Riding Tandem on the Big Wave of AI

Last week, I attended the Conference Board’s People First: Strategic Transformation event and heard from leaders deep in the work of organizational change. They shared stories of mergers, digital overhauls, and cultural redesign. But the thread running through nearly every session? AI.

Not the future of it, but the now of it.

Daniel Schreiber, CEO of insurance company Lemonade, opened with an eye-opening perspective: AI is already reshaping the size and structure of organizations, redefining roles, and accelerating decision-making. The message was clear: adapt or risk falling behind.

Cue my OMG moment.

I talk about AI a lot. I’ve moved from experimenting with it to fully integrating it into my coaching practice and my personal life. (You can read my drunk bestie AI bio [here] if you want proof.)

I’ve done the reading, taken the courses, stayed current. But hearing it from business leaders inside the transformation? That hit differently.

Because it wasn’t theoretical. It was operational. And at scale.

This wasn’t about what AI might do. It was about what’s already happening – real-time org chart rewrites, sped up decision-making, shrinking headcount.  It wasn’t being debated. It was being done.

The companies that will thrive aren’t the ones with the flashiest dashboards. They’re the ones shifting from rigid hierarchies to fluid, networked ways of working that include AI. And that shift isn’t just technical, it’s deeply human. It demands new leadership. And new stewardship.

At Moderna, technology and HR were merged into a single role: Chief People and Digital Technology Officer, held by Tracey Franklin. Her mandate? Redesign teams around what people do best and what AI can take on. It’s a bold example of aligning talent and technology at scale, and a clear signal: human and tech strategies must now evolve in lockstep.

As Diane Cafritz of CarMax said, “People first and digital first are not mutually exclusive.” That line gets to the heart of it: leaders today must integrate care for people with the speed of digital acceleration.

If AI is changing how we work, we need to rethink how we measure, support, and reward that work. We can’t drop transformative tools into old systems and expect them to work. 

The tech is moving fast. But meaning, context, and culture? Those need to move with it.

This is where coaching becomes essential.

In my work, I support leaders and teams navigating high-stakes transformation. I help them build the capacity to lead in uncertain terrain. To name what’s shifting, align around what matters, and keep people connected through it.

Because leadership isn’t just about managing outcomes. It’s about creating conditions where people can adapt, contribute, and grow.

After the conference, one speaker messaged me:

“AI is less transformative on its own, and just another tool (even if it is an incredibly fancy one). Nimble cultures will absorb it into their DNA. Rigid cultures will bolt it on and it’ll get rejected, or just drag along.”

That lands.

Daniel Schreiber also offered a metaphor I can’t stop thinking about: surfing. Those who learn to ride the wave – who feel the thrill and the risk, but still get up – will find their way forward. Those who stay still? They risk being wiped out.

When I first heard it, I pictured a few confident leaders on their surfboards and the rest struggling to stay afloat. But adaptive change isn’t a solo act.

There’s more room on the surfboard than we think. We don’t have to go it alone. It’s time to ride the wave… together.

That’s the leadership move I’m committed to: staying with the wave. Staying in the conversation. Supporting others as they navigate the redesign of work, culture, and capacity.

Because we’re here now. And we get to shape what happens next.

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If your team or organization is navigating the uncertainty of AI and transformation, let’s talk. This is exactly the kind of moment coaching is made for.