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The Weird Question I Ask Every Candidate I Interview

By Sasanka Atapattu

“What’s the riskiest thing that you’ve done that would horrify your parents?”
For those VPs, Directors, and Managers that have worked with me, you know that this is one of my favorite questions when interviewing potential Business Development or Sales Development Representatives. Over the course of hundreds of interviews the answers have been thoughtful, surprising, and most importantly insightful.

So why do I ask this question? Mainly it’s to understand how a person thinks through their answer. I'm screening for a number of qualities that are necessary for success in the SDR role: grit, adaptability, propensity for risk-taking, ability to think on their feet. It also allows me to get to know a candidate on a more human level.

There is no wrong answer to the question, and while I’ve definitely heard some strange answers including being arrested and working at a strip club, the best answers are the ones where candidates think about a time where they were challenged in an unfamiliar situation and then tell that story.

For example, when someone answers that they were in the middle of Europe with no money and no idea where they were, and they describe what they did, it allows me to see how they might be able to get through some of the toughest challenges that our growing community of 200+ SDRs face every day.

Great startups go through a series of mini evolutions. I love asking this question to understand how a candidate thinks about risk and how he or she is able to adapt to a particular situation. It allows me to see how a candidate can quickly adapt to a curveball question during a conversation.

This question is also great to get to know a candidate outside the context of a stuffy, formal interview. I often see candidates pause, smile, and loosen up with this question and usually end up with some insight into cultural fit as well.

Interviewing is time-consuming but it can be enjoyable if you find a way to tap into the human side of your interviewee. Regardless of whether or not a candidate is selected for our program, our team always enjoys listening to the stories of some great people.

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