Recently, I gave an interactive keynote in Cartagena, Colombia for the Global Youth Entrepreneurship Summit. This amazing group from 35+ countries helped me re-learned a lesson I had forgotten:  

The simplest questions are often the most powerful questions  

American humorist, Jack Handey, illustrates the power of simplicity in a playful way with one of his “deep thoughts” copied below.  

Instead of raising your hand to ask a question in class, how about individuals push buttons on each desk? That way, when you want to ask a question, you just push the button and it lights up a corresponding number on a tote board at the front of the class. Then all the professor has to do is check the lighted number against a master sheet of names and numbers to see who is asking the question. 

Sometimes the best questions you can possibly ask are also the simplest questions. Here are 4 of my favorites questions which are all under 4 words. 


1. What struck you?

This question is perhaps my favorite “debrief” question as it is totally flexible. And it allows both “thinkers” and “feelers” to answer the question after a meeting, experience, presentation, conference, etc. You can customize it easily by adding a few words to the end: what struck you about … your interview? That conversation? This idea? Etc.

2. How might we?

Famously used in design thinking circles, this question can also be very useful to open up an idea-generating dialogue. One where possibility is at the forefront of doubts and negativity float to the back.

3. What else?

One of my mentors who is an extremely skilled counseling psychologist gave me this question. It’s so open and offers a quick way to peel a layer off the onion so to speak. It can be used at the end of nearly every point in a conversation…although you probably wouldn’t want to do that.

4. What brings you joy?

Each one of these questions could have an article of their own as there is so much to unpack. But I want to share a story that came from what is currently my partner Will Wise’s favorite question: What brings you joy?

After sharing this specific question in a LinkedIn post on the power of simple questions, a reader and communication expert, Claire Laughlin, responded with this story: 

I was recently co-facilitating a session with some colleagues who I hadn’t worked with before. I suggested starting our workshop with the “what brings you joy?” question. 

My co-facilitators were reluctant. 

They thought it might be too hard or too personal of a question for some to answer. 

So I walked over to the CEO who had hired us, and said, “Would you mind? What is one thing that brought you joy today?” 

He looked surprised and told a very touching story about watching his daughter walk confidently into school. 

Then he looked at me and said, “thank you for asking me that. It feels so good to talk about it.” 

Needless to say, my colleagues were convinced and we started the workshop with the “joy” question. 

David Whyte, a renowned English poet, once said that “no self survives a conversation.” Claire and this CEO would probably agree. Brain research and data about how we respond to curiosity and questions would also tend to agree. 

Questions are like keys that unlock the lifetime of un-Googleable experience we walk around with each day. Asking powerful questions opens a window into these life experiences, commonalities, differences, and possible contributions or collaborations that we each carry in our minds.

I did not spark this engagement. Questions did. A well crafted question does all the work for you. 

All that said…what else?

We-connect-card-question

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