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WelcomeEnjoy this excerpt from our:FeaturedinWantthe fullbook?

About the AuthorsWill Wise and Chad Littlefieldare also the creators of:WillChadBooking1-774-260-2577hello@weand.meOur team will respond within 48 hours with availability andpricing for your virtual or in-person event of 5 to 5,000 people.

Praise for Ask Powerful QuestionsFrom my experience of working with Will and Chad for many years,I know firsthand that they live what they teach. This book is an anthemto Will and Chad’s potent teaching, waking people up to themselves andothers—for the benefit of us all.Dr. Laurie L. Mulvey, Executive DirectorWorld in Conversation, Center for Public DiplomacyIn a world where certainty is valued and judgment often replaces discernment, Ask Powerful Questions builds a compelling case for fosteringcuriosity, finding clarity, and creating connections. If you dare, followthe simple (but not easy) path that Will Wise provides to help you findself-awareness, empathy, and personal transformation.Maren Showkeir, CoauthorAuthentic Conversations: Moving from Manipulation to Trust and CommitmentListening is our most fundamental tool for healing the world’s woundsand I thought I was pretty good at it. But after reading Wise and Littlefield’s book, I realize 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 goodlistening—e.g., the traps to avoid, the dispositions to cultivate, the toolsto hone. Wise provides all this and more through personal stories, compelling examples and effective practices. The result: A concise treatiseon the fundamentals of transformative listening.Dr. Christopher Uhl, AuthorTeaching as if Life Matters: The Promise of a New Education Culture

CreateConversationsThat M atterWiLL WiSECHAD LiTTLEFiELD

Ask Powerful QuestionsCreate Conversations That MatterCopyright 2017All rights reserved. No part of this book may be reproduced inany form without the written consent of the author except for briefcitations in reviews or quotations. Proper credit must be given.Cover design by Erik Tyler, Sunny DiMartinoEditing by Paula Hofmeister, Rebecca ThomasContent editing by Kirstin WaldkoenigPackaged by Round Table CompaniesPO Box 1603, Deerfield, IL 60015Printed in the United States of AmericaSecond EditionLibrary of Congress Control Number: 2017905930North Charleston, SCAsking Powerful Questions Pyramid is a trademark of We and Me Inc.

To my rock, whose abilityto share so authentically and transparentlymakes asking questions fun—and sometimesa bit, just a bit, scary.Thanks for choosing to be my wifeand life partner.—Will WiseTo my son, Otto. I’m writing this sentencejust days before you are even born.Yet, you have already ignited my curiosity.My intention is to channel that curiosityinto our relationship, so that I get to meetyou each and every day as if it is thefirst time our paths crossed.—Chad Littlefield

ContentsIntroduction . xiWho Is This Book For? . xxiThe Science of Asking Powerful Questions . xxviiOverview . xxxiiiChapter 1IntentionThe Power of Clear Intention.2How Intention Can Be Applied in GroupsSummary of Intention.Self-Work for Intention.232728Chapter 2RapportThe Power of Being Present . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 32How Rapport Can Be Applied in Groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 74Summary of Rapport.Self-Work for Rapport.8080Chapter 3OpennessThe Power of Being OpenOpen-Ended Questions.84.91The Power of How and What and the Weakness of Why Questions . . . . . . . . . . 93How Openness Can Be Applied in Groups.117Summary of Openness . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 118Self-Work for Openness . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 120

Chapter 4ListeningThe Power of Reflective Listening.124How Listening Can Be Applied in Groups . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 155Summary of Listening.Self-Work for Listening.156157Chapter 5EmpathyThe Power of Connection.How Empathy Can Be Applied in Groups162. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 206Summary of Empathy. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 208Self-Work for Empathy. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 209Chapter 6Advanced SkillsDebate and DialogueSilence.214. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 225Web Building. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 239Defining Words. . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 249Managing the Overtalkers.251Steering into the Curve . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 254Working with Co-Facilitators . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 258Summary . 261Acknowledgments . 267Notes . 270Endnotes . 271About the Authors . 276About We and Me Inc. . 278

IntroductionNothing 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 literallyinformed by our questions.-Sam Keen1 -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 matterwhere I landed, my list continued to grow and I continued to landin a lot of new places. There were some years when I worked insix different states. There were other years in which I travelledaround the world, looking for a place to fit in. I didn’t know thenwhat 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 hasalways been this way. I can’t even think of a time when I havetruly fit in—even as a child, I was separated from my family. Later,as an adopted member of a new family, I tried so hard to fit inthat I failed to understand who I was. I didn’t even know howto hug until I was in college. It was my roommate’s friends whowere part of an InterVarsity Christian Fellowship Club and whotaught me how to hug and even what a real hug is. Then whenit came time to enter the work force, I consistently landed jobsthat placed me on the periphery of an experience, like when Iwas leading prisoners through the desert as part of a maximumxi

security wilderness program or when I traveled to Nepal for thePeace Corps. In each case I was participating with others, but asthe lone outsider looking in.Now, with time and practice, I might make fewer social fauxpas, but I can still clearly see signs of the mistakes that I make.Perhaps these challenges are a gift because they have allowed meto connect with many people in many places. Failure is commonand it offers data on what is working and what is not. The intentof 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. Itwas far safer for me to blend in, to be in the shadows. If someonedid 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 schoolwhen I was traveling around to check out college campuses.I was traveling north on a Greyhound bus heading tosomeplace that I can no longer remember, maybe to tour acollege campus. I do clearly remember throwing on a cloakof invisibility, wanting to hide from the world. I peeredfrom beneath it, watching the world go by, questioningwho I was, questioning what I wanted to get from theworld. Then quite suddenly, someone was shaking me outof my hiding. Not physically, though it might as well havebeen. It was with a simple question from one strangerto another. An Amish man said hello and asked me aquestion, “What’s your story?” Immediately I wondered,xii

“How did he see me? Is he talking to me?” When I lookedup into his eyes, I could see his sincere, intense curiosity.He wanted to know. When I got on the bus, I was thinkingabout “me.” Now this man was seeing me as an equal andinviting me into his world. A world that was so muchbigger than just me, and so different from my own. I choseto accept this invitation into his world and was rewardedwith a fulfilling dialogue. We each learned things aboutthe other’s life. Until he said, “I’m thinking of adopting.”In that moment, the world stopped. All the carszooming past us froze. This kid bouncing up and downin the seat behind us was suddenly still. “How did heknow my secret?” The secret that I had been hiding fromeveryone was instantly exposed from its home in a dustyold banker’s box, covered with chains, locked, and burieddeep within. Even when folks said, “You look like yourmom,” I would smile and nod affably, but knew that sheand I were not related.Of course, when I paused, I realized that this man’sremark was just happenstance and that he didn’t actuallyknow my secret. Still, in that moment, it felt like muchmore then pure coincidence.He continued: “But I’m not sure if it’s the right thingto 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 mansaw me and I knew I needed to do something differently.I needed to share my secret for the first time with axiii

stranger—for no other reason than that it could be helpfulfor him and some future child. I knew in that momentthat I could have an impact on how he saw the world. SoI made a new choice. I took out the banker’s box, blew offthe 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 tome.” Long pause, another loud breath, then I continued: “Itmight have even saved my life.”Our eyes connected, and I could see his fear washaway. Like magic, the banker’s box became a treasurechest full of jewels. A gift for him, but also a gift for me.I was no longer in a small isolated bubble. Now I wasa part of something in which we were creating somethingnew together, maybe a new life for a child in need, maybea man who wanted to be a loving father. Maybe . . . Morequestions effortlessly as we explored this new space. Hewas full of curiosity. His world shifted and so did mine.Instead of getting something from the world, I suddenlyhad a desire to give. To give all I had.As I got off the bus, I was floating and found myselfsaying, “Yes, Yes, yes!” I was seen, I was heard, someoneunderstood me, and not only knew but valued my lifeexperience, maybe for the first time in my life—and it feltlike a weight had been lifted. I was accepted for who I was,and that was all that mattered.To this day, I would love to have the chance to say “thank you!”to this man. I am deeply grateful for his choice to connect withxiv

a random stranger while riding a bus . . . He taught me the valueof connecting. Perhaps the most important lesson is that peoplewant to be heard and understood. It may be the highest callingof our humanity.Since that moment, I have dedicated myself to exploringways to connect and invite “real” conversation to be a part of ournormal lives. From my perspective, what is missing are questions. powerful questions! Questions that allow for unscriptedresponses, leading us to places of the unknown. Conversationsin which deep listening can happen almost effortlessly.The Asking Powerful Questions Pyramid After years of working with others to teach them the importanceof real conversation, I experienced another pivotal moment inmy life, one which propelled me to write this book. The catalystmoment happened during a ten-day silent retreat. I was reflecting on my life, my teaching, and suddenly connections betweenconcepts clicked. I could see clearly how I would set about sharingthis knowledge about powerful questions with a larger audience.The Asking Powerful Questions Pyramid appeared. Ever sincethat moment, I have been sharing these concepts with folks inmany different professions, from CEOs of global corporationslike Mead and GE to entrepreneurs at tech start-ups. My life hasnot been the same since.As we move through the text, we will start from the bottomof the Pyramid with Intention and travel upwards. The foundational skills at the lower end of the Pyramid increase your abilityto work on skills further up the Pyramid. Each skill builds uponits predecessor. As you ascend, you will strengthen your ability toxv

ask powerful questions in a variety of situations. Students excelwhen they practice a level before moving to the next level.It is also useful to note that if you are practicing skills at aparticular level and things are not working, you can diagnose theproblem by stepping down the Pyramid, checking on your toolsat each level and ensuring that you are fully implementing them.For example, if you are using skills on the Empathy level and arefinding it difficult to connect, you revisit your Listening skills. Ifsomething still feels awry, readdress Openness. Still not workingfor you? Step down to Rapport. Finally, take another pass at exploring your Intention. Head backward down the Pyramid, stoppingat each step and examining your tools. One exception to this procedure is the concept of intention. Intention and its tools are sofoundational that you can return to this level at any time, from anyother skill on the Pyramid. We will discuss this more in Chapter 1.xvi

The Science of AskingPowerful QuestionsWe wrote this book with your mind in mind. More specifically,we wrote this book with both the right and left sides of your brainin mind. Whether you tend to be a more analytical, rational, andlogical thinker or you love to eat emotions and creative storytelling for breakfast, this book is for you.Will has infused the book with personal stories and examplesfrom his life to make the tools we share come alive as we unpackthe art of asking powerful questions. Chad complements Will’spersonal stories and examples with fascinating facts and nuancesin neuroscience that underpin the art of asking. In the pagesto follow, the art and science of asking join together to create asimple and powerful framework. When we facilitate our interactive keynotes or workshops, we often invite people to “ruthlesslymisinterpret everything we say and apply it to their own context.”The same invitation applies here as we dive into some of the research and data to set the stage for the book.As humans, we are wired to connect. And we are trying toconnect. On average, we spend about ten hours per day2 “connected” through a screen. However, Sherry Turkle, researcher atMIT, reminds us of the reality that all these “sips” of online connection never actually add up to a “gulp” of human connectionthat can satisfy our thirst.3With the rise of infinite amounts of always available information being just a click or tap away, answers have become cheap.xxvii

Cheap answers have contributed to a national curiosity deficit—as we call it. With a shortage of curiosity about each other andthe world around us, our research is finding that great questionsare becoming the new currency. One of our ongoing clients at amajor university orientation program said it best: “Even studentleaders are struggling with the question ‘What do we say?’ Whilewaiting in line for food or walking between classes, ‘What do wesay?’“Forget about “saying” and telling for a moment. What aboutasking? With the sounding board of social media, it seems wespeak more in declarative or exclamatory statements and lessin questions. This national curiosity deficit fuels division andseparation and prevents us from building trusting, healthy connections. Let’s use our mental muscles to bend our exclamationpoints into questions marks. Right! I mean . . . right? Questionsare like keys that unlock the lifetime of ungoogleable experiencewe walk around with each day. Asking powerful questions opensa window into these experiences, commonalities, differences, andpossible contributions or collaborations that we each carry in ourminds. For example, think of a colleague that may be difficult toget along with. What might happen if you were to ask, “Whatbrings you joy?” If we let go of assumptions just for a moment,what might we learn? After sharing this specific question in anarticle on our website on the power of simple questions, a readernamed Claire responded with this story:I was recently cofacilitating a session with some colleagueswho I hadn’t worked with before. I suggested starting ourworkshop with the “What brings you joy?” question.xxviii

My cofacilitators were reluctant.They thought it might be too hard or too personal of aquestion for some to answer.So I walked over to the CEO who had hired us, andsaid, “Would you mind? What is one thing that broughtyou joy today?”He looked surprised and told a very touching storyabout seeing his daughter walking into school.Then he looked at me and said, “Thank you for askingme that. It feels so good to talk about it.”Needless to say, my colleagues were convinced, and westarted the workshop with the “joy” question.It put the audience at ease, set a positive tone, allowedparticipants to be vulnerable with one another withoutfeeling as much risk. And it ignited the trust process.I find this question also primes our brains foropenness, learning, and creativity.David Whyte, a renowned English poet, once said that “no self. . . will survive a real conversation.”4 Data about how our brainsrespond to curiosity and questions would tend to agree. Thepurpose of this section of the book is to unpack a bit of that science and research.What is the downside to creating conversations that matteroffline and in person? There is no backspace, no “undo send,” andno ability to draft a communication and consider the ramifications for a couple hours. Face-to-face, live conversation introduces us to social and emotional risk. Our brains are wired toavoid social and emotional risk in the same way we used to avoidxxix

sabertooth tigers. Neuroscientists have even found that “socialpain” and physical pain activate the same regions in the brain!5It’s easier to avoid social pain or risk than it is to take the chanceof connection.But data suggests that the reward sitting on the other sideof the social risk required to ask powerful questions is massive.For the leaders and learners reading this book who wantto know about the science behind the “art” of asking powerfulquestions, we have

I know rsthand that they live what they teach. is book is an anthem to Will and Chad’s potent teaching, waking people up to themselves and others—for the bene t 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 o en replaces dis-

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