Will Wise - Ask Powerful Questions: Create Conversations That Matter

From my experience of working with Will and Chad for many years, I know firsthand that they live what they teach. This book is an anthem to Will and Chads potent teaching, waking people up to themselves and othersfor the benefit of us all.

Dr. Laurie L. Mulvey , Executive Director

World in Conversation, Center for Public Diplomacy

In a world where certainty is valued and judgment often replaces discernment, Ask Powerful Questions builds a compelling case for fostering curiosity, finding clarity, and creating connections. If you dare, follow the simple (but not easy) path that Will Wise provides to help you find self-awareness, empathy, and personal transformation.

Maren Showkeir , Coauthor

Authentic Conversations: Moving from Manipulation to Trust and Commitment

Listening is our most fundamental tool for healing the worlds wounds and I thought I was pretty good at it. But after reading Wise and Littlefields book, I real ize that I have a long way to go. At the same time, I am excited because now I have become aware of the basics of good listeninge.g., the traps to avoid, the dispositions to cultivate, the tools to hone. Wise provides all this and more through personal stories, compelling examples and effective practices. The result: A concise treatise on the fundamentals of transformative listening.

Dr. Christopher Uhl , Author

Teaching as if Life Matters: The Promise of a New Education Culture

Ask Powerful Questions

Create Conversations That Matter

Copyright 2017

All rights reserved. No part of this book may be reproduced in any form without the written consent of the author except for brief citations in reviews or quotations. Proper credit must be given.

Cover design by Erik Tyler, Sunny DiMartino

Editing by Paula Hofmeister, Rebecca Thomas

Content editing by Kirstin Waldkoenig

Packaged by Round Table Companies

PO Box 1603, Deerfield, IL 60015

Printed in the United States of America

Second Edition

Library of Congress Control Number: 2017905930

North Charleston, SC

Asking Powerful Questions Pyramid is a trademark of We and Me Inc.

To my lovely rock, whose ability to share so authentically and transparently makes asking questions funand sometimes a bit, just a bit, scary. Thanks for choosing to be my wife and life partner.
Will Wise

To my son, Otto. Im writing this sentence just days before you are even born. Yet, you have already ignited my curiosity. My intention is to channel that curiosity into our relationship, so that I get to meet you each and every day as if it is the first time our paths crossed.
Chad Littlefield

Nothing shapes our lives so much as the questions we ask, refuse to ask, or never dream of asking. Our minds, bodies, feelings, and relationships are literally informed by our questions.

Sam Keen

This book is a result of failure.

I had failed so many times in my life that in my youth I began to create a long list of reasons why I did not fit in. No matter where I landed, my list continued to grow and I continued to land in a lot of new places. There were some years when I worked in six different states. There were other years in which I travelled around the world, looking for a place to fit in. I didnt know then what I was looking for, but in hindsight I can see it more clearly.

I am socially awkward. Fitting in is not natural for me. It has always been this way. I cant even think of a time when I have truly fit ineven as a child, I was separated from my family. Later, as an adopted member of a new family, I tried so hard to fit in that I failed to understand who I was. I didnt even know how to hug until I was in college. It was my roommates friends who were part of an InterVarsity Christian Fellowship Club and who taught me how to hug and even what a real hug is. Then when it came time to enter the work force, I con sistently landed jobs that placed me on the periphery of an experience, like when I was leading prisoners through the desert as part of a maximum security wilderness program or when I traveled to Nepal for the Peace Corps. In each case I was participating with others, but as the lone outsider looking in.

Now, with time and practice, I might make fewer social faux pas, but I can still clearly see signs of the mistakes that I make. Perhaps these challenges are a gift because they have allowed me to connect with many people in many places. Failure is common and it offers data on what is working and what is not. The intent of this book is to add something to the experience of being human that I have seen as missing.

My own social backwardness was a result of not being seen for so long that I was afraid of someone actually seeing me. It was far safer for me to blend in, to be in the shadows. If someone did see me, it was shocking and I would run. Once I made a different choice and it made all the difference.

The first new choice moment I recall happened in high school when I was traveling around to check out college campuses.

I was traveling north on a Greyhound bus heading to someplace that I can no longer remember, maybe to tour a college campus. I do clearly remember throwing on a cloak of invisibility, wanting to hide from the world. I peered from beneath it, watching the world go by, questioning who I was, questioning what I wanted to get from the world. Then quite suddenly, someone was shaking me out of my hiding. Not physically, though it might as well have been. It was with a simple question from one stranger to another. An Amish man said hello and asked me a question, Whats your story? Immediately I wondered, How did he see me? Is he talking to me? When I looked up into his eyes, I could see his sincere, intense curiosity. He wanted to know. When I got on the bus, I was thinking about me. Now this man was seeing me as an equal and inviting me into his world. A world that was so much bigger than just me, and so different from my own. I chose to accept this invitation into his world and was rewarded with a fulfilling dialogue. We each learned things about the others life. Until he said, Im thinking of adopting.

In that moment, the world stopped. All the cars zooming past us froze. This kid bouncing up and down in the seat behind us was suddenly still. How did he know my secret? The secret that I had been hiding from everyone was instantly exposed from its home in a dusty old bankers box, covered with chains, locked, and buried deep within. Even when folks said, You look like your mom, I would smile and nod affably, but knew that she and I were not related.

Of course, when I paused, I real ized that this mans remark was just happenstance and that he didnt actually know my secret. Still, in that moment, it felt like much more then pure coincidence.

He continued: But Im not sure if its the right thing to do. What do you think?

Red Alert, lights flashing, abort! I wanted to run. Or at least the old me would have run. In this moment, however, the situation was different; the Amish man saw me and I knew I needed to do something differently. I needed to share my secret for the first time with a strangerfor no other reason than that it could be helpful for him and some future child. I knew in that moment that I could have an impact on how he saw the world. So I made a new choice. I took out the bankers box, blew off the dust, and used his question like a key to open the lock.

I took a breath (more like a gasp) and said meekly, Being adopted was the best thing that ever happened to me. Long pause, another loud breath, then I continued: It might have even saved my life.