Seven Great Questions to Ask an Interviewer

By Shawn Lipton


At the end of an interview, you will always have an opportunity to ask a couple of questions. This may be the last impression that you leave with the interviewer, so you want to ensure that your questions are impactful and make the interviewer think.

Avoid the simple nuts and bolts questions, such as what a typical day looks like or how will you collaborate with so and so, since they don’t really add anything to the conversation.
I have had hundreds of clients ask the following questions during interviews with good results.

1. If I am fortunate enough to get this position, let’s say at the end of six months or a year, how would you go about determining whether or not I was a success?

This is a good question for a few reasons. First, it could lead to more conversation which is exactly how you want an interview to end. They may provide a couple of areas that are important and if appropriate, you can comment or reiterate how that connects with your background. Second, if you ask this to the first interviewer in the loop, you’re getting great insight as to what the team looks for in a candidate and you can naturally weave those qualities in to your stories. Finally, if you do get an offer, you can evaluate what the team considers important and confirm that it aligns with your professional values and motivations.

2. What do you see as the great opportunities as well as the great challenges in this position?

Instead of simply asking what the team or individual may be working on, this question can show some of the tougher problems that you may face in this role as well as get you excited about the opportunities. I’ve had clients ask this and are surprised how open the interviewer is about the challenges that they may face.

3. In thinking about someone that you recently hired that was an absolute top performer, what are some of the qualities and characteristics they possess?

Similar to the first question, you are getting a lot of insight on the aspects that are most important to the team and company. Based on what they say, you may be more or less excited about the role. This question gets to culture of the company, environment, and what leadership values.

4. When friends and family ask you why you like working at ABC company, what do you tell them?

Instead of simply asking, ‘why do you like working here’, this question gets at the same information, but people end up thinking about what they actually tell friends and family about their team and company and often times leads to much deeper insight about the culture and atmosphere.

5. In thinking strategically about your work and what needs to get done over the next 12-24 months, what keeps you up at night?

This is an ideal question for the hiring manager, skip level, or bar raiser. This question gets at the most challenging problems the team or department may be facing and when you learn about them, it may get you more or less excited about the position. Responses tend to be more high-level so if you’ve done your research, it can often times lead to a rich conversation of how to effectively deal with the more stubborn problems the organization is facing. Instantly, you’ve moved from an on-the-surface-interview to a deeper connection.

6. What is the top priority for the person hired into this position?

This is a more common question but good to have on your list. It provides solid information about what the interviewer considers important and you may get different responses depending on who you’re asking.

7. Is this a place where you can fail, make mistakes, ask questions openly, and learn?

I don’t always have clients ask this question, but if you really want to be part of company that embraces risk, is pushing the envelope, and is genuinely innovating, then you want to ask this and consider the response. If one of your core professional values and motivations is to have variety, change, ambiguity, and challenge, the worst thing that can happen is for you to go to a company that values stability, is risk-averse, doesn’t have a growth mind-set, and is hierarchical. This question can start to get at that.

Best of luck on your interviews and I hope these questions take you over the top.

Shawn Lipton

Shawn Lipton
The Trusted Coach

I have been a coach for 15 years, first working at Seattle University and the last almost seven years running my own career and corporate coaching practice. There is nothing I love more than helping people identify what may be a fulfilling career and then teaching them how to develop their story to land an ideal role.

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