Hiring Out of the Box: My Favorite Interview Questions and Why They Work

We all want to hire smart, capable people, right?

People are the lifeblood of a company, and a brand will only be as good, as creative, as dynamic as the people behind it. With that in mind, hiring well is one of the most important jobs–if not the most important–that any business owner has.

A brand will only be as good, as creative, as dynamic as the people behind it. Hiring well is critical. Click To Tweet

I’ve read and listened to tons of different business experts talk about optimizing the hiring process, and there are so many significant steps to ensure success. My favorite part, though, is the initial in-person interview.

There are those intangibles of being face-to-face that tell you so much about a person: how they shake your hand, what they’re wearing, how they read the room and respond, the confidence they exude…

But the centerpiece of reading those intangibles–the place where you as an employer can really dig into the key strengths of that person–is through the questions you ask.

I love interviewing, and I’m constantly a collector of awesome questions.

Here are eight of my current favorite interview questions.

1- If you could choose two celebrities to be your parents, whom would you choose and why?

This question rocks because it catches people off guard, especially after a series of more “traditional” questions. It’s not serious, it’s not expected, and it’s not often asked. I love it because–regardless of the answer–you see how a person responds in an unanticipated situation. Do they look startled and have trouble recovering? Do they sit there and say, “Ummmm, ummm”? Or do they laugh, play it cool, and respond quickly and confidently? How they behave in an interview is how they’ll behave in front of a client.

2- When is it ok to break the rules?

This question serves a dual person. First, it’s another that potentially catches someone off guard and allows you to see their response in a “surprise” situation. But secondly, it gives you a peek into how they see rules, integrity, and rebellion. (In my book, rebellion–assuming it’s not hurting anyone–is the key to progress and innovation, so I’m all for it!) I’ve hired employees who say, “Never!,” another one who said, “When no one’s looking,” and another that said, “All the time, as long as no one dies.” There’s no right answer, but whatever the response, it speaks directly to how this person views boundaries and the status quo.

3- If you could choose a theme song to represent your work ethic, what would it be?

This question lightens the mood and, yet again, requires someone to think on their feet. This industry moves so quickly that we can’t afford to have a slow or uncertain decision-maker on board. I love hearing the responses, as well, because it informs me about this person’s perspective on work ethic: what it means, what they value, how they tick in regard to dedication and hard work.

4- What are you currently reading?

If I’ve said it once, I’ve said it a million times: good marketing requires continual learning. I’m a book nerd myself, and reading is one of the most significant ways to soak up expert knowledge. I’m looking to hire readers. Not only is reading a habit of some of our world’s most successful people, but marketing reading is a strong indicator that this person is interested in the field and dedicated enough to take the initiative to learn and grow in their spare time.

5- What other brands are you inspired by in our space/sector?

Like the book question above, this question also lets me see how much a candidate knows about the industry and how much effort they’ve made to learn about our space, our competition, and our potential clients. If they can speak intelligently about brands within our niche, I’m impressed. If they can speak intelligently about brands without our niche and offer savvy commentary about what they’re inspired by and what work is good work… I’m majorly impressed. This is a really key question.

6- What do you not like doing at work?

Everyone rehearses their way around the negative questions, right? People know all too well how to prepare for the “What are your three weaknesses?” inquiry, somehow spinning fantastic things in a “dark” light. (“I really just care too much about my work.” Don’t lie. You’ve done it too!) So I like to throw out negative questions that they’re not prepped for. This one is fun because it can come with a deep, intense answer or a light-hearted one, but either way, it says a lot about someone’s honesty, workplace presence, and suitability for the role at hand.

7- If we’re sitting here 12 months from now celebrating the success of your first year, what will you have accomplished?

This question is a fun one because it gets the candidate imagining life in your organization. You can often tell how excited someone is about the position by their energy in answering. Plus, it sets them to really speak to the mission of your organization (Do they know it?) and their own particular strengths. It allows you to assess whether they understand what you do and what this role is. I always think to myself, “Is a ‘win’ for them the same as a ‘win’ for our organization?” That’s such an important part of an employee’s role.

8- If you could get rid of one state in the U.S., what would you choose and why?

This question, like a couple others above, is fun and hits on the unexpected. Catch ‘em off guard and see how it goes! What I love even more, though, is that this one hits on the “why” very strongly. Do they make rash, emotional decisions? Well-reasoned, logical decisions? What does their thought process look like? Do they hit on research and current knowledge of the day to answer? Is it a quick answer, or awkwardly belabored?

I know the celebrity parents of everyone I’ve hired, along with their favorite states, current books, and top songs. Fun random facts. But more importantly, I know how they respond to the unexpected, how they reason and make decisions, and whether they take the initiative to stay up on industry trends. Hands down, that information is far more important than any fluffed-up description of their last job or a rehearsed recitation of their strengths.

Lots of people can do a job. But it takes the right person to rock a job. These interviews questions are just a handful of my favorite ammo to find strategic, creative “rock a job” people.


  • Junior N Monica Martinez

    I laughed at some of these questions because of how “off the wall” they are. I am actually going into an interview today, and thinking of these questions has me loose. Thanks!

    By the way, this is an upper management position; landing it means I run interviews in the future. Guess where I am getting some of my material? :). Awesome post!

    • It’s not about the responses they give, but how they think on their feet. That tells me so much about a person. Granted, their answers also say a lot about their personality.

  • I love these, Chad. I just may use these with podcast guests!

  • I love these, Chad. I just may use these with podcast guests!

    • So awesome, Tsh. The answers you get are very interesting. 😉

  • Lisa Cannon

    I must admit I have conducted and attended many interviews over the years and never heard of any of these, but I like them a LOT! Leave it to Chad to come up with some rather unique questions!