuable gauge for several qualities. It assesses the candidate’s level of self-awareness and their willingness to be open and honest. It also offers clues about whether the candidate would be a cultural fit for the role based on their preferences. Additionally, the way they manage tasks they don’t enjoy can shed light on their problem-solving capabilities and overall maturity. – Anna Anisin, DataScience.Salon
5. How did you manage your work and time while cooped up during Covid?
This question is insightful because it tells me how much discipline the candidate has, and it also tells me about their management skills. This works well for me because our company is 100% remote and we look for people who know how to work through the distractions of everyday life while working remotely. – Benjamin Rojas, All in One SEO
6. What’s something you learned recently that made you pause and think?
“Tell me something you learned recently. It doesn’t have to be work related per se, but just something that made you pause and think.” What I want to hear is: first, the level of depth when sharing something that is interesting to them; next, if they really are constantly learning or curious about information and if they have awareness of retaining knowledge and are potentially applying it too; finally, the vulnerability of showing they are not perfect. To say, “I don’t know the answer” is difficult, and we need consultants to be confident in their knowledge and even more confident that it is okay if they don’t have all the knowledge. – Marjorie Adams, Fourlane
7. What’s a professional goal you failed to achieve, and what did you learn?
One of my favorite questions to ask a potential hire in an interview is, “Tell me about a professional goal that you failed to achieve in the past. What did you learn from that experience?” The answer to that question usually reveals if the person can reflect on their past failures, whether they were able to grow professionally and how that failure in particular triggered the growth. – Andrey Chshelokovskiy, 360 Painting of Dallas
8. Can you describe a challenging situation you faced at work and how you dealt with it?
This question is particularly insightful because it sheds light on the candidate’s problem-solving skills. Through their answer, I can discern whether the candidate is methodical, innovative or perhaps reactive in their approach. For instance, if the challenge revolved around team conflicts, the answer might reveal their conflict resolution abilities and communication skills. A candidate’s description of how they navigated unexpected hurdles can offer a glimpse into their adaptability quotient. Additionally, candidates who reflect on their experiences and contemplate alternate approaches exhibit a commendable degree of self-awareness and continuous improvement. – Julia Rodgers, HelloPrenup
9. Why should I hire you?
Turnover rate in the restaurant industry is high, so I’m used to interviewing lots of potential hires for various positions. One of my favorite questions is, “Why should I hire you?” Their responses tell me how confident they are with themselves and their skill sets. Sometimes, I don’t even base their hiring on their resumes. Their accomplishments and experiences matter to me just a little bit; what matters the most is who they are now and how they present themselves. Of course, this depends on which position they’re applying for. For example, if they are applying for front of house (server, bartender), then their personality and communication skills must be on point. On the contrary, if they are applying for back of house (chef, dishwasher, line cook), then it’s more based on skills. – Fritz Colcol, Simply Thalia
10. Can you describe a project or situation where you had to collaborate with a diverse team?
My favorite question to ask potential hires in an interview is, “Can you describe a challenging project or situation where you had to collaborate with a diverse team to achieve a goal?” This question provides insights into their teamwork, communication, adaptability and problem-solving skills. Their response demonstrates their ability to work effectively in a team and reveals their attitude toward diversity and challenges—essential qualities for success in today’s workplace. – Alfredo Atanacio, Uassist.ME
11. What has your experience with our product been like?
I think that it’s very important that any hire uses our products and is familiar with our business. The answer they give will tell us everything we need to know about how prepared they are and whether they know what they’re going to be working with. I would use this question or a variation depending on the role and the brand the person is going to work for. It will help decide which candidate is best and most likely to fit with the company the fastest. – Syed Balkhi, WPBeginner
12. Can you tell me your story?
Opening up the floor for candidates to paint a picture of who they are will help you understand many of their attributes. Storytelling is an important quality for any creative job or client-facing position. Being able to decide what’s important is also a quality many managers look for. This question also puts people on the spot, and how the potential hire acts under pressure might reveal some other attributes that would be beneficial to learn before hiring the individual. – Chase Williams, Market My Market
13. What has been the toughest form of feedback to swallow in your career?
How candidates handle feedback and how they interpret it is vital to organizational success. Where someone levels blame on someone else or deflects a question like this can be a red flag. On the other hand, when someone discusses how they are able to digest tough feedback and take accountability, it shows strength of character and their willingness to lean into feedback culture. We always have something to learn. Entrepreneurs should pay very close attention to how candidates describe experiences with both negative and positive feedback to look for accountability cues or lack thereof. – Matthew Capala, Alphametic
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