On Culture: Courage Begins with Curiosity

Myste Wylde
May 30
8 min read

Dear Culturati Insider,

What is Courageous Leadership at this time, in the face of these geopolitical headwinds, during the accelerating era of AI? Not in theory but in practice, in this moment, when risk is real, while trust is fraying, and the stakes extend beyond just short term returns?

That was the prompt behind Tuesday’s gathering of senior leaders to explore the working theme for Culturati: Summit 2C26. With Brian Johnson, founder of Heroic and author of Areté, and Rev. Steven Tomlinson, PhD, we weren’t there to reach consensus or even a single definition. The goal was to test the premise, challenge assumptions, and begin identifying the real questions of what constitutes Courageous Leadership and if it is called for today. We left with an understanding that there are multiple possible frames.

The shift from seeking clarity to confronting complexity surfaced the tensions leaders must now face. When does courage reflect a commitment to principle, and when is it simply a well-branded performance? Are our organizations equipping leaders to navigate risk in service of something greater or merely conditioning them to comply efficiently? How do we build cultures that normalize dissent, reward integrity under pressure, and align authority with accountability?

Brian reminded us of Aristotle’s belief that courage is the virtue that activates all others—and that it doesn't stand alone. It relies on the constant interplay of wisdom, discipline, and love. Love was not introduced sentimentally, but structurally. Love as the foundation for principled risk. Love as the conqueror of fear. Discipline as the practice of value-aligned behavior. Wisdom as the discernment to act with clarity in moments of uncertainty. When those forces are present, courage becomes less a personal trait and more a systemic function. A special thanks to Chris Taylor for hosting us at Red Fridge Society and helping create the kind of setting where honest, unguarded conversation could unfold.

This lens reframes what we’re seeing across organizations today. Fear is widespread. Korn Ferry reports that 69% of employees withhold ideas, while 85% don’t feel safe challenging unethical directives. We also see how hierarchy influences values. One study of 5,500 financial services firms found that removing a single layer of management changed the cultural makeup of teams—not through hiring, but through attrition. Openness, conscientiousness, and agreeableness all increased, but restructuring must be co-led and deliberate. Flattening alone doesn’t build trust; without alignment to identity and values, it risks drift and unintended loss.

The same principle applies to growth. Just as structure shapes culture, informal development pathways shape who gets seen—and who gets left behind. Stretch assignments, long treated as vehicles for merit-based advancement, don’t reward everyone equally. In a large-scale study of early-career engineers, white and Asian men saw significantly greater gains in promotions and compensation, compared to women and peers from Black, Indigenous, Latinx, and other underrepresented backgrounds. The difference wasn’t effort or output—it was recognition. If development pathways mirror bias, the cost isn’t just stalled advancement; it’s the quiet erosion of trust, motivation, and belonging.

Externally, the pressure is no less acute. Michèle Flournoy’s research highlights that 85% of leadership teams are unpracticed in aligning during a crisis. Most boards still rely on static risk charts rather than live coordination. In this climate, resilience must be rehearsed. And while the headlines change, the internal cost is steady. Burnout mentions on Glassdoor rose 32% in Q1 alone. Adam Grant’s work points to practical, research-backed tools like innovation tournaments, generosity rituals, and memory-future reframing but these only work when embedded into how teams operate, not bolted on as a fix.

What threads all of this together is a call for alignment. Does Courageous Leadership require more than character? Does it requires systems that reinforce and reward it? It shows up in who is heard, who is developed, who is protected, and whether those decisions reflect values or convenience.

LaToya Collins-Jones (founder/CEO of Culture by Design and former VP of People, Culture & Inclusion at Dell Technologies) suggests we don’t need more rules or another corporate playbook. We need clarity. We need audacity. In our next Culturati:LIVE (June 24), LaToya invites leaders ready to trust their gut to design cultures that reflect who they truly are. She will share how to build high-performance environments without burning out or selling out, and why the boldest move you can make is to lead from alignment. We hope you'll join us.

Inquisitively yours,

Myste Wylde, COO

P.S.

If your week allows for one more click—here’s a bonus read worth your time: “From Gods to Code: A Brief History of Human Meaning.” (Because I’ve never met a timeline of human consciousness I didn’t want to annotate—and nothing soothes AI-induced existential dread like a tour through 10,000 years of meaning-making.)

Courage As Currency: How Brave Cultures Outperform Safe Ones

Forbes

By Margie Warrell, PhD

Summary: Fear is the hidden tax draining organizational performance, silencing innovation, enabling ethical blind spots, and stalling decision-making. Korn Ferry reports 69% of employees hold back ideas out of fear, and 85% don’t feel safe challenging unethical directives. The antidote? Courage. Organizations that invest in psychological safety and courageous leadership see up to 40% higher engagement, 30% more innovation, and 35% stronger crisis response. Courage can be innate, even heroic—but it’s also learnable and scalable. When modeled from the top, it accelerates trust, agility, and retention. In today’s environment, the edge belongs to leaders willing to take smart risks in service of what’s right—not just what’s safe.

READ ARTICLE IN FULL

Building Geopolitical Resilience: A Conversation with Michèle Flournoy

McKinsey & Company

By Andy West and Michèle Flournoy

Summary: Most corporate strategies are built for a bygone era of stability. Michèle Flournoy, former U.S. Undersecretary of Defense and cofounder of WestExec Advisors, argues that geopolitical resilience now demands clearer risk exposure mapping, scenario planning, and team-wide readiness. With 85% of leadership teams unpracticed in crisis alignment, Flournoy advocates for tabletop exercises to pressure test roles, communication plans, and decision speed. Boards, too, must move beyond static risk charts to active participation. The goal isn’t prediction—it’s preparation. Companies that embed geopolitical foresight into core governance and strategy processes are better positioned to respond fast, adapt continuously, and seize competitive openings amid global disruption.

LISTEN NOW

People Follow Structure: How Less Hierarchy Changes the Workforce

MIT Sloan Management Review

By Markus Reitzig and Kathrin Heiss

Summary: Organizational design is culture-shaping. A study of 5,500 U.S. financial services firms found that flattening hierarchies—specifically removing one layer of management—led to measurable shifts in workforce composition: a 2.0% rise in conscientiousness, 3.6% in agreeableness, and 3.4% in openness. These changes were driven by attrition, not hiring, revealing that structure silently selects for certain behaviors and values. Skill levels remained flat, but personality fit shifted—indicating that hierarchy isn't just operational, it's cultural. For CEOs, this means org charts are levers for workforce self-sorting. For CHROs, it underscores the need to co-lead restructuring efforts to protect high performers and prevent culture drift. Flatter doesn’t always mean better—unless leaders actively align structure with identity, incentives, and trust.

READ ARTICLE IN FULL

The Right Way to Implement Stretch Assignments

Harvard Business Review

By Shannon K. Gilmartin, Samantha Brunhaver, Sara Jordan-Bloch, Gabriela Gall, Caroline Simard and Sheri D. Sheppard

Summary: Stretch assignments are powerful tools for career acceleration—but when mismanaged, they quietly reinforce cultural inequities. A study of 600 early-career engineers found that White and Asian men gained the most from stretch work in terms of expected raises and promotions, while women and Black, Latinx, Indigenous, and Pacific Islander peers saw little to no benefit—despite equal or greater participation. These gaps weren’t about effort or ability, but recognition. For CEOs and CHROs, the message is clear: informal development pathways often mirror existing bias. To build a truly inclusive culture, organizations must track who gets stretch assignments, clarify their connection to advancement, and ensure rewards are distributed equitably.

READ ARTICLE IN FULL

Adam Grant’s 3 Best Ways to Beat Chaos Fatigue (Beyond Just Consuming Less News)

Inc.

By Jessica Stillman

Summary: With burnout mentions on Glassdoor up 32% year-over-year in Q1 2025 (reaching record highs) and 78% of employees reporting that news events are draining their energy at work, chaos fatigue has become a measurable organizational threat. To address this growing strain, Adam Grant outlines three research-backed strategies: First, use “mental time travel”—revisiting past resilience and imagining positive futures helps counter emotional overload. Second, encourage acts of generosity; studies show they reduce stress as effectively as medication. Third, engage teams through innovation tournaments, which shift energy from anxiety to problem-solving and reinforce agency. Leaders looking to stabilize morale should treat chaos fatigue not as a personal issue, but as a design challenge with cultural and operational implications.

READ ARTICLE IN FULL

BONUS: From Gods To Code: A Brief History Of Human Meaning

Forbes

By Tomas Chamorro-Premuzic

Reflection: Meaning has always been our most essential operating system—an evolving interface between consciousness and culture. From 10,000 BCE onward, humans found purpose through mythic and tribal identity (“we are one with the gods”), where belonging to the collective was survival. By 600 BCE, the Axial Age ushered in religious meaning, positioning life as a moral test under divine law. With the Enlightenment (1500–1800), meaning secularized—Descartes’ cogito crowned rationality as purpose, and thinkers like Kant redefined agency as ethical self-determination. During the Industrial Era (1800–1945), purpose industrialized: labor became identity, and output equaled worth. Existentialists responded to the disillusionment of war and mechanization with absurdism (1945–1980s)—Sartre’s “condemned to be free” marked a shift from divine mandate to radical autonomy. By the 1980s, neoliberalism transformed identity into a lifestyle brand—“I shop, therefore I am”—while the 2000s turned inward, linking meaning to mindfulness, self-optimization, and therapeutic growth.

Now, in the age of AI, we stand at an existential inflection point. Generative machines can write our stories, forecast our strategies, mimic our empathy. The very capacities we once believed made us indispensable are now duplicable at scale. If labor, cognition, and even creativity can be outsourced, what’s left of the self? What happens to meaning when agency erodes—not through oppression, but automation?

Viktor Frankl, writing from the abyss of Auschwitz, warned that the loss of meaning is more dangerous than suffering itself. And modern neuroscience agrees: meaning is not decorative—it’s neurological infrastructure. It’s how the brain stitches together memory, emotion, identity, and time. For leaders and fellow deep thinkers, this moment demands more than innovation or resilience. It demands an ontological reckoning. What does it mean to lead when performance can be simulated? To create when ideas can be auto-generated? To choose, when the algorithm knows what you’ll prefer before you do?

In every previous age, meaning evolved alongside the tools we built. But this is the first time our tools threaten to render meaning obsolete—by making us observers of our own relevance. The ultimate question is no longer “What is the future of work?” but “What is the future of being?” The most visionary leaders won’t just ask how to integrate AI. They’ll ask: "What can never be automated?" What remains sacred, slow, hard-won, and deeply human? In that answer lies not only the future of meaning—but the future of us.

READ ARTICLE IN FULL

LaToya Collins-Jones suggests we don’t need more rules or another corporate playbook, but that leading with clarity and audacity is the way. In this session, LaToya is calling in leaders ready to trust their gut and create cultures that reflect who they truly are. She'll explore how to build high-performance environments without burning out or selling out—and why the boldest move you can make is to lead from alignment. This conversation assumes leaders are here to shake things up—and ready to start with one powerful, unapologetic step.