Interviewing Your Interviewer: What To Ask & Why

Hiring at its core is a transaction. A company has a need to have something done and they are willing to exchange money for skill and time to get those things done. There is a sense of equality when you think about hiring in these terms. And with that concept in mind, I always encourage candidates to enter the interview with their own questions to make the transaction amenable to their needs as well. Related: 8 Simple Interview Questions To Ask Hiring Managers The interview should serve to show both the company and the candidate that the relationship is not only going to be solid, but that it will be sustainable and put in a position to ultimately flourish. Turnover is around 7%, people do not stay in jobs as long anymore and I think part of this is that there are not enough candidates interviewing their employers before accepting a position. So, let this serve as your permission slip to ascertain your personal and culture fit with them as much as they are looking to do the same with you. Getting a new job is stressful, and so is interviewing. But not as stressful as showing up in your first month and realizing that you made a mistake. Don’t make the mistake - ask as many questions as it takes to make sure you are making a good decision. Before I dive in, two points that are incredible important:

  1. Do not ask yes/no questions
  2. Do NOT be afraid of silence
For me, questions fall into three buckets: Culture, management, and the role.


You are selling time - your precious time. This is something you cannot get back. In some cases, you are selling this time to a company that you really value their mission and values on they list on their website. The challenge is seeing how they live these values in the interview and making sure that they align with yours. I usually ask some of the following questions:
  • Tell me about how the culture manifests itself regularly.
  • How important is the culture to the everyday associate?
  • What’s most exciting to you about the company today?
  • What’s a little scary?


This is where you will focus the bulk of your questions. Your manager is the company and the culture to you and this person can make or break your work experience. You need to find out how well you will work together, their management style, and what they can expect from you.
  • What are you most proud of in your career here?
  • Tell me about how you make decisions?
  • Tell me about your favorite direct report. What was it that made them your favorite?
  • Tell me about someone who you did not like working with. What did they do that was challenging?
  • Tell me about your management style.
  • What keeps you up at night?


As we all know, the job description is about as honest as an advertisement you see. It is only mostly accurate. And as CAREEREALISM touts: Every job is temporary. These questions will help you determine how much of the job description is true and accurate or how much is BS and falls into “Other duties as assigned."
  • Tell me about my average day here? What do you see me doing?
  • What does success look like for this role?
  • What would your direct reports tell me about working for you?
  • How do you see this role progressing over time?
Feel free to build on these and make them your own, but the spirit is true, to ensure you are making a good decision, you need to ask a lot of questions to make sure that this is the right job for you. These questions will help guide your decision making process should you get offered a position and also to really understand what you are getting into when you are a few months into the new job.

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