Shoes that Help You Ask Powerful Questions


Note from Bob: I want to give a BIG THANKS to Will Wise and Chad Littlefield for their terrific series this week of 5 Guest Posts/Excerpts from Will’s book: Ask Powerful Questions: Create Conversations that Matter which focuses not just on what questions to ask, but on how you build genuine relationships of trust by asking powerful questions.  In today’s final Post in this series – Will shares about how to build trust and clear communication through the power of empathy. I am guessing that you have already clicked on the link below to purchase Will’s terrific new book! (Or that you will do so today!)

Ask Powerful Questions: Create Conversations that Matter by Will Wise

Video length: 177 seconds

We often think of empathy as, “walking a mile in their shoes”. If that was the case we end up with some poor fitting shoes and the other would be a mile away (and in need of a shoe store).

Will Wise gives several tips and tricks in his book, Ask Powerful Questions, that outline how to forge deeper, more meaningful connections with those around us. While each topic is different, they all express the importance of stepping outside of ourselves and working harder to value another’s perspective. In the fifth chapter, Will expresses the significance of empathy when working with others.

Asking Powerful Questions Pyramid™ by Will Wise and We and Me, Inc.

Asking Powerful Questions Pyramid™ by We!

Will suggests that there are three ways we can respond to any situation: with apathy, with sympathy, or with empathy. One is better than the rest when it comes to building relationships of trust with people.

Apathy lacks an emotional response, it based on facts, and it may make a person feel as if they are not valued, making it more difficult for them to trust you. “I don’t care about you, your perspective, or your shoes. At least you have shoes.”

Sympathy is awashed with feelings. What is tricky here is that their experience has triggered our own experiences that are similar to theirs. Now I’m thinking about me.  “Your smelly shoes, remind me how smelly my own shoes are. Let’s do some retail therapy and get new shoes.”

Empathy is rooted in the experiences of the other as well as your own. Will describes it as walking in another’s shoe. One foot goes in their shoe, but the other remains in our own. Their experience reminds us of our own, just enough that it informs us. We can understand what it means for them and we become explorers to see how this moment shows up for them, right now. “Let me try one of your shoes for a bit, and walk together, so I can see how you experience the world.”

Tool for building empathy and understanding: describe the world as they see it.

Even when you are lost, and emotions are high and you’re not sure how to respond. Share with them a description of how they see the world. It is as if you’ve become the narrator, standing offstage, sharing with them and the audience how their life is occurring to them in this present moment. Your focus is on them. Combined with your desire to ask powerful, impactful questions, this Tool is a doorway to an empathetic world. Asking yourself these questions might help you streamline your description:

  • How do they see the world?
  • How do they see themselves in that world?
  • How does the world push on them?

For more information visit the “behind the scenes” video for Chapter 5 of Ask Powerful Questions.

If you missed Will Wise’s & Chad Littlefield’s posts from earlier this week you can read

  • Monday’s Post “Build Trust by First Focusing on Intention”  by clicking “HERE.”
  • Tuesday’s Post “How to Build Trust and Productivity at Work” by clicking “HERE.” 
  • Wednesday’s  Post:  “Stop Asking ‘Why?’ Questions” by clicking “HERE.”
  • Thursday’s Post: “Two Wise Ways to Practice Better Listening” by clicking “HERE.”

You can purchase your copy of the #1 Amazon Best Selling book, Ask Powerful Questions: Create Conversations that Matter and practical tools like We! Connect Cards™ by clicking the toolkit below.

We and Me Connection Toolkit




Chad Littlefield, M.Ed. is a speaker and professional facilitator. Leaders and conference organizers call Chad when they want to make their events more interactive and engaging. He has spoken at TEDx and is the creator of We! Connect Cards™, which are now being used to create conversations that matter on campuses and companies in over 50 countries around the world. Feel free to connect with Chad through his interactive learning letter right here.

WiLL WiSE, M.Ed., has over two decades of experience custom building leadership programs for corporate and nonprofit groups. Leaders call Will when there is a lack of trust getting in the way of results. Tens of thousands of people have been empowered with positive communication skills after spending some time with WiLL and We!™ Most recently, WiLL has been passionate about sharing his #1 Amazon Bestselling Book, Asking Powerful Questions: Create Conversations that Matter.



Note from Bob:  I just recently found this marvelous new book!  It is a Great Read! I was delighted when...


Note from Bob:  I just recently found this marvelous new book!  It is a Great Read! I was delighted when...

Ask The Right Questions

Note from Bob:  I just recently found this marvelous new book!  It is a Great Read! I was delighted when...

42 Questions to Test Your Knowledge of American Independence

How well do you know the story of American independence? It’s time to put your knowledge to the test!...


Guest Post by Dusty Rhodes  There is a popular quote you may have heard in recent years, which says… We...

20 Best Performance Review Questions To Ask Your Manager

Guest Post By Indeed Editorial Team Previously posted at  Throughout your time at a company,...

One Engaging Question

Excerpted with permission from Chapter 5 of “The Power of Conscious Connection” by Talia Fox Pam was...

Leave a Reply

Your email address will not be published. Required fields are marked *

This site uses Akismet to reduce spam. Learn how your comment data is processed.