The 10 Best Interview Questions to Ask

May 1, 2012

By: Dona DeZube

The best interview questions tell you about the person behind the resume, revealing the job candidate’s personality, strengths, weaknesses, knowledge, skills and abilities.

The best interview questions also benefit job seekers by giving them an opportunity to speak to details that don’t fit on a resume.

While a savvy interviewer always includes questions tailored to the position, our list of the 10 best questions works across a variety of industries and job descriptions:

1. From everything you’ve learned about this role, me and our company, tell me how you feel you’d make a contribution.

This interview question sorts people into two categories: contenders and also-rans.

“Those who have really prepared will love this opportunity to shine and stand out, demonstrating that they have done all the homework that can absolutely be done in today’s world of instant information,” says Darrell W. Gurney, career coach and author of Never Apply for a Job Again: Break the Rules, Cut the Line, Beat th....

“Those who haven’t will stumble and try to put some generic response together, which will be obvious.”

2. Why should we hire you?

This is among the best interview questions because it asks job candidates to define what sets them apart from the intense competition in today’s job market, says Doug Schade, principal & supervising executive recruiter, Winter, Wyman & Company -- New York Accounting & Finance.

Faced with a big stack of resumes telling a similar story, this question helps you determine the best candidate.

An interviewee who does a great job explaining how her unique experience, education, industry credentials, and personal interests will power your business will do the same thing for your company once hired.

3. If you could start your career over again, what would you do differently?

While no one likes to dwell on past regrets, this can be a good question to ask, says Brendan Courtney, president of staffing firms Randstad Finance & Accounting and The Mergis Group, Boston.

Asking a candidate to explain the major decisions he has made, highlighting the positive and negative, reveals the person’s ability to make calculated decisions based on past professional and personal experiences.

It also lets candidates share their vision for the future and their ambitions.

4. When I contact your last supervisor and ask which area of your work needs the most improvement, what will I learn?

“I love this question because it’s the one that actually garners an honest response from the candidate,” says career coach Lauren Milligan of ResuMayday, a Warrenville, Illinois, career-counseling firm.

“No amount of finesse will influence this answer because when the supervisor is brought into the conversation, the candidate knows the truth will come out anyway. Essentially, it’s the same question as ‘what is your biggest weakness,’ phrased in an unexpected way.”

5. Describe the best boss you ever reported to.

This is a great interview question because it tells you about past relationships, says Kathy Downs, recruiting manager, Robert Half Finance & Accounting, Menlo Park, California.

“Because it highlights the personality and work types the applicant meshes with best, the interviewer can gain greater insights into the candidate’s communication skills, work style and potential cultural fit,” she says.

Follow up with questions about what made the relationship click -- was it personality, performance, or perhaps a cheerleader type of boss? Does the candidate prefer autonomy to handholding, or was he inspired by a mutual drive to achieve organizational goals?

6. Tell me about what motivates you. 

7. What frustrates you?

Ask these questions in sequence to better understand the interviewee’s motivations, explains Janette Marx, SVP with Adecco Staffing US, Melville, N.Y.

If what drives the interviewee matches the position and your corporate culture, you have a winner.

When the candidate then talks about past frustrations, he reveals details about his personality, diplomacy skills and ability to work on teams.

Does the candidate answer by discussing minor irritations -- or ways that he successfully resolved serious conflicts over time, budgets, or priorities? The latter are candidates who have positive intelligence.

8. Tell me about the toughest negotiation you’ve ever been in.

Every job involves negotiation, and this question yields insight, not only in their direct negotiation skills, but also how the job seeker navigates difficult situations, Marx says.

The best negotiators answer this question by laying out both sides of the problem and then explaining how they aligned the issues or followed a process to a mutually-agreeable solution.

9. How do you involve your staff when an important company strategy decision needed to be made?

The candidate’s answer tells you whether a manager is secure enough to involve others in strategic decision-making, says Jayne Mattson, senior vice president, Keystone Associates, Boston, a career management firm.

How the job seeker involves his staff -- via written communication, one-on-one or in a group setting -- tells you a lot about their management style.

10. Where do you see yourself in five years?

With this question, it's not what the candidate says but how she says it that’s important, says Joey V. Price, CEO of Jumpstart HR, a managed HR services firm in Washington, D.C.

“If you see someone's eyes light up at the thought of the future, then you can tell this is a very ambitious person who knows where they want to go and will do everything in their power to help ensure your organization gets them there.”