The Single Most Important Interview Question You Can Ask

Jared Belsky Leadership

If I had only one question to ask on an interview, I would use it in order to figure out if the candidate had HUSTLE in them. I deeply believe you can teach soft skills like trust building, persuasion, and active listening. I have seen you can teach folks statistics, digital media, copywriting, finance, welding or needle point. So, what is almost impossible to teach? Hustle. More specifically, the love of hustle. So….what is that signature and simple question you can ask:

{Interviewer to Candidate}: How did you make money before you were 21?

Asking the question is easy. Understanding what to look for is a bit more nuanced. You are essentially looking for three things in the answer:

Body Language – Is the candidate excited? Is the candidate smiling? Is the candidate leaning forward? Is the candidate beaming with pride? You see…when a hustler tells their stories from their youth, they do so with immense pride. Because, they are addicted to the hustle. Those memories are foundational to who they are. They are happy you have finally asked them something that is uniquely ownable by them, and not some forced tired old question. You can read this if you look…so look for the clues.

Detail – Is the candidate sharing specifics about their paper route? Is the candidate talking about the multiple cup sizes at their lemonade stand where they were able to make more money per ounce with the bigger ones? Is the candidate talking about specific baseball card shows they hustled cards at and specific locations (ie – Nassau Coliseum 1991)? Is the candidate painting vivid pictures of how they roped their best friends into some sort of snow-shoveling syndicate pyramid scheme? Is the person proud as hell about the two jobs they worked during college to pay their own way? Whatever the story might be, a person on the hustle who truly loves the hustle will have abundance of detail.

Frequency – The person you want does not have just one story. You know, that one story they rehearsed in case they got asked this question. The person you want has 10, 20 and 100 stories where they worked the system, found the edge, made some money, and got it done.

One note folks. Like anything I ever share in this newsletter series, you have to use judgement. There are times and moments where this is not appropriate. There are many other more elegant ways to ask the question differently and still learn the same things. You could instead ask “Tell me how you hustled for some goal while you were in your formative years?” So, as always, take the idea and be thoughtful about when/where/how you use it.

This article is part of my LinkedIn Newsletter series entitled “Great Client Partnerships.” Subscribe (its easy, just press the subscribe button and no other next steps) and join the almost 40,000+ other leaders who receive my weekly leadership note on this topic, or just follow. Either way. Always practical, never too long.


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