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AI is messy: here’s how to clean up your data before it derails your strategy

Most AI rollouts fail due to messy data, not bad models. Three practical steps to build the data foundation your AI strategy actually needs.

Matthew Finlayson

By Matthew Finlayson

AI is messy: here’s how to clean up your data before it derails your strategy
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I’ve seen a frequent pattern with AI deployments. A team blames the model or the vendor when their AI rollout stalls, but the real problem was sitting in their data the whole time: scattered across systems, poorly governed, never structured for AI to use. This piece I wrote for TechRadar walks through three specific steps to get your data AI-ready.

Originally published in TechRadar

Getting AI-ready while building your data infrastructure is like learning to drive a manual transmission on the wrong side of the road.

It’s complicated and requires potentially dangerous multitasking.

Organizations with immature data-handling processes that are adopting AI are trying to solve multiple technology problems at once, and risk stalling out.

Unsurprisingly, 48% of enterprises cited data-related issues as their top challenge to AI adoption in NVIDIA‘s 2026 State of AI report.

Most enterprise AI programs don’t fail because of the model or solution selected. They fail because underlying data is fragmented, inconsistent and poorly governed.

Get Your Data Foundation in Order

Enterprise data is messy in layers. It’s scattered across many systems, making it hard to pull together into a coherent picture. Even when you can consolidate it, you often will run into granularity or identifier mismatches. One application may store account numbers as plain digits, while another adds “ACCT” as a prefix. That small inconsistency creates an extra reconciliation step every time you join those data sets.

Data governance compounds the problem. Without a system intentionally designed to control who accesses data, where it moves and what protections are in place, gaps emerge fast. PII exposure is the most obvious risk: an email address that ends up in the wrong hands can trigger a serious breach. Raw, unstructured data also yields mediocre AI outputs and is more expensive to process.

Clean, structured data yields better results at lower cost. A third gap, explainability, is quickly becoming a legal requirement. Many countries and several U.S. states now require organizations to demonstrate how AI-driven decisions were reached. Cut corners on the data foundation and you may not be able to show that chain of reasoning.

At that point, you’re either in compliance violation territory or your model is producing outputs you can’t defend.

Three Steps to Get Your Data AI-Ready

Define governance before you deploy. Classify your data: what is it, where did it come from and who can touch it. Separate the roles of technical decision-making and compliance oversight. Keeping those responsibilities with different people prevents a compromising situation where the same person sets the rules and monitors compliance.

Run cross-functional AI governance as a standing function. Assign a representative from every department and meet monthly to discuss what teams are working on, what concerns have surfaced and what support they need from one another.

Approach larger AI-readiness initiatives like any other business project: assign a project manager, designate an executive owner, set a weekly cadence, build a task list and work through it.

Collect behavioral data even before you need it. The outcomes you get from AI vary enormously depending on how skilled the operator is, ranging from using it as an expensive search engine to developing autonomous workflows. Without visibility, you might be pouring money into AI licenses and getting Google-level output in return.

You don’t know who needs training, whether they have the right tool in front of them or what outcomes they’re achieving. The risk is that you make the wrong strategic call as a result—abandoning a rollout, for example, when the real fix was better training or a different tool.

Further considerations

Here’s another layer to consider. When an experienced worker completes a task, with AI assistance, they leave more skilled than when they started. The output and the learning happen together. That’s what behavioral data should demonstrate over time – not just task completion, but upward skill trajectories.

When someone at the beginning of the learning curve accepts whatever AI produces without critically engaging with it, you get the output but not the growth. Behavioral data is how you catch that gap early, before it becomes a long-term cost you can’t unwind.

Stay curious and look for the easy wins. Focus your data readiness efforts on the workflows where work actually happens, and prioritize tools that let you get at that data.

A recent example illustrates the payoff. A product manager ran an AI-powered analysis of quarterly bug patterns using data from the department’s most commonly used tools. The results were unexpected. One team carried a disproportionate share of incoming tickets, most of them requests for manual workarounds to a missing product feature.

While other teams split their time roughly 75% on new work and 25% on incoming bugs, that team was closer to 50-50. By not building a single feature, the organization was effectively operating 1.5 people below capacity.

The entire analysis took about 45 minutes. None of it would have been possible without data that was organized, tagged by team, connected to individual contributors, accessible via existing AI connectors and protected by role-based access controls.

The organizations that get the most from AI are the ones that empower their people to ask “I wonder if there’s something here” — and have data to diagnose in an afternoon. That only happens when the foundation is already in place.

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Meet the author

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Matthew Finlayson
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Matthew Finlayson is CTO at ActivTrak, where he leads engineering, security and support for a platform serving 9,500+ customer organizations and more than one million users worldwide. He oversees a 65-person organization while staying hands-on: roughly 1/3 of hi... Read more
Matthew Finlayson is CTO at ActivTrak, where he leads engineering, security and support for a platform serving 9,500+ customer organizations and more than one million users worldwide. He oversees a 65-person organization while staying hands-on: roughly 1/3 of his working hours go to developer tools, and he writes and ships code nearly every day.

Matthew brings 26 years of technology experience across QA, development, consulting and leadership. The thread running through all of it: learning the work from the inside, and building technology worth using himself. That has taken him from a social software company through its IPO, to a cloud cost management startup that helped create an industry category, to a workforce intelligence company now defining how organizations measure the impact of AI on work.

At Jive Software, Matthew served as Principal Engineer on Cloud Management and Infrastructure Operations. He helped scale the platform from $46 million to $204 million in revenue while serving 15 million users across 600+ enterprise customers, including HP, SAP, T-Mobile and UBS. He developed the public cloud hosting environment that accounted for 59% of product revenue during the enterprise social software category's peak years, supporting Jive's NASDAQ IPO in December 2011, which raised $161.3 million.

At Cloudability, Matthew joined a 20-person team and helped build it to 50 as the platform grew to manage more than $9 billion in enterprise cloud spending across AWS, Azure and Google Cloud for 250+ enterprise customers. He helped formalize the FinOps discipline, bridging finance and engineering to manage cloud costs more effectively — work that has since become an industry category with its own foundation and certification program.

Matthew studied at a technical school with serious liberal arts coursework, including serving as the editor in chief of the college newspaper. He treats writing as a thinking tool and credits that habit as the fastest path to getting people aligned. His leadership style follows the same logic: kindness is underrated in technical leadership, and how a decision is communicated is as consequential as the decision itself.

As ActivTrak's technical leader, Matthew drove the engineering organization through 26% revenue growth in 2025. That year, ActivTrak secured a strategic investment from Francisco Partners, bringing total funding to $77.5 million across Francisco Partners, Elsewhere Partners and Sapphire Ventures. Those who work with Matthew describe him as a listener who is mindful about how decisions land and a leader who pushes organizations to operate as one team rather than separate functions.

Matthew is an expert in cloud infrastructure, engineering leadership at scale, AI adoption and measurement and FinOps. He has spent 26 years building and leading technology organizations from startup to enterprise scale. He also serves as an Operating Advisor at Elsewhere Partners.

Matt's thought leadership has been featured in top tier media including Fast Company, Dataversity, Aerospace Trends and more.
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