May 14, 1970 – November 12, 2021

Husband, Teacher, Dad, Mentor, Coach, & Author

Read About WillView His Works

The following is written by Chad Littlefield, WiLL’s friend, student, co-author, and collaborator for 10 years.

Are you ready for your life to change?

WiLL asked this question to thousands of students on the first day he met them over the years. If your answer was “no”, he was happy to show you the door. Most people might ease into a question like that. WiLL’s shocking directness was one of his many gifts to the planet. 

Now it’s our turn to be direct: William Samuel Wise has died. 

He passed early in the morning on November 12, 2021, at home with his loving and loyal wife, Heather House, asleep on the floor next to him. Before he died, they caught the last episode of Ted Lasso and (much) more importantly one final, deep hug where Heather felt WiLL say—not in words—”the way that we love each other is all that matters.” He is finally at peace. And achieving peace was one of his life’s deepest desires. 

And as WiLL would remind us: 

“You are what your deepest desire is. 

As is your desire, so is your intention. 

As is your intention, so is your will. 

As is your will, so is your deed. 

As is your deed, so is your destiny.”

It’s not possible to capture who WiLL was using the English language. His dyslexia would probably agree. But the real reason that words won’t be nearly enough is because he focused much of his effort on who he was being—and less on what he was doing. No matter the circumstance, he was adamant about being present. Being happy. Being the best listener most of us ever met. And being curious. Whether you were a student, a friend, son, daughter, or wife to WiLL, you experienced him being curious. He’d want his being to continue. 

Just before bed on the night WiLL passed away, his son Sylvan made a beautiful observation of how their daddy’s being will continue to live on. Sylvan noted that “Cypress got dad’s curiosity, Fern got daddy’s ability to love, and I got daddy’s playfulness.” 

Continuing the impossible attempt of capturing who he was, below are three of his favorite questions

And continuing his life’s work of asking powerful questions and creating conversations that matter, we—and he—would encourage you to spend at least 60 seconds of silence with each of the questions below. 

What brings you joy?

[Enjoy your 60 seconds of silence with this question before you read on.]

WiLL saw this question as a gateway to creating your future. On the day WiLL died, his oldest son, Cypress, pulled out a fortune cookie out of a box that Will kept on his desk to remind people to create their future rather than leaving it up to a cookie. Cypress’s fortune read something like, “every moment is a golden one to the person who recognizes it.” Cypress then looked out at a small group of family and friends and said, “Dad realized this. He truly did.” 

Being a master of turning each moment into one worth remembering, WiLL was known for pulling a bouncy ball—seemingly out of thin air—and tossing it out to an unsuspecting recipient. At the beginning of a class or in the middle of the mall, he’d reach into his pocket—the true permanent home of the bouncy ball—and infuse play into the space. Play was WiLL’s greatest teacher. He was committed to it and the joy and learnings that came along with it. Even in pain, he would find a way to play. He would love for you to move toward joy in each choice you make.

Second question…

What is this moment teaching you right now?

[Silence was one of WiLL’s favorite ingredients to a conversation that matters. That means that it is time to pause again.]

While WiLL was one of the best teachers, he knew that he was no match for Experience, the ultimate teacher. Right up until his last days even while he was struggling to utter each word, he was trying to share how to approach life even while you are dying. He used to say that “the moment you stop learning is the moment you start dying.”

Please, on WiLL’s behalf, keep learning. Keep living. 

And the final of WiLL’s favorite three questions…

What is a crossroads you are at?

The outdoor educator and nontraditional school principal in WiLL, loved seeing lessons in nature. Climbing rocks was just a meeting with Fear. Canoeing down the river was a one-to-one mentoring session with Control. Traveling into a cave was your chance to go stare Darkness head on in order to understand your light more clearly. 

WiLL understood that in each moment he had a choice. Listen to understand or listen to win. Openness or the need to be right. Learning or knowing. Exploring possibilities or making assumptions. 

Perhaps the crossroads that WiLL most commonly encountered was the choice to be driven by fear or living to love. He often faced fear, but rarely—if ever—did he ever choose it. 

In fact, he chose expansive love. 

Over and over again. 

And you can too.

He’d like it if you did.

“More than anything, I will miss being held in Will's loving and gentle presence. Who he was as a husband, father, colleague, seeker, teacher, and friend will inspire me for the rest of my life."

Allan Cohen | Will’s Coach & Mentor

“Will has an amazing gift — his lessons were life-altering for me and I still hear his voice in my ear day today when I'm dealing with conflict."

Tara Sollman

"Will really was expansive love. He was the change that he wanted to see in the world."

Tilly Stevens

"All of his curiosity, presence and happiness came from a core of the deepest compassion for us, each of us wherever we were."

Kimberly Fauss

Will Wise and Chad Littlefield


WiLL WiSE, M.Ed., was the co-author of the #1 Bestseller, Ask Powerful Questions: Create Conversations that Matter. He asked powerful questions for over two decades as a corporate development consultant, non-traditional school principal, university instructor, adventure guide and facilitator for team development.

WiLL was passionate about bringing out the best in people. He earned a reputation as one who could cut to the heart of what mattered most. Tens of thousands of people have been empowered with positive communication skills after spending some time with Will. 

In addition to his wife of 11 years, WiLL leaves behind three children, Cypress (10), Sylvan (8) and Fern (8). He is survived by his mother, Linda, and brothers, Ken (aka “Joe”) and Donny Wise.  

Why the strange grammar in WiLL WiSE’s name you might ask?
As he would say, “it’s to remind me to put less ‘I’ in the world—and focus more on we.” It drove Chad and Heather crazy 😊 , but he made this choice with intention.

WiLL’s Works

WiLL had a gift of blending his humanity in with his work. These two resources he leaves behind could just as well be titled “one last conversation with WiLL.” 

Also Available on Amazon & Audible

Guided Journal to Ask Powerful Questions

Also Available on Amazon


This book should be required reading for humanity.

Will presents very powerful and practical tools that can be applied in so many settings. This book has had profound effects on how I approach my interactions with others. I highly recommend it!


What can each moment teach you?

This book is a phenomenal tool to make one think about how they interact 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!


This book will help you communicate better in every aspect of your life.

Whether you are a consultant, a business owner, an employee, a parent, or a friend “Ask Powerful Questions” is a MUST for deepening relationships and for having conversations that matter.


This is one of the best books I’ve read on communication and leadership.

Not only because of the great practical tips and strategies but because Will infuses his own experience and shares impactful stories that reveal how powerful these questions are in real life situations.


Questions to guide you into wonderfully rewarding personal reflection

This book should be in the hands of anyone who facilitates groups, manages people, or wants to have deep, meaningful conversations… Easy to read and then to apply, Will has written a book that is truly a one stop shop for communications.


Couldn’t put it down.

If you like theory but NEED examples, this is perfect for you. This well written book is packed full of examples. Buy one for yourself and one for every supervisor in your organization. Use it as a textbook for supervisory training! Following the guidance in this book will dramatically change how you communicate; in a positive way.

In this video, Will Wise teaches a group to use their natural curiosity to create rapport with others. Length: 2:42

On WiLL’s behalf, please continue to be present, be intentional, be joyful, be curious, be a better listener, be empathetic, and be peaceful.

Will Wise Peaceful