Breakthrough Learning
for
Leadership and Life
For over 25 years, I’ve been driven by one mission: to unlock breakthroughs in learning that lead to bold, unexpected possibilities. I’ve pursued that mission with executives, with businesses, with school systems, and with communities.
This journey has taken me back and forth through the worlds of business and education leadership, where I’ve discovered how real impact happens and what makes it stick.
Here are a few highlights. (For my official bio and press kit, head here.)
In 2024, I released
The people around us hold vital insights that we rarely access—because we don’t ask, or don’t ask in the right way. That’s why I developed the Ask Approach: a research-backed method for surfacing powerful perspectives, feedback, and ideas that often go unheard.
Ask became a #1 new release in two categories, earned an Amazon’s Editor’s Choice Award, and was named a “Must Read” and a Top Leadership Book of 2024 by the Next Big Ideas Club.
I’ve since had the privilege to teach and give keynotes to leaders around the world who are seeking the kinds of breakthroughs that come when you truly get curious, ask better questions, and listen more deeply.
Learn more at: www.AskApproach.com.
In 2015, alongside Aylon Samouha, I co-founded Transcend, a cutting-edge innovation organization that works to fundamentally reimagine education for the 21st century. Transcend supports communities to design learning environments where everyone can thrive, while developing leaders who create the conditions for lasting change.
Throughout our first decade, as co-CEOs, we led Transcend through rapid growth (averaging 50% year over year), impacting schools and systems in over half the U.S. states and beyond. In 2024, along with our Chief Learning Officer, Jenee Henry Wood, we co-authored Extraordinary Learning for All: How Communities Design Schools Where Everyone Thrives, which captures the most powerful and practical lessons our team learned in Transcend’s first decade.
I currently serve on the board and also lead Transcend Labs, with a mission to create global partnerships and incubate new ventures.
Learn more at www.TranscendEducation.org.
In 2005, after I’d consulted for five years to Wendy Kopp, founding CEO of Teach for America, she invited me to lead part of this iconic organization. I initially signed on for two years (as a leave of absence from my consulting firm) but ended up staying for a decade, unable to resist TFA’s transformational mission and ambitious culture.
As Chief Learning Officer, I helped lead TFA through a period of intense growth—scaling by 300% while overseeing tens of thousands of teachers serving over a million students in some of the nation’s most challenging schools.
It was a trial-by-fire decade for me, filled with humbling lessons about what it takes to lead a large, diverse, people-intensive organization—and to build systems that help others grow and thrive.
Before stepping into operational roles, I spent nearly a decade at international strategy consulting firm Monitor Group (now Monitor-Deloitte), advising corporate executives across a range of industries – from pharmaceuticals to tourism to semiconductors to financial services. I also had the opportunity to serve as a founding member of Lattice Partners, Monitor’s business unit focused on leadership and organizational development.
This was an incredibly formative chapter—one where I had the rare privilege to learn from and work alongside pioneering thinkers like Harvard’s Chris Argyris and Dr. David Kantor, as well as their protégé Dr. Diana Smith, who chaired the applied doctoral program I completed in Human Dynamics and Change in Organizations. I had the opportunity to see firsthand the powerful impact of their ideas and tools every time I taught them to consultants or clients around the world. My book Ask builds on so much of what I did and learned there, and Monitor gave me the opportunity to create a software product called the Virtual Coach ™, an early use of technology to scale and embed interpersonal skills.
Education is a treasured value in my family, and I’ve been fortunate to have incredible opportunities throughout my life.
I earned a B.S. with honors in Psychology from Brown University and Master’s and Doctoral degrees in Adult Learning and Leadership from Columbia University.
For my doctoral dissertation, I developed and studied a new methodology called “collaborative organizational innovation” to unlock the collective genius that often lies dormant in organizations.
I’m also honored to be surrounded by some of the world’s most inspiring change-makers as a Fellow in the Aspen Global Leadership Network and in New Zealand’s Edmund Hillary Fellowship.
Beyond my formal education, I’ve come to believe that the most powerful learning happens in everyday moments—if we open ourselves to it. Every conversation, every conflict, every person holds the potential to teach us something important. I truly believe that hidden wisdom holds the potential to change our lives and our worlds, and my greatest hope is that we can all tap into it every day.
I live in New York with my wife, Dr. Jennifer Goldman-Wetzler, and our family – including our cherished puppy, Breeze. I love hiking, playing tennis, riding horses, and playing the guitar (campfire style).
Books
I wrote Ask because I saw over and over again (and also experienced myself) that leaders too often fail to find out what’s truly on others’ hearts and minds. Not for lack of desire, but because they don’t know how to ask the right questions in ways that would draw out the insights, feedback, and ideas they most need to hear.
The book introduces the Ask Approach, an ultra-practical, research-backed method for discovering what other people truly think, know, and feel. In my own leadership journey—and in coaching leaders around the world—I’ve seen the Ask Approach consistently sparks breakthroughs in decision-making, feedback, innovation, change, and culture.
I’m honored that Ask was named an Amazon Editor’s Pick for Best Books of 2024 and a Top Leadership Book of the Year. I’m also deeply grateful for the generous praise it’s received from experts and thought leaders like Adam Grant, Seth Godin, Jim Collins, Kim Scott, and Amy Edmondson, who authored the Foreword—as well as from CEOs and top executives from companies like Kraft/Mondelez, Medtronic, and JPMorgan.
Most of all, I’m encouraged by the impact Ask is having out in the world—helping leaders connect more deeply, listen more courageously, and unlock the wisdom that so often goes unspoken.
To learn more about how to bring the Ask Approach to your conference or organization, visit www.AskApproach.com/offerings.
I co-authored Extraordinary Learning for All with my dear colleagues Aylon Samouha and Jenee Henry Wood to paint a hopeful yet realistic portrait of how we can and must reinvent education for this century. The book draws on the voices and experiences of real school communities we’ve worked with at Transcend, who are on that very journey.
In the book, we share vivid case examples which illuminate the specific actions that school and system leaders can take to spark innovative design journeys in their communities. Extraordinary Learning for All emanates from our team’s direct, in-the-trenches partnerships with innovators, and it portrays in genuine detail what makes this work hard―but also what makes it possible.
To learn more about the work of Transcend and how we support schools and systems in the U.S. and around the world, visit www.TranscendEducation.org.
SPEAKING
Since Ask launched, I’ve had the good fortune to speak with thousands of leaders—across many industries and countries—from major corporations like Microsoft and Deloitte, to executive education programs at places like MIT and Harvard’s Institute of Coaching, to the TEDx stage and other major conferences, to over 75 podcasts and media interviews.
In every conversation, we tackle a simple but powerful question:
What happens when we stop trying to have all the answers…and start asking better questions?
It’s hard to explain the full energy of those rooms in words. So, we pulled together this short reel to convey what the work looks like in action.
I’m passionate about sharing what I’ve learned in practical and inspiring ways. If you’re planning a conference, offsite, or leadership event, I’d love for you to check it out.
To learn more about inviting me to speak about Ask at your next event, or for media or podcast inquiries, click here.
And to learn more about inviting me to speak on the topic of education innovation, click here.
PODCAST
Stay tuned for the Hidden Wisdom podcast, which I co-host with Rishi Jaitly. In every episode, we uncover the profound insights and life lessons that exist all around us, carried by everyday people whose voices often go unheard. Our podcast features intimate conversations with individuals who haven't written bestselling books or amassed social media followings, but whose experiences and perspectives offer deep wisdom about life, love, work, and what it means to be human.
From the retired teacher who transformed hundreds of lives, to the neighborhood barber who's been a quiet pillar of his community for decades, to unlikely pairs of people who disagree but are now finding common ground – we explore the extraordinary wisdom that emerges when we truly listen to each other. Our guests are regular people – your neighbors, coworkers, and friends – whose profound insights are hiding in plain sight.
Join us as we challenge the notion that wisdom only comes from recognized experts and public figures. Through authentic, unscripted conversations, Hidden Wisdom reminds us that some of life's most valuable lessons come from unexpected sources – we just need to know how to ask.
Stay tuned for more!