What happens when the rush toward AI collides with the messy reality of enterprise data that was never designed for it?

That is exactly where this fast-tracked episode with Kevin Dattolico from Syntax begins. Before we even hit record, we were swapping stories about music, travel, and a certain farewell concert that set the tone for a conversation that was both grounded and unexpectedly human. But once we got going, the discussion quickly shifted to one of the biggest blind spots I keep hearing about at tech conferences around the world. AI ambition is running far ahead of data readiness.

Kevin leads Syntax across the Americas, working with organizations that rely on SAP, Oracle, and complex cloud environments to run their businesses. In our conversation, he shares why many AI initiatives stall or quietly reset the moment they touch real production data. Proofs of concept can look impressive in isolation, but once AI starts interacting with live operational systems, the cracks appear. Inconsistent data, duplicated records, missing context, and governance gaps all surface at once. The result is confusion, unpredictable outputs, and a growing realization that the issue is rarely the model itself.

We dig into why ERP data has traditionally been trusted, while unstructured data across emails, documents, sensors, and logs often tells a very different story. Kevin explains where the real friction shows up when companies try to bring those worlds together, and why assumptions about data quality tend to break long before the technology does. It is a refreshingly honest look at what usually goes wrong first, and why leaders are often blindsided even after years of investment.

One of the strongest themes in this episode is the shift Kevin sees from AI-first thinking toward a data-first mindset. That does not mean abandoning AI spend. It means rebalancing priorities so those investments actually deliver outcomes the business can stand behind. We talk about what consolidation, cleansing, and transformation look like at enterprise scale, especially for organizations carrying decades of technical debt and fragmented systems.

The conversation also takes a thoughtful turn around governance, trust, and leadership. Kevin shares how the role of the chief data officer is changing from gatekeeper to enabler, and why modern governance has to support speed without sacrificing accountability. Along the way, he reflects on the risks of pushing ahead with weak data foundations, particularly in regulated industries where the cost of getting it wrong can be operational, reputational, or worse.

And then there is the moment that caught me completely off guard. When I asked Kevin to look back on his career and reflect on someone who made a difference, his answer led to one of the most moving stories I have heard in thousands of interviews. It is a reminder that behind every transformation story, there are people who quietly shape the path forward.

If you are wrestling with AI expectations, data reality, or simply wondering whether everyone else feels just as overwhelmed by this shift, this episode will resonate. The challenges Kevin describes are far more common than most leaders admit, and the opportunities for those who get the foundations right are real.

So as AI continues to dominate boardroom conversations, are you confident your data is ready to support the decisions you are asking it to make, or is it time to pause and rethink what sits underneath it all?

Useful Links

• Connect with Kevin Dattolico
• Learn more about Syntax

Thanks to our sponsors, Alcor, for supporting the show.