Getting ready to hire?  We often spend much of our focus on the candidate’s match to the competencies required for the open position.  However, we all know that it tends to be some of the softer skills and the candidate’s ability to fit within the culture of the organization that makes a great hire.  So yes, check to make sure the candidate has the competency to do the job.  Then spend more time on cultural fit and their attitude and approach to work.

Here are 14 unusual questions that tend to yield interesting information during a job interview:


Cultural Fit:

  1. “Assume that you come to work here. One year from now you go home on a Friday evening thinking that accepting this job was the best thing you ever did. What happened during the year for you to feel that way?”  The answer here may give you a sense for what is truly important to them in their work.
  2. What kind of oversight and interaction would your ideal boss provide?​
  3. Tell me about a time when you were happiest at work. Why did you feel that way?
  4. What types of behaviors do you find most annoying or frustrating in a client or team member? If they name something that you know exists at your firm, this may be a red flag. If it’s something that you too tend not to tolerate, then it’s a match.
  5. “Is it better to be perfect and late, or good and on time?” Based on your firm’s culture or the specific job, this is a really good question.
  6. “Pretend you are a product or brand. Who are you and why?”  I love this one.  It forces candidates to describe themselves in a totally different way and provides you with insight into who they really are.
  7. “If your boss asked you to jump, would you ask how high? Or, would you ask, why do you want me to jump?” Another good one that helps you test to see if there is a match with your culture.
  8. “You’re a new addition to the crayon box. What color would you be and why?”  Fun… like the brand question, this compels people to think about themselves in a creative way.


  1. Ask the candidate to rate a series of random items. They can be common things based on your company and the job.  How and why they rate them can prompt a good discussion.  Don’t make it obvious – we recently used these four items: a joke book, a watch, a spreadsheet, and a coffee mug.
  2. “What was the worst day you’ve ever had at work and why?”
  3. What’s your definition of hard work?”
  4. Name one person, alive or dead, that you would want to meet and why.” The thought process behind this can elicit some interesting perspectives about the candidate that you may not get otherwise.

 Service Orientation:

  1. If asked to clean the toilets here, how would you respond?” You can see how they address being asked to do menial tasks. This can be especially important in small companies, where everyone needs to pitch in to make it all work.
  2. Ask the candidate to describe a cell phone to someone who has never seen one. This tests their ability to communicate clearly and understand their audience.

While skills and education are often easy to find on a resume, the interview is where you want to probe and discover if the candidate is a cultural fit for your company.  A cohesive team can be difficult to create, but well worth the effort in the long run.  For help making a career transition, schedule a meeting by clicking below, contact Joni Lindquist –, or call (913) 345-1881.

Joni Lindquist, MBA, CFP®, is a Principal at Aspyre Wealth Partners, specializing in Financial Planning and Executive/Career Coaching. For help with your specific situation contact Joni Lindquist at, (913) 345-1881 or visit our website at We help successful people Master What’s Next® – whatever phase of life they are in.