5 unconventional interview questions to ask candidates

Last updated:
February 2, 2021
December 16, 2021
min read
Sim Samra
Table of contents

Most interviewers don't ask unconventional interview questions. Most stick to a standard list of unoriginal and uninspired questions because the person doing the interviewing assumes that's "just what you do."  

And then there are questions designed to elicit answers that force a candidate to dig deep, demonstrate what they bring to the table, and articulate why they are a great fit for the job. If you want to get the most out of your next interview, below are the 5 best unconventional interview questions to ask.

1. Would you be open to further education?

That is to say: if a role, at some point, necessitated that you develop or acquire a new skillset, and that required some form of education, would you be open to or willing to undertake that? Depending on the industry in question, it is not uncommon for top talent to be asked to complete graduate-level degrees and time-intensive designations outside working hours.

An organization might ask an employee to return to college to complete an MBA, or potentially a professional designation like a project management professional course. The thought of such an undertaking might be off-putting to certain candidates, and their hesitation or enthusiasm when entertaining the prospect is a good indicator of where their priorities lie.

Relevant: Creating employee development plans that work

2. What do you see as a major challenge facing our industry?

If you want to know if the person you are talking to sees the role they are applying for as more than just a way to pay the bills, it is always a good idea to test their industry knowledge.

That is not to say that you should expect them to be experts--especially if they are recent graduates or have little work experience. But it is not unreasonable to expect the people you bring on board to be interested in the state and fate of the industry they will be working in.

A lack of understanding or interest is often a good sign that a person is not in something for the long-haul. If they are not informed on the industry, they might get the job and soon find out that it is not for them and jump ship. At this point, you'd have already invested a considerable amount of time, money, and opportunity cost in onboarding and training them.

3. Describe a weakness and not "I'm too much of a perfectionist" or "I work too hard"

Many hiring managers think that this is, most of the time, a pointless question. Too many interviewees take this question as a kind of game you ask them to play, where the point is to demonstrate how good they are at feigning humility while avoiding saying anything disqualifying or off-putting.

If asked correctly, with the appropriate qualifier, the real point of this unconventional question is to ascertain whether the person you are interviewing can be self-critical and reflective.

There is still a slight element of trickery to it. If a candidate reveals that they lack a skill that is non-negotiable (e.g., they are interviewing for a data analyst role, and they say their biggest weakness is their attention to detail), you can still rule them out.

4. What kind of organizational culture do you think you would best fit into?

Every organizational culture is different, and not all of them are appropriate for every candidate. Some places are entirely top-down operations that value performance over all else and take a dictatorial approach to office relationships.

Others ask their people to consider the social and environmental impact of everything they do and encourage employees to take advantage of the nap room and meditation space on their lunch breaks.

The point being is that some people are better suited to certain kinds of organizational cultures than others. Employees are often quitting, not because they aren't happy with the job, but because they aren't happy with the culture. Having a candidate spell out what they are looking for in an organizational culture is a great way to determine whether they are a good fit.

Relevant: Cultural fit interview questions to ask

5. How do you prefer to handle conflict?

Human beings butt heads. It is so rare for any relationship to be completely free of conflict, and it is unreasonable to expect that conflict will not arise in the workplace. The important thing is how people handle it.

Organizational well-being is, in many ways, predicated on accepted and widely-practiced conflict resolution skills. You need to be sure that the person you are bringing into the fold is not a loose cannon or unwilling to compromise or behave diplomatically with others. You learn a lot about someone when you ask them to describe how they handle conflict.

6. Why do you work?

This might seem too profound or philosophical of an unconventional question to ask an interviewee, and depending on the role in question, it might be. But if the role is sufficiently sophisticated, with high potential for growth and professional expertise, questions that seek to understand why a person works can shed a lot of light on how they will approach their job.

If a person is concerned primarily with financial gain, it is not necessarily a bad thing. Still, people who solely chase money tend to burn out faster or dissatisfied if the money does not come quickly enough.

Other reasons a person may work are to finance a rich and varied life outside of work, or because they are in love with what they do or believe it gives their life meaning or think it has a positive impact on the world.

Understanding what motivates a person to come into work every day offers a tremendous amount of insight into how much of themselves they are willing to invest in the role.

Relevant: 5 best job fit interview questions to ask candidates


You should approach every interview with a candidate as if that person will potentially be around long-term. This is not always how labor relationships work. Still, suppose you ask professional and personal questions under the assumption that they will be.

In that case, you stand a better chance of not only eliciting real substance from an interviewee but shining more light on who they are as a person.

Keep the above unconventional interview questions in mind and make sure your new hires are the right fit for the organization's role and that you are not wasting their or your time.

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