The 10 Best Interview Questions to Ask Candidates

1. How Would You Address This Real-World Business Problem?

My best interview questions are actual business problems that we are currently facing. I want to understand how the candidate works through a real-world case. If we’re hiring a designer and are currently planning a website redesign, I might ask, “How would you redesign our checkout flow?” or “What do you think can be improved with our current homepage?” If we’re hiring a social media manager and heading into the holiday season, I may ask, “What are some grassroots tactics we should try this year to engage our customers before Black Friday?” This allows me to experience their thought process in real time – and who knows, you may even get a couple good ideas in the process.

— Scott Zakrajsek, Managing Partner and Analytics Lead, Sproutward 

2. What Is the Biggest Misconception People Have About You?

This question gives the candidate a chance to express their self-awareness. Sometimes, you’ll get really, really honest answers. Sometimes, you’ll get total B.S. answers in which candidates are still trying to paint themselves as perfect.

At my company, authenticity is really important, so this question lets us know who is comfortable being authentic and honest and who isn’t.

– Rachel Betterbid, Inbound Marketing Team Lead, Coalmarch Productions 

3. What Is the Most Courageous Thing You’ve Done in Your Life?

This question tells me about 75 percent of what I need to know about a person. It give me insight into how they think, how curious they are, and how self-aware they are.

— Bryan Clayton, CEO, GreenPal 

4. What Is Your Greatest Non-Work, Non-Academic Achievement?

Any reasonable candidate should be able to tell you about their academic achievements or a time they’ve excelled professionally. This question gives valuable insight into what the candidate values in their personal life.

Better yet, you’re almost guaranteed to get a wide variety of answers, even from pools of similarly experienced candidates. Someone might say they’re proud of having done a skydive, while another person might state that their children are their greatest achievement. Every answer will tell you more about someone personally than a question like “Tell me about yourself” or “What do you do for fun?” ever would. Given the importance of getting culture fit right, this is a powerful question to have in your repertoire.

— Arron Richmond, Digital Marketing Executive, High Speed Training 

5. If You Were an Ice Cream Flavor, What Would It Be and Why?

It sounds like a silly question, but it helps determine if candidates can think on their feet quickly. Do they just tell you a flavor they like, or do they give you an answer that’s relevant, such as, “I’d be cookies and cream because just like how cookies and cream work together to create something delicious, I can work well with any team!”

— Brandon Hoffman, Director of Digital Marketing, KEA Advertising 

6. Why Are You Interested in This Job?

This question is great because the answer can tell you a lot. It will share whether or not the job seeker is running from a bad situation. It tells you how interested they are in this job. It can also reveal other important details, like whether or not the person is looking to relocate.

— Angela Copeland, Career Coach, Copeland Coaching 

7. If There Are Two Types of People in the World, What Are They and Which One Are You?

I always end the interview with this same question.

Now, I know the question sounds very black and white, but I am curious about how candidates respond. Some candidates use the question as a chance to set themselves apart from other people (e.g., “There are people who take the initiative and people who don’t. I take the initiative”); others use it to show their creativity (e.g., “There are fork people and spoon people. My little sister ate her mac and cheese with a fork, and I used a spoon. I always had a more gentle approach to situations then she did”); others like to clarify that they don’t believe in just two types of people and will give me three types instead. These are all good answers.

In practice, the question is so basic it usually catches the candidate off guard. As a result, they give really candid responses. Again, there are no wrong or good answers. The point of the question is to draw a candid and real response to a silly question.

— Christina Wong, Customer Success Manager, Badger Maps, Inc. 

8. Are You Playing to Not Lose, or Are You Playing to Win?

What drives the candidate? Are they a risk-taker or a protector? When you find out what their motivators are, you will have a better idea of whether they will fit into the office culture.

— Tonya Lanthier, CEO, DentalPost 

9. When Working on a Team, What’s Hardest for You?

Cross-functional teams require employees who exhibit the ability to recognize emotions in other people and thrive as part of a healthy, collaborative team. Consider asking these questions about teamwork to learn more about your candidate’s ability:

– When working on a team, what’s hardest for you?

– Tell me about a time when you worked on a difficult team. What was your role and experience?

– What makes you happiest and most effective when working with others?

— Kristen Hamilton, CEO and Cofounder, Koru 

10. Tell Me About Your Current (or Most Recent) Boss or Supervisor.

I love this one because it gives me a chance to see how the candidate relates to authority. I can evaluate the candidate’s current (or most recent) relationship with their boss and hear what words they use to describe their association.

This question also gives me the chance to see whether the candidate will violate the all-important rule of “don’t badmouth your current employer.” Even if the candidate is unhappy with their current situation, there are ways to answer this question without going into anything negative. I’m hoping the candidate will choose to take the high road.

If the candidate likes their current boss, that’s all the better. The best predictor of future behavior is past behavior. If the candidate is happy with their current boss, it’s highly likely they’ll be happy with the next one, as well.

Some candidates will answer this question by describing the “official” relationship with their boss: “I report to Bianca, the head of operations. She gives me my weekly assignments and tells me what calls I need to make.”

Others immediately go into the more personal stuff: “Oh, I just love Mark. He’s so funny. He checks in with me every day and always has something hilarious to talk about.”

Again, I like to listen and see where the candidate takes the question. These types of open questions are sort of like Rorschach tests. Will the candidate play it straight or will they weave the human component into their answer?

– Denise Dudley, Author, Work It! Get In, Get Noticed, Get Promoted