What Can Six Bold Thinkers Teach Us About Leading Through Chaos?
Hear How To Lead With Imagination, Empathy, and Purpose
Some stories break through the noise—and stay with you. For me, it was the recent murders in Minnesota. The violence was heartbreaking, but what’s lingered is the deeper question it raises...
What kind of society are we creating if every disagreement becomes a declaration of war?
We’ve grown too quick to assume intent, too eager to take sides. We’ve lost the ability to disagree without breaking something. That breakdown isn’t just political—it’s personal, cultural, and it’s showing up everywhere.
We can—and must—do better. I shared more of my thoughts in this short LinkedIn post.
That’s also why this week’s newsletter feels especially timely. Because if the world is getting more complex, leadership can’t just be about control or speed. It has to be more human.
In this edition of Humanity at Scale, I’ve pulled together insights from six powerful conversations—with voices from across AI, design, psychology, and operations—who are rethinking how to lead when the playbook stops working.
I hope you enjoy this edition. If you do, I’d love for you to subscribe and share it with others who might benefit. Let’s dive in.
Leading Through Complexity with Imagination, Empathy, and Purpose
We’re living in a world that just won’t sit still. Technology is accelerating, expectations are shifting, and the pace of change keeps outrunning the systems designed to handle it. It’s not just chaotic—it’s complex. And that complexity isn’t going away.
That’s what makes leadership harder—and more important—than ever. In this kind of environment, reacting faster isn’t enough. Today’s leaders need to think differently, act more intentionally, and lead in ways that are deeply human. Over the last six episodes of the Humanity at Scale: Redefining Leadership podcast, I’ve had conversations with remarkable thinkers who are showing what that looks like—from AI pioneers and futurists to workplace strategists and operational CEOs.
Each guest brought a different lens—neuroscience, design, psychology, operations—but they were all wrestling with the same challenge: how do we lead in ways that make sense in a world that often doesn’t?
Leadership Lessons From Six Smart Voices
Below are snapshots from those six episodes, each offering a distinct but connected piece of the leadership puzzle:
The Ethics of Empowerment: How AI Can Make Us Stronger with Dr. Vivienne Ming
Empathy, AI, and the New Rules of the Human Workplace with Erica Keswin
Innovate or Stagnate: Mastering Leadership in a Dynamic World with Charlene Li
Beyond Right and Wrong: Rethinking Moral Disagreements with Dr. Kurt Gray
Scaling with Heart: How Safelite Balances Growth, People, and Purpose with Renee Cacchillo
Designing the Future: How to Be a Good Ancestor with Lisa Kay Solomon
1) Designing The Future: How to Be a Good Ancestor
In this episode, I sat down with Lisa Kay Solomon—futurist, educator, and designer-in-residence at Stanford’s d.school—to explore how leaders can expand their imaginative capacity in a world defined by speed and uncertainty. With decades of experience helping students and executives design better futures, Lisa shares why imagination isn’t a luxury for leaders—it’s a necessity. We talked about the pressures of short-termism, the practice of possibility, and what it means to lead with empathy and legacy in the age of AI.
Imagination is a leadership muscle—and we’ve stopped using it. Lisa warns that our institutions—from classrooms to boardrooms—have systemically trained imagination out of us. “We reward right answers,” she says, “not better questions.” That’s a problem in an era shaped by exponential change. To lead effectively, she argues, leaders must relearn how to ask ‘what if?’ and embrace possibility as a daily practice—not a luxury. “The future isn’t something that happens to us,” she says. “It’s something we shape.”
Empathy and values are the compass for navigating complexity. With AI accelerating and volatility increasing, Lisa urges leaders to pause and clarify their design criteria—not just what they want to build, but what they won’t. “The future will reward clarity,” she notes, “but it will punish certainty.” Grounding decisions in empathy and purpose, especially during moments of ambiguity, allows leaders to stay human-centered even when the path ahead is unclear.
We need to lead like good ancestors. At the heart of Lisa’s work is a powerful challenge: to lead not just for quarterly returns, but for long-term impact. She encourages leaders to practice “legacy thinking”—planting seeds they may never see grow. That shift starts with mindset, but it’s brought to life through small, intentional actions. Whether it’s designing with inclusion in mind or simply making space to think beyond today’s demands, leadership in the age of AI is about shaping futures we’re proud to leave behind.
2) The Ethics of Empowerment: How AI Can Make Us Stronger
In this episode, I sat down with Dr. Vivienne Ming—neuroscientist, entrepreneur, and visionary technologist—to explore how leaders can unlock human potential in an AI-driven world. With a career spanning neurotech, predictive modeling, and global philanthropy, Vivienne brings an extraordinary blend of science and soul to every conversation. We talked about designing AI that supports growth, the strategic power of imperfection, and why human insight is still our greatest advantage.
Human-centered AI starts by asking better questions. Vivienne challenges leaders to stop thinking about what AI can do and start asking what it should do. From hiring algorithms to productivity tools, too many systems optimize for the wrong goals simply because leaders fail to own the question. “AI doesn’t understand anything,” she explains. “It just implements whatever question you give it.” Her advice? Start with purpose, stay grounded in context, and design for growth—not just efficiency.
We need tech that makes people better when it’s turned off. Not all progress is positive. Vivienne warns that some technologies erode core human capacities—even while appearing helpful. Tools like GPS, she notes, may improve navigation, but they dull our spatial memory. That’s why she asks a bold design question: Are people better after they stop using your product? Whether it’s mapping software or generative AI, the goal should be to amplify—not outsource—our human strengths.
Imperfection is a feature, not a flaw. One of the most powerful themes in Vivienne’s work is the value of embracing our weaknesses. Drawing from massive data sets, she found that the highest performers aren’t perfect—they’re self-aware. They know where they struggle and develop strategies to adapt. “You don’t need to be flawless,” she says. “You just need to understand your limits and practice being the person you want to be.”
3) Empathy, AI, and the New Rules of the Human Workplace
In this episode, I sat down with Erica Keswin—bestselling author, workplace strategist, and champion of human-centered leadership—to explore how leaders can build organizations where people truly belong. Drawing from her Human Workplace Trilogy, Erica explains why connection is the currency of modern leadership. We talked about the power of rituals, the evolving role of middle managers, and how to design employee experiences that last—from onboarding to offboarding.
Human leadership is about honoring relationships. At its core, Erica’s philosophy centers on one simple idea: leadership is a daily act of honoring relationships—with colleagues, customers, and ourselves. In a world increasingly shaped by AI and automation, she challenges leaders to be more intentional in how they communicate and connect. “Left to our own devices,” she warns, “we’re not going to be connecting.”
Rituals bring values to life and make culture real. Erica defines rituals as intentional actions with meaning, rhythm, and emotional depth—something that goes beyond routine. From company-wide onboarding ceremonies to informal daily moments, rituals help employees feel grounded in something bigger. “Begin with your values,” she advises. “And look for moments where people already feel most connected.”
Retention starts with connection—and doesn’t end at goodbye. The old playbook for retaining talent no longer applies. Erica urges leaders to shift from controlling tenure to designing meaningful journeys—where people feel seen, supported, and even celebrated if they leave. Whether through offboarding rituals, boomerang programs, or mentorship roles, she reframes retention as a long-term relationship, not a transaction. “It’s about creating a culture,” she says, “where people want to stay connected.”
4) Innovate or Stagnate: Mastering Leadership in a Dynamic World
In this episode, I sat down with Charlene Li—bestselling author, disruption strategist, and transformation expert—to explore how leaders can move from managing change to creating it. With deep experience guiding organizations through uncertainty, Charlene shares why disruption isn’t just an event—it’s a skill. We talked about building cultures ready for change, leading with vision, and finding stability in values.
Disruption starts with discomfort—on purpose. Charlene’s challenge to leaders is clear: “If you’re comfortable, you’re not doing it right.” Growth demands a tolerance for uncertainty, and the best disruptors develop that muscle intentionally. Leaders must create safe but stretching environments—where people feel supported enough to take risks, but uncomfortable enough to evolve. “You want to stretch people, not stress them,” she said. That balance is where transformation begins.
Vision matters—but buy-in matters more. You can’t lead transformation alone. As Charlene put it, “The boat has already left the harbor—are you on it?” Change leaders must create compelling visions of the future, then connect that vision to individual motivations and fears. It’s not just about direction—it’s about co-ownership. “Invite people to come along and dream with you,” she said. When people feel agency in the journey, resistance gives way to momentum.
Culture is your anchor in times of chaos. True disruptors don’t thrive on chaos—they thrive on clarity. While everything else shifts, a strong culture provides stability. “Everything else can change, but you need a bedrock,” Charlene said. Values, mission, and shared beliefs give people orientation and safety—even when decisions are fast, failure is frequent, and the path forward is unclear. That’s what enables innovation that’s bold and grounded.
5) Beyond Right and Wrong: Rethinking Moral Disagreements
In this episode, I sat down with Dr. Kurt Gray—psychologist, neuroscientist, and author of Outraged—to unpack the science behind moral conflict. We explored why people see the same issue in wildly different ways, and how leaders can build bridges by understanding the moral frameworks driving disagreement. In a polarized world, Kurt’s work offers leaders a new lens for empathy, trust, and ethical leadership.
Moral conflict stems from different views of harm. According to Kurt, most people—regardless of ideology—are motivated by protection. “Everyone condemns acts they see as harmful. The problem is, folks on the left and right sometimes focus on different harms.” What looks like malice from afar is often fear up close. Leaders who understand this can move past surface-level conflict and address the underlying concerns people are trying to defend against.
Facts don’t change minds—but stories of vulnerability can. When people talk past each other, it’s often because they argue from positions, not from personal experiences. “We wrongly think throwing facts at folks is going to convince them,” Kurt said. Instead, sharing personal stories—especially ones rooted in fear or hardship—can shift conversations from debate to understanding. That’s where leaders can unlock empathy and build bridges across seemingly entrenched divides.
Ethical leadership requires revealing your moral tension. Leaders often face moral trade-offs with no clear “right” answer. What matters, Kurt argues, is not always what decision is made, but how it’s communicated. “If you acknowledge competing values and show that you’re grappling with the dilemma, people are more likely to trust your intent.” In gray-zone leadership, transparency about tensions becomes more powerful than certainty.
6) Scaling with Heart: How Safelite Balances Growth, People, and Purpose
In this episode, I spoke with Renee Cacchillo—CEO of Safelite—about what it takes to operationalize humanity at scale. Leading a $3B+ business with 14,000 employees, Renee offers a masterclass in integrating purpose, empathy, and frontline intelligence into enterprise strategy. We talked about how Safelite designs systems that support care, why vulnerability builds trust, and how to align big goals with everyday decisions.
Operational excellence is a delivery mechanism for empathy. Renee’s approach to leadership is rooted in the belief that care isn’t a side program—it’s a system. From redesigning workspaces through employee-led 5S processes to embedding real-time safety feedback loops, she’s engineered the business to support physical, emotional, and cognitive capacity on the frontline. “The easier we make it for them, the more energy they have to serve customers with care,” she explained. Empathy doesn’t scale through messaging—it scales through infrastructure.
Vulnerability isn't weakness—it's a precondition for adaptive leadership. Renee reframed vulnerability as a strategic asset that enables learning and trust across functions. “I had to walk into rooms where I knew nothing about telecom, or how to create a TV spot. And I had to admit it,” she said. That posture didn’t undermine her authority—it allowed her to cultivate teams with deeper expertise and stronger buy-in. Her leadership model breaks from heroic individualism and embraces distributed intelligence as a source of resilience.
Purpose is a discipline of alignment, not aspiration. For Renee, purpose isn’t an abstract ideal—it’s a practical standard for how decisions get made and how change takes root. “If a decision isn’t aligned with being both people powered and customer driven, we don’t do it,” she explained. That alignment doesn’t happen behind closed doors; it’s forged in partnership with the people doing the work. “We don’t just explain the change—we design it with them.” By grounding purpose in shared decisions, not corporate messaging, Safelite ensures it shows up where it matters most—at the point of action.
Sparking New Leadership Thinking
Leaders who want to elevate humanity inside their organizations don’t need to wait for a grand transformation. Across these six episodes, a shared insight emerges: bold leadership is less about having all the answers, and more about the discipline of asking better questions, creating room for possibility, and staying anchored in purpose—even as the world shifts. Here are five actionable ways to bring that into practice:
Make imagination part of the leadership job. We’re operating in systems built for efficiency, not possibility. But leaders must carve out space to imagine alternative futures—not just react to forecasts. Lisa Kay Solomon encourages teams to practice “backcasting”: envisioning a future 10 years out, then working backward to define what must be true to get there. Her Stanford class, View from the Future, invites leaders to learn from pattern-breakers across industries. Vivienne Ming echoes the need for this kind of thinking, reminding leaders that technology is only as visionary as the humans shaping it.
Slow down to design with purpose. Urgency can push leaders to chase quick wins over enduring impact. But designing for humanity requires reflection, not just reaction. Lisa Kay Solomon challenges leaders to define their “design criteria”—what they must, should, could, and won’t do—to stay aligned with their values. Renee Cacchillo reinforces this discipline at Safelite by embedding purpose into decision-making frameworks, ensuring every change supports both people and performance.
Build rituals that reinforce what matters. Culture isn’t built through slogans—it’s built through rhythm. Erica Keswin stresses the power of intentional rituals to connect people, especially in hybrid or fast-changing environments. Whether it’s onboarding ceremonies or offboarding reflections, rituals offer moments of shared meaning that build belonging. Renee Cacchillo brings this to life through employee-led workplace design processes that create ownership and trust at scale.
Practice leadership transparency in moral gray zones. In complex, polarized environments, leaders can’t always offer certainty—but they can offer honesty. Kurt Gray found that people trust leaders more when they acknowledge moral tension rather than mask it. Instead of pretending there’s one right answer, he urges leaders to reveal the competing values they’re navigating. Vivienne Ming shared similar insight: ethical leadership begins with asking the right question, not just optimizing the right answer.
Design technology to amplify human strengths. AI is powerful—but without human-centered design, it risks eroding the very capacities it should enhance. Vivienne Ming warns against technologies that diminish core skills, like how overreliance on GPS can impair spatial reasoning. She urges leaders to ask: “Are people better after they stop using your product?” Erica Keswin applies that lens to workplace tech, pushing organizations to ensure their tools foster real connection—not just surface efficiency. Done right, technology becomes a lever for growth, not just automation.
The Bottom Line
The most impactful leaders aren’t just reacting to change—they’re actively shaping the future with imagination, empathy, and purpose. These six conversations reveal a powerful truth: designing human-centered organizations requires clarity of values, comfort with uncertainty, and a deep commitment to elevating people—not just performance.
Humanity At Scale: Redefining Leadership Podcast
Listen in to my podcast, Humanity at Scale: Redefining Leadership, where I talk with leaders and thinkers who are reimagining what leadership looks like in a fast-changing world. We explore how putting people first—employees, customers, communities—isn’t just the right thing to do, it’s a smarter path to success. Along the way, we dig into the human side of leadership—how our brains work, what drives behavior, and how technology is reshaping it all.
If you haven’t tuned in yet, it’s a great time to start.
The podcast is available on Apple Podcasts, Spotify, and YouTube.
Humanity at Scale is a movement to inspire and empower leaders to create humanity-centric organizations