Smart Questions to Ask Interviewers

Finding a job is rarely a simple process with little stress. From finding an open role that seems like a good fit, to creating a resume tailored to the requirements, and finally, interviewing, you have to do a lot to get the right job offer.

Interviewing is a particularly challenging part of the process, because it requires communication skills with at least one other person who ultimately decides your fate at that time. The advice about what questions to ask or be ready to answer varies, so how can you feel confident?

One resource I find especially aligned to my understanding of the career management process, and interviewing success, is Work It Daily. I recently watched a YouTube video: 8 Smart Questions To Ask Hiring Managers In A Job Interview. The video content is presented by J.T. O’Donnell, CEO of Work It Daily, who has 18+ years of experience in all things career-related, and a professional whose writing is featured in business publications.

In this video, she suggests asking some questions that I had never considered. Some of these questions are easy for me to consider asking, while others might make me feel a little less comfortable (for example, asking the interviewer what might have been lacking in my interview approach or my resume).

I think the advice applies to job seekers of all ages, and I’ve summarized some of the main concepts here. If you struggle during interviews or are just looking for some new questions to ask, I recommend watching the video and reading the comments submitted by other viewers.

O’Donnell breaks down her interviewing advice into four categories and reminds viewers to never say you don’t have any questions when the interview turns it over to you!

The 4Cs of interview categories are:

  • Connect
  • Culture
  • Challenges
  • Close


You need to connect with the interviewer to create rapport and convince him or her that your skills and your personality are an asset to the company.

O’Donnell suggests starting with this question: “How did you come to work here?”

I hadn’t thought to ask this before but think it’s a great plan. First, think about how your nerves settle in during in an interview, and even with thoughtful planning, you can forget what you planned to ask. This question is easy to remember!

Second, this question shows you are interested in the interviewer and can connect with his or her story. People like to talk about themselves and share the successes they have in their careers.

Third, by getting the interviewer talking, you can take a breather from talking, and instead show you can be an attentive listener.

Fourth, if you get hired and end up working with this person, you already have a good understanding of his or her background, role, successes, and interests.


Is this the right company culture for you? Sometimes you might not feel like you have the luxury of caring (for example, if you’re new to the workforce or you’ve suffered a long-term stint without work), but if you can find the right fit, you’ll likely do a better job for the company, have more opportunities, and encounter stresses that are more manageable than if you can’t stand the company values or views on work-life balance.

I found her suggestion to ask the interviewer about the most successful recent hire or the one who just didn’t work out for the company interesting. I think it could feel awkward to ask, but if you listen closely to interviewer’s comments, you can quickly decide if your own skills and approach will be applauded or admonished.


What challenges are most important to the organization, and how do your unique skills and experience help overcome them?

O’Donnell suggests not just asking what the company is facing as its biggest challenge for the year, but also how the job you’re applying for can play a part in overcoming the challenge. It shows your interest in helping the company (not just on making the cash) and shows that you know each role in the company is critical to the company’s success.

She also mentions asking how the company will measure your performance against these objectives. If you are expected to contribute, but when you ask about how your performance will be measured against objectives, you can’t get a solid answer, it’s a red flag that you might not want to work there. With expectations that could be ambiguous, it leaves you open to blame or potential firing for no clear reason.


You want to end on a high note and leave with clear next steps. It is good for you to ask what the next steps are, hoping you’ll be told a date by which you should be contacted. If you’re not contacted by that date, it’s appropriate to reach back out to the company to let them know you’re still interested.


What are some of the questions you’ve asked during an interview that helped you land the role? Have you asked any that you immediately regretted?