Creative Interview Questions for Finding the Right Candidate

Interview questions usually revolve around a candidate’s work history, experience and unique qualifications. While these questions can help determine how qualified a candidate is in terms of life experience, it won’t tell you if a candidate can fit into your culture and team. 

Creative questions can help. They can provide insight into a candidate’s sharpness, personality, sense of humor and industry knowledge. Creative interview questions can also ease tensions at the beginning of an interview, or serve to break up the strings of business-focused questions. They can be used to make connections and develop rapport. The following creative interview questions can yield results that traditional interview questions wouldn’t.

Before You Ask…

Make sure to clarify that the interview will be shifting to a few less-serious questions. Be sure not to ask anything illegal, such as whether candidates are planning to have a family, questions about their race, or other questions that may make them uncomfortable. While this is a change to a more lighthearted section of the interview, it should never make the candidate uncomfortable. 

Additionally, try to be transparent; expecting candidates to pick up on some hidden meaning in what is meant to be a lighter question might not yield the best results. A good way to test these questions is to ask coworkers and even come up with an answer for yourself.

1. If You Were a Vending Machine, What Would You Vend?

This question requires a bit of creativity to answer. Candidates’ answers can tell you about their values. For example, they might say they’d sell some particular thing because it resembles their beliefs in some way. It can also give some insight to their personality with what snack characteristics they relate to themselves – such as sweet, reliable, old-fashioned, etc. If they don’t elaborate on why they picked that, make sure to ask follow-up questions to understand the thought process behind their answer. 

2. Where Should I Go On Vacation?

This question is particularly good for sales positions. Instead of telling you their favorite place they’ve been, a great salesperson might ask where you’ve been in the past that you’ve enjoyed, or things you’d like to do while on your vacation. 

Keep in mind that this question, like many creative interview questions, may not allow you to directly assess a person’s qualification for the position. However, this will let you see how the candidate considers all the information. If they want to answer the question in a thoughtful way, they will find out your needs and wants before making the pitch. The more considerations they take, the more of a connection you can see in their potential as a candidate.

3. Is There a Fictional Character You Identify With?

A candidate’s answer to this question can tell you a lot about how they see themselves. It can demonstrate both the values they care about, and the type of person they aspire to be or a character flaw they see in themselves as well. 

This is another question where the ‘why’ is equally as important as their answer. If you don’t get the why, you’ll want to ask more questions to find out the thought process. It can also be a good way to get to know the candidate’s interests and how they use perspective to relate to others. 

4. What Industry Resources Do You Follow?

While this question is less ‘fun,’ it can tell you a lot about how invested the candidate is in the industry as a whole, and whether they stay up to date on new developments. Do they stay up to date on any certifications, course work or local meetings? This can be another way to assess their knowledge of the industry without it being about their personal experiences.

5. What is Your Favorite Work Memory?

This question can tell you about the value a candidate places on culture, which is crucial in many roles. One purpose of many of these creative interview questions is to assess how well a candidate will mesh with your company. 

If their favorite memory clashes with your company’s values, then this would be a key indicator of a poor fit. This can also show you how a candidate bonds with fellow coworkers or supervisors, or give insight to why the candidate might have left a particular job. 

6. If You Could Switch Places with Anyone, Who Would it Be?

There are many questions like this you could ask, but they all serve the same purpose. The answer isn’t the important part; rather, their reasoning or explanation for ‘why’ is what matters, and can give you an insight as to what kind of person they are. This might tell you what they believe they are missing in their life, or some of their goals. If it is a well thought out answer, it can show their analytical side or if they ask questions such as, “How long would I switch places with the person?”, then you can see that they have a long-term focus and understand time constraints. 

7. What Questions Were You Expecting That We Didn’t Ask? Why?

This spin on the common question ‘do you have any questions for us?’ is a more interesting one. It allows the candidate to provide answers to questions they may be very prepared for that highlight some of their experience or qualifications for the role, but weren’t asked in the interview. 

It also shows you how they prepared for the interview. If any of the questions interest you, then you can use that as a segue to ask the question and find out their answer and reasoning behind it. 

8. What’s the Best Mistake You’ve Ever Made?

This question forces candidates to draw learning lessons from experiences that might have been less than ideal, but also shows you how they can deal with criticisms, conflicts, or major issues. It highlights their problem solving skills as well as their outlook. Does their answer indicate a short-term or long-term focus? Are they a big picture or little picture kind of thinker? Overall, it gives you insight to their values and morals as well. 

9. What Did You Want to Be When You Were Younger?

This question often gets candidates to open up a bit about how their interests have changed over time, how they ended up in this field, and whether they’re passionate about it. This can be one of those questions that help show you if they fit into the company culture. 

For example, if they wanted to be a nurse because they like to help people and your company values giving back, then you could see that they value similar things. It also might give you more of an idea about what skills they have. Maybe they were on the path to go to a different field and have certifications or training in areas that your company is lacking.Building a successful team is important for any business. And having the right insurance coverage in place is critical. To learn more about protecting your business, contact your local Society Insurance agent today.


As a mutual insurance company, we operate and exist for the benefit of our policyholders. For more than 100 years, Society has been helping businesses overcome the unexpected with comprehensive coverage packages and outstanding claims handling, underwriting and risk management.

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