Small Business

What Is Your Best Job Interview Question?

Congratulations, graduates! All those early-morning classes and late-night cramming sessions and what's your reward? A lousy job market. Sure, we've seen a steady, albeit modest, drop in the unemployment rate over the past several months, but the job market remains anything but robust. Just ask the millions who are still desperately looking for work. For them, and for new job seekers, the key question remains, "How can I stand out?"

Resumes, of course, still matter. (And lying on them, as recently departed Yahoo CEO Scott Thompson learned the hard way, can be a big mistake.) But for many companies, especially smaller ones with close-knit staffs, interviews play an increasingly central role in the recruitment process. Whether it's a series of one-on-one interviews, group interviews or even psychological tests, in-person conversations are more likely than ever to make -- or break -- your candidacy.

Here's the good news. Despite an unemployment rate north of 8 percent, many employers say they still can't find the right people to fill open positions -- which means if you can get your foot in the door, a winning interview just may keep you there.

So what is the person on the other side of that desk really looking for? We decided to ask members of our Board of Directors, some of whom are hiring as we speak, for their toughest interview questions. For other entrepreneurs out there, these should help your own hiring process. And for job seekers, consider it a cheat sheet for your next big sitdown.

JJ Ramberg

Host, MSNBC's Your Business and Co-Founder, GoodSearch

"The Host"

"Would you be willing to put together an IKEA bookshelf?"

"From the early days of hiring for GoodSearch, I've always asked this. In the beginning, this was actually a necessary question, as we moved offices a lot and we in fact did put together a lot of IKEA bookshelves! But there is more to the question than the practicality of gauging their handiwork. Asking this question sends a message to the candidate that we are the type of company that acts like a family, and when things are needed for the company, no matter what they are and no matter what your position, all hands are on deck."

Tom Szaky

Founder, TerraCycle

"The Eco-Capitalist"

"What do you want out of this role and the company? And where do you see yourself in five years?"

"Basically, what are their goals and desires? Many times, this is a telling question, as people answer it more honestly than other questions. People often only tell you what they think you want to hear. In contrast, it's a 'watch out' if someone is looking to do something unrelated five years from now.

"I also like to ask what someone's biggest, most glorious screw-up was. I can't tell you how many times people say they 'can't think of something' or they 'don't make mistakes.' When I hear that, I immediately discount the person's fit, as everyone makes mistakes. And at TerraCycle, we want to encourage a team mentality of risk-taking and experimenting."

Tate Chalk

Founder and CEO, Nfinity

"The Matador"

"Why us?"

"When I meet with someone, that's what I want to know most. That can tell me a lot about a person. Most people don't take the time to write a cover letter when they apply and, for the most part, don't do their due diligence before they sit down in front of you."

Lawrence Gelburd

Lecturer, The Wharton School

"The Rock 'n' Roll Professor"

"What are the three most important decisions you have made affecting your professional career?"

"I am always informed by the way interviewees frame their responses and how specific they are. This gives me a great window into their 'big picture.'"

Phil Town

Investor and Author of Rule #1 and Payback Time


"If you're working here and I think you're doing a terrible job, how do you want me to handle it?"

Elizabeth Busch, Anne Frey-Mott And Beckie Jankiewicz

Co-Founders, The Event Studio

"The Clipboard Queens"

"How do you work? Can you fit into our culture?"

"We are a unique company with a very virtual team spread out across the country, so that's really the most important question we're asking."

Bob Parsons

Founder and Executive Chairman, The Go Daddy Group

"The Renegade"

"How would you make a difference in our organization?"

"I like to get a sense of the person and what they are most passionate about. I can tell a lot about a candidate by hearing their answer."

Jennifer Hill

Startup Advisory and Venture Lawyer, Gunderson Dettmer LLP

"The Advocate"

"If you weren't doing [fill in the blank here], what would you do?"

Clint Greenleaf

Founder and CEO, Greenleaf Book Group

"The Cowboy"

"When I call your old boss, what will she say about you?"

"It absolutely depends on the candidate, but we use the Topgrading method, which is awesome. I highly recommend it. To understand it, read the book 'Who' by Geoff Smart -- it's a perfect primer. The best question has several steps, but it's about references. Note that it's not 'references' in general, it's a specific person who knows the candidate's work style. And it's not 'if' but 'when.' The candidate is forced to be more honest. It fleshes out his or her true character."

Eric Ryan

Co-Founder and Chief Brand Architect, Method

"The Soap Guy"

"How will you keep our company weird?"

"At Method, our best question comes during the 'homework assignment,' which is the final stage of a candidate's journey. Think of it as a live audition where they are given three questions. Two are related to the specific position and the last one is always this one. We ask because it's a cultural value, because we want people who can think differently, and let’s face it, the weirdest people are the ones who change the world."