Insightful Questions to Ask When Interviewing Someone

During an interview, there are essential questions to ask, related to the job at hand, and about the candidate’s resume. That said, it is also important to ask additional questions that give you more insight on the candidate’s personality and morals, which can help you determine how they would contribute to a company’s culture and inclusivity. This article demonstrates some useful questions to ask, and what answers may tell you about who you are interviewing.


What is your favorite childhood memory?

By asking this, one can gain insight on how a candidate grew up, and if he or she had to help with family issues, how many siblings they have, or if they got along with friends in school. These answers can reflect positively on soft skills such as leadership, dependability, and teamwork.


Tell me a story about a meaningful experience in your life.

This gives the candidate a chance to talk about something they could have overcome, how they helped someone, or a time they had clarity. The candidate’s story will give you great insight on what is important to them in their life, which could relate to how they interact in a workplace. Depending on their story, you may learn how they have grown from an experience, and about what inspires them to keep working hard.


When was a time you failed, and how did you react to it?

Many people see failing as a negative thing to happen; however if you handle a situation well, there should be no need to feel negatively about it. We all fail at some point, it is human nature. What is important is how we deal with our failures and learn from them.

When asking this question, you shouldn’t be worried about what they failed at, as it’s not likely to happen again if they handled it well. Focus on what they did after they realized a mistake. You want someone who takes responsibility for their mistakes, and does their best to fix the issue.


What is a project you have done in the past, alone or in a group, that you are proud of?

The candidate’s answer to this question will give you insight on how they may prefer to work, either in a group or alone. You will also be able to see how they take pride their work, which is important in seeing how work ethic will be used in the position you are offering.

You can even make the question broader by adding that it could be a project from outside of work. By adding that, you can learn about hobbies and causes they care about while not at work. This question also is a gateway to follow up questions such as, do you think working in a group would’ve benefitted the project, or how did working in a team help or hurt the project.


Tell me about a time in your life you had to make a difficult decision.

The candidate’s response will show you the actual thought process they went through. It is not only important that they can make decisions, but that they care about the consequence of that decision, whether it be good or bad.  This question can also be a way to find out if they would be willing to ask for help with a decision, or other tasks. If they would ask for help, it shows they know their strengths and when they need the support. If they wouldn’t ask for help, maybe they are more independent and like to figure things out on their own. Either way you get a deeper insight on how they work best, and if they would be a good fit for this position.


Have you ever had to deal with a difficult person, in or out of the workplace?

With this question you will be able to learn how they handle conflict in relationships. Being able to work through conflict is an important skill to have, especially when working with a team. Conflict also isn’t a negative thing; sometimes we need conflict to make our work or relationships better, but that only works if it is handled correctly. If a person is just being difficult, it is important to know how to deal with that. You want your candidate to be a calm person, and a type of mediator when working with someone difficult.

If they cannot handle a conflict or difficult person, it may cause more issues that would not make them a good fit. You want your candidate to give you an example of when they had to deal with this for a better understanding, not them just saying how they would handle it.


When asking any insightful question, it is important to be able to understand the meaning behind the candidate’s answer, otherwise the question is less useful. A mistake a lot of interviewers make is by talking more than the candidate. You should want to hear what they have to say. By asking more insightful questions, it will make the interview more comfortable for the candidate, as it feels more personal, and the questions can be answered in a storytelling manner, rather than by listing off skills.  

You may also be interested in..

Related Posts

Lorraine West: Artisanry Adorned


How to Be a Better Active Listener at Work


Maura Green Jewelry: A Coven of Gems to Protect & Inspire


WJA: Fabulous at 40