Courageous Leadership in the Age of AI: Why Culture Will Decide Who Thrives

Artificial intelligence is changing the workplace faster than almost anything we’ve seen before. Companies are pouring billions into AI initiatives, but as Brené Brown said in her recent interview with the New York Times, “it looks like a complete shit show.” Fear and scarcity are driving huge investments not even aligned with strategy. Leaders are panicked. Employees are confused. And what’s really at stake isn’t just technology. It’s culture.

This isn’t a tech transition. It’s a culture transformation.

Fear-Based AI Adoption vs. Courageous Leadership

AI is exposing a massive leadership divide.

On one side, we see fear-based leadership: frantic decisions, constant churn, and “chicken-with-your-head-cut-off urgency,” as Brown describes in her interview. It produces quick activity but little impact. And as Brené points out, fear has a very short shelf life.

On the other side, we see courageous leadership: the ability to “settle the ball,” create space where none exists, and make smart, values-aligned decisions. Leaders who practice this kind of clarity, trust, and discipline don’t just survive disruption. They thrive.

The data backs it up. Organizations with courageous leaders consistently outperform on engagement, retention, and long-term performance.

Why AI Is a Culture Issue

Too many executives treat AI as a systems or process challenge. But the real risk (and the real opportunity) is cultural:

• Communication: Are leaders honest and clear about what AI means for their people?

• Trust: Do employees believe leadership is investing in them, not just in tools?

• Alignment: Are AI decisions connected to the company’s strategy and values, or just panic-driven?

Without cultural alignment, AI adoption feels like chaos. With courageous leadership, it becomes a catalyst for innovation, resilience, and growth.

My Perspective as a Cultural Anthropologist

I’ve spent my career studying how cultures form, thrive, and fracture. In every organization, culture is the soil everything else grows in. AI is simply the newest storm hitting that soil.

When I work with leaders, I help them:

• Anticipate disruption without creating panic.

• Design programs and processes that support employees through uncertainty.

• Anchor change in values and trust, so culture becomes a competitive advantage—not collateral damage.

In this moment, leaders don’t just need to implement AI. They need to cultivate culture as their operating system.That’s what I help them do.

Join the Conversation: The Culture Collective Book Club

Leaders don’t have to navigate this alone. I’m launching The Culture Collective Book Club, a free community space where we’ll read and discuss Brené Brown’s Strong Ground: The Lessons of Daring Leadership, the Tenacity of Paradox, and the Wisdom of the Human Spirit to kick us off.

Our first discussion will take place in October.

If you’d like to join, let me know! Feel free to join even if you know you aren't going to read the book.

Final Word

AI will reshape every organization, but it won’t be the companies with the flashiest tools or those who measured butts in seats that win. It will be the ones with the strongest cultures. Courageous leadership, not fear-based reaction, is what will separate the disruptors from the disrupted.

And if you’re a leader ready to face this shift with clarity and courage, I’d love to work directly with you, advising you and your team, and helping you build the programs and processes that will carry you through.

Because, like all change initiatives, culture is what determines whether your AI strategy succeeds.

Schedule a call with me here.

Read the full interview here.

Pre-order the book here.