Ask Genuine Questions to Get Others Thinking

By: Dylan Nunn 


"How was was your weekend? " or "How are you?"-->  Most people who ask this question will answer "good", "great"; one word responses that drive me nuts. In my eyes, these responses mean that you really could care less about the interaction and are just conforming to what ever is convenient for you. 




Anyone who knows me well knows my obsession with digging deep by asking genuine questions in order to learn the most from people.


This obsession may have started from my pet peeve which is..  that's right!   Empty questions......  eliminate questions that illicit common/basic and all around plain answers. 

--> When a waiter asks "How is everything?" does the waiter really care or are they just repeating what many other waiters have said to them. Please, Please, Please! I long for creativity here, take more initiative, tailor your question specifically to the ones your serving. 

We simply don't know what to say.

We are hard wired to take the easy way out, short cuts.  These days our communication methods are changing massively along with our attention spans.  It takes less energy to text/email each other than it does to walk down the hall and knock on their door. Human interactions are more important than ever. 

The best way to judge someones character is to ask them genuine questions that elicit tough genuine responses. The goal is to catch people off guard, we want them to dig deep so they reveal their flaws, their inner workings, and their values. 

We want to emotionally connect to the people we start conversations with.  

Questions we should love asking:

  • What's the most exciting thing that's happened to you lately? 
  • What was the high point and low point of your weekend/month/summer year?
  • What have you learned today from the moment you stepped out of bed this morning? 
  • What was the last action you did to give back to society? 
  • If you could change one thing about yourself what would it be? ( this opens people up to be vulnerable) 
  • How are you changing or improving the world with what your doing? If not, how can you start?
  • If money was no object what would you be doing with your life?
  • If there
  • What are three words to describe how your feeling right now? (good, great, ect. words not allowed here) 
  • What's the most unique characteristic about you?

Asking these questions takes empathy. You can be the smartest person in the room but if you don't have the empathy to connect with others you have nothing going for you. 

What questions have sparked your interests in the past? What questions do you hate to answer? What questions tell you the most about people?