14 Unique Interview Questions to Ask Your New Hire

14 Unique Interview Questions to Ask Your New Hire

Unique interview questions are an essential part of hiring the right candidate. They should provide insight into the person’s thinking skills and personality. 

Here are 14 of the most interesting and unusual interview questions to ask your next candidate.

Icebreaker Interview Questions

We all know that interviews are nerve-wracking. Even the strongest candidates can be thrown off by the interview process and may not demonstrate their true aptitude. To help mitigate this problem, add some icebreaker questions to your docket to loosen their nerves.

Question 1: If you could visit any planet, which one would you go to and why?

Who doesn’t love an outlandish (literally) question such as this? It’ll be interesting to watch the interviewee’s thought process with this unique interview question.

Question 2: Dogs or cats?

An age-old debate!

Question 3: Describe this job to an extraterrestrial who just landed on your front lawn.

This is one of those unique interview questions that kills two birds with one stone. It helps loosen nerves, but it also allows you to get a first glance into a candidate’s understanding of the job.

Creativity Interview Questions

Many jobs require creativity and quick thinking. These unique interview questions are your first attempt to understand the candidate’s ability to be creative. How does their thought process work, and are you impressed by their out-of-the-box thinking?

Question 4: How would you pitch our company to a friend?

You want to uncover how much the candidate knows about your company. The best interviewees are the ones who come prepared with knowledge of the company. 

Is it clear they looked at your website, understand your ICP, read your blog, checked out your social media, and more? Can this candidate make sense of your unique selling point, competitors, strengths, and weaknesses?

Question 5: Name five uses for a picture frame, other than its intended use.

This is a thinker, especially when you aren’t expecting it. The five uses a candidate comes up with don’t matter as much as their thought process. Ask them to explain why they chose those five uses and talk aloud as they arrive at each conclusion.

Question 6: How would you transport a herd of elephants safely from Africa to Asia?

This unique interview question may seem silly, but in reality, it’s a great way to gauge how a candidate tackles an unexpected question. There’s almost no way they wrote down and recited an answer to this!

As with all of these creativity questions, a candidate’s exact answer doesn’t matter; instead, their thought process and rationale are interesting.

Question 7: What are three things you’d change about our website and why?

First, this forces an answer to the question of whether or not the candidate did their homework and checked out your site. It’s probably a red flag if they answer: I didn’t actually look at your site.

This unique interview question is excellent because it supplies you with valuable and practical information. Perhaps one of the suggestions is so strong you want to run with it. This gauges a candidate’s aptitude within the realm of actually doing work for your company.

Emotional Intelligence Interview Questions

Some studies suggest that up to 90% of top performers are highly emotionally intelligent. With that in mind, you want to gauge your candidate’s emotional aptitude with these unique interview questions.

Question 8: If you have more projects than time to dedicate to them, how would you manage your workload?

Dealing with stress and staying organized are significant components of emotional intelligence. Is this candidate able to sort projects effectively? Do they ask supervisors about priorities? Do they stay calm, or do they get flustered?

Question 9: How do you handle conflict in the workplace?

We encourage you to throw this one into the mix when considering which strategic interview questions to ask candidates. It’s one of those unique interview questions that allows you to understand how a candidate would handle a real-life occurrence that many of us go through.

Conflict is inevitable, and how a person handles it speaks volumes about their emotional intelligence. You want a candidate who reacts rationally, controls their emotions, and manages the situation diplomatically.

Question 10: How do you pick out birthday gifts for your friends?

It doesn’t matter if your candidate is a good gift giver or not; what matters is how they go about figuring out what gift to give their friend. 

Part of emotional intelligence is empathizing with others and understanding their needs — does this candidate apply that logic to picking a gift?

Question 11: How does it make you feel when someone criticizes what you’ve done?

The most emotionally intelligent people value feedback. Is this candidate one who gets defensive or prefers not to receive criticism? Or do they keep an open mind and use it to improve? Consider adding this in when figuring out what questions to ask when interviewing someone.

Behavioral Interview Questions

How does a candidate work through specific situations? What’s their behavior like in certain scenarios? These unique interview questions help you find out.

Question 12: If you were the CEO of our company, what’s the first change you’d make?

You can gain significant insight from this unique interview question. What does the candidate see as your company’s biggest challenge? What’s their leadership decision-making like?

Question 13: Tell me about a time when you disliked your work, and why?

Self-awareness is a large part of success. Can this candidate recognize when their work wasn’t up to par, and what was their reaction? How did they rectify the situation?

Question 14: What’s a goal you set recently and how did you achieve it? 

Being goal-oriented is another component of success, personally and professionally. How does this candidate set goals and follow a roadmap to accomplishing them? Does it seem like this person accomplishes their goals frequently, or do they fall short?

Final Word

Unique interview questions help you glean essential parts of a person’s candidacy. Do they seem like the type of person who’d work well at your company?

Looking to hire for a senior leadership position with these unusual interview questions? Jennings Executive can help you simplify the recruiting process and find the best candidate possible. Learn more today!

Related: Top 7 Best Recruitment Strategies For 2021

Kerry Ward

Director of Strategic Operations

Kerry is the Director of Strategic Operations at Jennings Executive Search. Starting her career with a boutique bank management consulting firm specializing in revenue enhancement and regulatory compliance, her engagements with financial institutions within all 12 Federal Reserve Districts propelled her interest for blending client interaction and strategic financial operations. She later transitioned to tax consulting and wealth management becoming registered with FINRA and the SEC and becoming licensed in insurance. Moving into a big four investment bank, and working in a boutique ultra high net worth investment advisory firm, her history spans various aspects of capital markets – both public and private.


Here at Jennings Executive Search, Kerry applies her two decades of experience along with her knack for interpersonal communications in aligning the interest of all stakeholders. Joining the team was a natural return to a highly specialized firm where she can work across all business functions using her energetic candor, enthusiasm for growth and improving processes while fostering relationships with our clients to reach their talent development and overall strategic growth goals.


Kerry graduated with a Bachelor of Business Administration degree from Georgia State University, and earned her MBA in Finance. Outside of the Jennings office, she enjoys traveling with her family for outdoor music festivals, golf and sports.

Daniel Wilkinson

Vice President of Strategic Initiatives & Client Success

DANIEL WILKINSON IS THE VICE PRESIDENT OF STRATEGIC INITIATIVES & CLIENT SUCCESS. HE BRINGS OVER TWO DECADES OF EXPERIENCE IN COMMERCIAL AND PRICING STRATEGY, HAVING HELD KEY LEADERSHIP ROLES AT DELTA AIR LINES AND DELTA VACATIONS. HIS CAREER IS MARKED BY A PROVEN TRACK RECORD IN DRIVING SIGNIFICANT BUSINESS TRANSFORMATION THROUGH INNOVATIVE DATA-DRIVEN STRATEGIES, CROSS-FUNCTIONAL TEAM LEADERSHIP, AND ENHANCED PROFITABILITY. DAN’S EXPERTISE IS IN HIS ABILITY TO INTEGRATE DATA ANALYTICS WITH STRATEGIC PLANNING, ENABLING ORGANIZATIONS TO OPTIMIZE THEIR REVENUE MANAGEMENT AND PRICING STRATEGIES IN DYNAMIC MARKET ENVIRONMENTS.

AT DELTA VACATIONS, DAN SERVED AS VICE PRESIDENT OF STRATEGIC BUSINESS/IT PLANNING & REVENUE MANAGEMENT, WHERE HE SUCCESSFULLY LED TEAMS IN DELIVERING SCALABLE TECHNOLOGY SOLUTIONS, DEFINING GO-TO-MARKET STRATEGIES AND DRIVING SIGNIFICANT INCREMENTAL REVENUE AND PROFIT.

DAN RECEIVED A BACHELOR OF SCIENCE FROM TAYLOR UNIVERSITY AND AN MBA WITH A FINANCE CONCENTRATION FROM EMORY UNIVERSITY’S GOIZUETA BUSINESS SCHOOL.

Brian Banister

EXECUTIVE RECRUITER

BRIAN BANISTER IS AN EXECUTIVE RECRUITER AT JENNINGS EXECUTIVE SEARCH. BRIAN HAS A BROAD RANGE OF EXPERIENCE, HAVING WORKED IN STRATEGY & CORPORATE DEVELOPMENT, FINANCIAL PLANNING & ANALYSIS, AND PUBLIC ACCOUNTING ROLES FOR LEADING COMPANIES AND CLIENTS IN THE HOSPITALITY, REAL ESTATE, MANAGEMENT CONSULTING, AND TECHNOLOGY, MEDIA, AND TELECOM (TMT) SECTORS. HE BEGAN HIS CAREER AT DELOITTE & TOUCHE, WORKING AS A LICENSED CPA. AFTER DELOITTE, BRIAN PIVOTED INTO CORPORATE FINANCE, WHERE HE HELD POSITIONS IN STRATEGY & CORPORATE DEVELOPMENT AT INTERCONTINENTAL HOTELS GROUP (IHG) AND COX COMMUNICATIONS, AS WELL AS AN FP&A ROLE AT BOSTON CONSULTING GROUP (BCG). THESE ROLES ALLOWED BRIAN TO GAIN VALUABLE EXPOSURE IN AREAS LIKE CLIENT SERVICES, STRATEGIC CONSULTING & PLANNING, FINANCIAL ANALYSIS, AND M&A AND INVESTMENT ACTIVITY.

BRIAN’S EDUCATION INCLUDES BOTH A MASTER OF ACCOUNTANCY DEGREE AND A BACHELOR OF BUSINESS ADMINISTRATION IN ACCOUNTING FROM THE UNIVERSITY OF GEORGIA.

Lori Shad

EXECUTIVE RECRUITER

DRIVING TRANSFORMATION THROUGH PEOPLE IS OUR MISSION AND LORI’S PASSION AS AN EXECUTIVE RECRUITER WITH JENNINGS EXECUTIVE SEARCH. SHE CONDUCTS THOROUGH RESEARCH ON EACH ROLE AND BUILDS STRONG RELATIONSHIPS WITH CANDIDATES TO HELP CONNECT PROFESSIONALS WITH THEIR NEXT GREAT OPPORTUNITY. LORI SPENT 22 YEARS AT A FORTUNE 500 INSURANCE COMPANY IN PRODUCT MANAGEMENT, SALES/BUSINESS CONSULTING, AND RECRUITING ROLES. SHE USES THIS EXPERIENCE AS SHE SEARCHES FOR THE BEST TALENT TO HELP DRIVE CLIENT SUCCESS FORWARD. SHE’S FOCUSED ON DELIVERING RESULTS AND GETS THERE THROUGH EFFICIENCY AND TENACITY WITH AN EMPATHETIC, COMPASSIONATE, FUN, GENUINE, AND POSITIVE APPROACH. SHE HAS BEEN INSTRUMENTAL IN HELPING CLIENTS ACHIEVE BUSINESS OBJECTIVES THROUGH UNDERSTANDING NEEDS, CREATING INDIVIDUAL, DATA-DRIVEN SOLUTIONS, AND SOLVING PROBLEMS, AS WELL AS POSITIVE RELATIONSHIP BUILDING AND TEAMWORK.

LORI GRADUATED WITH A BACHELOR OF SCIENCE DEGREE FROM THE UNIVERSITY OF GEORGIA.

Justin Graves

EXECUTIVE RECRUITER

JUSTIN GRAVES IS AN EXECUTIVE RECRUITER AT JENNINGS EXECUTIVE SEARCH.

JUSTIN HAS A VARIETY OF EXPERIENCES WORKING WITHIN PUBLIC AND INDUSTRY ACCOUNTING. HE BEGAN HIS CAREER WITH PATHSTONE FAMILY OFFICE PREPARING TAX RETURNS FOR HIGH NET WORTH INDIVIDUALS AND CORPORATIONS IN THE ATLANTA AREA. IN JANUARY 2015, HE JOINED COHNREZNICK, LLP, A TOP 10 PUBLIC ACCOUNTING FIRM, IN AUDIT & ASSURANCE WORKING PRIMARILY IN THE COMMERCIAL REAL ESTATE AND HOUSING MARKET. PRIOR TO JOINING JENNINGS EXECUTIVE SEARCH, JUSTIN WORKED AT A FAST GROWING TECHNOLOGY COMPANY, SS&C TECHNOLOGIES, WHERE HE WORKED IN THE REAL ASSETS DEPARTMENT DOING FUND ADMINISTRATION.

JUSTIN GRADUATED WITH A BACHELORS OF SCIENCE DEGREE IN ACCOUNTANCY FROM OGLETHORPE UNIVERSITY.

Justin Jennings

EXECUTIVE RECRUITER

JUSTIN JENNINGS IS AN EXECUTIVE RECRUITER AT JENNINGS EXECUTIVE SEARCH. HE COMES FROM THE HEALTHCARE INDUSTRY WITH 15 YEARS OF MEDICAL SALES EXPERIENCE. HE ATTRIBUTES HIS SUCCESS IN SALES TO LISTENING AND LEARNING FROM HIS CUSTOMERS AND ENJOYS THE PROCESS OF SOLVING PROBLEMS. HE IS SKILLED AT DEVELOPING THE RIGHT ACTION PLAN FOR EACH OF HIS CLIENT’S UNIQUE NEEDS AND COMMITTED TO HELPING THEM CHOOSE THE BEST SOLUTION. JUSTIN HAS TAKEN HIS SPIRIT AND PASSION FOR SELLING TO THE WORLD OF RECRUITING. HE HAS A GOAL OF SURPASSING HIS CLIENT’S EXPECTATIONS AND ASSISTING THEM WITH TALENT ACQUISITION.

JUSTIN GRADUATED WITH A BACHELOR OF SCIENCE IN MANAGEMENT FROM GEORGIA INSTITUTE OF TECHNOLOGY. WHEN NOT AT WORK, YOU CAN FIND HIM ON HIS MOUNTAIN BIKE, THE GOLF COURSE, OR SKIING OUT WEST IN THE WINTERS.

Chip Locke

PRACTICE LEAD, TECHNOLOGY RECRUITING

CHIP LOCKE IS THE TECHNOLOGY RECRUITING PRACTICE LEAD FOR JENNINGS EXECUTIVE SEARCH. CHIP BRINGS 15 YEARS OF EXPERIENCE IN TECHNOLOGY AND RECRUITING INCLUDING HANDS-ON WORK AS A SOFTWARE DEVELOPER AND BIG 4 SYSTEMS CONSULTANT. HE IS A TRUSTED CIO ADVISOR WITH EXPERIENCE ACROSS INDUSTRY VERTICALS AND A DEEP UNDERSTANDING OF TECHNOLOGY PLATFORMS AND THE FUNCTIONAL AREAS OF DELIVERY THAT ENABLE BUSINESS OPERATIONS. HIS EXPERIENCE INCLUDES RECRUITING EXECUTIVES AND COLLABORATING ON STRATEGIC PLANNING AND IMPLEMENTATION OF IT ORGANIZATIONS.

HIS CLIENT SUCCESS STORIES CAN BE FOUND AT COMPANIES RANGING IN SIZE FROM STARTUP TO FORTUNE 500 ACROSS AVIATION, ENERGY, FINANCE, HEALTHCARE, TECH, MANUFACTURING, RETAIL AND TELECOMMUNICATIONS. CHIP GRADUATED FROM THE UNIVERSITY OF GEORGIA WITH A BACHELOR OF BUSINESS ADMINISTRATION DEGREE IN MANAGEMENT INFORMATION SYSTEMS.

Brian Gelfand

PARTNER

BRIAN GELFAND IS A PARTNER AT JENNINGS EXECUTIVE SEARCH. HE BEGAN HIS CAREER AT DELOITTE & TOUCHE IN AUDIT AND ENTERPRISE RISK SERVICES, WITH A FOCUS ON THE FINANCIAL SERVICES AND REAL ESTATE INDUSTRIES. AT DELOITTE, BRIAN GAINED VALUABLE CORPORATE EXPERIENCE WORKING WITH A MULTI-BILLION DOLLAR PUBLIC MORTGAGE SERVICING CORPORATION, AND A NOT-FOR-PROFIT FOUNDATION WITH OVER $10 BILLION IN ASSETS. BRIAN PASSED THE CPA EXAM BUT ULTIMATELY DECIDED ASSISTING CLIENTS WITH THEIR PEOPLE STRATEGIES WAS HIS PASSION.

BRIAN’S EDUCATION INCLUDES A MASTER OF ACCOUNTANCY FROM KENNESAW STATE UNIVERSITY AND A BACHELOR OF BUSINESS ADMINISTRATION IN ACCOUNTING FROM GEORGIA COLLEGE & STATE UNIVERSITY

Jon Jennings

FOUNDER / MANAGING PARTNER

JON JENNINGS IS THE FOUNDER AND MANAGING PARTNER OF JENNINGS EXECUTIVE SEARCH. ESTABLISHED IN 2014, HIS VISION WAS TO SHAPE A FIRM ANCHORED IN TRANSPARENCY AND VALUE CREATION. OVER THE YEARS, JON HAS HAD THE DISTINCT OPPORTUNITY TO ENGAGE WITH AND LEARN FROM LEADING INDUSTRY EXECUTIVES, GLEANING INSIGHTS FROM THEIR EXPERIENCES AND COMBINING THIS KNOWLEDGE WITH THOROUGH RESEARCH. THIS HAS EQUIPPED HIM TO OFFER A DEEPER, MORE STRATEGIC PERSPECTIVE ON ORGANIZATIONAL DESIGN AND TALENT IDENTIFICATION. WITH AN INITIAL FOCUS IN FINANCE, THROUGH JON’S LEADERSHIP THE FIRM HAS PIVOTED INTO BROADER COMMERCIAL AND TECHNICAL STRATEGIES AS WELL AS PROFESSIONAL SERVICES.

TOGETHER WITH HIS EXPERIENCED TEAM OF EX-CONSULTANTS AND INDUSTRY PROFESSIONALS, JON COLLABORATES WITH PREMIER CONSULTING FIRMS TO ENHANCE THEIR PRACTICES. SIMULTANEOUSLY, HE ASSISTS PRIVATE EQUITY GROUPS AND THEIR PORTFOLIO COMPANIES IN REFINING AND FORTIFYING THEIR COMMERCIAL AND FINANCIAL STRATEGIC OPERATIONS.

THE CULMINATION OF THESE EFFORTS IS A BOUTIQUE FIRM THAT INC.COM CELEBRATED AS ONE OF THE COUNTRY’S FASTEST-GROWING COMPANIES. BETWEEN 2019 AND 2022, THE COMPANY WITNESSED A STAGGERING GROWTH RATE OF NEARLY 600%.