Best Interview Questions to Ask a Candidate

How to Find Out: Can They Do the Job? Will They Fit In?

best interview questions to askTo wrap up on this month’s theme of “Interview Like a Champion” I want to close with thoughts on interviewing from the hiring manager side of the desk. How can you determine if the candidate before you is not only a great technical fit, but also a cultural fit? What are the best interview questions to ask a candidate?

If you have never interviewed a candidate, you might dread the process and wonder how to find the best one. You may already be an experienced veteran of interviewing and building teams, in which case, I welcome your thoughts on the best questions to ask.

During the years I spent focused solely on executive search, I learned a lot about how hiring managers think. I collaborated with some great leaders who knew just what they wanted, as well as executives who hated the hiring process. In both instances, we collaborated on designing the types of questions that would reveal the caliber of person before us. Some of the questions my clients relied on over the years, and the types of responses we received, follow.


What is the single accomplishment you are proudest of so far?

What we were looking for with this question, in part, was whether or not the answer was career-related. If the candidate couldn’t come up with a career-related accomplishment, that was a red flag.

We also hoped to learn about the candidate’s level of focus, discipline, and self-motivation. What the candidate chose to highlight as a proud accomplishment could reveal much about interests, skills, and alignment with the position and company.


Who is your favorite boss so far, and why?

The response to this question can reveal much about how a candidate prefers to be managed. It tells whether or not they appreciate being challenged and if they expect their boss to be a friend, as opposed to a mentor or leader.


Who is your least favorite boss so far, and why?

The response to this question can give you insights into who this candidate struggles to get along with, and how they cope with conflict. No one can be expected to like everyone. How a candidate responds to conflict is an important indicator of their emotional intelligence.


What do you excel at in your work, and what do you struggle with in your work?

This question acknowledges that no one loves every aspect of a job. The intention here is to get a sense of the candidate’s self-awareness and gauge their honesty about handling the parts of their job that are less than ideal.


Give an example of a time when you failed in a goal or objective.

We have all faced failure. Some managers I have worked with have a strong belief in the value of failure as a teacher. The answer to this question could provide great insights into a candidate’s honesty, resiliency, determination, and ability to overcome obstacles.


Who is the smartest person you know. Why do you choose them?

In one unfortunate instance, we had a candidate who said, “I am accustomed to being the smartest guy in the room.” As you might suppose, that interview ended soon and the candidate was not invited back. With this question, we were hoping to learn who had inspired and shaped this candidate as a professional. Whose values and expertise did he aspire to emulate?


If we were to hire you, what would you do in your first 30 days here?

This question is designed to learn how the candidate approaches new situations. Will she seek to understand before recommending changes, or will she disrupt the culture by forcefully offering unfounded opinions?

The object of interviewing is not to pose “trick” questions or to hold your cards so close to the vest that the candidate has no clue how he’s doing. Likewise, it’s not about determining if you want to hang out and have a beer with your potential new hire. I have seen hiring managers take each of these approaches, only to regret their hire.

No matter which side of the interview desk you’re on, I hope you will see it as an opportunity for a discovery and exploration of the best fit for all involved.


What’s the best interview question you have asked?

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