The most impressive job interview questions

Dave Kerpen
Founder and CEO, Likeable Local
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Interviewing for your next job is tough work!

Last year, I published The 1 Thing You Must Do In Every Job Interview. The article received a lot of feedback—some in support and some in opposition. Interviews have remained a hot topic for me over the past year, especially as I work to scale our team at Likeable Local. This year, I thought I’d ask my friends over at the Young Entrepreneur Council (YEC) about the 1 most impressive interview question to ask.

The YEC is an invite-only organization comprised of the world’s most promising young entrepreneurs. I asked these CEO’s and entrepreneurs what single most impressive interview questions applicants have asked (or they they wish applicants would ask). These are their answers, followed by mine:

1. What New Skills Can I Hope to Learn Here?

This is just my perspective, but I’ve always secretly hoped to hear this question. It signifies a few positive things: the applicant acknowledges they don’t know everything and it signals both humility and potential. This individual is actively seeking knowledge and using that as a criteria to judge opportunity. They know that skills are important, not just knowledge. – Brian Honigman, BrianHonigman.com

2. How Do You See This Position Evolving in The Next Three Years?

When job applicants ask this question, it means they’re looking for a position where they can blossom long term. They’re committed to their own career growth and being selective about only accepting offers from companies that will give them the framework for that growth. And they’re also tactful and strategic enough to let me know in a polite, subtle way. – Jared Brown, Co-Founder, Hubstaff

3. What Can I Help to Clarify That Would Make Hiring Me an Easy Decision?

At Launch Academy, we always coach our graduating students to ask this question at the end of an interview. It shows that that you’re eager to get the job, you’re amenable to feedback, you’re confident in your abilities and that you can clear up any uncertainty. – Dan Pickett, Co-Founder,Launch Academy

4. How Can ‘X’ Scenario Move ‘Y’ Idea Forward?

I love when an engineering applicant asks a question about our business model, or a marketing applicant asks about our development process. At a small company, holistic thinking is essential to make a killer product: You have to combine business needs with technical expertise, and the people who are interested in both areas often come up with the most creative solutions – AJ Shankar, CEO, Everlaw, Inc.

5. If You Could Improve One Thing About The Company, What Would It Be?

Any qualified candidate should be interviewing the prospective employer as much as they are being interviewed. By asking about where the company can improve, the interviewee not only establishes that the interview process is a two-way street, but may also find out some important information to use in her decision making. If the answer given is not candid, there is information in that as well. – Peter Minton, Founder & President, Minton Law Group, P.C.

6. What’s The Most Frustrating Part of Working Here?

This and other courageous questions demand a thoughtful response. We encourage questions that require courage to ask and thoughtfulness to answer. If you can do it in an interview, you can probably do it with customers. And every day we need to have courageous — sometimes uncomfortable — conversations with customers. – Avery Fisher, President, Remedify

7. Who’s Your Ideal Candidate And How Can I Make Myself More Like Them?

No matter if they’d like to admit it or not, every CEO and hiring manager has their picture perfect “ideal” candidate for the job. If an employee asked this question or something similar during their interview, it would not only show me that they’re sincerely interested in the job, but willing to do whatever it takes to become the best employee possible. –Phil Laboon, President, Eyeflow Internet Marketing

8. How Did You Get Your Start?

When asked this question as a CEO, it shows that the individual you are interviewing is interested in your past and what you have accomplished up to this point. You want employees who buy into you and your idea, so it is imperative that you hire people who are on board with your vision. – Jayna Cooke, CEO, EVENTup

9. What Is Holding the Company Back?

Every company has immediate challenges that prevent it from achieving it’s full potential. A great employee will identify those bottlenecks, develop a plan to solve them and then execute on the strategy. A great candidate will be doing whatever she can to start identifying these challenges even before getting the offer. – Sathvik Tantry, Co-Founder and CEO, FormSwift

10. What Keeps You Up at Night?

I love this question because it demonstrates an adherence to our culture of challenging everyone while also indicating that the candidate understands that our existence is always in flux as a startup. When a candidate shows that she has a similar feeling and/or the outline of a way to think about addressing that fear, it goes a long way. – Kofi Kankam, Chief Executive Officer, Admit.me

11. What Concerns/Reservations Do You Have About Me for This Position?

This question shows that the candidate is being thoughtful about the job, and cares about truly earning the role and excelling if they join the team. It’s also smart because it allows them to address concerns on the spot and in person. – John Berkowitz, Co-founder and Chief Revenue Officer, Yodle


Those are the 11 favorite interview questions from the YEC. As for me, my favorite interview question is:

How will the work I’ll be doing contribute to the organization’s mission?

This article is published in collaboration with LinkedIn. Publication does not imply endorsement of views by the World Economic Forum.

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Author: Dave Kerpen is the founder and CEO of Likeable Local, as well as the co-founder and Chairman of Likeable Media.

Image: An interviewee answers questions during a job interview. REUTERS/Francois Lenoir.

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