Three unexpected (and unfiltered) insights from CEOs moving fastest on AI adoption
By now, everyone knows AI can bring major productivity and efficiency gains for companies who use it well. But it’s evolving so quickly that leaders have far bigger (and more interesting!) opportunities to explore.
So over the last few months, I’ve been asking guests on my podcast, How Leaders Lead: How are you using AI?
And their answers are fascinating. These are CEOs who lead massive teams and make big decisions at global brands like Bumble, Royal Caribbean, Siemens, Upwork, Oura, Thrive Market, and more.
I’m noticing some trends in their answers, so today, I’d like to share with you what I’m seeing. So here’s an inside look at what smart leadership looks like in the age of AI:
They’re not afraid to dive in
One of the biggest patterns I’ve seen in my conversations is how quickly top leaders move when it comes to AI. They’re not waiting for perfect information, and they’re not operating from fear.
Klaus Kleinfeld, former CEO of Siemens and Alcoa, didn’t mince words when I asked him what mindset leaders have right now: “If you’re not engaging with AI, you’re toast.”
In his view, there isn’t a single function that won’t be reshaped by it, so sitting on the sidelines simply isn’t an option.
Richard Fain, longtime CEO of Royal Caribbean, echoed that sentiment. He told me that “it’s too late to just experiment,” meaning leaders need to make AI a real part of how they operate. But he also stressed that urgency shouldn’t come at the expense of intention. As he put it, “You have to go at this clearly and with intentionality.”
That balance — moving fast, but not blindly — is exactly what Hayden Brown, CEO of Upwork, demonstrated when ChatGPT was only two months old. Her leadership team was split between “wait and see” and “move now.” She stepped in and made the call: “We couldn’t just wait,” she told me. “We had to get our hands dirty and learn by doing.”
Leadership takeaway:
Don’t wait for the dust to settle. Start applying AI in small, meaningful ways and learn as you go. Momentum is your advantage, and intentional experimentation is how you build real capability.
They’re tapping AI tools for personalized leadership coaching
We all have blind spots. And we all know how it feels when a situation goes sideways because you missed a critical perspective or didn’t ask the right questions soon enough.
So I love seeing just how many leaders are privately using AI as a real-time thought partner. It’s an invaluable way to pressure-test their thinking, widen their perspective, and work through tough situations more clearly.
For example, Bumble Founder and CEO Whitney Wolfe Herd has built custom AI “coaches” inside ChatGPT — including one she calls Sally, which pushes back on her assumptions and challenges her blind spots. She also created another coach that helps her reframe decisions through a more reflective, spiritual lens.
Nick Green, the CEO of Thrive Market, didn’t come to leadership naturally, so he puts a high value on getting feedback. And for him, AI is a great way to get it. By providing a little context, he can ask for feedback that helps him understand a situation better or reframe it entirely. He describes it as an uncannily effective “thought partner” that elevates the way he leads.
Leadership takeaway:
AI gives leaders a reliable place to think out loud. The instant feedback it provides can accelerate your growth as a leader. Use it to explore perspectives you might otherwise miss and strengthen your decision-making over time.
They’re recognizing the paradigm shift and looking for opportunities
Top CEOs aren’t just looking to AI to speed up what already exists. They’re considering the big picture, imagining how it will reshape the way we live. And they’re positioning their companies to build for what’s coming next.
Oura CEO Tom Hale is trying to make the world’s best health and wellness wearable, so he’s paying close attention to AI’s potential to reinvent the healthcare industry. He described a study from Hippocratic AI where people received daily wellness check-ins from an AI nurse. At first, participants were resistant — “are you a robot?” But by the end of the call many were opening up about their lives and worries.
Tom is seeing how AI creates space for care in ways traditional systems often can’t: unlimited time, patience, and emotional bandwidth. In his view, AI won’t replace clinicians, but it could expand care in ways our current health systems simply can’t scale.
Whitney Wolfe Herd (Bumble) sees a similar breakthrough opportunity in relationships. She believes AI can eliminate the friction and fatigue of modern dating and instead become the world’s most intelligent, emotionally aware matchmaker.
Her vision is a dating experience where AI helps with “true compatibility and self-discovery,” matching people through deep emotional alignment, not just surface-level preferences. She’s not interested in AI for artificial relationships, but she sees a huge opportunity to accelerate people into real—and better—ones.
Leadership takeaway:
Great leaders see the opportunities in new technologies. But they don’t just look for the ways it can improve how the world works now. They’re asking bigger questions about how it’s going to completely transform it, and they’re building their businesses accordingly.
Wrapping it up
I’m grateful that my podcast gives me the chance to hear directly from top leaders about how they’re navigating big shifts like AI. It’s an exciting moment, but it’s also a moment that calls for real intention and thoughtfulness.
Richard Fain put it well when he told me that AI can be “seductive.” It gives you fast answers. It moves at incredible speed. And if you’re not careful, you can lose the deeper thinking and human intuition that leadership demands.
AI can offer us powerful shortcuts for efficiency and productivity. But when it comes to high-level thinking and strategy, AI should be a catalyst, not a shortcut.
These top leaders use it intentionally to elevate the things only humans can bring to the table: curiosity, judgment, perspective, and the ability to build strong, adaptive cultures.
That’s the example we can all follow as we lead our organizations into the next era of work
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