The Hardest AI Questions Aren't About Technology

Last month, I had the opportunity to attend and speak at the Henry Stewart Creative Operations Conference in New York. I left thinking less about what AI can do and more about who we want to be in a world where it can do so much.

Across keynotes, panels and hallway conversations, AI came up again and again. Workflow automation. Creative production. Analytics. Measurement. Planning. Every session seemed to explore another way AI could transform the way we work.

And somewhere along the way, it became clear that the room wasn't really debating whether AI could do these things anymore. The harder, more important conversation, the one that stayed with me, was what happens to the people who do them today. Not just as a leadership question. As a human one.

If you're leading a content or marketing operations function right now, that tension is likely already sitting somewhere in your organisation, whether or not it's being named out loud. The question isn't simply, ‘can we use AI here?’ It's, ‘what happens to your people, your brands and your decisions once you do'.

That, I think, is the question most organisations haven't actually answered yet. And it's the one worth sitting with before the next pilot programme gets greenlit.

Moving Past the Problem-in-Search-of-a-Solution Phase

What I appreciated most about the conversations at Henry Stewart was that they felt more grounded than the typical AI hype. People were excited. They should be. The technology is evolving incredibly quickly. But there was also a growing recognition that excitement isn't a strategy.

What struck me wasn't one keynote or one conversation. It was the pattern that emerged throughout the day. There were dozens of examples of successful pilots. Creative workflows were becoming faster. Reporting was becoming smarter. Teams were experimenting with new ways of working.

But I heard far fewer stories about organisations fundamentally changing because of those successes. One example that stuck with me came from Ryan Day at Wayfair, whose role has evolved from a traditional Creative Operations PM into one focused on AI capability. It was a small but tangible reminder that the future isn't only about replacing work. It's also about creating entirely new kinds of work. That felt different. It was one of the few examples I heard that wasn't just about making work more efficient. It was about intentionally evolving the organisation alongside the technology, starting with the people.

Technology rarely transforms organisations on its own. Leadership does. And leadership happens through people. One thing I've learned from helping organisations redesign the way they work is that operating models don't succeed because the process is better. They succeed because people understand how they fit into what’s coming next. AI doesn't change that. If anything, it makes it even more important.

The Conversation We Keep Dancing Around

The topic that stayed with me most after the conference was one that tends to sit just beneath the surface at events like this. Jobs. People. Teams. The future of work.

Most leaders understand that AI will change how work gets done. Many are already seeing it happen. What remains uncomfortable is talking openly about what that means for the people doing that work today. So let's be honest.

Part of AI's value proposition is reducing human effort. Sometimes that means helping people work faster. Sometimes it means changing roles, reducing the need for certain skills or eliminating positions altogether. That's an uncomfortable thing to say out loud.

Not because leaders don't care. In my experience, they do. They care deeply about building teams, creating opportunities and helping people grow. At the same time, they're being asked to prepare their organisations for a future that may require different skills, different team structures and, in some cases, fewer people doing certain types of work. That's where the tension lives.

The question isn't whether AI will impact jobs. It already is. The question is whether you’re willing to talk honestly about that impact before it becomes unavoidable.

Do you wait until disruption forces your hand? Do you proactively reskill employees? Do you redesign roles? Do you intentionally create new opportunities, like Wayfair did? Do you slow adoption in areas where human expertise remains a competitive advantage? Or do you pursue efficiency wherever possible?

None of those choices is inherently right or wrong. But pretending they aren't choices doesn't make them disappear. These aren't technology decisions. They're leadership decisions. And they can't be delegated to a vendor or solved with another pilot programme.

What Kind of Organisation Do You Want to Be?

Ultimately, I think that's the conversation AI is forcing every organisation to have. How do you balance business performance with responsibility to your workforce? What do you owe employees whose roles may look fundamentally different three years from now? How do you help people build the skills they'll need for work that doesn't fully exist yet? And if difficult decisions become necessary, how do you make them in a way that reflects our values, not just your quarterly targets?

Those questions don't have universal answers. Nor should they. Every organisation will draw the line differently. But the organisations that navigate this transition well won't be the ones that avoid these conversations.

They'll be the ones willing to have them early, honestly and intentionally.

What Happens Next

The most interesting thing I heard at Henry Stewart wasn't a product announcement or a new capability. It was the growing acknowledgement that we've moved beyond asking whether AI will impact our organisations. We're now in the part where we have to decide what to do about it.

Better, faster and cheaper are easy goals to align around. The harder questions are: Better for whom? Faster at what cost? Cheaper according to whose definition of value?

Those are leadership questions. Those are the conversations we're increasingly having with clients at ICP. Not because they're asking us to implement AI, but because they're trying to understand what AI means for the way their marketing organisations actually operate, how teams are structured, and how people continue to create value as the work changes.

The organisations that navigate this moment well won't be the ones with the most AI pilots. They'll be the ones willing to answer those questions honestly and make decisions that reflect who they actually want to be, not just what technology makes possible.

The organisations that emerge stronger won't be the ones with the most AI pilots. They'll be the ones willing to answer the hardest questions before the technology forces them to. The organisations that emerge stronger won't be the ones with the most AI pilots. They'll be the ones willing to answer those questions honestly and make decisions that reflect who they want to be, not simply what the technology makes possible.