Note from Bob: Recently I came across a book called Ask Powerful Questions: Create Conversations that Matter by Will Wise. There are over 80 “Leading With Questions” type books on my shelf, yet none of them are like Will’s book. Will’s book focuses not just on what questions to ask, but on how you build genuine relationships of trust by asking powerful questions. It’s no wonder it recently became a #1 Bestseller on Amazon! This week, with Will’s help we are doing something that we have never done before on this blog. There will be guest posts by Will every day this week sharing highlights from 5 chapters of the book and the Asking Powerful Questions Pyramid™. In today’s Post – Will shares about how to build trust and clear communication through the power of curiosity. I am guessing that by the end of the week – probably even before you finish watching Will’s short video clip (about 2 minutes) and reading the excerpt below – you will be clicking on the link below to purchase Will’s terrific new book!

Ask Powerful Questions: Create Conversations that Matter by Will Wise

Video length: 173 seconds

We often enter new situations with a sense of vulnerability, and as a result, we build protecting walls that prevent us from connecting to the people around us. Imagine you and a new colleague are expected to come up with a solution to “reduce lengthy morning meetings in the office.” This situation is likely to go in one of three directions:

  1. You shake hands, introduce yourselves, and take turns spit-firing potential solutions that are mostly small changes to what is already happening.
  2. One person offers a suggestion while the other explains why that won’t work, until a “safe option” is found, and you both go on your way.


  1. You choose to prioritize connection and establish a relationship of trust that allows you to be more comfortable collaborating to create something entirely new that has never been done before. And you both love it and you’re wondering if the other team members will go for it.

Rapport is about connection. It’s about building relationships of trust so that Option #3 above becomes normal rather than abnormal. You know trust is high when you hear things like, “Our idea….” or “We’ve got this idea….” rather than “My idea is…” or “I got this idea…” The “me” moments shift to “we” moments and the idea is born and then built upon in the space between the individuals. Author of Ask Powerful Questions, Will Wise, reveals a practical tip on how to establish this trust and connection in the second chapter of his book:

Find something on or around the person that they are wearing, carrying, or sharing and follow your natural, genuine curiosity by asking a question about it.

People generally want to be seen and heard. And curiosity is the doorway to making that connection. The second level of the Asking Powerful Questions Pyramid™ explores the concept of building rapport – quickly and genuinely.

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

Asking Powerful Questions Pyramid™ by We!

According to Will, if we connect before diving into content with our colleagues, we will spend less time shooting down ideas because we will be comfortable enough to listen and build on the ideas of others. Peter Block once said that “without relatedness, no work can occur.” Creativity and innovation happens best in an environment of psychological safety where we trust our co-workers have our best interest in mind. That safety is larger developed through personal and social connections.

Will’s invitation: in your next meeting, take a few minutes and focus on connection before content.

Start out your next meeting discussing a question in groups of three that connects to purpose, allows for for vulnerability and authenticity, thus allowing people to connect to each other.

For more information regarding rapport, check out Will’s “behind the scenes” of Chapter 2.

You can purchase your copy of the book, Ask Powerful Questions: Create Conversations that Matter by clicking the book below or this link here.

Ask Powerful Questions: Create Conversations that Matter book by Will Wise and We and Me, Inc.

If you missed Yesterday’s (Monday’s) Post “Build Trust by First Focusing on Intention” you can read it by clicking “HERE.”

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.

Chad Littlefield and Will Wise from We and Me



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