“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. There is no wrong answer with the question, and while I’ve heard some of the strangest 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.

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 a what they did, it allows me to see how they may 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.

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. Most importantly for the BDR/SDR position, it allows me to see how a candidate can quickly adapt to a “very different” type of question during a conversation.

Interviewing is time-consuming but can be enjoyable if you find a way to tap into the human side of your interviewee. Regardless of if a candidate is selected for our program, our team enjoys listening to the stories of some great people.

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