1. If we're sitting here a year from now celebrating what a great year it's been for you in this role, what did we achieve together?
"For me, the most important thing about interviews is that the interviewee interviewsus. I need to know someone's done his or her homework, truly understands our company and the role, and really wants it.
"The candidate should have enough strategic vision to not only talk about how good the year has been but also to answer with an eye toward that bigger-picture understanding of the company--and why he or she wants to be here."
Randy Garutti, Shake Shack CEO
2. When have you been most satisfied in your life?
"Except with entry-level candidates, I presume reasonable job skill and intellect. Plus, I believe smart people with relevant experience adapt quickly and excel in new environments where the culture fits and inspires them.
"So, I concentrate on character and how well someone's matches that of my organization.
"This question opens the door for a different kind of conversation, in which I push to see the match between life in my company and what people need to be their best and better in my company than they could be anywhere else."
Dick Cross, Cross Partnership founder and CEO
3. If you got hired, loved everything about this job, and were paid the salary you asked for, what kind of offer from another company would you consider?
"I like to find out how much the candidates are driven by money versus working at a place they love.
"Can the person be bought?
"You'd be surprised by some of the answers."
Ilya Pozin, Ciplex founder
4. Who is your role model, and why?
"The question can reveal how introspective the candidate is about personal and professional development, which is a quality I have found to be highly correlated with success and ambition.
"Plus, it can show what attributes and behaviors the candidate aspires to."
Clara Shih, Hearsay Social co-founder and CEO
5. What things do you not like to do?
"We tend to assume people who have held a role enjoy all aspects of that role, but I've found that is seldom the case.
"Getting an honest answer to the question requires persistence, though. I usually have to ask it a few times in different ways, but the answers are always worth the effort. For instance, I interviewed a sales candidate who said she didn't enjoy meeting new people.
"My favorite was the finance candidate who told me he hated dealing with mundane details and checking his work. Next!"
Art Papas, Bullhorn founder and CEO
6. Tell me about a project or accomplishment that you consider to be the most significant in your career.
"I find that this question opens the door to further questions and enables someone to highlight him- or herself in a specific, nongeneric way.
"Plus, additional questions can easily follow: What position did you hold when you achieved this accomplishment? How did it impact your growth at the company? Who else was involved, and how did the accomplishment impact your team?
"Discussing a single accomplishment is an easy way to open doors to additional information and insight about the person, his or her work habits, and how the person works with others."
Deborah Sweeney, MyCorporation owner and CEO
7. Tell me how...
"I don't have one favorite question, because I believe a great interview takes on a life of its own, becoming more of a conversation than a formal process.
"Ultimately, we're looking for people who are motivated, disciplined, and good spirited, possessing skills and passion, so I ask indirect questions about the creative process, about articulating and demystifying the process of creating great food and great service.
"Then I trust my instincts. Reading the eyes of the candidate is a final test I've come to rely on--because the eyes never lie."
Eric Ripert, Le Bernardin chef and co-owner
8. What's your superpower, or what's your spirit animal?
"During her interview I asked my current executive assistant what was her favorite animal. She told me it was a duck, because ducks are calm on the surface and hustling like crazy getting things done under the surface.
"I think this was an amazing response and a perfect description for the role of an EA. For the record, she's been working with us for more than a year now and is amazing at her job."
Ryan Holmes, HootSuite CEO
9. Why have you had x amount of jobs in y years?
"This question helps me get a full picture of the candidate's work history. What keeps the person motivated? Why, if the person has, did the person jump from job to job? And what is the key factor when he or she leaves?
"The answer shows me the person's loyalty and reasoning process. Does the person believe someone always keeps him or her down (managers, bosses, etc.)? Does the person get bored easily?
"There is nothing inherently wrong with moving from job to job--the reasons are what matters."
Shama Kabani, The Marketing Zen Group founder and CEO
10. We're constantly making things better, faster, smarter, or less expensive. We leverage technology or improve processes. In other words, we strive to do more--with less. Tell me about a recent project or solution to a problem that you made better, faster, smarter, more efficient, or less expensive.
"Good candidates will have lots of answers to this question. Great candidates will get excited as they share their answers.
"In 13 years we've only passed along one price increase to our customers. That's not because our costs have decreased--quite the contrary. We've been able to maintain our prices because we've gotten better at what we do. Our team, at every level, has their ears to the ground looking for problems to solve.
"Every new employee needs to do that too."
Edward Wimmer, RoadID co-founder and co-owner
11. Discuss a specific accomplishment of yours in a previous position that indicates you will thrive in this position.
"Past performance is usually the best indicator of future success.
"When candidates can't point to a prior accomplishment, they are unlikely to be able to accomplish much at our organization--or yours."
Dave Lavinsky, Growthink co-founder and president
12. So, (insert name), what's your story?
"This inane question immediately puts an interviewee on the defensive, because there is no right answer or wrong answer. But there is an answer.
"It's a question that asks for a creative response. It's an invitation to the candidate to play the game and see where it goes without worrying about the right answer. By playing along, it tells me a lot about the character, imagination, and inventiveness of the person.
"The question, as obtuse as it might sound to the interviewee, is the beginning of a story, and in today's world of selling oneself, or one's company, it's the ability to tell a story and create a feeling that sells the brand--whether it's a product or a person.
"The way the candidate looks at me when the question is asked also tells me something about the person's likability. If someone acts defensive, looks uncomfortable, and pauses longer than a few seconds, it tells me the person probably takes things too literally and is not a broad thinker. In our business we need broad thinkers."
Richard Funess, Finn Partners managing partner
13. What questions do you have for me?
"I love asking this question really early in the interview--it shows me whether the candidate can think quickly on his or her feet, and also reveals the person's level of preparation and strategic thinking.
"I often find you can learn more about people from the questions they ask versus the answers they give."
Scott Dorsey, ExactTarget co-founder and CEO
14. Tell us about a time when things didn't go the way you wanted--like a promotion you wanted and didn't get, or a project that didn't turn out how you had hoped.
"It's a simple question that says so much. Candidates may say they understand the importance of working as a team, but that doesn't mean they actually know how to work as a team. We need self-starters that will view their position as a partnership.
"Answers tend to fall into three basic categories: 1) blame, 2) self-deprecation, or 3) opportunity for growth.
"Our company requires focused employees willing to wear many hats and sometimes go above and beyond the job description, so I want team players with the right attitude and approach. When candidates point fingers, blame, go negative on former employers, communicate with a sense of entitlement, or speak in terms of their role as an individual as opposed to their position as a partnership, they won't do well here.
"But if someone takes responsibility and is eager to put what he or she has learned to work, the person will thrive in our meritocracy."
Tony Knopp, Spotlight Ticket Management co-founder and CEO