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On Culture: Let's Not Say Goodbye



The best questions do more than produce answers. They change the person asking them.


I learned that long before I knew anything about leadership. Through storytelling, my grandfather taught me to pay attention to what others overlook, follow my curiosity, and trust that the next good question is usually worth more than the last good answer. Years later, that instinct has become the throughline of my work.


This edition is about change, but perhaps the more interesting subject is what change reveals.


That posture is what makes continuous reinvention possible. Strong leaders question successful models before performance forces the issue: Which assumptions are aging? Where are needs moving? What does technology now make possible? Which systems should be redesigned or retired? They use disruption to create better products, stronger relationships, and more capable people, while purpose and trust provide the necessary continuity.


And through all of it, questions matter. The right one can interrupt a rehearsed answer, reveal an assumption everyone else has accepted, or make another person feel genuinely heard. Curiosity gives change both intelligence and humanity. It moves us beyond “How do we preserve what we have?” toward questions with greater possibility: What remains worth carrying? What is ready to evolve? What might become possible from here?

Those questions are personal for me now.

After nearly five years helping build Culturati into a year-round executive learning community, this will be one of my last On Cultures (though I hope to guest author from time-to-time). Culturati: Summit is on pause while Eugene and I step off payroll and reevaluate the organization’s mission and direction. We will continue stewarding Culturati in a volunteer capacity and welcome thoughtful ideas about what its evolution might look like at info@culturatisummit.com.


In the interim, Annie will remain as administrator and Eugene’s personal assistant. I will continue to monitor my inbox for some time, but I encourage you to connect with me at myste@mystewylde.com as well or on LinkedIn. Eugene plans to continue On Culture, likely in an evolving format, and I look forward to the distinct perspective, experience, and questions he will bring to it.


On that note, I am tremendously grateful to Eugene, Josh, Steven, our team, partners, advisors, contributors, attendees, and you, our readers. You brought rigor, generosity, and lived experience to the work. Thank you to every person who shared an idea, challenged an assumption, entrusted us with a story, attended a gathering, opened this newsletter, or carried one of these conversations into your own organization. You changed how I think.


The privilege of this work has been proximity to people thinking seriously about consequential things: how authority should be exercised, how trust is earned, how technology changes human behavior, and what organizations owe the people whose lives they shape. I'm so glad I've had the opportunity to build around those questions, write through them, and create spaces where leaders could examine them together. After taking a few weeks to reset, I plan to continue writing on Substack about leadership, AI & human flourishing, and the questions shaping our shared future. 


One of the most important things I've learned is that thoughtful leadership begins with humility. The wisest people I've encountered hold strong convictions and remain willing to revise them. They listen with genuine interest. They understand that every strategy eventually touches a human life, and they care about becoming the kind of person capable of holding that power responsibly.


As we move further into the age of AI, the human capacities that determine how power is used will become even more consequential. How do we build institutions worthy of human potential? How do we cultivate judgment, trust, wisdom, and courage? How do we direct increasingly powerful tools toward a more humane world? How do we create places where people leave more capable, more conscious, and more fully themselves than when they arrived?


Those are the questions I intend to keep pursuing. I do not yet know what the next chapter will look like, but I look forward to meeting it with the same curiosity I have spent years encouraging here. On Culture gave my many questions a home, and I hope the relationships formed will give them a life beyond it.


So, if you have ever thought we should get to know one another better, this is a great time to reach out. I love talking with people who are building, questioning, imagining, leading, learning, or trying to make sense of what comes next. Leadership, AI, human flourishing, books, history, travel, dogs, moral philosophy, the nature of reality, strange questions—all are fair game. I would be glad to hear from you. 


There are many questions left to ask. 


To what comes next, with love,


Myste Wylde

The Power of Strategic Centering

Harvard Business Review

By Rita McGrath

 

Summary: Change becomes more navigable when we know what must remain true. With roughly 90% of corporate value now concentrated in intangible assets such as knowledge, relationships, brands, and capabilities, leaders need a clear center to guide decisions as roles, structures, and circumstances evolve. That center may be a mission, a community, a problem worth solving, or a principle that gives coherence to what comes next. The same applies personally: a title can end while the values, relationships, questions, and capacities formed through the work continue. Transformation asks us to release the container while carrying forward what gave it meaning.


Three Hidden Reasons Why Leaders Resist Change

Fast Company

By Ryan Gottfredson

 

Summary: 71% of organizations now consider leading through constant change critical, yet only 18% of leaders feel capable of doing it. The barrier often sits beneath strategy and skill: leaders become attached to proving their worth, controlling outcomes, and protecting their competence, even when transformation requires experimentation, shared ownership, and humility. Those instincts may have fueled past success, but under pressure they create burnout, bottlenecks, and closed systems that block the insight leaders need most. Change-ready leaders are secure enough to distribute authority, invite ideas, and enter uncertainty with curiosity, replacing the impulse to protect their identity with a more useful question: What does this moment require of me?


Today’s Great Leaders Disrupt Themself Before Someone Else Does

Forbes

By Robert Reiss

 

Summary: Continuous reinvention turns disruption into a source of momentum. The strongest leaders challenge their own assumptions, operating models, and definitions of success while the business is still performing, using each shift in technology, customer behavior, or market conditions to create new possibilities. UPS is reimagining what will carry a 120-year-old company into its next century, while others are applying AI to deepen creativity, judgment, service, and customer connection. What gives that evolution coherence is a purpose-aligned culture built on trust and shared values. Products and technology can be replicated; an organization capable of changing bravely without losing its humanity becomes far harder to copy.


The Great Untangling: The Smarter Way to Rebuild Your Identity After a Career Pivot

Inc.

By Daniela Pierre-Bravo

 

Summary: When work carries our belonging, security, and sense of worth, a career change can feel like losing the language we used to explain ourselves. U.S. employers announced more than 1.2 million job cuts in 2025, while the independent workforce grew to 72.9 million, signaling a wider separation between identity and any single title or institution. Research suggests that what comes next is built through small experiments rather than discovered through introspection alone: a project, a client, an advisory role, a conversation that reveals another way forward. The deeper work is learning to treat success and failure as information rather than judgments on our value, then deciding which parts of the person we became through the role are still ours to carry.


The Secret to Good Questions

The Economist

By Bartleby

 

Summary: Better questions begin with genuine curiosity rather than a desire to display what we already know. They are relevant enough to advance the conversation, unexpected enough to interrupt rehearsed thinking, and followed by the discipline to listen for what changes. Research found that hard-to-predict but contextually grounded questions were more likely to surface new information and drive meaningful shifts in judgment. Consistency also matters when evaluating people or ideas, since uneven questioning creates room for bias. As leaders become more senior, inquiry becomes a larger part of the job: testing assumptions, uncovering what others have missed, and creating the conditions for clearer thinking. The quality of a question is ultimately measured by whether it opens something that certainty would have kept closed.


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