5 unconventional interview questions that get real answers from candidates


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In any startup, the interview process can be one of the most time-consuming activities. While it takes time, it is also essential because it ensures that you are bringing in the best talent to set your business up for success.

Unless you have an in-house recruiter, the founder, co-founder, or department manager usually ends up being responsible for recruiting efforts and selecting candidates. If you balance several other initiatives, a few questions arise. How do you make sure you nail down the interview process? How can you ask the right questions to understand the full reach of your candidates? How do you know when you are ultimately making the right decision?

Think about everything you are trying to accomplish. You want to know a person’s qualifications, skills and background, but you also want to know what kind of person the interviewee is. Will it fit into the corporate culture? Will he or she face the pressure? Does he think outside the box? Will he remain committed for the long term?

At this point, many interviewees are familiar with common questions that arise, even those designed to encourage them to think on their feet. Between LinkedIn, Glassdoor, and similar resources, they may actually already know the questions you’re going to ask. This allows them to plan their responses in advance and ultimately will not give you any real insight into the identity of the candidate.

To get people to really open up, you have to ask them really 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 a basic truth that you believe in that most of the world does not agree with?

A famous interview question by one of the most successful entrepreneurs and venture capitalists of all time, Peter Thiel, this question shows whether the candidate can stand alone in his convictions. Does the candidate have their own original thoughts and aren’t they afraid to support them? In an interview, it’s tempting to just say what the employer wants to hear, but it shows whether an interviewee is confident enough to hold on.

It can orient conversations towards politics, society, ethics, morals. This question simply requires honesty as it requires quick thinking and trust. This often brings a passionate response with the right candidate and is a great strategy for finding free thinkers and passionate people you would like to work with.

Related: 25 questions you need to know in a job interview

2. If I gave you $ 100 million now, would you be there?

It’s a big picture, 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 discuss the things that they are 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, this gives you insight into an entrepreneurial trait, as the candidate may decide to use the money to start a business.

If the candidate’s answer is “yes”, the interviewer must dig into that to decide if it is a lie. If not, you can conclude that he is really passionate about the company and the role. But let’s be honest, this is rarely the case. You can also ask questions such as, “Why wouldn’t you do this yourself with that kind of capital, rather than working for someone else?” Or lead to a series of questions that ask the candidate how he or she would do things differently with this kind of monetary resource. This is a great question for determining someone’s authenticity and finding out more about their passions. Both answers can elicit equally interesting answers that give you different types of information.

3. Describe your sense of humor

This one is still a lot of fun but tends to make people nervous. Everyone knows their sense of humor, but it’s often something that takes a long time to manifest in the workplace. This very quickly gives insight into how a candidate might fit into the culture of the company, and generally candidates can share their answers very quickly and honestly.

It also tends to bring in a few laughs, which is a great way to make a candidate feel more comfortable. There is no wrong answer to this question, but it allows you to see if someone does not fit the culture of the company the best. If you don’t laugh at the end of this answer, or if that doesn’t elicit some kind of genuine joke, the candidate might not be the right fit.

Related: 9 questions to ask candidates’ references

4. Why don’t we hire you for this role?

This is a variation of the common question “What is your biggest weakness?” He encourages the candidate to be honest with their weaknesses and not to give a generic answer. This is a great opportunity to make him think introspectively and discuss the concerns that arise from it. Another way to ask the question is, “If you and I had been best friends and knew all about you, what would I be concerned about when I had to make the decision to hire you?” “

When a candidate does not have time to prepare an answer, it often manifests itself in many answers and leads to productive ramblings. This is when the truth comes out as there is no time to refine the answer.

Related: Executives: Here’s the # 1 thing you shouldn’t do when interviewing candidates

5. What is your goal both personally and professionally?

This is a question that should be asked with confidence or it may seem a bit too open-ended. However, it can also be the most impactful. This is where the interviewer learns where the individual wants to go in life and what he or she wants to accomplish. Again, this is an alternative way to ask the common question of “Where do you see yourself in three to five years” and get much more personal and authentic answers. Big answers here earn big points. You want to bring dreamers and actors into your business who act and function with a purpose.

6. Bonus question

An additional tactic to superimpose on these interview questions is to keep looking for answers. Never stop at face value; if you keep pressing you will find out what the candidates weren’t prepared for. One tactic, especially with “Tell me about an hour” questions, is to ask for another example in addition to the first one they gave you. Then, after receiving your second response, ask a third time. Most people tend to come up with one or two answers, but the idea is to keep pushing until you get a really genuine answer or no answer at all.

Asking these unconventional interview questions keeps potential candidates on their toes, encourages honesty, and allows the interviewer to gain valuable insight into potential hires. Always remember that the interview is a two-way street and you both decide whether or not you are a good fit for each other. With that in mind, it makes sense to be straightforward, honest, and sometimes vulnerable. When people are embarrassed, they can produce their best answers and can just say exactly what you want to hear, or the thing you least expect.

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