17 Quirky Questions to Evaluate Your Next Potential Hire

Question: What is one unique interview question that you ask to every potential new employee?

Question by: Elsie

TV Queens and Bookworms?

"When you ask, "Tell me about your favorite show/book?" see if they are passionate about what they are talking about. When I hire people onto my Sweet T Team, I am looking for high-energy and passionate teammates. If they can't express how much they love they favorite show/book, they'll never be passionate about our brand."

- Nancy T. Nguyen | President & CEO, YMH, Inc.
Verify Your Value System

"If you want to be sure you're hiring someone who will be a good fit for a specific position, it's wise to ask about the candidate's top threevalues. Answers like "perseverance" and "ambition" likely mean she or she is a good fit for a sales-oriented role, while answers like "peacefulness" and "creativity" may indicate well-suitedness to an entirely different area."


How Shall I Praise Thee?

"I ask: "How would you like me to tell you you're doing a great job?" Knowing what motivates people—cash, awards, recognition—helps me keep them happy when they're performing well."


Dream Occupations

""If you could be doing anything, what would it be?" As a startup, we want to make sure we're bringing people on board who are passionate and excited about their work. Knowing what a potential employee loves to do, above all else, is critically important in aligning their passions and skills with the core needs of the business, to create a harmonious and prosperous relationship."

- Matt Cheuvront | Founder/CEO, Proof Branding
As If You Were Already Hired

"What is a "blind spot" in our business and how would you implement improvement? This one question will give you everything you need to know. Have they done their homework about your business or are you just "another interview" to them? Are they results-oriented and understanding of how to comprehensively improve a product or service? What value will they bring in exchange for their pay?"

- Josh Shipp | TV Host & Bestselling Author, Josh Shipp Productions
Count Parking Lots, Please

"Never had the chance to ask it, but I've heard this is a great question: "How many cars are in the United States?" Do they blurt out a random number with no thought? Do they mumble and stumble and say nothing? Do they use some logic and try to figure it out? It's not about knowing the number, it's about their process for finding an answer."

Are You Looking Up?

"I ask candidates interviewing for positions with Thinking Caps to tell me about a role model and why the interviewee looks up to that person. Not only does the question require the candidate to respond with a thoughtful answer, but it also gives me an opportunity to hear about the candidate's values and goals."

- Alexandra Mayzler | Founder and Director, Thinking Caps Tutoring

Turn the Tables

"I start every interview with the same question: "What would you like to ask me?" I learn more about the person from their first question then I do from the rest of the interview. If they ask about pay or vacation time, I already know what they are looking for. If they start to ask about things they saw on one of my websites, then I know I have someone who is serious about the job."

- Roger Bryan | Managing Partner, Enfusen Digital Marketing
Superman? Batman?

""What superhero would you be?" Sounds cheesy but it's amazing to see the answers people come up with, and then to see those that literally freeze. It's a simple question and it's mostly to how creative they can be and how quick they can be answer. In business, you can't teach "personality" and this question gives you a quick glimpse into theirs."

- Ashley Bodi | Co-Founder, Business Beware

Who Do You Really Want to Work With?

"Every time we bring a potential new employee through the door we ask them a series of questions pertinent to the position. The one question we always end with is, "If you could work on a project for any company in the world, who would it be, and why?" This shows us where their interests really are, and it's really all about identifying people's passions."

- Bobby Emamian | CEO, Co-Founder, Prolific Interactive
Which Drink Would You Be?

"We use this question to see how quickly someone can think on their feet and how creative they are. We've had answers that run the gamut from ice water to Jack Daniels, to Guiness to orange juice. Each answer reveals something about the person who is answering and because we like to have a great time in the office, seeing how someone reacts to this question shows how well they will fit in."

- Nathan Lustig | Co-Founder, Entrustet

Let's Go to the Theater!

""What was the last movie you saw?" It's crucial to make sure all employees have a life outside of the office and are capable of talking about things other than business."

- Josh Weiss | Founder and President, Bluegala
Literary Tightrope

"This is our make-or-break question: "What do you read on a weekly basis?" If a potential employee can't list at least one resource that he or she reads to keep up on what's happening in the world, how can we expect them to keep up with changes in our industry?"

- Allie Siarto | Co-Founder, Fare Oak
Why Are Manhole Covers Round?

"Most people will not know this answer, but I am just curious if they are going to BS me or tell me the truth. If they don't know, they can always tell me they can get me the answer; if they make something up, they're out. How could I trust them with me or my customers?"

What Do You Think You Are Best in the World At?

"When building a team, you have to learn what is most important to your potential employees and if they are a fit within your company. At our company, want to be best in the world at certain things and leave a legacy through the work that we do. This question sets standards for employees upfront, and as an employer you begin to understand what your candidates values, strengths and aspirations are."

- Matt Wilson | Adventurer in Residence , Under30Experiences
The Stickiest Question

""Here's a roll of duct tape. What are ten things you can do with it?" It doesn't have to be duct tape; it can be any item sitting anywhere in the room. The reason we ask this question is to measure an interviewee's creativity (and limitations). If they can come up with ten things to do with an item, we know they're a good fit. Why? Because creativity is seeing what others don't."

- Brett Farmiloe | Employee 01: Digital Marketing Auditor, Markitors
Time to Prioritize

""If I ask you to put together a list of clients from our database and you see the database is corrupted with incomplete and duplicate entries, what would you do: put together the list I asked for first or fix the database first?" Their answer tells me many things about their personality—shortsightedness, attitude towards work, detail orientation, and time management. "


The Young Entrepreneur Council (YEC) is an invite-only nonprofit organization comprised of the world's most promising young entrepreneurs. In partnership with Citi, the YEC recently launched #StartupLab, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses via live video chats, an expert content library and email lessons.

About YEC

The Young Entrepreneur Council (YEC) is an invite-only organization comprised of the world's most promising young entrepreneurs. In partnership with Citi, YEC recently launched StartupCollective, a free virtual mentorship program that helps millions of entrepreneurs start and grow businesses.

Leave a Reply

Your email address will not be published. Required fields are marked *

You may use these HTML tags and attributes: <a href="" title=""> <abbr title=""> <acronym title=""> <b> <blockquote cite=""> <cite> <code> <del datetime=""> <em> <i> <q cite=""> <strike> <strong>