Best Oddball Interview Questions

Posted by Bradley Metz on 11/8/18 1:12 PM

In Leadership, Management, Hiring Tips, interviewing

Interviews are critical as they take your time and depending on the success of the interview, the results can have implications for years to come. Asking the wrong questions or even useless questions in an interview can be confusing for both parties and you might leave an hour later having not learned much. An interview is intended to gather insights about many different aspects of your candidate such as their problem solving abilities, their loyalty, insight into the way they think, but how do we get this information just from their answers and without them lying? The trick is to ask planned questions that are developed to reveal specific characteristics. 

There are a number of interview questions already out there; however these are our favorite oddball interview questions that will really separate the best from the rest. 

How will I know you are struggling or need help? 

This question can also be phrased as "tell me about a time where you struggled during a project or task and how did you overcome your struggle?". This is a great question to determine (you guessed it!) how your candidate deals asking for help or approaches difficult problems. 

What did you do to prepare for this interview today?

This is one of our top interview questions at imatters. You can learn so much from a candidate just by asking them how they prepared for the interview. An unprepared candidate will stumble over their answer and and find it hard to form a cohesive response rather than just admit they didn't prepare. A candidate that is excited about the career opportunity, who is eager to progress and learn will tell you all about how they studied up on the company, the position, the industry, etc. If a candidate can't properly illustrate how they prepared for your career, it speaks volumes about how they will prepare for projects, tasks, meetings, etc. once they actually have the job.  

What about this opportunity interests you the most?

In our opinion, a proper response to this question indicates that your candidate enjoys and is passionate about the work they do. Someone looking for a stepping stone in their career will tell you that they're looking for growth, they love the idea of the position or the title. Do not immediately write a candidate off because they don't seem to be passionate or 'into the work' however a candidate that loves what they do will be more inclined to get their projects and tasks done on time and completely. 

How are your basic math skills?

This is a bit of a trick question. Most candidates will respond with something like "excellent or great or above average". That is when you ask them a simple, however tricky, math question such as "what is 20 percent of 35". Most of the time they will rattle off some guess. The objective of this interview question is not to gauge their math skills, but to find out how they handle making a mistake. Some will respond positively, some will not. 

After you leave today, what are the top things that you want me to have heard about you? What do you want me to remember the most?

This is an excellent question as it allows the candidate to recap their perceived value to your company. They might not tell you anything you haven't heard already, however they might reveal something that wasn't covered in the interview. They might go over some of their soft skills that you missed out on in the interview or they might just recap why they are the perfect candidate for the career. After asking this question, you have given the candidate every chance at sharing the knowledge, interests, skills and any other information relevant to your career opportunity.

How would you rate your memory?

This question gives the candidate the opportunity to show vulnerability. No one really has a perfect memory and if they do, you'll probably know it before you ask this question. It shows a candidates honesty and gives them a chance to really analyze their memory 'skill' and justify their answer. The best answer will consist of some confidence in the candidates memory along with a demonstration of their memory with examples of memory-dependent tasks completed in other roles.

Estimate how many windows are in New York.

This is a fun question that really chokes candidates up. Some candidates will crumble and wont even attempt to answer. Take note of that and move on it they do, however a strong candidate will break the question down and attempt to answer it with what they know. 

A strong response will involve the candidate clarifying some assumptions, making some estimates and finally drawing conclusions with some simple calculations. Problems are never solved immediately. They take analysis and assessment and some time. Give the candidate some time if they ask. Offer them a pen and paper to write some things down. Notice the details that the candidate includes. There is no right answer, rather the information you are looking for is in the process the candidate uses to come up with an answer. 

The candidate might ask if the answer is correct. You of course do not know the correct answer. You only want to see how they approach an unfamiliar problem and the process they use to arrive at a conclusion. 

Up to this point in your life, what is the achievement you are most proud of? 

Asking this towards the end of the interview, before asking what else your candidate would like you to remember the most, helps your candidate leave the interview on a positive note. This question can give you insight into what the candidate values the most and can clue you in on the candidates long term goals.

When have you had to learn a new skill, what was your process and what did you learn about yourself? What was the end result? 

In our opinion, the most important part of this question is the "what did you learn about yourself". It is a great behavioral insight question.

Tell me about a time when you felt a change needed to be made in how a process was done. How did you come to this conclusion and how did you get the support for change?

Everyone has room for improvement. Recognizing the opportunity to improve takes a unique perspective to actually notice room for improvement and the ability to make that happen. 

Listen closely to the details about the change, how it was discussed and most importantly they steps they took to implement that change.

What is your personal definition of success? 

Everyone's definition of success is different. How you define your success can be a huge clue into your habits, work ethics, participation and motivation. How one defines success can really tell a lot about the person. 

What is the hardest thing you have ever done?

The candidate may answer this question personally or professionally. The what is not as important as the why, how and the details. What were the hurdles? How did they overcome them? Did the ask for help? The question can also define what the candidate thinks is "hard" and how they might fare with challenges in your business.


Your interviews should have a goal. You should go into your interviews knowing the questions you will ask and the information you would like to gather from those questions. This will give you something to fall back on if you go off on a tangent or get off track and will guide the interview toward revealing the information you are actually need.

In the eye care industry, quality candidates are hard to find. ANY candidates are hard to find! imatters has a network of over 150,000 eye care professionals waiting to meet you and interview for your career opportunity. Give us a call to get in touch with one of our recruiters or get started below!

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