What is Your Most Effective Interview Question?


This month, we asked our members the following: When interviewing a potential employee, what is your most effective interview question?

Here are some highlights from the responses we received.

Dan Hoffman, M5

By far, my favorite question is, “What can I tell you?” This isn’t just me being lazy. I can instantly tell if they’ve prepped. I can tell if they can listen. I can quickly tell if they are genuinely curious about us, and what they are curious about. Strategy? Culture? Something specific to the role? I can gauge confidence—are they really interviewing me? Doing this early in the conversation can throw people off balance, which I enjoy.

Jordan Finger, Ardis Health

I ask an open ended question such as, “Why are you the perfect fit for this position?” It makes them think on their feet, and people tend to run on and disclose other things about themselves.

Damon Gersh, Maxons Restorations Inc.

In a late stage interview, I will often frame the hiring process as one of “risk management” for both the candidate and our company. This way we acknowledge the reality and help the candidate understand that we are both assuming risks in considering an employment opportunity. I then ask, “What are the most significant risks that you would be taking by joining our team?” This question allows me to better understand and address the candidate’s specific concerns, unspoken objections, and potential obstacles to finalizing a deal to have them join our team.

Alexander Gordin, Broad Street Capital Group and The Princeton Council of World Affairs

My most effective question thus far has been: “Please tell me about your biggest failure and how you dealt with it.” I purposely do not qualify whether the failure is business or personal. Asking this kind of question lets me do a couple of things. It allows me to gauge a candidate’s reaction and observe how comfortable they are dealing with negative subjects. It also allows me to learn about the level of adversity they have faced thus far in their lives and their ability to deal with it. Finally, I look at the way they can present negative information and spin it into positive factor for the position for which they are applying.

Divya Gugnani, Send the Trend and Behind the Burner

The question I always asking prospective hires is, “Tell me about your biggest failure.” Everyone who’s been successful at any point has also failed. There’s no such thing as a perfect person and making mistakes allows you to learn from them. This question allows me to understand a person’s ability to accept/embrace failure as a part of their career, and in a start-up, that’s a daily occurrence. If someone is unable to admit to failure they are also unable to accept mistakes, which won’t work in a learning environment like Send the Trend or any other startup. It’s key to learning how to move on and grow.

Alexa von Tobel, LearnVest

The LearnVest team has been quickly growing, so I’ve done many interviews recently. I keep coming back to my favorite question: “What makes you get out of bed in the morning?” I think it explains so much about who the interviewee is as a person. It gets to the core of what motivates, inspires, and drives him or her.

Edward Solomon, Net@Work

Recruiting is extremely important to Net@Work. Our consultants and engineers spend most of their time with our clients. Our internal support staff also interacts with our clients or supports those that do. Even as we have grown to more than 150 employees, my partner (and brother) Alex and I are still actively engaged in the recruiting process. We want to make sure that we are hiring the best and the brightest. When interviewing a new candidate, I do have a few key questions that I ask which help me to understand and get to know the candidate.

Question 1: What did you think of the Net@Work website?

If a candidate doesn’t prepare for the interview by reviewing our website then the likelihood of the candidate getting a job with us is virtually nil.

Question 2: What do you enjoy most about your current job?

Candidates have a hard time bluffing on this one. If there are issues this usually draws them out, and if they love their current job, then how serious are they about finding a new one? You don’t want to waste the time on people that are not serious about the job search.

Question 3: What would the people that you have reported to in the past say about you and your performance? And if this is for a management position, what would the people that reported to you say about you and your performance?

I love this question. It allows the candidate to comfortably brag about themselves in third person. It generally draws out examples of interactions with former managers and staff. Plus, as we will be following up with reference checks, we will be able to compare the candidate’s response to their reference’s response.

Stephen Hindy, Brooklyn Brewery

Asking about previous work experience can be very revealing of a person's focus, commitment and curiosity. I look for people who have bounced around a bit and learned along the way. And I always check references.

Jeff Stewart, Lenddo

At my core, I am a technologist, so I always want to understand the candidate’s relationship with technology. Even non-technical roles, I will ask, “Tell me about a time you used software to solve a problem,” or “What is your favorite web based application, and how do you use it?” Also critical is references, so in advance of calling references I want to understand the candidate’s relationship with their former coworkers. A common question is, “References are very import to us, and we will be talking with many people you have worked with. What do you think will be the worst thing we may hear?” This question has proven to be quite insightful, and we have also had candidates choose to drop out of the process once they understand we do check references. 

Ronn Torossian, 5WPR

Generally when an employee candidate makes it to my office, they have been screened by our HR department and senior team so I trust that the basics have been screened. So by the time I am interviewing, I want to better understand work ethic and attitude.

I’ll ask one of two questions:

  • A challenge that the candidate has faced in life and how they overcome it
  • Their favorite, or first, job

Understanding what one views as a challenge gives an insight into their work ethic, and problem solving abilities. We want to understand the strategic thinking someone has and what they view as difficult. Owning a PR agency, clients always want more, and we have to always over-deliver. So people who aren’t resilient won’t have an easy time succeeding in this industry, and particularly at this public relations firm.

When asking about someone’s favorite or first job, once again it’s a chance to understand work ethic and attitude—what inspires them, what excites them. Even in a first job, if it’s someone like myself who worked for years in a fast food restaurant (pizza for me), they understand that elbow grease matters and everything in an entrepreneurial environment has to be done to succeed. Service counts and matters.