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5 Unconventional Interview Questions That Get Real Answers From Candidates Interview questions that get past the pre-planned answers and get you in front of the real candidate.

By Patrick Frank Edited by Amanda Breen

Opinions expressed by Entrepreneur contributors are their own.

In any startup, the interviewing process can be one of the most time-consuming activities there is. Though time-consuming, it is also critical, as it ensures that you are bringing on the best talent to set your company up for success.

Unless you have an in-house recruiter, typically the founder, co-founder or department leader ends up being the one in charge of the recruitment efforts and screening of candidates. If you are balancing several other initiatives, a few questions arise. How do you ensure that you nail down the interview process? How can you ask the right questions to understand the full scope of who your candidates are? How do you know that ultimately you are making the right decision?

Think of everything you are trying to accomplish. You want to know about a person's qualifications, skills and background, but you also want to find out what kind of person the interviewee is. Will he or she fit into the company culture? Will he or she cope under pressure? Does he or she think outside the box? Will he or she stay committed for the long haul?

At this point, many interviewees are familiar with the common questions that come up, even the ones that are designed to encourage them to think on their feet. Between LinkedIn, Glassdoor and similar resources, they can actually already know the questions you are going to ask. This allows them to pre-plan their answers and ultimately will not give you the real insight on who the candidate is at his or her core.

To get people to really open up, they need to be asked truly unconventional questions.

If you want your next round of potential hires to give you unique and insightful answers to inform your decision, take a look at the questions below.

1. What is one fundamental truth that you believe in that the majority of the world disagrees with?

A famous interview question by one of the most successful entrepreneurs and venture capitalists of all time, Peter Thiel, this question shows if the candidate can stand alone in his or her beliefs. Does the candidate have his or her own original thoughts and is he or she unafraid to stand by them? In an interview setting, it's tempting to simply say what the employer wants to hear, but this demonstrates if an interviewee is confident enough to stand his or her ground.

It can turn the conversations towards politics, society, ethics, morals. This question quite simply demands honesty as it requires quick thinking and confidence. It often brings out a passionate answer with the right candidate and is a great strategy to find free thinkers and passionate people whom you would want to work with.

Related: The 25 Questions You Should Know in a Job Interview

2. If I gave you $100 million right now, would you be in this seat?

It's a big picture one, but also a bit of a trick question. If the candidate gives the honest answer, which is 99% of the time "no," he or she will usually go on to discuss the things he or she is passionate about, and he or she will inevitably talk about what matters to him or her in his or her personal life. In some cases, it gives you an insight into an entrepreneurial trait as the candidate may decide to go the route of using the money to start a business.

If the candidate's answer is "yes," the interviewer must dig into this to decide if it is a lie. If not, then you can conclude he or she is truly passionate about the company and the role. But let's be honest, this is rarely the case. You can also follow up with questions like, "Why wouldn't you just go do this yourself with that kind of capital, rather than working for someone else?" Or lead into a series of questions that ask the candidate about how he or she would do things differently with these kinds of monetary resources. This is a great question to determine someone's authenticity and learn more about his or her passions. Both answers can prompt equally great responses that give you different types of insight.

3. Describe your sense of humor

This one is always a lot of fun but tends to make people nervous. Everyone knows his or her sense of humor, but it's often something that takes a while to come out in the workplace. This very quickly provides an insight into how a candidate might fit in the company culture, and typically candidates can share their answers very quickly and honestly.

It tends to bring a few laughs as well, which is a great way to allow a candidate to feel more comfortable. There is no wrong answer to this question, but it does allow you to see if someone may not be the best fit for the company culture. If you aren't laughing by the end of this answer, or if it doesn't prompt some type of authentic banter, the candidate may not be the right fit.

Related: 9 Questions to Ask Candidates' References

4. Why would we not hire you for this role?

This is a variation to the common question of "What is your biggest weakness?" It encourages the candidate to be honest with his or her weaknesses and not give a generic answer. It's a great opportunity to have him or her think introspectively and talk through concerns that are raised as a result. Another way to ask this is: "If you and I had been best friends, and I knew everything about you, what would I be concerned about when I had to make a decision to hire you?"

When a candidate doesn't have time to prepare for an answer, it often manifests in many answers and leads to productive rambling. This is when the truth comes out as there's no time to polish the response.

Related: Leaders: Here's The No. 1 Thing You Shouldn't Do When Interviewing Job Candidates

5. What is your purpose both personally and professionally?

This is a question that needs to be asked confidently or it may come off as a little too forthcoming. However, it can also be the most impactful. This is where the interviewer gets to learn about where the individual wants to go in life and what he or she wants to accomplish. Again, it is an alternative way to ask the common question of "Where do you see yourself in three to five years" and get answers that are much more personal and authentic. Big answers here earn big points. You want to bring dreamers and doers into your company who act and operate with purpose.

6. Bonus question

A bonus tactic to layer on top of these interview questions is to keep digging for answers. Never stop at face value; if you continue to press, you will find what candidates did not prepare for. One tactic, especially with "Tell me about a time" questions, is to ask for another example on top of the first one they gave you. Then, after you receive your second answer, ask a third time. Most people tend to have one to two answers prepared, but the idea is to keep pushing until you get a truly authentic response or no response at all.

By asking these unconventional interview questions, it keeps potential candidates on their toes, encourages honesty and allows the interviewer to gain some valuable insight into potential hires. Always remember that interviewing is a two-way street and that you are both deciding whether or not you are a good fit for each other. In that spirit, it only makes sense to be direct, honest and sometimes vulnerable. When people are put on the spot, they can produce their best responses and may just say exactly what you want to hear, or the thing you were least expecting.

Patrick Frank

COO of PatientPartner

Patrick Frank is the co-founder and COO of PatientPartner, a platform that connects pre-surgical patients with fully recovered patients who went through the same surgery. He has worked in consumer technology across a variety of industries including retail banking, law, real estate and health care.

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