Will Wise – May 14, 1970 – November 12, 2021

Note from Bob: Last Friday – November 12 I lost a dear friend.  If you knew Will Wise, you loved him! If you didn’t know Will Wise you would have loved him if you had ever met!  Today I am honored to share with the kind permission of Will’s dear friend and business partner Chad Littlefield, his wonderful Tribute to his dear colleague of 10 years.

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.


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 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.” 

Note from Bob:  Thank You Chad for your wonderful Tribute! 

Click HERE to purchase one or both of Will’s books

Here are several “Guest Posts” by my friends Will Wise and Chad Littlefield that are my favorites:




Chad LIttlefield


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 co-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.



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