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Ask Powerful Questions: Create Conversations That Matter by Will Wise

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Pre-release copy without final edits NEW EDITION COMING SOON What is revealed when you authentically connect with the people around you? In Ask Powerful Questions, Will Wise explains how the questions we traditionally ask are virtually meaningless when it comes to establishing connection. Introducing a set of practical tools for accessing and understanding others by changing the way we ask questions, Will shows how to transform "How are you?-I'm fine, thanks" into a conversation that changes not only how you lead, but who you are as a person. Business professionals, personal coaches, teachers and anyone in a position of leadership will relate to the personal successes and failures Will shares as he unpacks the art of asking questions that elicit unconventional answers. This book invites the reader on a journey that the clarity of intent, connecting though rapport, creating openness, reflective listening, and empathy. How can we explore the space between ourselves and others, and exchange meaningful perspectives? Just ask-powerfully.

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Will Wise

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5 stars
161 (34%)
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166 (36%)
3 stars
98 (21%)
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31 (6%)
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Displaying 1 - 30 of 41 reviews
Profile Image for Kony.
446 reviews259 followers
October 2, 2022
This is an earnest, thoughtful, organized manual on how to connect meaningfully with fellow humans. I appreciate the author's overarching framework, which is depicted as a pyramid with intention ("I am willing to know you") at the base. The layers above that are rapport ("I see you"), openness ("I hear you,"), listening ("I get you"), and empathy ("I'm with you"). Each layer gets a chapter that offers practical tools and examples to help bring the advice to life.

This could serve as a guide for teachers, managers, coaches, or group facilitators who are new to the job and/or find it challenging to build connections within their role. As someone who's played all of the above roles, I found this book summarized a lot of the lessons I've had to learn through trial-and-error.

It's written in a friendly, accessible tone. I knocked off a star or two because it could use tighter editing -- and also the descriptions of "diversity" or interracial conversations strike me as outdated and a bit white savioristic.
Profile Image for Trang Do.
37 reviews4 followers
May 3, 2021
Although this book is about asking powerful questions, I find it also a book about listening/how to listen.
The book offers a set of practice tools to understand others by changing the way we ask questions. It is noticeable that the authors believe for every conversation to start, it starts with clear intention.
In the "asking powerful questions pyramid" (trademark) in the book, there are steps to create powerful questions which are:
1. Intention (= I am willing to know you)
2. Rapport (= I see you)
3. Openness (= I hear you)
4. Listening (= I get you)
5. Empathy (= Get you)

This is a long book and I am not easily absorbed by the book if I read it all straight away. I then found that it would be more practical/useful to read the book by chapter, pause then practice for ourselves (as the book has the "self-practice" by end of each chapter), then continue with the next one. Or I guess it might be interesting to read the book in pairs/group so that we can exchange the thoughts/practice the tools mentioned together.

My key take away is the power of getting very clear intention in every conversation/action and also the power of being present. By being present (in a conversation), you will find yourself easily let go of "already/always listening", be more open to unscripted answers so that you can ask more powerful questions. There are also some techniques of asking questions with the How/What and the pros/cons of Why questions that shared some commons I found in "Never Split the Difference" and "Start with Why".

Two more thing I like about this book are (1) every chapter starts with a quote that is somehow speaks to the intention of the chapter and I can quickly grab a first glance what the chapter is about and the quotes are so interesting for you to keep for yourself; and (2) the authors themselves give real example of how they have been successful/unsuccessful in asking powerful questions, which reminds me that listening and asking powerful questions are not one-off experience but an on-going practice.
Rate the book 3.75/5 (round up to 4/5 hehe) on Goodreads as some parts lands on more like a theory in textbook.
Profile Image for Mary Erickson.
670 reviews3 followers
September 16, 2019
Another title could be: How to be an excellent listener. The book is applicable for many situations--whether you want to get to know a new neighbor, or whether you are a group facilitator. It takes you through five stages of conversation and connection. 1: Intention (being honest about why you want to know the person better) 2: Rapport (being truly curious about the other person) 3: Openness (being non-judgmental) 4: Listening (reflective dialogue) 5. Empathy (truly connecting with the other person, despite any potential conflicts or differences). Surely wanting to truly know what makes another person tick--why they think and act the way they do--is a a useful skill for anyone who cares about creating relationships that go beyond, "How are you? I am fine."
Profile Image for Elana A.
141 reviews14 followers
June 30, 2024
Fantastic! A really beautiful and well articulated book packed full of humanity and evident lived experience, great for anyone facilitating conversations, working with people or seeking to improve communication skills.
Profile Image for Lorraine.
1,253 reviews24 followers
August 24, 2021
UPDATE: I've also bought the companion Guided Journal, which is a great way to work through the book. Using the two together is like learning alongside a master who coaches you. What's great is that the questions, like yoga, don't try to get you "there," because there is no "there" or end goal. It's all about moving forward with incremental improvements. Which means that once I've worked through the journal, I can start all over and do it again, and again, and again. I can also use it to coach others forward. So useful!

Section1 is great for getting yourself set to move forward towards a goal -- any goal, be it corporate, team, personal, big or small. The steps walk you through the intention-setting logically and progressively. Magical.
Section 2, on rapport, takes more time as you need to really reflect on how you interact with people. Take a question at a time and observe yourself with other people using that question's lens. It moves from general interactions to a specific connection, so great when you're looking to network.
Section 3, openness, is about digging into your own baggage that may prevent openness. It requires time to reflect and observe oneself -- but with compassion to keep trying.
Section 4 involves deep work on self-awareness to be a good listener.
Section 5 on empathy proposes that now that you've looked deep into yourself, learn to look deeply into others.
Section 6 helps you to bring all that work on yourself forward into the world to achieve your goals.

REVIEW OF THE BOOK:
After watching so many of Chad Littlefield's YouTube videos (which are great!) I felt compelled to get the book, which he shamelessly but convincingly references frequently. (He is pointing out the consistency in his work and messaging as much as promoting the book, so no criticism here).
The book is full of great ideas and help for facilitators who want to connect with a group and lead that group through important and meaningful conversations. I think the hint is in the choice of "create" conversations rather than "have" conversations that matter. This really is a guide for facilitators, though coaches and conversationalists can find takeaways as well. It is a how-to and I know I will go back to the book multiple times to learn and relearn the processes.
I found the personal examples useful in illustrating some of the concepts explained, and I could have read more of them. I also would have welcomed more of the Did You Know? sidebars. But maybe that's what the YouTube videos are. I'll keep watching them, too.
341 reviews1 follower
July 24, 2022
I read this because my principal asked me to. Initially I was excited and thought it would help me connect to my students. But the more I read, the less convinced I became that these ideas work. Reading during the summer made it difficult to try the concepts out through implementation. I will mine some things out of it for use in the fall. But, in general, I found myself questioning this guys credibility. One of the earliest concepts that the book teaches is to follow your curiosity to ask meaningful questions. So, if you see someone with a ridiculous hat, you might ask, "What made you chose that hat today?" However, I feel that a large number of people, myself included, may not be enough of an actor to pull off a question like that without our tone giving away our dislike of the hat. Later in the book he talks about some of the things that happened during Diversity training classes that he led. Here is where I seriously questioned his credentials. In fact, when I worked as a trainer in a large company, I won an award for a Diversity training that I wrote and facilitated. The things he thought were okay to single-out and focus on were appalling to read about.
So, in the end, this book contains a few flecks of gold in the pan, but not enough to strike it rich.
Profile Image for Derrick Jones.
10 reviews
December 30, 2017
Knowledge is Power

Will Wise provides you with the knowledge needed to ask meaningful and powerful questions that provide you with the ability to create strong relationship bonds.
Profile Image for Jason Watkins.
149 reviews1 follower
March 6, 2021
Just a fantastic book! As a leader, coach, facilitator, and educator this is now on my personal reading list I will suggest to people. Will Wise prescribes a simple to follow pyramid process towards evoking powerful questions, but it goes deeper than that. He begins with the idea of intention which is really about clear communication of one’s own intentions combined with not assuming someone else’s intention. Following this idea he provides practical tools to build connections (rapport)...a concept which I fully believe is fundamental to leadership and education. The next rung is “openness” where he expresses the trap many people succumb to while conversing, that of getting trapped in content (the What) versus the art of the process (the How). Next is listening, which delves into various reflective listening styles and techniques. The last rung is empathy where Wise adds a richer understanding of empathy, through some great examples. Finally, the last chapter provides facilitators some practical tools to encourage healthy dialogue over that of toxic debates in group settings. This is such a useful book! I have tabbed it, bookmarked it throughout and will lean on it going forward in team development! Recommend!
This entire review has been hidden because of spoilers.
Profile Image for Evelien Vandeplassche.
75 reviews
July 19, 2025
Ja super hé dit boek. Ideaal als je net zoals mezelf professioneel bezig bent met coaching en facilitatie. Veel zaken die Will beschrijft zijn een echte eyeopener en zijn ook zaken waarvan ik persoonlijk denk dat we er veel te weinig bij stil staan in het echte leven. Hoe vaak we gaan we gesloten vragen stellen of gebruiken we het woordje "waarom?", of gaan we heel vaak "maar" toevoegen aan het einde van een uitleg? In dit boek krijg je enorm veel inzichten over waarom deze vragen of zinsbouw eigenlijk niet ideaal zijn en welke vragen je dus in de plaats kan stellen. Echter, om effectief uit te oefenen wat hier in het boek staat zal je enorm veel oefening nodig hebben, dit pas je niet toe op enkele dagen. Ik heb ook graag dat gesprekken natuurlijk verlopen zonder dat ik steeds diep moet nadenken over wat correct is om te zeggen of hoe het beter kan. Dus neem het boek af en toe met een korrel zout en vergeet ook niet de flow van je gesprek te vergeten. Sowieso neem ik veel dingen mee uit dit boek in mijn job en zal ik het zelfs mijn teamleden aanraden dit boek te lezen!
117 reviews1 follower
March 17, 2018
"You can tell whether a man is clever by his answers. You can tell whether a man is wise by his questions." — Naguib Mahfouz, Nobel Prize Winner

I received this book for free as a promotion, and had very little expectations for it. In my experience, books around topics related to emotional intelligence often end up being quite superficial in nature. This one turned out to be quite the opposite. I was pleasantly surprised by how many sections of the book really felt insightful and applicable to my life. There were several key conversational techniques described that I could immediately begin experimenting with.

Although I had hoped that there'd been a bit more pragmatic "If someone says X, Y is a good question", ultimately, I really enjoyed the more holistic approach the author takes towards approaching conversations. A worthwhile read!
Profile Image for Oscar Romero.
296 reviews
July 2, 2020
If there is a book that I think we should all read and practice--this is one of them. Will really takes the time not only to explain about his concepts about these questions but to provide examples of how it is we currently use these type question and how we could change into a much better question that will, no doubt in my mind, enable us to work better together. I have identified so many question just the way I usually ask them--and his alternatives sure make sense to me. Now I just need to practice and practice until I can make a new habit with my new improved questions.

What I find puzzling is the fact--that we just keep using those questions in a way that most times causes people to become defensive--I guess we do too-if anyone ask us the same way.

Do take the time to read this book--it can only help us, for sure. Thank you Will--you sure did an amazing job at writing it.
6 reviews
October 13, 2022
The goal of this book is to teach readers to ask questions that will require the listener to think and respond with fresh and new answers. The book is organized to discuss intention, rapport, openness, listening and empathy. The base for good conversation is to understand the intention. The author uses excellent examples through out the book, including why intention is the base of all good communication, understanding intention allows one to solve and address the key issues not necessarily what the people will find easy to address with a simple or evasive answer. Overall, I enjoyed the book and found it helpful.
If you like theory but NEED examples, this is perfect for you. This well written book is packed full of examples.
3 reviews
February 17, 2023
While on the subway on my way home, a guy leaned over and asked me about my speed reading. He had noticed that I was using a tracking technique with my figure as I was moving through a book. We proceeded to have a fantastic conversation where he asked such unique and interesting questions. His ability to ask questions stuck with me and put me on a journey to understand conversations/question-asking.
This was one of the books I came across and I felt like it was exactly what I was looking for. I do already feel like I've more consciously and intentionally engaged in conversations. I'm not only looking for what relates to me but now seeking to listen and understand, allowing my natural curiosity to take me further into the conversation.
Profile Image for Warren.
393 reviews4 followers
April 4, 2021
Will Wise has put together a wonderful manual for any of us who have the need or desire to learn more about others. In my line as a wilderness guide, getting to know the people I work with is the first step in understanding what might be a struggle for them, and how I can best help them be their best. I know that I'm going to be reading this book again in the future, and I'll be recommending it to my company to put our the shelf.

If you work in an industry where learning about people will be of benefit (hint: you do), or just want to brush up on your overall conversation skills, this is a great book to get you started. Highly recommended.
Profile Image for antony .
359 reviews8 followers
November 6, 2017
When I first started this book I wasn't expecting much. However the author demonstrates a firm grasp of the subject and presents many examples for clarifying your understanding. There is an orderly methodology to assist with your practicing what you learn. This is a thorough book that does not wander aimlessly through its subject as many do. Also unlike many books you will come across on Amazon these says this is a real book, not a pamphlet, and not a collection of someone else work repackaged.
Profile Image for Yoric.
178 reviews9 followers
November 14, 2018
The book was unexpectedly good to me: "it sounds real". The author speaks from his real experience, and thus it's moving. We can feel he really worked on making connections with people throughout his life. He really had a trauma in the first part of his life (social phobia), then really had a breakthrough, which convinced him to dedicate his life to this purpose.

The result is a subtle set of concepts, a framework, helping to truly connect with someone else, and make a difference, not only in that person's life but also in one's own life.
188 reviews9 followers
October 29, 2022
Really good book. Would highly recommend for anyone wanting to become a facilitator. It takes you through the stages of connection (Intention, Rapport, Openness, Listening, Empathy, We) with explanations, practical examples, tools, common traps, antidotes to them, how to apply the concepts in groups, and scientific research backing up each idea. Clear, easy to follow and understand. This book will stay on my bookshelf to refer to for years to come.
14 reviews
November 21, 2022
Ummm it has some good things, but like he states at the end of the book. He is not a writer. He is difficult to understand. I had a horrible time understanding chapter 1 and the last chapters, which were the most important. I did got some good things out of this, but again. Don't go in there thinking your reading a jk Rowling book where words are beautiful and everything is cohesive. It was difficult to get through this book but i did it.
40 reviews
September 27, 2024
Becoming a Weologist. Mastering the art of being with others. Follow your curiosity to ask powerful questions.

Empathy I feel with you. Listening I get you. Openness I hear you. Rapport i see you. Intention i am willing to know you. Starting at the bottom of the pyramid people want to know that there are others that want to get to know them. They want to be seen. They want to be heard. They want people to get them and be really understood. They want to know that others feel what they feel. Asking powerful questions of others you can start to explore worlds other than just your own. Your world will open up and you see things that you didn’t see before.

Tools
- create intentions that stretch you to include the needs of others
- Following your natural genuine curiosity when connecting with others
- Shifting from judgment to openness by dropping why based questions.
- Listening for anything rather than listening for how you might be right
- Describing how they see the world

Mastery of being with others - as a weologist. To be present to the possibility of what we might create together.
8 reviews
January 20, 2025
For me, this book was just OK. It's nothing groundbreaking, but it has some nuggets of wisdom. I wish it had been a little shorter, though. Some chapters seemed to go on for ages. It's also a bit confusing at times and makes it difficult to understand how the things I read relate and can be applied in real life.

Overall, this book is just average. There are some interesting things, but there is also a lot of long and slightly confusing writing.
Profile Image for Rhiannon.
26 reviews13 followers
April 7, 2018
It wasn't what I thought it would be, but it definitely had some good information. Some of it I found useful for what I was reading it for. I thought other information would be useful in a different situation. Maybe someone who works in group situations as a leader would find this book very helpful.
Profile Image for Mandie Pendola.
69 reviews
December 12, 2023
It was a 3/4 star for me. Tons of great ideas and phrases I pulled out to use for future conversations, but it felt like it was more geared towards teachers or more specifically, college professors, rather than the workplace. It also felt a bit dated, but when I checked the release date, it was fairly new. Lastly, I wish it also approached some more introvert-friendly solutions.
73 reviews
May 18, 2024
A lot to late

This book was full of great information that I wished I had read when I was actively working at a large corporation where I facilitated a variety of meetings.
Although, I am retired, I am still leading and facilitating now in Christian leadership and will take advantage of this information. Thanks for practical and useful information.
Profile Image for Otis.
372 reviews2 followers
July 7, 2024
4.5 stars. Such an insightful and well thought out book. The examples were spot on and useful. The information within is something | will be able to immediately apply in several areas in my life; i.e: work, relationships, meeting new people, etc. The entire concept of be intentionally purposeful when attempting to connect with others can make a life changing impact. Recommended.
Profile Image for Clint Heitz.
235 reviews13 followers
October 17, 2017
This book is a phenomenal tool to make one think about how he/she interacts with others, particularly when having difficult conversations. Will's authentic, honest voice presents a powerful approach to opening communication and owning powerful conversations. Truly a must read!
1 review
May 22, 2020
Open mind

Very interested book pointing ways for us to be aware of ourselves to not be a robot asking meaningfulness questions. It helps a lot in the communication with others in all areas, even with strangers.
2 reviews
June 4, 2021
Powerful

Powerful questions start with introspection and are an amalgamation of who we are, our curiosities and fears. Wonderful articulation of what lyes beneath a powerful question.
21 reviews
January 23, 2022
The book has very powerful ideas, but listening to the audiobook I found it not very engaging. The narration was a bit boring and I felt like it was not well-written. Will have to listen to it again as it requires a bit of focus and mental energy.
Profile Image for Jean Gallagher.
26 reviews
March 28, 2024
The tips and tools in this book are very practical. Although I was skeptical of yet another pyramid model to learn about, this one was good. Not quite 5-star level, but a book I will refer back to and will probably recommend to others.
27 reviews
July 9, 2019
I think I have to be very mindful of the questions I ask now. I made a lot of highlights in this book.
Displaying 1 - 30 of 41 reviews

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