25Founders: 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?