Regrets, Motivations, and More: 8 Questions to Ask Every Candidate Who Walks Through Your Door

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Welcome to Recruiter Q&A, where we pose employment-related questions to the experts and share their answers!

Today’s Question: What is one question you always ask when interviewing a candidate for a job?

The answers below are provided by YEC Next, an invitation-only community for the world’s most promising early-stage entrepreneurs.


reb1. Why Do You Want This Job?

It’s important to ask applicants why they are interested in the job, why they would want to work for your company, and why they would want this particular role within your organization. Understanding why an applicant sees themselves as the right person for the role is very useful in determining fit.

Reb Risty, REBL Marketing  

michael2. How Will This Role Help You Achieve Your Goals in Life?

A candidate may be satisfied to complete the job’s duties in the short term, but unless the job helps the applicant achieve their own personal long-term goals in some way, it’s unlikely they will be a permanent fit.

Michael Miglio, ICO Law Group 

jason3. What Would You Enjoy Doing 40 Hours a Week?

To get to the heart of whether a candidate will end up performing well in a role, I always ask a simple question: “If money were not a concern, what would you enjoy doing 40 hours a week, every week?” If their answer relates to their planned role with the company, we proceed. If it’s something far off, I know the chances are extremely high they won’t be around for long.

Jason Keyz, Keyz Group, Inc. 

ajmal4. What Motivates You to Perform Well?

If someone is not motivated or encouraged, or if you have to constantly push an employee to do better, hiring that person might just mean signing up for more work for yourself! A person with good motivators — emotional, material, or financial — will always do a better job than someone who just wants to get by.

Ajmal Saleem, Suprex Learning  

Ron5. Tell Me About a Problem You Encountered

When interviewing anyone for any role, I always ask them to explain a problem they’ve encountered, their solution to the problem, and the outcome of the solution. This provides deeper insight into the prospect’s leadership potential. I only like working with leaders; it makes the day-to-day much simpler.

Ron Lieback, ContentMender  

zahra6. Why Should We Not Hire You?

This simple question serves a hidden purpose, as it tests how honest the candidate is. Some candidates refer to a minor quality that has little or no effect on their role. Others tailor the answer to describe their ideal work environment. Both are acceptable answers, as long as they are candid.

Zahra Timsah, AMCL  

turath7. Do You Have Any Regrets in Life?

When interviewing someone for a job, I like to ask them if they have any regrets in life. If so, what do they wish they could’ve done differently, and what have they learned from those experiences? Their answers can give me insight into their perspective on achieving goals and persevering through setbacks or failures.

Turath D’hont, San Diego Moving Company  

jose8. Where Do You See Yourself in the Next Few Years?

Most recruiters have been shying away from this question in recent times, but I believe it’s a great question to ask, depending on the context.

For example, if I am recruiting team members for a startup, I will look for people whose long-term goals are aligned with the company’s. It has to be a win-win situation. The new team member and company have to be able to say: “We will both be together in 2-3 years.”

Jose Magana, Yellowberry Hub  


By Recruiter Q&A