These Strange, Unorthodox Interview Questions Can Help You Hire Better Employees

Interviews over the years have become… predictable. The same old questions, the same old answers – it’s become a case of two complete strangers doing a familiar dance they’ve done with countless partners before.

And why? Because often, employers and job seekers alike tend to forget that the best interviews are ones that are unique and lively conversations. At its heart, an interview is a meeting of two people, looking to find out if they are compatible to work in a professional environment together. Arguably, interviews are less about confirming qualifications and more about first impressions, personality, and fun!

Finding your hiring process is getting stale and repetitive? Take a page from big business players like Apple and Google and toss in a fun curveball question. These questions are less straightforward, and really allow the employer insight into the way the candidate assesses situations, and more importantly, views themselves.

1. You just won the lottery for $10 million dollars. What do you do with your winnings?

Sure, the safe response is to put it in a savings account, but individuals who are passionate about things in their lives will likely come up with interesting answers. Perhaps they would donate to a charity that’s close to their hearts, share it with friends, invest in a business, or something else completely!

2. Say you could choose anyone in the world to be your mentor (celebrity, historical figure, etc.) – who would they be, and why?

This is a fantastic question if you want to get a sense of your candidate’s aspirations. A mentor is someone you hope to model yourself against, and depending on their answer, you can get to know who they hope to become and what they hope to achieve as an individual.

3. If you could pick any animal in the world to represent you as a person, what would it be and why?

We all had a favorite animal or two when we were kids, but picking one that represents ourselves is more challenging than you’d think. It really takes someone who is in touch with themselves and knows who they truly are to come up with an answer and complete explanation to this question.

4. I have a stapler right here. I need you to sell me this stapler right now – go!

Hiring for a job that requires selling? This is a great way to keep your candidate on their toes and see how quickly they can assess a product and produce a pitch on the fly. It’s also handy for getting to know their selling style and how they’ll interact with customers.

5. What do you think you’ll have the most trouble with at this job?

We all like to pretend that there’s a “perfect person” for every job, but let’s be real: we’re all human, and we all have flaws. The interviewee who can answer this question showcases a real knowledge of their strengths and weaknesses, and is able to anticipate challenges so they can (hopefully) compensate and overcome them!

6. Imagine you could create the perfect manager or supervisor. What traits or qualities would they have?

We don’t always get to choose our work families, so hiring someone who will mesh well with your existing team is incredibly important. This is especially important when it comes to management – after all, the number one reason employees leave their jobs is because of their managers. Getting to know their expectations and ideal management style early on will help you determine their fit and whether they’ll be content working with your staff.

7. If you don’t get this job, what’s your backup plan?

This question is sure to catch your interviewee’s attention – after all, most job seekers are trained to showcase confidence that they will land the job. However, this is a great way to tell how your candidate might handle rejection and how they plan for and deal with setbacks.

8. Let’s say I hire you right now, but I don’t have anyone available to sit with you and train you. How would you handle this situation?

Sure, this isn’t an ideal situation for anyone, but this imaginary scenario can give you a glimpse into how your candidate would work under pressure. More importantly, it’ll showcase their resourcefulness – are they the type to refer to a written manual? Would they ask questions from their fellow coworkers? Do they actively seek feedback or would they wing it?

9. If you could go back in time to when you were 10 years old, what advice would you give yourself?

It is incredibly valuable to have people on your team who are able to learn from their mistakes and apply the lessons to their own lives. This is a great opportunity to have them highlight some of the most important things they’ve learned, so you can get a better sense of who they are and what they value.

10. If money was no object, what would keep you happy at your job?

If everyone in the world honestly answered the question “why do you want to work here?” they’d probably say “for the paycheque!”. But if rent and food were free, what motivates them to do a great job each and every day? This is an important factor to know before hiring, as it can make of break the working relationship.

What other questions would you add to this list? If you’re looking to boost your hiring efforts, connect with our Hiring Experts! Email us at or visit our Applicant Tracking System page!

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