Alan Gregerman: Small Steps, Big Changes and the Wisdom of Ignorance
Release Date: 09/29/2025
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info_outlineOn this episode of On the Brink with Andi Simon, I had the pleasure of speaking with Alan Gregerman, an internationally recognized authority on business strategy, innovation, and the hidden potential within all of us. Known as the “Robin Williams of Business Consulting,” Alan brings humor, humanity, and deep insight into how we can adapt, grow, and innovate in a world changing faster than ever before.
I couldn't wait to share this podcast with you! My friend and innovation mentor, Alan Gregerman, joined me on On the Brink with Andi Simon for a stimulating conversation that digs into the interesting challenges facing all those who want to find their own best way of innovating. The "Robin Williams of Business Consulting," Alan injects humor, humanity, and leading-edge thinking into the brutal truth about how we need to adapt, change & innovate so now we win in a world changing faster than ever.
Alan's latest book, "The Wisdom of Ignorance: Why Not Knowing Can Be a Catalyst for Innovation in an Uncertain World," reminds us that our lack of knowledge can be the source of the greatest discovery. During our conversation, we discussed his unique personal journey, his desire to help others reinvent themselves, and the most critical skills for all of us to cultivate to succeed in a world of disruptions.
Curiosity Begins Early
Alan revealed that his interest in other cultures began in early life. His mother, a specialist in world history, and one cherished gift — an atlas — prompted him never to stop learning and exploring. That early sense of curiosity would eventually form the basis of his career: to help businesses and individuals look beyond what they know, he tells them, to find new ideas in unexpected places.
This investigative spirit has characterized his writing, from Lessons from the Sandbox (about reclaiming the creativity of childhood) to Surrounded by Geniuses (on how ordinary people and ideas can spur innovation) to The Necessity of Strangers (for why we must connect with people unlike ourselves). Now, with The Wisdom of Ignorance, he contends that expertise is not sufficient: we must develop the courage to say "I don't know" and use that humility to drive our future expos.
Why Adults Resist Change
A common refrain in our conversations was how hard it is to make a change. Alan reminded us that whereas 10% of people are quick to embrace new concepts, and another 10% resist vigorously, the rest of us tend to be somewhere in between. This resistance is not only cultural — it's neurological. Because our brains are wired to conserve energy, they will always prefer established habits over new things to learn.
It's why Alan emphasized that innovation frequently demands creating small, quantifiable experiments. We can try ideas out incrementally rather than insisting on wholesale change overnight. These experiments help build confidence, reduce fear, and allow us to adjust more organically to the world as it changes.
Watch our video of our podcast on YouTube.
Wisdom of Ignorance
Alan's methodology is based on what he dubs the six fundamental skills for flourishing in uncertain times. Central to them is purpose. Without something transformative and exciting enough to wake up for, innovation merely wanders around aimlessly. Clarity of purpose, whether it's in a for-profit or not-for-profit organization, is what leads to curiosity and experimentation, which begets growth.
"When I speak with people at non-profits, one of the common themes you'll hear is a greater sense of purpose than businesses," Alan says that both sectors need to revisit and sharpen their "why constantly." "Best is a space that's kind of a moving target," as he put it. What works today is no guarantee of relevance tomorrow, and without purpose, even the greatest idea can lose its impact.
The Six Essential Capabilities of an Innovative Organization
Alan boiled it down to six related skills - all of which are the building blocks of his book and consulting practice:
1. Purposefulness – Commit to something worth doing that is meaningful.
2. Curiosity – Ask for inspiration and you will find it, remembering that behind most great ideas is the thinking of others.
3. Humility – Acknowledge we don't have all the answers, discovery starts with an open mind.
4. Respect – Respect everybody and everything, they are coming from somewhere unexpected.
5. Focus Forward – Peer into the future with a focus on newer trends, cultures, and ideas.
6. Paranoia: Stay aware of the fact that competitors and threats are always on your heels.
These habits together prompt us to adopt what Santayana gleefully termed "enlightened ignorance" — a stance that appreciates not knowing as yet as the beginning rather than the end of knowledge.
Lessons for Leaders
As an anthropologist, Alan's take felt eerily familiar. We both believe that growth is often staring organizations in the face, disguised in plain sight — if only they can look beyond their routines and assumptions. Leaders need to push teams out of their comfort zones, provoke new ways of thinking, and acknowledge progress along the journey.
Alan cautioned us that our customers aren't loyal because they're devoted to us — they stay with us because switching to another provider seems more complex. But they'll leave as soon as something better comes along. Innovation, therefore, isn't optional. It's survival.
Human-Centered Change
All this talk of disruption nowadays is mainly centered on technology — and current trend words like AI, Bitcoin, blockchain, or the Fourth Industrial Revolution — but Alan warned us to remember that much more critical forms of change are human and social. From changing values across generations to increasing loneliness and shifting work habits post-COVID, leaders need to pay attention to the people side of transformation.
He urges us to reach out to strangers, listen more closely, and pay attention to the subtle signs of change that are all around us. In it, we can transform ignorance into discovery and shape futures that count.
A Final Thought
Alan's lesson is that you don't have to have all the answers in your mind to do something remarkable. All you need is a sense of purpose, curiosity, humility, respect for others, and a focus on the future — together with just enough paranoia to keep you from being complacent. Most of all, you need to warm up to the wisdom that eighth graders get every single day going into high school: not knowing.
For, as these people remind us: "We all actually do have the ability to make a difference. It's something we can attain if we engage in a few crucial behaviors each day."
His new book, The Wisdom of Ignorance, was published on October 14 and is available wherever fine books are sold.
Key Takeaways:
• Lean into what you don't know — that's where the wonder is, and that's where you'll feel becoming.
• Purpose orients; small experiments build confidence.
• Remain curious, humble, respectful of norms and traditions while remaining future-oriented, and a bit paranoid.
• The human and social change is at least as important as the technological disruption.
• Each and every one can make a difference one step at a time.
Connect with Alan:
Alan’s Profile: linkedin.com/in/alan-gregerman-a33b236
Website: alangregerman.com/ (Personal
Connect with me:
- Website: www.simonassociates.net
- Email: info@simonassociates.net
- Books: Learn more about our books here:
Listen + Subscribe:
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