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Advice / Succeeding at Work / Management

10 Entrepreneurs Tell Us: The Interview Questions You Should Be Asking

Most job interviews fit a certain mold. You explain the position and company mission, ask a few questions, and decide whether the candidate's skill set would fit within your organization.

But is there anything else you can do during the interview process to determine who’s truly the right fit for your team? To learn more, we asked 10 successful entrepreneurs to reveal their go-to interview questions—the ones that really weed out the good apples from the bad. Here's what they ask every time to ensure they're picking the right men and women for the job.

1. What Do You Want Out of This Experience?

I look for answers that feel personal and authentic and are about more than ‘career development.’ Once I feel I have a good candidate in front of me, this question lets me think about projects he or she might enjoy. If people are happy at work and love what they do, they are more productive, they will stay longer, and they will help recruit other passionate people they know."

Santiago Halty, Senda Athletics

2. What is Your Dream Job?

It's absolutely vital to ask a candidate what his or her dream job is. I actually learned this from a very good friend and mentor of mine. The question is: ‘If you had a paintbrush and a blank canvas and you could paint the perfect job for you, what would that painting look like?’ This helps ensure that the role is the absolute right fit for the person. It also lets him or her know you genuinely care."

Mike Cuesta, CareCloud

3. Where Do You Go on a Night Out?

We work in a lifestyle industry, and I want to make sure that a candidate’s lifestyle and culture fits in with the rest of our staff and our clients. I also want to know that he or she can be a representative for us when out and about."

Alex Frias, Track Marketing Group

4. What is Your Ambition?

More than wanting to know that a candidate has taken the time to think through his or her goals in life, I want to know how those goals align with the opportunities at my company. This question is a great way to uncover how deeply the candidate has thought about his or her own life and how powerful the alignment could be."

—Kuty Shalev, Clevertech

5. How Can You Make the Company Better?

I like prospective hires to set themselves apart by telling me what individual skills or characteristics they bring to the table. Culture is so important in startups, and every single hire matters. It's important to not only find someone with the qualifications to do the job, but also someone who is uniquely driven to help make the company the absolute best it can be."

Brittany Hodak, 'ZinePak

6. Which Three Adjectives Describe Your Strengths?

This question often catches candidates off guard, and I have found that they tend to be honest with their perceived strengths. Make sure you assess the strengths they list against the core skills you are seeking in the role. At least half of the time, I identify a concern that warrants further questioning."

Chuck Cohn, Varsity Tutors

7. What Do You Want on Your Resume in Two Years?

We ask all of our interviewees how they want their resume to look in two years. This gives us great insight into their development goals and whether they are aligned with our needs. More importantly, when we hire, this question helps us guide their responsibilities and growth. Tailoring projects and ownership to employee goals builds their happiness."

Aaron Schwartz, Modify Watches

8. What Are Your Expectations for This Position?

I ask this for several reasons. First, I want some insight into where the person wants the position to go, his or her work culture expectations, if he or she anticipates management responsibilities, and what his or her comfort level is. This gives us an opportunity to see if this person meets the expectations for the position or falls short, and whether he or she is a good culture fit for Chocomize."

—Fabian Kaempfer, Chocomize

9. Could You Live Here?

By directly asking candidates if they wouldn't mind spending a great deal of time at the office, the idea is merely to gauge their initial reaction. If someone’s face shows a bit of sadness or surprise, you know that he or she might not be as passionate as a candidate who immediately perks up with delight. Afterward, you should of course tell candidates it was a test to make sure they don’t think you're a crazy boss."

Logan Lenz, Endagon

10. What Would You Do With Unlimited Resources?

Aspirations are an important and neglected talking point in interviews. Asking candidates what they would do over the next five years if they had unlimited resources gives you deep insight into their true personal or career goals. This is a great opportunity to see if someone’s ethos fits with your company and can help build organic rapport right off the bat."

Sarah Ware, Markerly

Tell us! What are your must-ask interview questions?

Photo of woman interviewing courtesy of Shutterstock.