The best interview question you’re not asking …

— freestyle rap?!

I have one interview question that seems to filter people out better than anything I’ve ever tried.

It’s an absurd question, one that will catch you off-guard and get you to scratch your head, BUT, I guarantee this question will tell me if you’re a good fit for what I’m looking for.

It’s not so much of a question as it is a request. One that flexes all the creative muscles of the mind simultaneously. One that challenges even the best of thinkers.

What is this question/request?

“I’m going to give you a random word and you’re going to create a freestyle rap for me…ready?!”

Freestyle rap?! What the hell does that have to do with my ability to perform on the job?!?!

This question always gives me one of two responses —

  1. I can’t do it
  2. I’ve never done it, but I’ll give it a try.

Why do I ask this question? Why do I want to know if you can freestyle?

How you respond to a question like this will tell me a lot about how you respond to something you’ve never tried before. It shows me the type of problem solver that you are. I don’t care if you can freestyle, but I do care about your default reaction when a challenge comes your way. I don’t care if your “freestyle” is “uuuuhhhhhhhh blue. you! two! I like to wear shoes!” — what I care is that you tried to make an attempt. You put your best effort forward in a moment where you were vulnerable and could fail miserably. I respect that.

I like to isolate someone’s “default reaction”. Many people come to an interview prepared with a set of canned replies to make sure they nail it. It’s important to catch them off guard and surprise them with something they couldn’t prepare for. By catching them off-guard, you see how they react in a real life situation.

The people who reply “I’ve never done it but I’ll try”, show me that when a problem arises, they stay cool and try to figure it out. They make an attempt at solving the problem on their own first, and then will seek support after they have tried (and perhaps even failed). Instead of seeing the obstacle, they devise ways to work around it.

If you replied “I can’t do it” — then this is probably how you think when a challenge arises. Instead of trying to figure out a solution you simply say, “I’ve never done this, I can’t do it.” It’s a defeatist mindset. Instead of seeing the ways around the obstacle, all they see is the obstacle itself.

How does this translate to the workplace? The people who say “I’ll try” are the ones who troubleshoot problems on their own and then come to you saying, “I ran into this problem, here’s how I tried to solve it, here were my results, what do you think?”. The people who say “I can’t do it” are the ones who come to you and say “Here’s a problem that I can’t solve — can you help me solve it?”

Problems will inevitably arise in the workplace. Problems that you probably have never dealt with before either. Do you want someone who comes running every time something goes wrong? Or do you want someone who figures out potential solutions and tries to get the job done on their own?

There’s a key difference here. The people who try are able to overcome challenges. The people who say they can’t are the ones who buckle in the face of adversity. I ask this question to discover the people who say “i’ll try” in the face of a challenge.

My experience: In the past I’ve ignored my gut and hired people who failed this test — and everyone who failed the test also failed to exemplify the type of thinking and problem solving that I look for. For example, we hired one engineer who failed this test. When the time came for him to get outside of his comfort zone he buckled in the face of a challenge and gave up. When work was in his comfort zone he was a stud, but the second he went outside the box everything crumbled.

On the flip side, we hired one person who passed this test with flying colors. He was someone who was constantly pitching ideas, creating designs, and researching how to do things that were outside of his comfort zone. He didn’t care if he never did something before, he would figure out how to do it and only come to me and express where he was stuck. He lasted with us for a year before he moved on (our project was complete).

The point is, in an interview it’s more important to discover how someone thinks in high pressure moments. Do they shut down in the face of a challenge, or become even more resourceful? Do they think clearly and put their best effort forwards, or do they self sabotage when they get confused? Do they say “I’ll try” or “I can’t”. Choose wisely.

Note: I understand that it’s not always this black and white when looking at how to evaluate people. There are grey areas, and people who perform poorly on this test can do incredibly well in other areas. I don’t believe that it’s the fairest way to interview people, nor is it the sole basis for my decision. It’s a fun challenge I enjoy giving, and it does show me a lot about how someone views challenges. I am in no way saying that if you fail this test you always buckle under pressure — I’m making generalizations for the purposes of illustration. Thanks for reading 😃

Do you have any examples of ways that you test for these attributes in your own interviews? Similar techniques to discover how people think? Let me know in the comments below!

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