The 16 Best and Most Revealing Interview Questions Ever

Posted by Robert Norton on

These questions are in no particular order, as they should be customized to the particular position and person.  You want to mix up the tougher ones with more social, calming questions, so people do not feel they are getting the first degree. 

Always do your questions first and theirs second, by saying upfront you have some questions first and then will answer any questions they have later. This way they cannot sell specifically to your needs. You are in charge and should control the first interview completely. Only after they have proven that they are a viable candidate should you start revealing potentially sensitive company information.  If this person is not a good candidate, you can terminate the interview early and save everyone time.  Real candidates will need and deserve this sensitive information, but you would not want this to be generally available.  Good candidates will often try to control the flow of the interview and learn more early. You need to gently prod them to your questions first, so they cannot answer every question specifically for your need, but must answer for them honestly.

1. What are the biggest strengths you will bring to this organization? 

Purposely open-ended to allow them to sell their abilities. Looking for specifics and past accomplishments that are relevant to the position before revealing what these are.

2. What are the things you do not like to do, and not want to work on?

Test for honesty. A less threatening way to ask about weaknesses.  We all have weaknesses, are they willing to take a risk, be honest and explain where they might need help? People are good at what they enjoy and not so good at what they do not enjoy.


3. Please walk me through a typical day at your current/previous job and about your boss and relationship with them?

Tests their resume and title against their actual duties. Probes their level of supervision by their boss and how much autonomy are given? Tell me about the people you hired in your last position? How long did they stay? What percentage worked out? Tests knowledge of turn-over, training, and honesty too (since no one has a 100% success rate).

4. What adjectives would your references use to describe you?

Keeps it short and can be compared to actual reference comments to see how self-aware they are about their strengths and weaknesses?  

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The "Anti-refs" Question (One of the BEST and most revealing, spend some time digging in.)  Think of someone you have had problems with within your career, as we all do, who you would NEVER use as a reference. Tell me the adjectives (to keep short) they might use to describe you and why they had this perception?  Then we can discuss how you dealt with the situation.

This is a great backdoor to the weaknesses questions and far more effective.  It is very open-ended and often brings up events or issues that they would never volunteer that are indicative of issues.  Gets at potential reference points they will not volunteer and companies, or environments, where they may struggle. Tests honesty, as anyone saying they never had any issues with someone else is probably not being totally honest. Tests their ability to deal with difficult situations? Tests their impressions of the resolution of the problem(s) and if the company's mission still got done in spite of personal issues. Give you things to ask references about that force more honesty.

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5. Tell me what are the first 5 things you would do if you got this position?

Tests the level they think at, how they go about solving problems, how quickly they will dig in. How much research and investigation they will do before implementing changes to be sensitive to the organization, history, and other company-specific issues.

6. What accomplishment in your career to date are you most proud of?

7. What level is the accomplishment at? Is it big or small? Does it show skill, luck, focus, hard work, long-term career objectives?

8. Where would you like to be in 3-5 years in your career? What would you like to be earning?

Shows ambition, ability to think ahead and plan, and tests their plans against the company's goals for the person and position.

9. Tell me how you would go about _________ (installing a new system, implement a new procedure)? This is a position-specific question to test specific technical or managerial knowledge. Too many people do not ask specific deep technical questions, because they do not know them or are worried about offending. You need a few domain knowledge questions that are deep, technical, and esoteric enough to prove they understand their technical landscape

10. What do you think are the most important five (3-7) things for you to be successful in this position?

The candidate will most often cite what they believe to be their strengths, which may or may not agree with your corporate priorities and goals. 

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11. What are some things your current employer could do differently to be more successful?

Sour grapes or constructive criticism? What is the level they are thinking about small or large ideas and concepts? If nothing but complaints, they could be a malcontent, who took no action to improve the situation or would have a negative impact on company morale. 

12. Why are you interested in this job? What do you know about our company?

13. A genuine interest here, or just another job? Shows knowledge of your company - Did they do their homework on your company, what level of information did they focus on and consider important? Do they talk about a career path that makes sense within your company?

14. What have been the biggest failures and frustrations in your career?

Brings out attitudes about failure, risk, and self-responsibility versus just blaming others and outside factors. Learning experiences, ability to pick up and move on, etc.

15. Why have you decided to leave your current position?

Dig deeply into this with follow-up questions on their answers?  Whatever is driving this is critical to how they see the world and work. What did they do to try to correct what was driving them away? Was it out of their control, or a projection of their own issues?

16. What risks did you take in your last position?

Studies indicate that people who take risks are generally more successful than those who do not! As optimists are far more successful than pessimists.  Discussion on this can be very revealing. In early-stage organizations, you will not want to hire people who are not too risk-averse, as they may jump at the first new opportunity after learning how up and down things can be. You will also need people willing to fail more rapidly in small ways to help figure out the company's secret sauce.


In my opinion, these are some of the best and most revealing interviewing questions. More should be added with the job or industry-specific questions, and this can be done with a forty-five-minute interview.  Use the same questions for people in the same position and process, so you can compare apples to apples and have some consistency when comparing candidates.

Always understand their salary requirements and commute distance, as these can vary enormously by the candidate and be major factors visa vie your ability to close the deal.

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Bob Norton is a long-time Serial Entrepreneur and CEO with four exits that returned over $1 billion to investors. He has trained, coached and advised over 1,000 CEOs since 2002. And is Founder of The CEO Boot Camp™ and Entrepreneurship University™. Mr. Norton works with companies to triple their chances of success in launching new companies and products. And helps established companies scale faster using the six AirTight Management™ systems. And helps companies successfully raise capital.

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